<?xml version="1.0" encoding="UTF-8"?>

<!--XBRL Document Created with Wdesk from Workiva-->
<!--Copyright 2023 Workiva-->
<!--r:9104fffc-1f68-4cb5-852b-c4fe3a706d02,g:280f7ca0-018d-443c-9174-3bd0ed7833d4-->
<link:linkbase xmlns:link="http://www.xbrl.org/2003/linkbase" xmlns:xlink="http://www.w3.org/1999/xlink" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xsi:schemaLocation="http://www.xbrl.org/2003/linkbase http://www.xbrl.org/2003/xbrl-linkbase-2003-12-31.xsd">
  <link:roleRef roleURI="http://www.xbrl.org/2009/role/negatedPeriodStartLabel" xlink:type="simple" xlink:href="http://www.xbrl.org/lrr/role/negated-2009-12-16.xsd#negatedPeriodStartLabel"/>
  <link:roleRef roleURI="http://www.xbrl.org/2009/role/netLabel" xlink:type="simple" xlink:href="http://www.xbrl.org/lrr/role/net-2009-12-16.xsd#netLabel"/>
  <link:roleRef roleURI="http://www.xbrl.org/2009/role/negatedNetLabel" xlink:type="simple" xlink:href="http://www.xbrl.org/lrr/role/negated-2009-12-16.xsd#negatedNetLabel"/>
  <link:roleRef roleURI="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="simple" xlink:href="http://www.xbrl.org/lrr/role/negated-2009-12-16.xsd#negatedTerseLabel"/>
  <link:roleRef roleURI="http://www.xbrl.org/2009/role/negatedPeriodEndLabel" xlink:type="simple" xlink:href="http://www.xbrl.org/lrr/role/negated-2009-12-16.xsd#negatedPeriodEndLabel"/>
  <link:roleRef roleURI="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="simple" xlink:href="http://www.xbrl.org/lrr/role/negated-2009-12-16.xsd#negatedLabel"/>
  <link:roleRef roleURI="http://www.xbrl.org/2009/role/negatedTotalLabel" xlink:type="simple" xlink:href="http://www.xbrl.org/lrr/role/negated-2009-12-16.xsd#negatedTotalLabel"/>
  <link:labelLink xlink:role="http://www.xbrl.org/2003/role/link" xlink:type="extended">
    <link:label id="lab_us-gaap_BusinessAcquisitionAxis_3afd40b3-fcd6-4125-b46b-f71f78a08e6d_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Business Acquisition [Axis]</link:label>
    <link:label id="lab_us-gaap_BusinessAcquisitionAxis_label_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Business Acquisition [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessAcquisitionAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_BusinessAcquisitionAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessAcquisitionAxis" xlink:to="lab_us-gaap_BusinessAcquisitionAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInReinsuranceRecoverable_3591fcd4-9ba5-4a79-bc41-edb0f93962a2_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInReinsuranceRecoverable" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance recoverables</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInReinsuranceRecoverable_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInReinsuranceRecoverable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Increase (Decrease) in Reinsurance Recoverable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInReinsuranceRecoverable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInReinsuranceRecoverable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInReinsuranceRecoverable" xlink:to="lab_us-gaap_IncreaseDecreaseInReinsuranceRecoverable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RelatedPartyTransactionsAbstract_label_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Related Party Transactions [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RelatedPartyTransactionsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RelatedPartyTransactionsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RelatedPartyTransactionsAbstract" xlink:to="lab_us-gaap_RelatedPartyTransactionsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProvisionForDoubtfulAccounts_be8bef09-11ff-4434-a66e-ebcc74ac20f7_terseLabel_en-US" xlink:label="lab_us-gaap_ProvisionForDoubtfulAccounts" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Provision for bad debts</link:label>
    <link:label id="lab_us-gaap_ProvisionForDoubtfulAccounts_label_en-US" xlink:label="lab_us-gaap_ProvisionForDoubtfulAccounts" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accounts Receivable, Credit Loss Expense (Reversal)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProvisionForDoubtfulAccounts" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ProvisionForDoubtfulAccounts"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProvisionForDoubtfulAccounts" xlink:to="lab_us-gaap_ProvisionForDoubtfulAccounts" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_SMA1Member_b20ebefa-70db-4723-a465-b850ec30b03b_terseLabel_en-US" xlink:label="lab_skwd_SMA1Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SMA1</link:label>
    <link:label id="lab_skwd_SMA1Member_label_en-US" xlink:label="lab_skwd_SMA1Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SMA1 [Member]</link:label>
    <link:label id="lab_skwd_SMA1Member_documentation_en-US" xlink:label="lab_skwd_SMA1Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SMA1</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_SMA1Member" xlink:href="skwd-20221231.xsd#skwd_SMA1Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_SMA1Member" xlink:to="lab_skwd_SMA1Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredIncomeTaxAssetsNet_85844e7c-8c60-4fce-bf34-ae000774235c_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredIncomeTaxAssetsNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred income taxes</link:label>
    <link:label id="lab_us-gaap_DeferredIncomeTaxAssetsNet_label_en-US" xlink:label="lab_us-gaap_DeferredIncomeTaxAssetsNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Income Tax Assets, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredIncomeTaxAssetsNet" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DeferredIncomeTaxAssetsNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredIncomeTaxAssetsNet" xlink:to="lab_us-gaap_DeferredIncomeTaxAssetsNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentCarryingAmount_0861edcb-ba1e-45ff-9be8-b8b5ce8159f5_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentCarryingAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Principal</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentCarryingAmount_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentCarryingAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long-Term Debt, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentCarryingAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtInstrumentCarryingAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentCarryingAmount" xlink:to="lab_us-gaap_DebtInstrumentCarryingAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock_49326e47-5335-4069-b37b-27c2c026aed0_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Unrealized Loss Position, Fair Value</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Unrealized Loss Position, Fair Value [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue_d1ff314d-e750-4393-8820-22a7cc50df84_terseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">12 Months or More</link:label>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue_label_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Held-to-Maturity, Continuous Unrealized Loss Position, 12 Months or Longer, Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue" xlink:to="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentAbstract_label_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Property, Plant and Equipment [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PropertyPlantAndEquipmentAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentAbstract" xlink:to="lab_us-gaap_PropertyPlantAndEquipmentAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ContingentlyIssuableInstrumentsPreferredSharesIfConvertedMember_8c4619c6-6016-4e8e-8b8f-4c04a31e23cb_terseLabel_en-US" xlink:label="lab_skwd_ContingentlyIssuableInstrumentsPreferredSharesIfConvertedMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred shares, if converted</link:label>
    <link:label id="lab_skwd_ContingentlyIssuableInstrumentsPreferredSharesIfConvertedMember_label_en-US" xlink:label="lab_skwd_ContingentlyIssuableInstrumentsPreferredSharesIfConvertedMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Contingently Issuable Instruments, Preferred Shares, If Converted [Member]</link:label>
    <link:label id="lab_skwd_ContingentlyIssuableInstrumentsPreferredSharesIfConvertedMember_documentation_en-US" xlink:label="lab_skwd_ContingentlyIssuableInstrumentsPreferredSharesIfConvertedMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Contingently Issuable Instruments, Preferred Shares, If Converted</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ContingentlyIssuableInstrumentsPreferredSharesIfConvertedMember" xlink:href="skwd-20221231.xsd#skwd_ContingentlyIssuableInstrumentsPreferredSharesIfConvertedMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ContingentlyIssuableInstrumentsPreferredSharesIfConvertedMember" xlink:to="lab_skwd_ContingentlyIssuableInstrumentsPreferredSharesIfConvertedMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PreferredStockSharesOutstanding_a746400e-3b23-43e8-9321-edc4ff5c966d_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred stock, shares outstanding (in shares)</link:label>
    <link:label id="lab_us-gaap_PreferredStockSharesOutstanding_label_en-US" xlink:label="lab_us-gaap_PreferredStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred Stock, Shares Outstanding</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockSharesOutstanding" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PreferredStockSharesOutstanding"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PreferredStockSharesOutstanding" xlink:to="lab_us-gaap_PreferredStockSharesOutstanding" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense_f9fceabb-be1c-4687-a87e-cf2414ff68f2_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Liability for Unpaid Claims and Claims Adjustment Expense</link:label>
    <link:label id="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Liability for Unpaid Claims and Claims Adjustment Expense [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:to="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GainLossOnInvestments_0aae229b-4d3f-47d2-9050-d42da95a4480_terseLabel_en-US" xlink:label="lab_us-gaap_GainLossOnInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net investment (losses) gains</link:label>
    <link:label id="lab_us-gaap_GainLossOnInvestments_329c5716-6f08-47b3-a1ed-a1ff29891a54_totalLabel_en-US" xlink:label="lab_us-gaap_GainLossOnInvestments" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net investment (losses) gains</link:label>
    <link:label id="lab_us-gaap_GainLossOnInvestments_label_en-US" xlink:label="lab_us-gaap_GainLossOnInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gain (Loss) on Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GainLossOnInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_GainLossOnInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GainLossOnInvestments" xlink:to="lab_us-gaap_GainLossOnInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentAxis_3e151810-ac50-4327-bd05-d21a98b8dfd2_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument [Axis]</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentAxis_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtInstrumentAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentAxis" xlink:to="lab_us-gaap_DebtInstrumentAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TechnologySectorMember_68dcbe96-c2ee-4596-9909-b437ea8c32e9_terseLabel_en-US" xlink:label="lab_us-gaap_TechnologySectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Information technology</link:label>
    <link:label id="lab_us-gaap_TechnologySectorMember_label_en-US" xlink:label="lab_us-gaap_TechnologySectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Technology Sector [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TechnologySectorMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_TechnologySectorMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TechnologySectorMember" xlink:to="lab_us-gaap_TechnologySectorMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueOfFinancialInstrumentsPolicy_105b66ac-b67c-44bf-8534-9202a328b570_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueOfFinancialInstrumentsPolicy" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value of Financial Instruments</link:label>
    <link:label id="lab_us-gaap_FairValueOfFinancialInstrumentsPolicy_label_en-US" xlink:label="lab_us-gaap_FairValueOfFinancialInstrumentsPolicy" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value of Financial Instruments, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueOfFinancialInstrumentsPolicy" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FairValueOfFinancialInstrumentsPolicy"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueOfFinancialInstrumentsPolicy" xlink:to="lab_us-gaap_FairValueOfFinancialInstrumentsPolicy" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherIncomeAndExpensesAbstract_label_en-US" xlink:label="lab_us-gaap_OtherIncomeAndExpensesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other Income and Expenses [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherIncomeAndExpensesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OtherIncomeAndExpensesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherIncomeAndExpensesAbstract" xlink:to="lab_us-gaap_OtherIncomeAndExpensesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AdditionalPaidInCapital_add3e3f6-db40-4e4a-a515-14235bcbabac_terseLabel_en-US" xlink:label="lab_us-gaap_AdditionalPaidInCapital" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Additional paid-in capital</link:label>
    <link:label id="lab_us-gaap_AdditionalPaidInCapital_label_en-US" xlink:label="lab_us-gaap_AdditionalPaidInCapital" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Additional Paid in Capital</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdditionalPaidInCapital" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AdditionalPaidInCapital"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AdditionalPaidInCapital" xlink:to="lab_us-gaap_AdditionalPaidInCapital" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_877f82cb-288e-441e-9914-edbd564a5102_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reserves for losses and loss adjustment expenses</link:label>
    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_bfbc130b-d252-4a17-8a30-d1b626939e70_periodStartLabel_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reserves for losses and LAE, beginning of period</link:label>
    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_8d180c99-55e4-4032-82ef-7e33f719fe88_periodEndLabel_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reserves for losses and LAE, end of period</link:label>
    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability for Claims and Claims Adjustment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:to="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue_c9697fde-5420-4067-a3ad-062f205de119_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Due after five years through ten years</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Fair Value, Maturity, Allocated and Single Maturity Date, after Year 5 Through 10</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromDivestitureOfInterestInSubsidiariesAndAffiliates_055ff3ec-025e-4540-8ad9-0aa2f70bcb5e_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromDivestitureOfInterestInSubsidiariesAndAffiliates" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Sale of investment in subsidiary</link:label>
    <link:label id="lab_us-gaap_ProceedsFromDivestitureOfInterestInSubsidiariesAndAffiliates_label_en-US" xlink:label="lab_us-gaap_ProceedsFromDivestitureOfInterestInSubsidiariesAndAffiliates" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Proceeds from Divestiture of Interest in Subsidiaries and Affiliates</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromDivestitureOfInterestInSubsidiariesAndAffiliates" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ProceedsFromDivestitureOfInterestInSubsidiariesAndAffiliates"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromDivestitureOfInterestInSubsidiariesAndAffiliates" xlink:to="lab_us-gaap_ProceedsFromDivestitureOfInterestInSubsidiariesAndAffiliates" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueDisclosureItemAmountsDomain_af1c5b17-86fd-406c-8ec5-049583cbe045_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueDisclosureItemAmountsDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value Measurement [Domain]</link:label>
    <link:label id="lab_us-gaap_FairValueDisclosureItemAmountsDomain_label_en-US" xlink:label="lab_us-gaap_FairValueDisclosureItemAmountsDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value Measurement [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueDisclosureItemAmountsDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FairValueDisclosureItemAmountsDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueDisclosureItemAmountsDomain" xlink:to="lab_us-gaap_FairValueDisclosureItemAmountsDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain_e5e81ea7-922b-407f-8c4d-4a804f68c366_terseLabel_en-US" xlink:label="lab_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Financial Instruments [Domain]</link:label>
    <link:label id="lab_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain_label_en-US" xlink:label="lab_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Financial Instruments [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain" xlink:to="lab_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1_3227b82c-ef92-4ec4-a0d4-9b06a57db811_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Basis spread on variable rate</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Basis Spread on Variable Rate</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtInstrumentBasisSpreadOnVariableRate1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1" xlink:to="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_Depreciation_bd0d1348-3987-44d0-b6b3-717ca5aea001_terseLabel_en-US" xlink:label="lab_us-gaap_Depreciation" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Depreciation expense</link:label>
    <link:label id="lab_us-gaap_Depreciation_label_en-US" xlink:label="lab_us-gaap_Depreciation" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Depreciation</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Depreciation" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_Depreciation"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Depreciation" xlink:to="lab_us-gaap_Depreciation" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredTaxAssetsLiabilitiesNet_77e5bd5d-bff7-41ff-b93f-24fab3f10f41_totalLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsLiabilitiesNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred income taxes</link:label>
    <link:label id="lab_us-gaap_DeferredTaxAssetsLiabilitiesNet_label_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsLiabilitiesNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Tax Assets, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxAssetsLiabilitiesNet" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DeferredTaxAssetsLiabilitiesNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredTaxAssetsLiabilitiesNet" xlink:to="lab_us-gaap_DeferredTaxAssetsLiabilitiesNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage_672ac192-2a22-4803-a10e-74fa26a6d208_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stated interest rate</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Interest Rate, Stated Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtInstrumentInterestRateStatedPercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:to="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OperatingLeaseWeightedAverageDiscountRatePercent_b1214e04-7384-4099-bf59-6632389d7ec7_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingLeaseWeightedAverageDiscountRatePercent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Operating lease weighted-average discount rate</link:label>
    <link:label id="lab_us-gaap_OperatingLeaseWeightedAverageDiscountRatePercent_label_en-US" xlink:label="lab_us-gaap_OperatingLeaseWeightedAverageDiscountRatePercent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Operating Lease, Weighted Average Discount Rate, Percent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseWeightedAverageDiscountRatePercent" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OperatingLeaseWeightedAverageDiscountRatePercent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OperatingLeaseWeightedAverageDiscountRatePercent" xlink:to="lab_us-gaap_OperatingLeaseWeightedAverageDiscountRatePercent" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseTable_576e52b4-ddab-488b-846b-64d3193b03c3_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability for Claims and Claims Adjustment Expense [Table]</link:label>
    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseTable_label_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability for Claims and Claims Adjustment Expense [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseTable" xlink:to="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseTable" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_OfficePortfolioSegmentMember_4b065807-dadf-45e5-b09c-fff07d82c5c4_terseLabel_en-US" xlink:label="lab_skwd_OfficePortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Office</link:label>
    <link:label id="lab_skwd_OfficePortfolioSegmentMember_label_en-US" xlink:label="lab_skwd_OfficePortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Office Portfolio Segment [Member]</link:label>
    <link:label id="lab_skwd_OfficePortfolioSegmentMember_documentation_en-US" xlink:label="lab_skwd_OfficePortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Office Portfolio Segment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_OfficePortfolioSegmentMember" xlink:href="skwd-20221231.xsd#skwd_OfficePortfolioSegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_OfficePortfolioSegmentMember" xlink:to="lab_skwd_OfficePortfolioSegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ReinsuranceAgreementMember_549b7889-7e8d-4cda-b3f7-7939d2b9092c_terseLabel_en-US" xlink:label="lab_skwd_ReinsuranceAgreementMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance agreement</link:label>
    <link:label id="lab_skwd_ReinsuranceAgreementMember_label_en-US" xlink:label="lab_skwd_ReinsuranceAgreementMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Agreement [Member]</link:label>
    <link:label id="lab_skwd_ReinsuranceAgreementMember_documentation_en-US" xlink:label="lab_skwd_ReinsuranceAgreementMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Agreement</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ReinsuranceAgreementMember" xlink:href="skwd-20221231.xsd#skwd_ReinsuranceAgreementMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ReinsuranceAgreementMember" xlink:to="lab_skwd_ReinsuranceAgreementMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsAccidentYear2016Member_64372f74-c2aa-46d8-8812-582a1ac6183c_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsAccidentYear2016Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accident Year 2016</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsAccidentYear2016Member_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsAccidentYear2016Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Accident Year 2016 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsAccidentYear2016Member" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortdurationInsuranceContractsAccidentYear2016Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsAccidentYear2016Member" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsAccidentYear2016Member" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_GainLossOnHeldToMaturitySecuritiesAndEquityMethodInvestments_f1a929ee-72b4-49b2-a2ef-582988738c6d_negatedTerseLabel_en-US" xlink:label="lab_skwd_GainLossOnHeldToMaturitySecuritiesAndEquityMethodInvestments" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Earnings on illiquid investments</link:label>
    <link:label id="lab_skwd_GainLossOnHeldToMaturitySecuritiesAndEquityMethodInvestments_label_en-US" xlink:label="lab_skwd_GainLossOnHeldToMaturitySecuritiesAndEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gain (Loss) On Held-to-Maturity Securities and Equity Method Investments</link:label>
    <link:label id="lab_skwd_GainLossOnHeldToMaturitySecuritiesAndEquityMethodInvestments_documentation_en-US" xlink:label="lab_skwd_GainLossOnHeldToMaturitySecuritiesAndEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gain (Loss) On Held-to-Maturity Securities and Equity Method Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_GainLossOnHeldToMaturitySecuritiesAndEquityMethodInvestments" xlink:href="skwd-20221231.xsd#skwd_GainLossOnHeldToMaturitySecuritiesAndEquityMethodInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_GainLossOnHeldToMaturitySecuritiesAndEquityMethodInvestments" xlink:to="lab_skwd_GainLossOnHeldToMaturitySecuritiesAndEquityMethodInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LesseeLeaseDescriptionTable_1eb256e1-fb07-4b92-9895-1efe59f75e16_terseLabel_en-US" xlink:label="lab_us-gaap_LesseeLeaseDescriptionTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Lessee, Lease, Description [Table]</link:label>
    <link:label id="lab_us-gaap_LesseeLeaseDescriptionTable_label_en-US" xlink:label="lab_us-gaap_LesseeLeaseDescriptionTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Lessee, Lease, Description [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeLeaseDescriptionTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LesseeLeaseDescriptionTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LesseeLeaseDescriptionTable" xlink:to="lab_us-gaap_LesseeLeaseDescriptionTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems_899dad6a-b673-42c8-8ab1-b7991cd0924a_terseLabel_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]</link:label>
    <link:label id="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems_label_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems" xlink:to="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ApplicableMarginRateMember_413b0b9c-37a0-4b67-b9d8-0519f9c284c8_terseLabel_en-US" xlink:label="lab_skwd_ApplicableMarginRateMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Applicable Margin Rate</link:label>
    <link:label id="lab_skwd_ApplicableMarginRateMember_label_en-US" xlink:label="lab_skwd_ApplicableMarginRateMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Applicable Margin Rate [Member]</link:label>
    <link:label id="lab_skwd_ApplicableMarginRateMember_documentation_en-US" xlink:label="lab_skwd_ApplicableMarginRateMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Applicable Margin Rate</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ApplicableMarginRateMember" xlink:href="skwd-20221231.xsd#skwd_ApplicableMarginRateMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ApplicableMarginRateMember" xlink:to="lab_skwd_ApplicableMarginRateMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount_6bcf0f00-eaa5-44f1-8630-ac56f80a11ed_terseLabel_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Antidilutive securities (in shares)</link:label>
    <link:label id="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount_label_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Antidilutive Securities Excluded from Computation of Earnings Per Share, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount" xlink:to="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReceivablesFromStockholderMember_222ba97c-3de3-43f1-baec-65305461f035_terseLabel_en-US" xlink:label="lab_us-gaap_ReceivablesFromStockholderMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stock Notes Receivable</link:label>
    <link:label id="lab_us-gaap_ReceivablesFromStockholderMember_label_en-US" xlink:label="lab_us-gaap_ReceivablesFromStockholderMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Receivables from Stockholder [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReceivablesFromStockholderMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ReceivablesFromStockholderMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReceivablesFromStockholderMember" xlink:to="lab_us-gaap_ReceivablesFromStockholderMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_A2022EmployeeStockPurchasePlanMember_0eceb8f4-236b-4441-a004-4f73a7d5ee3e_terseLabel_en-US" xlink:label="lab_skwd_A2022EmployeeStockPurchasePlanMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">2022 Employee Stock Purchase Plan</link:label>
    <link:label id="lab_skwd_A2022EmployeeStockPurchasePlanMember_label_en-US" xlink:label="lab_skwd_A2022EmployeeStockPurchasePlanMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">2022 Employee Stock Purchase Plan [Member]</link:label>
    <link:label id="lab_skwd_A2022EmployeeStockPurchasePlanMember_documentation_en-US" xlink:label="lab_skwd_A2022EmployeeStockPurchasePlanMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">2022 Employee Stock Purchase Plan</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_A2022EmployeeStockPurchasePlanMember" xlink:href="skwd-20221231.xsd#skwd_A2022EmployeeStockPurchasePlanMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_A2022EmployeeStockPurchasePlanMember" xlink:to="lab_skwd_A2022EmployeeStockPurchasePlanMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearNine_c96621c0-9ffb-4522-a1db-905767e463cd_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearNine" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Year 9</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearNine_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearNine" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Historical Claims Duration, Year Nine</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearNine" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearNine"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearNine" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearNine" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossReclassificationAdjustmentFromAOCIForSaleOfSecuritiesNetOfTax_8806fc05-f43a-4005-bb45-4fddf7306f55_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossReclassificationAdjustmentFromAOCIForSaleOfSecuritiesNetOfTax" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reclassification adjustment for gains on securities no longer held, net of tax</link:label>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossReclassificationAdjustmentFromAOCIForSaleOfSecuritiesNetOfTax_label_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossReclassificationAdjustmentFromAOCIForSaleOfSecuritiesNetOfTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other Comprehensive Income (Loss), Reclassification Adjustment from AOCI for Sale of Securities, Net of Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossReclassificationAdjustmentFromAOCIForSaleOfSecuritiesNetOfTax" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OtherComprehensiveIncomeLossReclassificationAdjustmentFromAOCIForSaleOfSecuritiesNetOfTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherComprehensiveIncomeLossReclassificationAdjustmentFromAOCIForSaleOfSecuritiesNetOfTax" xlink:to="lab_us-gaap_OtherComprehensiveIncomeLossReclassificationAdjustmentFromAOCIForSaleOfSecuritiesNetOfTax" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OperatingLeaseLiabilitiesPaymentsDueAbstract_a336ef11-5932-47e3-8b3b-dda3a3f484e7_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingLeaseLiabilitiesPaymentsDueAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Lessee, Operating Lease, Liability, to be Paid [Abstract]</link:label>
    <link:label id="lab_us-gaap_OperatingLeaseLiabilitiesPaymentsDueAbstract_label_en-US" xlink:label="lab_us-gaap_OperatingLeaseLiabilitiesPaymentsDueAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Lessee, Operating Lease, Liability, to be Paid [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseLiabilitiesPaymentsDueAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OperatingLeaseLiabilitiesPaymentsDueAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OperatingLeaseLiabilitiesPaymentsDueAbstract" xlink:to="lab_us-gaap_OperatingLeaseLiabilitiesPaymentsDueAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationOtherAdjustments_c6a19364-df83-4aec-98ec-236e2418371d_terseLabel_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationOtherAdjustments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other</link:label>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationOtherAdjustments_label_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationOtherAdjustments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Effective Income Tax Rate Reconciliation, Other Adjustments, Percent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectiveIncomeTaxRateReconciliationOtherAdjustments" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EffectiveIncomeTaxRateReconciliationOtherAdjustments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectiveIncomeTaxRateReconciliationOtherAdjustments" xlink:to="lab_us-gaap_EffectiveIncomeTaxRateReconciliationOtherAdjustments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueAfterYearFive_2be11dd4-eca2-4e23-8c7d-1f14d79fd1e6_terseLabel_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueAfterYearFive" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Thereafter</link:label>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueAfterYearFive_label_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueAfterYearFive" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Lessee, Operating Lease, Liability, to be Paid, after Year Five</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueAfterYearFive" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueAfterYearFive"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueAfterYearFive" xlink:to="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueAfterYearFive" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetInvestmentIncome_4b95659b-c998-4664-b8bb-2f409b45ea90_terseLabel_en-US" xlink:label="lab_us-gaap_NetInvestmentIncome" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net investment income</link:label>
    <link:label id="lab_us-gaap_NetInvestmentIncome_c3894f71-bffa-49c0-9d32-1fd529b62290_totalLabel_en-US" xlink:label="lab_us-gaap_NetInvestmentIncome" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net investment income</link:label>
    <link:label id="lab_us-gaap_NetInvestmentIncome_label_en-US" xlink:label="lab_us-gaap_NetInvestmentIncome" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net Investment Income</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetInvestmentIncome" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetInvestmentIncome"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetInvestmentIncome" xlink:to="lab_us-gaap_NetInvestmentIncome" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityComponentDomain_96f0e994-7c63-4437-aa42-3d02e1d465a5_terseLabel_en-US" xlink:label="lab_us-gaap_EquityComponentDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Component [Domain]</link:label>
    <link:label id="lab_us-gaap_EquityComponentDomain_label_en-US" xlink:label="lab_us-gaap_EquityComponentDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Component [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityComponentDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EquityComponentDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityComponentDomain" xlink:to="lab_us-gaap_EquityComponentDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubsequentEventTypeDomain_c2cc9fcb-fea9-4659-b386-f2b5b4971263_terseLabel_en-US" xlink:label="lab_us-gaap_SubsequentEventTypeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subsequent Event Type [Domain]</link:label>
    <link:label id="lab_us-gaap_SubsequentEventTypeDomain_label_en-US" xlink:label="lab_us-gaap_SubsequentEventTypeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subsequent Event Type [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsequentEventTypeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SubsequentEventTypeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsequentEventTypeDomain" xlink:to="lab_us-gaap_SubsequentEventTypeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SecuredDebtMember_8544539e-8e5f-4ea0-87a3-1fdd9143921a_terseLabel_en-US" xlink:label="lab_us-gaap_SecuredDebtMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Secured Debt</link:label>
    <link:label id="lab_us-gaap_SecuredDebtMember_label_en-US" xlink:label="lab_us-gaap_SecuredDebtMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Secured Debt [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SecuredDebtMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SecuredDebtMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SecuredDebtMember" xlink:to="lab_us-gaap_SecuredDebtMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareReconciliationAbstract_9153b51b-2f03-4647-bc80-65f439a247e1_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareReconciliationAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Weighted-average common shares outstanding</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareReconciliationAbstract_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareReconciliationAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Earnings Per Share Reconciliation [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareReconciliationAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EarningsPerShareReconciliationAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareReconciliationAbstract" xlink:to="lab_us-gaap_EarningsPerShareReconciliationAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_OwnershipAxis_c8bc236c-1221-4eb3-9bef-e106978035d7_terseLabel_en-US" xlink:label="lab_srt_OwnershipAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ownership [Axis]</link:label>
    <link:label id="lab_srt_OwnershipAxis_label_en-US" xlink:label="lab_srt_OwnershipAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ownership [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_OwnershipAxis" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_OwnershipAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_OwnershipAxis" xlink:to="lab_srt_OwnershipAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_EquityMethodInvesteeNameDomain_8e0c3d6c-0ec8-4d3b-875d-76d63a215a2c_terseLabel_en-US" xlink:label="lab_srt_EquityMethodInvesteeNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment, Name [Domain]</link:label>
    <link:label id="lab_srt_EquityMethodInvesteeNameDomain_label_en-US" xlink:label="lab_srt_EquityMethodInvesteeNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment, Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_EquityMethodInvesteeNameDomain" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_EquityMethodInvesteeNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_EquityMethodInvesteeNameDomain" xlink:to="lab_srt_EquityMethodInvesteeNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearSeven_7c00c086-ebf3-42d8-94d5-b5f37717f29d_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearSeven" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Year 7</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearSeven_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearSeven" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Historical Claims Duration, Year Seven</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearSeven" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearSeven"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearSeven" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearSeven" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperationsTaxRateReconciliationAbstract_2cdc7772-e015-4f90-8229-e6cb637ee759_terseLabel_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperationsTaxRateReconciliationAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Percentage</link:label>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperationsTaxRateReconciliationAbstract_label_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperationsTaxRateReconciliationAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Effective Income Tax Rate Reconciliation, Percent [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectiveIncomeTaxRateContinuingOperationsTaxRateReconciliationAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EffectiveIncomeTaxRateContinuingOperationsTaxRateReconciliationAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectiveIncomeTaxRateContinuingOperationsTaxRateReconciliationAbstract" xlink:to="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperationsTaxRateReconciliationAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RelatedPartyDomain_2245a026-5c61-45da-b8c7-48ebace6e766_terseLabel_en-US" xlink:label="lab_us-gaap_RelatedPartyDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Related Party [Domain]</link:label>
    <link:label id="lab_us-gaap_RelatedPartyDomain_label_en-US" xlink:label="lab_us-gaap_RelatedPartyDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Related Party [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RelatedPartyDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RelatedPartyDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RelatedPartyDomain" xlink:to="lab_us-gaap_RelatedPartyDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LesseeLeaseDescriptionLineItems_36bec545-b4e4-437b-ba0a-78a19eba9a8e_terseLabel_en-US" xlink:label="lab_us-gaap_LesseeLeaseDescriptionLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Lessee, Lease, Description [Line Items]</link:label>
    <link:label id="lab_us-gaap_LesseeLeaseDescriptionLineItems_label_en-US" xlink:label="lab_us-gaap_LesseeLeaseDescriptionLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Lessee, Lease, Description [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeLeaseDescriptionLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LesseeLeaseDescriptionLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LesseeLeaseDescriptionLineItems" xlink:to="lab_us-gaap_LesseeLeaseDescriptionLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_GMICMember_f87e400d-2949-496a-8290-5127bf16f184_terseLabel_en-US" xlink:label="lab_skwd_GMICMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">GMIC</link:label>
    <link:label id="lab_skwd_GMICMember_label_en-US" xlink:label="lab_skwd_GMICMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">GMIC [Member]</link:label>
    <link:label id="lab_skwd_GMICMember_documentation_en-US" xlink:label="lab_skwd_GMICMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">GMIC</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_GMICMember" xlink:href="skwd-20221231.xsd#skwd_GMICMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_GMICMember" xlink:to="lab_skwd_GMICMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharePurchasesPortionFinancedByStockNoteReceivableMaximum_7aeae01f-d4e2-4b06-9bad-da98964e4761_terseLabel_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharePurchasesPortionFinancedByStockNoteReceivableMaximum" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Maximum finance option</link:label>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharePurchasesPortionFinancedByStockNoteReceivableMaximum_label_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharePurchasesPortionFinancedByStockNoteReceivableMaximum" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Share Purchases, Portion Financed by Stock Note Receivable, Maximum</link:label>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharePurchasesPortionFinancedByStockNoteReceivableMaximum_documentation_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharePurchasesPortionFinancedByStockNoteReceivableMaximum" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Share Purchases, Portion Financed by Stock Note Receivable, Maximum</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharePurchasesPortionFinancedByStockNoteReceivableMaximum" xlink:href="skwd-20221231.xsd#skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharePurchasesPortionFinancedByStockNoteReceivableMaximum"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharePurchasesPortionFinancedByStockNoteReceivableMaximum" xlink:to="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharePurchasesPortionFinancedByStockNoteReceivableMaximum" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract_c066bf7a-85b7-4c69-a146-860ac8b603c7_terseLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Available-for-sale and held-to-maturity, fair value</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract_label_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Unrealized Loss Position [Abstract]</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract_documentation_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Unrealized Loss Position</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract" xlink:href="skwd-20221231.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract" xlink:to="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SupplementalCashFlowInformationAbstract_261a5c92-defd-4df3-998f-d419ae5c975e_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalCashFlowInformationAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Supplemental disclosure of cash flow information:</link:label>
    <link:label id="lab_us-gaap_SupplementalCashFlowInformationAbstract_label_en-US" xlink:label="lab_us-gaap_SupplementalCashFlowInformationAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Supplemental Cash Flow Information [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalCashFlowInformationAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SupplementalCashFlowInformationAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SupplementalCashFlowInformationAbstract" xlink:to="lab_us-gaap_SupplementalCashFlowInformationAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions_789ffce7-6ff6-469f-bedf-85f3c62946d9_terseLabel_en-US" xlink:label="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unrecognized compensation cost</link:label>
    <link:label id="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions_label_en-US" xlink:label="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Payment Arrangement, Nonvested Award, Excluding Option, Cost Not yet Recognized, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions" xlink:to="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PlanNameDomain_cbfc842e-f24d-4e03-95c8-2c28c7808a21_terseLabel_en-US" xlink:label="lab_us-gaap_PlanNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Plan Name [Domain]</link:label>
    <link:label id="lab_us-gaap_PlanNameDomain_label_en-US" xlink:label="lab_us-gaap_PlanNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Plan Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PlanNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PlanNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PlanNameDomain" xlink:to="lab_us-gaap_PlanNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract_745f77f8-e111-4ec2-b920-1c69a1dcc620_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Earned</link:label>
    <link:label id="lab_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract_label_en-US" xlink:label="lab_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Premiums Earned, Net [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract" xlink:to="lab_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressStateOrProvince_18b58137-8b21-4736-a220-16839992a3de_terseLabel_en-US" xlink:label="lab_dei_EntityAddressStateOrProvince" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Address, State or Province</link:label>
    <link:label id="lab_dei_EntityAddressStateOrProvince_label_en-US" xlink:label="lab_dei_EntityAddressStateOrProvince" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Address, State or Province</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressStateOrProvince" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityAddressStateOrProvince"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityAddressStateOrProvince" xlink:to="lab_dei_EntityAddressStateOrProvince" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PrepaidReinsurancePremiums_5104a482-1b40-439b-8453-e618fee9ccf5_terseLabel_en-US" xlink:label="lab_us-gaap_PrepaidReinsurancePremiums" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ceded unearned premium</link:label>
    <link:label id="lab_us-gaap_PrepaidReinsurancePremiums_1c2c5077-dc80-4f37-9805-d954756f7432_verboseLabel_en-US" xlink:label="lab_us-gaap_PrepaidReinsurancePremiums" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ceded unearned premium</link:label>
    <link:label id="lab_us-gaap_PrepaidReinsurancePremiums_label_en-US" xlink:label="lab_us-gaap_PrepaidReinsurancePremiums" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Prepaid Reinsurance Premiums</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PrepaidReinsurancePremiums" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PrepaidReinsurancePremiums"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PrepaidReinsurancePremiums" xlink:to="lab_us-gaap_PrepaidReinsurancePremiums" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract_33b38a61-4000-4650-badb-433afec71aab_terseLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Comprehensive (loss) income:</link:label>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract_label_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other Comprehensive Income (Loss), Net of Tax [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract" xlink:to="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverables_1d520251-1769-4197-a11f-3b7decf0d174_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverables" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance collateral</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverables_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverables" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Recoverables, Including Reinsurance Premium Paid</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverables" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ReinsuranceRecoverables"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverables" xlink:to="lab_us-gaap_ReinsuranceRecoverables" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AwardTypeAxis_43306f81-fd34-4c5e-a1b7-1a102f8800dd_terseLabel_en-US" xlink:label="lab_us-gaap_AwardTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Award Type [Axis]</link:label>
    <link:label id="lab_us-gaap_AwardTypeAxis_label_en-US" xlink:label="lab_us-gaap_AwardTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Award Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AwardTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AwardTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AwardTypeAxis" xlink:to="lab_us-gaap_AwardTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CollateralizedSecuritiesMember_8170ee75-ee73-4efa-8562-fe01decb978a_terseLabel_en-US" xlink:label="lab_us-gaap_CollateralizedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Mortgage-backed securities</link:label>
    <link:label id="lab_us-gaap_CollateralizedSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_CollateralizedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Collateralized Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CollateralizedSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CollateralizedSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CollateralizedSecuritiesMember" xlink:to="lab_us-gaap_CollateralizedSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MortgagesHeldForSaleFairValueDisclosure_2b5c1d6f-be09-43b4-a1fa-4be240372a4a_terseLabel_en-US" xlink:label="lab_us-gaap_MortgagesHeldForSaleFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Mortgage loans</link:label>
    <link:label id="lab_us-gaap_MortgagesHeldForSaleFairValueDisclosure_label_en-US" xlink:label="lab_us-gaap_MortgagesHeldForSaleFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Mortgages Held-for-sale, Fair Value Disclosure</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MortgagesHeldForSaleFairValueDisclosure" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_MortgagesHeldForSaleFairValueDisclosure"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MortgagesHeldForSaleFairValueDisclosure" xlink:to="lab_us-gaap_MortgagesHeldForSaleFairValueDisclosure" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ValuationAndQualifyingAccountsDisclosureLineItems_8d03e402-e880-445c-b199-27451ec42606_terseLabel_en-US" xlink:label="lab_srt_ValuationAndQualifyingAccountsDisclosureLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-09, Valuation and Qualifying Accounts Disclosure [Line Items]</link:label>
    <link:label id="lab_srt_ValuationAndQualifyingAccountsDisclosureLineItems_label_en-US" xlink:label="lab_srt_ValuationAndQualifyingAccountsDisclosureLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-09, Valuation and Qualifying Accounts Disclosure [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ValuationAndQualifyingAccountsDisclosureLineItems" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_ValuationAndQualifyingAccountsDisclosureLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ValuationAndQualifyingAccountsDisclosureLineItems" xlink:to="lab_srt_ValuationAndQualifyingAccountsDisclosureLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable_4823a5c4-5f4b-4981-9aff-dd5ee22f34e9_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Antidilutive Securities Excluded from Computation of Earnings Per Share [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Antidilutive Securities Excluded from Computation of Earnings Per Share [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable" xlink:to="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerOtherMember_61dc81ca-5ffd-43b6-ab1a-6ed5e2c85f55_terseLabel_en-US" xlink:label="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerOtherMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other</link:label>
    <link:label id="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerOtherMember_label_en-US" xlink:label="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerOtherMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Managing General Insurance Agent And Broker, Other [Member]</link:label>
    <link:label id="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerOtherMember_documentation_en-US" xlink:label="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerOtherMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Managing General Insurance Agent And Broker, Other</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ManagingGeneralInsuranceAgentAndBrokerOtherMember" xlink:href="skwd-20221231.xsd#skwd_ManagingGeneralInsuranceAgentAndBrokerOtherMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ManagingGeneralInsuranceAgentAndBrokerOtherMember" xlink:to="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerOtherMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxReconciliationOtherReconcilingItems_dbe1a408-e599-4a20-b51b-d0cb73da952d_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxReconciliationOtherReconcilingItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other</link:label>
    <link:label id="lab_us-gaap_IncomeTaxReconciliationOtherReconcilingItems_label_en-US" xlink:label="lab_us-gaap_IncomeTaxReconciliationOtherReconcilingItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Effective Income Tax Rate Reconciliation, Other Reconciling Items, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxReconciliationOtherReconcilingItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncomeTaxReconciliationOtherReconcilingItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxReconciliationOtherReconcilingItems" xlink:to="lab_us-gaap_IncomeTaxReconciliationOtherReconcilingItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CostsAndExpensesAbstract_c13ea7a3-e31a-4113-b9ee-1350ba54e7c5_terseLabel_en-US" xlink:label="lab_us-gaap_CostsAndExpensesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Expenses:</link:label>
    <link:label id="lab_us-gaap_CostsAndExpensesAbstract_label_en-US" xlink:label="lab_us-gaap_CostsAndExpensesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Costs and Expenses [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CostsAndExpensesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CostsAndExpensesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CostsAndExpensesAbstract" xlink:to="lab_us-gaap_CostsAndExpensesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_EquitySectorMember_89071c52-ef48-482c-86ef-424b68ee852c_terseLabel_en-US" xlink:label="lab_skwd_EquitySectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity</link:label>
    <link:label id="lab_skwd_EquitySectorMember_label_en-US" xlink:label="lab_skwd_EquitySectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Sector [Member]</link:label>
    <link:label id="lab_skwd_EquitySectorMember_documentation_en-US" xlink:label="lab_skwd_EquitySectorMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Sector</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_EquitySectorMember" xlink:href="skwd-20221231.xsd#skwd_EquitySectorMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_EquitySectorMember" xlink:to="lab_skwd_EquitySectorMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherShortTermInvestments_2cc0e225-5579-4925-b7d2-b1fa6587c293_terseLabel_en-US" xlink:label="lab_us-gaap_OtherShortTermInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-term investments, at fair value</link:label>
    <link:label id="lab_us-gaap_OtherShortTermInvestments_label_en-US" xlink:label="lab_us-gaap_OtherShortTermInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other Short-Term Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherShortTermInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OtherShortTermInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherShortTermInvestments" xlink:to="lab_us-gaap_OtherShortTermInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredTaxAssetsUnrealizedLossesOnAvailableforSaleSecuritiesGross_7235e0d5-35ab-4093-95f8-7b8f5e178292_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsUnrealizedLossesOnAvailableforSaleSecuritiesGross" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unrealized losses on investments</link:label>
    <link:label id="lab_us-gaap_DeferredTaxAssetsUnrealizedLossesOnAvailableforSaleSecuritiesGross_label_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsUnrealizedLossesOnAvailableforSaleSecuritiesGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Tax Asset, Debt Securities, Available-for-Sale, Unrealized Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxAssetsUnrealizedLossesOnAvailableforSaleSecuritiesGross" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DeferredTaxAssetsUnrealizedLossesOnAvailableforSaleSecuritiesGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredTaxAssetsUnrealizedLossesOnAvailableforSaleSecuritiesGross" xlink:to="lab_us-gaap_DeferredTaxAssetsUnrealizedLossesOnAvailableforSaleSecuritiesGross" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockholdersEquityNoteSubscriptionsReceivable_5a998738-b479-4a68-8950-dfe53cffc304_terseLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquityNoteSubscriptionsReceivable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Sale of stock, stock note receivable</link:label>
    <link:label id="lab_us-gaap_StockholdersEquityNoteSubscriptionsReceivable_label_en-US" xlink:label="lab_us-gaap_StockholdersEquityNoteSubscriptionsReceivable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stockholders' Equity Note, Subscriptions Receivable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquityNoteSubscriptionsReceivable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StockholdersEquityNoteSubscriptionsReceivable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockholdersEquityNoteSubscriptionsReceivable" xlink:to="lab_us-gaap_StockholdersEquityNoteSubscriptionsReceivable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_Liabilities_c3b87615-ab6f-4045-a65e-a7c1b6ab852c_totalLabel_en-US" xlink:label="lab_us-gaap_Liabilities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total liabilities</link:label>
    <link:label id="lab_us-gaap_Liabilities_label_en-US" xlink:label="lab_us-gaap_Liabilities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liabilities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Liabilities" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_Liabilities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Liabilities" xlink:to="lab_us-gaap_Liabilities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInUnearnedPremiums_c5748f82-4964-4976-8f5c-f8981b0d7c41_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInUnearnedPremiums" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unearned premiums</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInUnearnedPremiums_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInUnearnedPremiums" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Increase (Decrease) in Unearned Premiums</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInUnearnedPremiums" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInUnearnedPremiums"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInUnearnedPremiums" xlink:to="lab_us-gaap_IncreaseDecreaseInUnearnedPremiums" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ContingentlyIssuableInstrumentsTreasuryStockMethodMember_59f209c3-39df-46b4-93c2-6df3957fd976_terseLabel_en-US" xlink:label="lab_skwd_ContingentlyIssuableInstrumentsTreasuryStockMethodMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Contingently issuable instruments (treasury stock method)</link:label>
    <link:label id="lab_skwd_ContingentlyIssuableInstrumentsTreasuryStockMethodMember_label_en-US" xlink:label="lab_skwd_ContingentlyIssuableInstrumentsTreasuryStockMethodMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Contingently Issuable Instruments, Treasury Stock Method [Member]</link:label>
    <link:label id="lab_skwd_ContingentlyIssuableInstrumentsTreasuryStockMethodMember_documentation_en-US" xlink:label="lab_skwd_ContingentlyIssuableInstrumentsTreasuryStockMethodMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Contingently Issuable Instruments, Treasury Stock Method</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ContingentlyIssuableInstrumentsTreasuryStockMethodMember" xlink:href="skwd-20221231.xsd#skwd_ContingentlyIssuableInstrumentsTreasuryStockMethodMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ContingentlyIssuableInstrumentsTreasuryStockMethodMember" xlink:to="lab_skwd_ContingentlyIssuableInstrumentsTreasuryStockMethodMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAccumulatedUnallocatedClaimAdjustmentExpense_429f46d1-a6cb-4e03-a64f-c445f138c353_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAccumulatedUnallocatedClaimAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unallocated LAE</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAccumulatedUnallocatedClaimAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAccumulatedUnallocatedClaimAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Liability for Unpaid Claims and Claims Adjustment Expense, Accumulated Unallocated Claim Adjustment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAccumulatedUnallocatedClaimAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAccumulatedUnallocatedClaimAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAccumulatedUnallocatedClaimAdjustmentExpense" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAccumulatedUnallocatedClaimAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OperatingLeaseWeightedAverageRemainingLeaseTerm1_815fbbfa-a9a7-4366-b7af-dbbf5d567bc3_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingLeaseWeightedAverageRemainingLeaseTerm1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Operating lease weighted-average remaining lease term</link:label>
    <link:label id="lab_us-gaap_OperatingLeaseWeightedAverageRemainingLeaseTerm1_label_en-US" xlink:label="lab_us-gaap_OperatingLeaseWeightedAverageRemainingLeaseTerm1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Operating Lease, Weighted Average Remaining Lease Term</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseWeightedAverageRemainingLeaseTerm1" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OperatingLeaseWeightedAverageRemainingLeaseTerm1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OperatingLeaseWeightedAverageRemainingLeaseTerm1" xlink:to="lab_us-gaap_OperatingLeaseWeightedAverageRemainingLeaseTerm1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems_016b34d2-1339-4c5a-aded-1e3b6b642957_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award [Line Items]</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract_fe508df2-cb48-4491-a237-a215c9dd889e_terseLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash flows from investing activities:</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net Cash Provided by (Used in) Investing Activities [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:to="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNet_13f38061-6acc-4a05-8aa1-da840bc1d084_totalLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total net reserves for loss and LAE</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNet_264b6711-dafc-4236-b3e4-33803b2f9868_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reserves for losses and LAE, net of reinsurance</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNet_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNet" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNet" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNet" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityCommonStockSharesOutstanding_87f31caa-612c-4196-ae5d-d7e0cb841b4b_terseLabel_en-US" xlink:label="lab_dei_EntityCommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Common Stock, Shares Outstanding</link:label>
    <link:label id="lab_dei_EntityCommonStockSharesOutstanding_label_en-US" xlink:label="lab_dei_EntityCommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Common Stock, Shares Outstanding</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityCommonStockSharesOutstanding" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityCommonStockSharesOutstanding"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityCommonStockSharesOutstanding" xlink:to="lab_dei_EntityCommonStockSharesOutstanding" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTable_44bbfa3c-30af-4baf-8908-1455960545fe_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Claims Development [Table]</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTable_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Claims Development [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTable" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain_081a62f2-e7e9-44be-8d57-02f16b0f601a_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value Hierarchy and NAV [Domain]</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value Hierarchy and NAV [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementsFairValueHierarchyDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FairValueMeasurementsFairValueHierarchyDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementsFairValueHierarchyDomain" xlink:to="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RevolvingCreditFacilityMember_f0857225-26eb-4c15-8a69-559114102fe4_terseLabel_en-US" xlink:label="lab_us-gaap_RevolvingCreditFacilityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Revolving Credit Facility</link:label>
    <link:label id="lab_us-gaap_RevolvingCreditFacilityMember_label_en-US" xlink:label="lab_us-gaap_RevolvingCreditFacilityMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Revolving Credit Facility [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RevolvingCreditFacilityMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RevolvingCreditFacilityMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RevolvingCreditFacilityMember" xlink:to="lab_us-gaap_RevolvingCreditFacilityMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_IndustrialPortfolioSegmentMember_087d29c9-58dd-453f-b9f1-fea450ed4ba3_terseLabel_en-US" xlink:label="lab_skwd_IndustrialPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Industrial</link:label>
    <link:label id="lab_skwd_IndustrialPortfolioSegmentMember_label_en-US" xlink:label="lab_skwd_IndustrialPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Industrial Portfolio Segment [Member]</link:label>
    <link:label id="lab_skwd_IndustrialPortfolioSegmentMember_documentation_en-US" xlink:label="lab_skwd_IndustrialPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Industrial Portfolio Segment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_IndustrialPortfolioSegmentMember" xlink:href="skwd-20221231.xsd#skwd_IndustrialPortfolioSegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_IndustrialPortfolioSegmentMember" xlink:to="lab_skwd_IndustrialPortfolioSegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_HospitalityPortfolioSegmentMember_b218039f-3445-4615-97d2-e82a086431c0_terseLabel_en-US" xlink:label="lab_skwd_HospitalityPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Hospitality</link:label>
    <link:label id="lab_skwd_HospitalityPortfolioSegmentMember_label_en-US" xlink:label="lab_skwd_HospitalityPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Hospitality Portfolio Segment [Member]</link:label>
    <link:label id="lab_skwd_HospitalityPortfolioSegmentMember_documentation_en-US" xlink:label="lab_skwd_HospitalityPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Hospitality Portfolio Segment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_HospitalityPortfolioSegmentMember" xlink:href="skwd-20221231.xsd#skwd_HospitalityPortfolioSegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_HospitalityPortfolioSegmentMember" xlink:to="lab_skwd_HospitalityPortfolioSegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentType_4c47cd8e-273b-4769-b042-9cbbe81b0577_terseLabel_en-US" xlink:label="lab_dei_DocumentType" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Document Type</link:label>
    <link:label id="lab_dei_DocumentType_label_en-US" xlink:label="lab_dei_DocumentType" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Document Type</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentType" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_DocumentType"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentType" xlink:to="lab_dei_DocumentType" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentUsefulLife_1c91d019-6e95-4266-bcc1-39d7cb9c5afb_terseLabel_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentUsefulLife" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Property, plant and equipment, useful life</link:label>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentUsefulLife_label_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentUsefulLife" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Property, Plant and Equipment, Useful Life</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentUsefulLife" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PropertyPlantAndEquipmentUsefulLife"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentUsefulLife" xlink:to="lab_us-gaap_PropertyPlantAndEquipmentUsefulLife" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingLoss_d55af5df-ffe1-4eff-9f1a-4dff933cbb1e_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross Unrealized Losses</link:label>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingLoss_label_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Held-to-Maturity, Accumulated Unrecognized Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingLoss" xlink:to="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition_700bad32-4bff-41df-b80b-a621bd6e2079_totalLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition_label_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Unrealized Loss Position</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition_documentation_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Unrealized Loss Position</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition" xlink:href="skwd-20221231.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition" xlink:to="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain_b0f05d24-3ba2-4125-9f18-916551c391ee_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Finite-Lived Intangible Assets, Major Class Name [Domain]</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Finite-Lived Intangible Assets, Major Class Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ShortTermInvestmentFairValueDisclosure_a47129bc-d268-46a9-a55e-e32394ca58a6_terseLabel_en-US" xlink:label="lab_skwd_ShortTermInvestmentFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-term investments</link:label>
    <link:label id="lab_skwd_ShortTermInvestmentFairValueDisclosure_label_en-US" xlink:label="lab_skwd_ShortTermInvestmentFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short Term Investment, Fair Value Disclosure</link:label>
    <link:label id="lab_skwd_ShortTermInvestmentFairValueDisclosure_documentation_en-US" xlink:label="lab_skwd_ShortTermInvestmentFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short Term Investment, Fair Value Disclosure</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ShortTermInvestmentFairValueDisclosure" xlink:href="skwd-20221231.xsd#skwd_ShortTermInvestmentFairValueDisclosure"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ShortTermInvestmentFairValueDisclosure" xlink:to="lab_skwd_ShortTermInvestmentFairValueDisclosure" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ProFormaMember_b28453dc-1b8b-4b5e-bb3a-c1b69699d9e6_terseLabel_en-US" xlink:label="lab_srt_ProFormaMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Pro forma</link:label>
    <link:label id="lab_srt_ProFormaMember_label_en-US" xlink:label="lab_srt_ProFormaMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Pro Forma [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ProFormaMember" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_ProFormaMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ProFormaMember" xlink:to="lab_srt_ProFormaMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue_29edb1a6-3bc7-4000-946f-48b61894051f_periodStartLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Non-vested, beginning period (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue_14ebf823-f57c-429a-85e2-ae94e13ba269_periodEndLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Non-vested, ending period (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Nonvested, Weighted Average Grant Date Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtInstrumentFixedInterestRatePeriodOneMember_7047f536-ae08-4d00-a4b7-7907beb96cc1_terseLabel_en-US" xlink:label="lab_skwd_DebtInstrumentFixedInterestRatePeriodOneMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Interest Rate, First 8 Years</link:label>
    <link:label id="lab_skwd_DebtInstrumentFixedInterestRatePeriodOneMember_label_en-US" xlink:label="lab_skwd_DebtInstrumentFixedInterestRatePeriodOneMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Fixed Interest Rate, Period One [Member]</link:label>
    <link:label id="lab_skwd_DebtInstrumentFixedInterestRatePeriodOneMember_documentation_en-US" xlink:label="lab_skwd_DebtInstrumentFixedInterestRatePeriodOneMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Fixed Interest Rate, Period One</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtInstrumentFixedInterestRatePeriodOneMember" xlink:href="skwd-20221231.xsd#skwd_DebtInstrumentFixedInterestRatePeriodOneMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtInstrumentFixedInterestRatePeriodOneMember" xlink:to="lab_skwd_DebtInstrumentFixedInterestRatePeriodOneMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_HudsonVenturesFund2LPMember_b077afdb-832e-4833-8f80-4b823632c86a_terseLabel_en-US" xlink:label="lab_skwd_HudsonVenturesFund2LPMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Hudson Ventures Fund 2 LP units</link:label>
    <link:label id="lab_skwd_HudsonVenturesFund2LPMember_label_en-US" xlink:label="lab_skwd_HudsonVenturesFund2LPMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Hudson Ventures Fund 2, L.P. [Member]</link:label>
    <link:label id="lab_skwd_HudsonVenturesFund2LPMember_documentation_en-US" xlink:label="lab_skwd_HudsonVenturesFund2LPMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Hudson Ventures Fund 2, L.P.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_HudsonVenturesFund2LPMember" xlink:href="skwd-20221231.xsd#skwd_HudsonVenturesFund2LPMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_HudsonVenturesFund2LPMember" xlink:to="lab_skwd_HudsonVenturesFund2LPMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredIncomeTaxExpenseBenefit_9477b9e4-5058-4cc6-911f-5e2ef479974c_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredIncomeTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred income tax, net</link:label>
    <link:label id="lab_us-gaap_DeferredIncomeTaxExpenseBenefit_label_en-US" xlink:label="lab_us-gaap_DeferredIncomeTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Income Tax Expense (Benefit)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredIncomeTaxExpenseBenefit" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DeferredIncomeTaxExpenseBenefit"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredIncomeTaxExpenseBenefit" xlink:to="lab_us-gaap_DeferredIncomeTaxExpenseBenefit" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentsAbstract_29a44e9d-f3d3-4ca5-8220-a474d0105280_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investments:</link:label>
    <link:label id="lab_us-gaap_InvestmentsAbstract_label_en-US" xlink:label="lab_us-gaap_InvestmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investments [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_InvestmentsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentsAbstract" xlink:to="lab_us-gaap_InvestmentsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ImpairmentOfIntangibleAssetFiniteLivedStatementOfIncomeOrComprehensiveIncomeExtensibleEnumerationNotDisclosedFlag_67a4173f-ff21-4168-be0d-23274c2dc6a6_terseLabel_en-US" xlink:label="lab_skwd_ImpairmentOfIntangibleAssetFiniteLivedStatementOfIncomeOrComprehensiveIncomeExtensibleEnumerationNotDisclosedFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Impairment Of Intangible Asset Finite Lived Statement Of Income Or Comprehensive Income Extensible Enumeration Not Disclosed Flag</link:label>
    <link:label id="lab_skwd_ImpairmentOfIntangibleAssetFiniteLivedStatementOfIncomeOrComprehensiveIncomeExtensibleEnumerationNotDisclosedFlag_label_en-US" xlink:label="lab_skwd_ImpairmentOfIntangibleAssetFiniteLivedStatementOfIncomeOrComprehensiveIncomeExtensibleEnumerationNotDisclosedFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Impairment Of Intangible Asset Finite Lived Statement Of Income Or Comprehensive Income Extensible Enumeration Not Disclosed Flag</link:label>
    <link:label id="lab_skwd_ImpairmentOfIntangibleAssetFiniteLivedStatementOfIncomeOrComprehensiveIncomeExtensibleEnumerationNotDisclosedFlag_documentation_en-US" xlink:label="lab_skwd_ImpairmentOfIntangibleAssetFiniteLivedStatementOfIncomeOrComprehensiveIncomeExtensibleEnumerationNotDisclosedFlag" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Impairment Of Intangible Asset Finite Lived Statement Of Income Or Comprehensive Income Extensible Enumeration Not Disclosed Flag</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ImpairmentOfIntangibleAssetFiniteLivedStatementOfIncomeOrComprehensiveIncomeExtensibleEnumerationNotDisclosedFlag" xlink:href="skwd-20221231.xsd#skwd_ImpairmentOfIntangibleAssetFiniteLivedStatementOfIncomeOrComprehensiveIncomeExtensibleEnumerationNotDisclosedFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ImpairmentOfIntangibleAssetFiniteLivedStatementOfIncomeOrComprehensiveIncomeExtensibleEnumerationNotDisclosedFlag" xlink:to="lab_skwd_ImpairmentOfIntangibleAssetFiniteLivedStatementOfIncomeOrComprehensiveIncomeExtensibleEnumerationNotDisclosedFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems_eb24491a-f8c8-41dc-9d0e-7bf17e6b81e6_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net Investment Income [Line Items]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems_label_en-US" xlink:label="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net Investment Income [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems" xlink:to="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_LongTermIncentivePlanMember_ed121c39-3f6f-4b6d-83d6-2179bd7f42bd_terseLabel_en-US" xlink:label="lab_skwd_LongTermIncentivePlanMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long Term Incentive Plan</link:label>
    <link:label id="lab_skwd_LongTermIncentivePlanMember_label_en-US" xlink:label="lab_skwd_LongTermIncentivePlanMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long Term Incentive Plan [Member]</link:label>
    <link:label id="lab_skwd_LongTermIncentivePlanMember_documentation_en-US" xlink:label="lab_skwd_LongTermIncentivePlanMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long Term Incentive Plan</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_LongTermIncentivePlanMember" xlink:href="skwd-20221231.xsd#skwd_LongTermIncentivePlanMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_LongTermIncentivePlanMember" xlink:to="lab_skwd_LongTermIncentivePlanMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsRollForward_8239d275-c645-4d60-b80a-38470394262c_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Finite-Lived</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsRollForward_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Finite-Lived Intangible Assets [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FiniteLivedIntangibleAssetsRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsRollForward" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ContractWithCustomerAssetAndLiabilityTableTextBlock_b7d8b23c-55e3-4d3e-9429-ae6285508814_terseLabel_en-US" xlink:label="lab_us-gaap_ContractWithCustomerAssetAndLiabilityTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Contract Asset</link:label>
    <link:label id="lab_us-gaap_ContractWithCustomerAssetAndLiabilityTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ContractWithCustomerAssetAndLiabilityTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Contract with Customer, Contract Asset, Contract Liability, and Receivable [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ContractWithCustomerAssetAndLiabilityTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ContractWithCustomerAssetAndLiabilityTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ContractWithCustomerAssetAndLiabilityTableTextBlock" xlink:to="lab_us-gaap_ContractWithCustomerAssetAndLiabilityTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleTable_f8133c91-3f85-44ce-871b-377f2b678730_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale [Table]</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleTable_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleTable" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfCostsOfRetirementPlansTableTextBlock_fcf75fff-9658-417b-bcbb-1f3f83762dba_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfCostsOfRetirementPlansTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Company's Matching Contributions</link:label>
    <link:label id="lab_us-gaap_ScheduleOfCostsOfRetirementPlansTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfCostsOfRetirementPlansTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Costs of Retirement Plans [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfCostsOfRetirementPlansTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfCostsOfRetirementPlansTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfCostsOfRetirementPlansTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfCostsOfRetirementPlansTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CapitalizationOfDeferredPolicyAcquisitionCostsPolicy_fd992c90-9d3c-4e2e-85f9-6439823d7d52_terseLabel_en-US" xlink:label="lab_us-gaap_CapitalizationOfDeferredPolicyAcquisitionCostsPolicy" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Policy Acquisition Costs</link:label>
    <link:label id="lab_us-gaap_CapitalizationOfDeferredPolicyAcquisitionCostsPolicy_label_en-US" xlink:label="lab_us-gaap_CapitalizationOfDeferredPolicyAcquisitionCostsPolicy" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Policy Acquisition Costs, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CapitalizationOfDeferredPolicyAcquisitionCostsPolicy" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CapitalizationOfDeferredPolicyAcquisitionCostsPolicy"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CapitalizationOfDeferredPolicyAcquisitionCostsPolicy" xlink:to="lab_us-gaap_CapitalizationOfDeferredPolicyAcquisitionCostsPolicy" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet_02bf2360-e8d2-4151-8133-61501dff653e_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Implied fair value of business</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet" xlink:to="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedNet" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_WestaimHIIGLPMember_0e87a228-72c4-458c-920d-779c9308009d_terseLabel_en-US" xlink:label="lab_skwd_WestaimHIIGLPMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Westaim HIIG LP</link:label>
    <link:label id="lab_skwd_WestaimHIIGLPMember_label_en-US" xlink:label="lab_skwd_WestaimHIIGLPMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Westaim HIIG LP [Member]</link:label>
    <link:label id="lab_skwd_WestaimHIIGLPMember_documentation_en-US" xlink:label="lab_skwd_WestaimHIIGLPMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Westaim HIIG LP</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_WestaimHIIGLPMember" xlink:href="skwd-20221231.xsd#skwd_WestaimHIIGLPMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_WestaimHIIGLPMember" xlink:to="lab_skwd_WestaimHIIGLPMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsWrittenOffRelatedToSaleOfBusinessUnit_95fe0319-5189-4135-b4ea-a6261307cf88_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsWrittenOffRelatedToSaleOfBusinessUnit" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Disposals</link:label>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsWrittenOffRelatedToSaleOfBusinessUnit_label_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsWrittenOffRelatedToSaleOfBusinessUnit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Indefinite-Lived Intangible Assets, Written off Related to Sale of Business Unit</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefiniteLivedIntangibleAssetsWrittenOffRelatedToSaleOfBusinessUnit" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IndefiniteLivedIntangibleAssetsWrittenOffRelatedToSaleOfBusinessUnit"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IndefiniteLivedIntangibleAssetsWrittenOffRelatedToSaleOfBusinessUnit" xlink:to="lab_us-gaap_IndefiniteLivedIntangibleAssetsWrittenOffRelatedToSaleOfBusinessUnit" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsForLossesAndLossAdjustmentExpense_56fa3742-506c-4156-bd8d-e039df08cb79_totalLabel_en-US" xlink:label="lab_us-gaap_PaymentsForLossesAndLossAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total paid</link:label>
    <link:label id="lab_us-gaap_PaymentsForLossesAndLossAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_PaymentsForLossesAndLossAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Claims Paid</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsForLossesAndLossAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PaymentsForLossesAndLossAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsForLossesAndLossAdjustmentExpense" xlink:to="lab_us-gaap_PaymentsForLossesAndLossAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtDisclosureAbstract_label_en-US" xlink:label="lab_us-gaap_DebtDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Disclosure [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtDisclosureAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtDisclosureAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtDisclosureAbstract" xlink:to="lab_us-gaap_DebtDisclosureAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ContingentlyIssuableInstrumentsCommonSharesMember_68987016-c27a-4fe8-8634-e1a55d21149b_terseLabel_en-US" xlink:label="lab_skwd_ContingentlyIssuableInstrumentsCommonSharesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common shares</link:label>
    <link:label id="lab_skwd_ContingentlyIssuableInstrumentsCommonSharesMember_label_en-US" xlink:label="lab_skwd_ContingentlyIssuableInstrumentsCommonSharesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Contingently Issuable Instruments, Common Shares [Member]</link:label>
    <link:label id="lab_skwd_ContingentlyIssuableInstrumentsCommonSharesMember_documentation_en-US" xlink:label="lab_skwd_ContingentlyIssuableInstrumentsCommonSharesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Contingently Issuable Instruments, Common Shares</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ContingentlyIssuableInstrumentsCommonSharesMember" xlink:href="skwd-20221231.xsd#skwd_ContingentlyIssuableInstrumentsCommonSharesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ContingentlyIssuableInstrumentsCommonSharesMember" xlink:to="lab_skwd_ContingentlyIssuableInstrumentsCommonSharesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_BookOfErrorsOmissionsBusinessMember_2936b335-e007-4ed1-9873-f43764bb16b8_terseLabel_en-US" xlink:label="lab_skwd_BookOfErrorsOmissionsBusinessMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Book of Errors &amp; Omissions Business</link:label>
    <link:label id="lab_skwd_BookOfErrorsOmissionsBusinessMember_label_en-US" xlink:label="lab_skwd_BookOfErrorsOmissionsBusinessMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Book of Errors &amp; Omissions Business [Member]</link:label>
    <link:label id="lab_skwd_BookOfErrorsOmissionsBusinessMember_documentation_en-US" xlink:label="lab_skwd_BookOfErrorsOmissionsBusinessMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Book of Errors &amp; Omissions Business</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_BookOfErrorsOmissionsBusinessMember" xlink:href="skwd-20221231.xsd#skwd_BookOfErrorsOmissionsBusinessMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_BookOfErrorsOmissionsBusinessMember" xlink:to="lab_skwd_BookOfErrorsOmissionsBusinessMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_GainOnSaleOfOtherInvestments_28b0c21c-df9d-4a38-b5a5-08c97edea54f_terseLabel_en-US" xlink:label="lab_skwd_GainOnSaleOfOtherInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other</link:label>
    <link:label id="lab_skwd_GainOnSaleOfOtherInvestments_label_en-US" xlink:label="lab_skwd_GainOnSaleOfOtherInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gain on Sale of Other Investments</link:label>
    <link:label id="lab_skwd_GainOnSaleOfOtherInvestments_documentation_en-US" xlink:label="lab_skwd_GainOnSaleOfOtherInvestments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gain on Sale of Other Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_GainOnSaleOfOtherInvestments" xlink:href="skwd-20221231.xsd#skwd_GainOnSaleOfOtherInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_GainOnSaleOfOtherInvestments" xlink:to="lab_skwd_GainOnSaleOfOtherInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersReservesForUnpaidClaimsAndClaimsAdjustmentExpense_0f9bed6b-2bba-4efb-98a5-f19e7bf7c7d8_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersReservesForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reserve for losses and loss adjustment expenses</link:label>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersReservesForUnpaidClaimsAndClaimsAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersReservesForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-18, Supplemental Information, Property-Casualty Insurance Underwriters, Reserve for Unpaid Claim and Claim Adjustment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersReservesForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersReservesForUnpaidClaimsAndClaimsAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersReservesForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:to="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersReservesForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinitelivedIntangibleAssetsAcquired1_46342290-22cb-4a2c-a1ea-7e386a9089c8_terseLabel_en-US" xlink:label="lab_us-gaap_FinitelivedIntangibleAssetsAcquired1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Additions</link:label>
    <link:label id="lab_us-gaap_FinitelivedIntangibleAssetsAcquired1_label_en-US" xlink:label="lab_us-gaap_FinitelivedIntangibleAssetsAcquired1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Finite-Lived Intangible Assets Acquired</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinitelivedIntangibleAssetsAcquired1" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FinitelivedIntangibleAssetsAcquired1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinitelivedIntangibleAssetsAcquired1" xlink:to="lab_us-gaap_FinitelivedIntangibleAssetsAcquired1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities_de611373-9e95-4b2c-80c2-4bd0e1250251_totalLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net cash provided by financing activities</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net Cash Provided by (Used in) Financing Activities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetCashProvidedByUsedInFinancingActivities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:to="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccountingPoliciesAbstract_label_en-US" xlink:label="lab_us-gaap_AccountingPoliciesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accounting Policies [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccountingPoliciesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AccountingPoliciesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccountingPoliciesAbstract" xlink:to="lab_us-gaap_AccountingPoliciesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LineOfCreditMember_c36e1143-aa3d-47b2-9a41-21236d0ea60a_terseLabel_en-US" xlink:label="lab_us-gaap_LineOfCreditMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Line of Credit</link:label>
    <link:label id="lab_us-gaap_LineOfCreditMember_label_en-US" xlink:label="lab_us-gaap_LineOfCreditMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Line of Credit [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LineOfCreditMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LineOfCreditMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LineOfCreditMember" xlink:to="lab_us-gaap_LineOfCreditMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GainLossOnSaleOfBusiness_8ed3b6d8-14a3-4fee-af95-181516d5a8f3_terseLabel_en-US" xlink:label="lab_us-gaap_GainLossOnSaleOfBusiness" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net realized gain on sale of business</link:label>
    <link:label id="lab_us-gaap_GainLossOnSaleOfBusiness_b6e46ae3-fe39-4f6c-a9ad-1bcd6cc75940_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_GainLossOnSaleOfBusiness" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net realized gain on sale of business</link:label>
    <link:label id="lab_us-gaap_GainLossOnSaleOfBusiness_label_en-US" xlink:label="lab_us-gaap_GainLossOnSaleOfBusiness" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gain (Loss) on Disposition of Business</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GainLossOnSaleOfBusiness" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_GainLossOnSaleOfBusiness"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GainLossOnSaleOfBusiness" xlink:to="lab_us-gaap_GainLossOnSaleOfBusiness" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CumulativeEffectPeriodOfAdoptionDomain_67893e47-9c5a-4de8-81f3-e40e4aa7e5fd_terseLabel_en-US" xlink:label="lab_srt_CumulativeEffectPeriodOfAdoptionDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cumulative Effect, Period of Adoption [Domain]</link:label>
    <link:label id="lab_srt_CumulativeEffectPeriodOfAdoptionDomain_label_en-US" xlink:label="lab_srt_CumulativeEffectPeriodOfAdoptionDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cumulative Effect, Period of Adoption [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_CumulativeEffectPeriodOfAdoptionDomain" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_CumulativeEffectPeriodOfAdoptionDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_CumulativeEffectPeriodOfAdoptionDomain" xlink:to="lab_srt_CumulativeEffectPeriodOfAdoptionDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost_bee76aab-2ddc-48c3-b12d-f491c689f115_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Due after one year through five years</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Amortized Cost, Maturity, Allocated and Single Maturity Date, after Year One Through Five</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisclosureOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTextBlock_c43d783f-fb3b-4f49-9272-b17d3f08ae95_terseLabel_en-US" xlink:label="lab_us-gaap_DisclosureOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Summary of Equity Awards</link:label>
    <link:label id="lab_us-gaap_DisclosureOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTextBlock_label_en-US" xlink:label="lab_us-gaap_DisclosureOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Disclosure of Share-Based Compensation Arrangements by Share-Based Payment Award [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisclosureOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DisclosureOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisclosureOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTextBlock" xlink:to="lab_us-gaap_DisclosureOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MunicipalBondsMember_391110c0-aef4-4a79-a69f-05c01a7b5e8e_terseLabel_en-US" xlink:label="lab_us-gaap_MunicipalBondsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Municipal securities</link:label>
    <link:label id="lab_us-gaap_MunicipalBondsMember_label_en-US" xlink:label="lab_us-gaap_MunicipalBondsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Municipal Bonds [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MunicipalBondsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_MunicipalBondsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MunicipalBondsMember" xlink:to="lab_us-gaap_MunicipalBondsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RelatedPartyTransactionLineItems_77c75575-fec1-436c-9b3a-b1324263ad0b_terseLabel_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Related Party Transaction [Line Items]</link:label>
    <link:label id="lab_us-gaap_RelatedPartyTransactionLineItems_label_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Related Party Transaction [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RelatedPartyTransactionLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RelatedPartyTransactionLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RelatedPartyTransactionLineItems" xlink:to="lab_us-gaap_RelatedPartyTransactionLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfComponentsOfIncomeTaxExpenseBenefitTableTextBlock_fff9eb5a-c33a-4dd3-8ae1-c5b9d92a4548_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfComponentsOfIncomeTaxExpenseBenefitTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Components of Income Tax Expense (Benefit)</link:label>
    <link:label id="lab_us-gaap_ScheduleOfComponentsOfIncomeTaxExpenseBenefitTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfComponentsOfIncomeTaxExpenseBenefitTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Components of Income Tax Expense (Benefit) [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfComponentsOfIncomeTaxExpenseBenefitTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfComponentsOfIncomeTaxExpenseBenefitTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfComponentsOfIncomeTaxExpenseBenefitTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfComponentsOfIncomeTaxExpenseBenefitTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ContingentlyIssuableInstrumentsMember_dbdda207-f6a6-4cab-b42f-4c0aeb13382a_terseLabel_en-US" xlink:label="lab_skwd_ContingentlyIssuableInstrumentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Contingently issuable instruments</link:label>
    <link:label id="lab_skwd_ContingentlyIssuableInstrumentsMember_label_en-US" xlink:label="lab_skwd_ContingentlyIssuableInstrumentsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Contingently Issuable Instruments [Member]</link:label>
    <link:label id="lab_skwd_ContingentlyIssuableInstrumentsMember_documentation_en-US" xlink:label="lab_skwd_ContingentlyIssuableInstrumentsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Contingently Issuable Instruments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ContingentlyIssuableInstrumentsMember" xlink:href="skwd-20221231.xsd#skwd_ContingentlyIssuableInstrumentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ContingentlyIssuableInstrumentsMember" xlink:to="lab_skwd_ContingentlyIssuableInstrumentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ResidentialMortgageBackedSecuritiesMember_d1a8ffc8-097d-408a-b817-f9594ae997de_terseLabel_en-US" xlink:label="lab_us-gaap_ResidentialMortgageBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Residential mortgage-backed securities</link:label>
    <link:label id="lab_us-gaap_ResidentialMortgageBackedSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_ResidentialMortgageBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Residential Mortgage-Backed Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ResidentialMortgageBackedSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ResidentialMortgageBackedSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ResidentialMortgageBackedSecuritiesMember" xlink:to="lab_us-gaap_ResidentialMortgageBackedSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedPeriodForRecognition1_ecb12051-9237-4b0b-8bc9-f5a52dc0f014_terseLabel_en-US" xlink:label="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedPeriodForRecognition1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unrecognized compensation cost, recognition period</link:label>
    <link:label id="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedPeriodForRecognition1_label_en-US" xlink:label="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedPeriodForRecognition1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Payment Arrangement, Nonvested Award, Cost Not yet Recognized, Period for Recognition</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedPeriodForRecognition1" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedPeriodForRecognition1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedPeriodForRecognition1" xlink:to="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedPeriodForRecognition1" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_PretaxImpactOfLossPortfolioTransfer_a0583b8f-29b6-4f2f-9c59-35a2a1fd39f5_negatedTerseLabel_en-US" xlink:label="lab_skwd_PretaxImpactOfLossPortfolioTransfer" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Losses and loss adjustment expenses</link:label>
    <link:label id="lab_skwd_PretaxImpactOfLossPortfolioTransfer_label_en-US" xlink:label="lab_skwd_PretaxImpactOfLossPortfolioTransfer" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Pretax Impact Of Loss Portfolio Transfer</link:label>
    <link:label id="lab_skwd_PretaxImpactOfLossPortfolioTransfer_documentation_en-US" xlink:label="lab_skwd_PretaxImpactOfLossPortfolioTransfer" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Pretax Impact Of Loss Portfolio Transfer</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_PretaxImpactOfLossPortfolioTransfer" xlink:href="skwd-20221231.xsd#skwd_PretaxImpactOfLossPortfolioTransfer"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_PretaxImpactOfLossPortfolioTransfer" xlink:to="lab_skwd_PretaxImpactOfLossPortfolioTransfer" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss_4eba8329-abb0-4ae7-bdd3-9809ef89e50c_negatedTotalLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTotalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Unrealized Loss Position, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueByBalanceSheetGroupingTextBlock_232e0759-8bcb-42b0-9f28-51e05c6c6aef_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueByBalanceSheetGroupingTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value, by Balance Sheet Grouping</link:label>
    <link:label id="lab_us-gaap_FairValueByBalanceSheetGroupingTextBlock_label_en-US" xlink:label="lab_us-gaap_FairValueByBalanceSheetGroupingTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value, by Balance Sheet Grouping [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueByBalanceSheetGroupingTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FairValueByBalanceSheetGroupingTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueByBalanceSheetGroupingTextBlock" xlink:to="lab_us-gaap_FairValueByBalanceSheetGroupingTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsToAcquireBusinessesGross_3abffe6a-7f5f-4e50-96ea-0a149020759e_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireBusinessesGross" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Purchase of business</link:label>
    <link:label id="lab_us-gaap_PaymentsToAcquireBusinessesGross_f4ffde45-7b12-4452-a865-c8046c4a8255_terseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireBusinessesGross" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Purchase of business</link:label>
    <link:label id="lab_us-gaap_PaymentsToAcquireBusinessesGross_label_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireBusinessesGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Payments to Acquire Businesses, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireBusinessesGross" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PaymentsToAcquireBusinessesGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsToAcquireBusinessesGross" xlink:to="lab_us-gaap_PaymentsToAcquireBusinessesGross" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityRegistrantName_373901c8-c244-4883-9e0f-a8ea140c3cc9_terseLabel_en-US" xlink:label="lab_dei_EntityRegistrantName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Registrant Name</link:label>
    <link:label id="lab_dei_EntityRegistrantName_label_en-US" xlink:label="lab_dei_EntityRegistrantName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Registrant Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityRegistrantName" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityRegistrantName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityRegistrantName" xlink:to="lab_dei_EntityRegistrantName" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivities_1e61899e-1ed6-4a92-bb4f-93c9f4d63d82_terseLabel_en-US" xlink:label="lab_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Adjustments to reconcile net income to net cash used in operating activities</link:label>
    <link:label id="lab_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivities_label_en-US" xlink:label="lab_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Adjustments to Reconcile Net Income (Loss) to Cash Provided by (Used in) Operating Activities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivities" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivities" xlink:to="lab_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivities" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_PurchaseOfCommonStockMember_38830dbd-aa43-4f7c-8547-bef8a08c1522_terseLabel_en-US" xlink:label="lab_skwd_PurchaseOfCommonStockMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Purchase Of Common Stock</link:label>
    <link:label id="lab_skwd_PurchaseOfCommonStockMember_label_en-US" xlink:label="lab_skwd_PurchaseOfCommonStockMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Purchase Of Common Stock [Member]</link:label>
    <link:label id="lab_skwd_PurchaseOfCommonStockMember_documentation_en-US" xlink:label="lab_skwd_PurchaseOfCommonStockMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Purchase Of Common Stock</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_PurchaseOfCommonStockMember" xlink:href="skwd-20221231.xsd#skwd_PurchaseOfCommonStockMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_PurchaseOfCommonStockMember" xlink:to="lab_skwd_PurchaseOfCommonStockMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ProceedsFromPaymentsForDepositAccounting_84748dbf-a8ef-4873-a1be-8d0da20a8449_terseLabel_en-US" xlink:label="lab_skwd_ProceedsFromPaymentsForDepositAccounting" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash provided by (used in) deposit accounting</link:label>
    <link:label id="lab_skwd_ProceedsFromPaymentsForDepositAccounting_label_en-US" xlink:label="lab_skwd_ProceedsFromPaymentsForDepositAccounting" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Proceeds From (Payments For) Deposit Accounting</link:label>
    <link:label id="lab_skwd_ProceedsFromPaymentsForDepositAccounting_documentation_en-US" xlink:label="lab_skwd_ProceedsFromPaymentsForDepositAccounting" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Proceeds From (Payments For) Deposit Accounting</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ProceedsFromPaymentsForDepositAccounting" xlink:href="skwd-20221231.xsd#skwd_ProceedsFromPaymentsForDepositAccounting"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ProceedsFromPaymentsForDepositAccounting" xlink:to="lab_skwd_ProceedsFromPaymentsForDepositAccounting" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsNumberOfReportedClaims_4950e2bc-8a45-45a7-ac6b-383831a5ceb4_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsNumberOfReportedClaims" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contract, Cumulative Number of Reported Claims</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsNumberOfReportedClaims_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsNumberOfReportedClaims" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contract, Cumulative Number of Reported Claims</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsNumberOfReportedClaims" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortdurationInsuranceContractsNumberOfReportedClaims"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsNumberOfReportedClaims" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsNumberOfReportedClaims" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubsequentEventsTextBlock_e04d4d60-220f-42d5-aa18-0553ac14febb_terseLabel_en-US" xlink:label="lab_us-gaap_SubsequentEventsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subsequent Events</link:label>
    <link:label id="lab_us-gaap_SubsequentEventsTextBlock_label_en-US" xlink:label="lab_us-gaap_SubsequentEventsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subsequent Events [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsequentEventsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SubsequentEventsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsequentEventsTextBlock" xlink:to="lab_us-gaap_SubsequentEventsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_LoansHeldForInvestmentTerm_b0fc205d-e561-4736-a3ee-14f334d8879e_terseLabel_en-US" xlink:label="lab_skwd_LoansHeldForInvestmentTerm" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Loans held-for-investment, term</link:label>
    <link:label id="lab_skwd_LoansHeldForInvestmentTerm_label_en-US" xlink:label="lab_skwd_LoansHeldForInvestmentTerm" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Loans Held-for-Investment, Term</link:label>
    <link:label id="lab_skwd_LoansHeldForInvestmentTerm_documentation_en-US" xlink:label="lab_skwd_LoansHeldForInvestmentTerm" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Loans Held-for-Investment, Term</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_LoansHeldForInvestmentTerm" xlink:href="skwd-20221231.xsd#skwd_LoansHeldForInvestmentTerm"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_LoansHeldForInvestmentTerm" xlink:to="lab_skwd_LoansHeldForInvestmentTerm" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent_bfc588eb-7029-452e-bbd1-e0112cce0d6f_terseLabel_en-US" xlink:label="lab_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accounts payable and accrued liabilities</link:label>
    <link:label id="lab_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent_label_en-US" xlink:label="lab_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accounts Payable and Accrued Liabilities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent" xlink:to="lab_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsIncurredClaimsAndAllocatedClaimAdjustmentExpenseNet_36b314a6-41c1-460e-a5a7-ed9768b4d5cc_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsIncurredClaimsAndAllocatedClaimAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Incurred losses and ALAE, net of reinsurance</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsIncurredClaimsAndAllocatedClaimAdjustmentExpenseNet_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsIncurredClaimsAndAllocatedClaimAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Incurred Claims and Allocated Claim Adjustment Expense, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsIncurredClaimsAndAllocatedClaimAdjustmentExpenseNet" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortdurationInsuranceContractsIncurredClaimsAndAllocatedClaimAdjustmentExpenseNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsIncurredClaimsAndAllocatedClaimAdjustmentExpenseNet" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsIncurredClaimsAndAllocatedClaimAdjustmentExpenseNet" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_UnsecuredSubordinatedNotesDue2039Member_d8ecf4df-62f0-4fd8-acbc-132a74a14209_terseLabel_en-US" xlink:label="lab_skwd_UnsecuredSubordinatedNotesDue2039Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subordinate Debt Due 2039</link:label>
    <link:label id="lab_skwd_UnsecuredSubordinatedNotesDue2039Member_label_en-US" xlink:label="lab_skwd_UnsecuredSubordinatedNotesDue2039Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unsecured Subordinated Notes Due 2039 [Member]</link:label>
    <link:label id="lab_skwd_UnsecuredSubordinatedNotesDue2039Member_documentation_en-US" xlink:label="lab_skwd_UnsecuredSubordinatedNotesDue2039Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unsecured Subordinated Notes Due 2039</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_UnsecuredSubordinatedNotesDue2039Member" xlink:href="skwd-20221231.xsd#skwd_UnsecuredSubordinatedNotesDue2039Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_UnsecuredSubordinatedNotesDue2039Member" xlink:to="lab_skwd_UnsecuredSubordinatedNotesDue2039Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PensionAndOtherPostretirementBenefitsDisclosureTextBlock_d212d071-bdd4-4a69-88a8-f2950cb4932e_terseLabel_en-US" xlink:label="lab_us-gaap_PensionAndOtherPostretirementBenefitsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Employee Benefit Plans</link:label>
    <link:label id="lab_us-gaap_PensionAndOtherPostretirementBenefitsDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_PensionAndOtherPostretirementBenefitsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Retirement Benefits [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PensionAndOtherPostretirementBenefitsDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PensionAndOtherPostretirementBenefitsDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PensionAndOtherPostretirementBenefitsDisclosureTextBlock" xlink:to="lab_us-gaap_PensionAndOtherPostretirementBenefitsDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SecSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersCurrentYearClaimAndClaimAdjustmentExpense_716f40b9-3e04-4480-9529-afd36f06a982_terseLabel_en-US" xlink:label="lab_us-gaap_SecSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersCurrentYearClaimAndClaimAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Losses and loss adjustment expenses (current year)</link:label>
    <link:label id="lab_us-gaap_SecSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersCurrentYearClaimAndClaimAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_SecSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersCurrentYearClaimAndClaimAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-18, Supplemental Information, Property-Casualty Insurance Underwriters, Current Year Claim and Claim Adjustment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SecSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersCurrentYearClaimAndClaimAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SecSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersCurrentYearClaimAndClaimAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SecSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersCurrentYearClaimAndClaimAdjustmentExpense" xlink:to="lab_us-gaap_SecSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersCurrentYearClaimAndClaimAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateFairValue_e0aa2f8a-796a-41f1-be77-14605a374b20_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Without single maturity date</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateFairValue_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Maturity, without Single Maturity Date, Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateFairValue" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LeasesAbstract_label_en-US" xlink:label="lab_us-gaap_LeasesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Leases [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LeasesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LeasesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LeasesAbstract" xlink:to="lab_us-gaap_LeasesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MutualFundMember_5ad38a96-391d-4924-a4fe-d257a6155799_terseLabel_en-US" xlink:label="lab_us-gaap_MutualFundMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total mutual funds</link:label>
    <link:label id="lab_us-gaap_MutualFundMember_b50c8709-ccdb-4199-9b38-be4774a049e7_verboseLabel_en-US" xlink:label="lab_us-gaap_MutualFundMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Mutual funds</link:label>
    <link:label id="lab_us-gaap_MutualFundMember_label_en-US" xlink:label="lab_us-gaap_MutualFundMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Mutual Fund [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MutualFundMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_MutualFundMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MutualFundMember" xlink:to="lab_us-gaap_MutualFundMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesUnrealizedGainLossAbstract_3f795f84-cd2c-4444-a97c-b251a2eab744_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesUnrealizedGainLossAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unrealized gains and losses on investments:</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesUnrealizedGainLossAbstract_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesUnrealizedGainLossAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Unrealized Gain (Loss) [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesUnrealizedGainLossAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesUnrealizedGainLossAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesUnrealizedGainLossAbstract" xlink:to="lab_us-gaap_DebtSecuritiesUnrealizedGainLossAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities_28dbd7ae-3331-4f7f-86db-41f56effbe66_negatedTerseLabel_en-US" xlink:label="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Payable (receivable) for securities sold</link:label>
    <link:label id="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities_label_en-US" xlink:label="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Payments For (Proceeds From) Sale and Collection of Securities</link:label>
    <link:label id="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities_documentation_en-US" xlink:label="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Payments For (Proceeds From) Sale and Collection of Securities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities" xlink:href="skwd-20221231.xsd#skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities" xlink:to="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredTaxAssetsOperatingLossCarryforwards_17bc0bfe-85cf-498d-9f58-efdc9290db45_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsOperatingLossCarryforwards" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net operating losses</link:label>
    <link:label id="lab_us-gaap_DeferredTaxAssetsOperatingLossCarryforwards_label_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsOperatingLossCarryforwards" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Tax Assets, Operating Loss Carryforwards</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxAssetsOperatingLossCarryforwards" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DeferredTaxAssetsOperatingLossCarryforwards"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredTaxAssetsOperatingLossCarryforwards" xlink:to="lab_us-gaap_DeferredTaxAssetsOperatingLossCarryforwards" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_MinimumMember_fd1b2194-9e49-4f98-ab76-457b8a45b33c_terseLabel_en-US" xlink:label="lab_srt_MinimumMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Minimum</link:label>
    <link:label id="lab_srt_MinimumMember_label_en-US" xlink:label="lab_srt_MinimumMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Minimum [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_MinimumMember" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_MinimumMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_MinimumMember" xlink:to="lab_srt_MinimumMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost_5b972e7b-511a-4e73-89ef-e6cbd9fe3c77_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Due in less than one year</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Amortized Cost, Maturity, Allocated and Single Maturity Date, Year One</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityEmergingGrowthCompany_137f8819-3149-433c-9d81-d86448de137a_terseLabel_en-US" xlink:label="lab_dei_EntityEmergingGrowthCompany" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Emerging Growth Company</link:label>
    <link:label id="lab_dei_EntityEmergingGrowthCompany_label_en-US" xlink:label="lab_dei_EntityEmergingGrowthCompany" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Emerging Growth Company</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityEmergingGrowthCompany" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityEmergingGrowthCompany"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityEmergingGrowthCompany" xlink:to="lab_dei_EntityEmergingGrowthCompany" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredTaxAssetsTaxDeferredExpenseReservesAndAccrualsUnearnedPremiumsReserve_fbecd77e-cecf-4026-9814-b7614f7e9ecc_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsTaxDeferredExpenseReservesAndAccrualsUnearnedPremiumsReserve" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unearned premiums</link:label>
    <link:label id="lab_us-gaap_DeferredTaxAssetsTaxDeferredExpenseReservesAndAccrualsUnearnedPremiumsReserve_label_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsTaxDeferredExpenseReservesAndAccrualsUnearnedPremiumsReserve" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Tax Assets, Tax Deferred Expense, Reserves and Accruals, Unearned Premiums Reserve</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxAssetsTaxDeferredExpenseReservesAndAccrualsUnearnedPremiumsReserve" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DeferredTaxAssetsTaxDeferredExpenseReservesAndAccrualsUnearnedPremiumsReserve"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredTaxAssetsTaxDeferredExpenseReservesAndAccrualsUnearnedPremiumsReserve" xlink:to="lab_us-gaap_DeferredTaxAssetsTaxDeferredExpenseReservesAndAccrualsUnearnedPremiumsReserve" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockParOrStatedValuePerShare_22a98ccd-9b3b-4462-86dd-d14fdd9cded8_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockParOrStatedValuePerShare" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common stock, par value (in USD per share)</link:label>
    <link:label id="lab_us-gaap_CommonStockParOrStatedValuePerShare_label_en-US" xlink:label="lab_us-gaap_CommonStockParOrStatedValuePerShare" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common Stock, Par or Stated Value Per Share</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockParOrStatedValuePerShare" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CommonStockParOrStatedValuePerShare"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockParOrStatedValuePerShare" xlink:to="lab_us-gaap_CommonStockParOrStatedValuePerShare" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ScheduleOfCommonStockNotesReceivableTableTextBlock_1d1f157c-8798-4d40-8c9f-3e5e91b88f7a_terseLabel_en-US" xlink:label="lab_skwd_ScheduleOfCommonStockNotesReceivableTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Common Stock Notes Receivable</link:label>
    <link:label id="lab_skwd_ScheduleOfCommonStockNotesReceivableTableTextBlock_label_en-US" xlink:label="lab_skwd_ScheduleOfCommonStockNotesReceivableTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Common Stock Notes Receivable [Table Text Block]</link:label>
    <link:label id="lab_skwd_ScheduleOfCommonStockNotesReceivableTableTextBlock_documentation_en-US" xlink:label="lab_skwd_ScheduleOfCommonStockNotesReceivableTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Common Stock Notes Receivable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ScheduleOfCommonStockNotesReceivableTableTextBlock" xlink:href="skwd-20221231.xsd#skwd_ScheduleOfCommonStockNotesReceivableTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ScheduleOfCommonStockNotesReceivableTableTextBlock" xlink:to="lab_skwd_ScheduleOfCommonStockNotesReceivableTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ValuationAndQualifyingAccountsDisclosureTable_391d0313-9619-46d3-a510-4810f00bb26f_terseLabel_en-US" xlink:label="lab_srt_ValuationAndQualifyingAccountsDisclosureTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-09, Valuation and Qualifying Accounts Disclosure [Table]</link:label>
    <link:label id="lab_srt_ValuationAndQualifyingAccountsDisclosureTable_label_en-US" xlink:label="lab_srt_ValuationAndQualifyingAccountsDisclosureTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-09, Valuation and Qualifying Accounts Disclosure [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ValuationAndQualifyingAccountsDisclosureTable" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_ValuationAndQualifyingAccountsDisclosureTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ValuationAndQualifyingAccountsDisclosureTable" xlink:to="lab_srt_ValuationAndQualifyingAccountsDisclosureTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommitmentsAndContingenciesDisclosureAbstract_label_en-US" xlink:label="lab_us-gaap_CommitmentsAndContingenciesDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Commitments and Contingencies Disclosure [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommitmentsAndContingenciesDisclosureAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CommitmentsAndContingenciesDisclosureAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommitmentsAndContingenciesDisclosureAbstract" xlink:to="lab_us-gaap_CommitmentsAndContingenciesDisclosureAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis_4dc021c7-8a08-42e3-8bb2-09f67754c561_terseLabel_en-US" xlink:label="lab_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment, Name [Axis]</link:label>
    <link:label id="lab_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis_label_en-US" xlink:label="lab_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment, Name [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis" xlink:to="lab_srt_ScheduleOfEquityMethodInvestmentEquityMethodInvesteeNameAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RevenueRecognitionPremiumsEarnedPolicy_21dbe6ee-257a-41ac-92cc-50bb95967a47_terseLabel_en-US" xlink:label="lab_us-gaap_RevenueRecognitionPremiumsEarnedPolicy" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Premiums</link:label>
    <link:label id="lab_us-gaap_RevenueRecognitionPremiumsEarnedPolicy_label_en-US" xlink:label="lab_us-gaap_RevenueRecognitionPremiumsEarnedPolicy" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Revenue Recognition, Premiums Earned, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RevenueRecognitionPremiumsEarnedPolicy" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RevenueRecognitionPremiumsEarnedPolicy"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RevenueRecognitionPremiumsEarnedPolicy" xlink:to="lab_us-gaap_RevenueRecognitionPremiumsEarnedPolicy" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueDisclosuresTextBlock_1a30d34f-7169-4d9c-a5bc-45c8bc83201b_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueDisclosuresTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair ValueMeasurements</link:label>
    <link:label id="lab_us-gaap_FairValueDisclosuresTextBlock_label_en-US" xlink:label="lab_us-gaap_FairValueDisclosuresTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value Disclosures [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueDisclosuresTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FairValueDisclosuresTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueDisclosuresTextBlock" xlink:to="lab_us-gaap_FairValueDisclosuresTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionAccumulatedLossAbstract_64cf6dc9-2729-4463-a4dd-61836838edd2_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Available for sale, gross unrealized losses</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionAccumulatedLossAbstract_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Unrealized Loss Position, Accumulated Loss [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionAccumulatedLossAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_TradingSymbol_a6f1c750-dcd1-4b53-a30e-664fadfcf5c2_terseLabel_en-US" xlink:label="lab_dei_TradingSymbol" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Trading Symbol</link:label>
    <link:label id="lab_dei_TradingSymbol_label_en-US" xlink:label="lab_dei_TradingSymbol" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Trading Symbol</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_TradingSymbol" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_TradingSymbol"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_TradingSymbol" xlink:to="lab_dei_TradingSymbol" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityFileNumber_0c3e70b7-29b2-4cac-a1a2-e46307958842_terseLabel_en-US" xlink:label="lab_dei_EntityFileNumber" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity File Number</link:label>
    <link:label id="lab_dei_EntityFileNumber_label_en-US" xlink:label="lab_dei_EntityFileNumber" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity File Number</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityFileNumber" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityFileNumber"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityFileNumber" xlink:to="lab_dei_EntityFileNumber" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_EverestReinsuranceCoMember_cd61055d-e6b4-4076-9b69-bf048ff82edf_terseLabel_en-US" xlink:label="lab_skwd_EverestReinsuranceCoMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Everest Reinsurance Co</link:label>
    <link:label id="lab_skwd_EverestReinsuranceCoMember_label_en-US" xlink:label="lab_skwd_EverestReinsuranceCoMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Everest Reinsurance Co [Member]</link:label>
    <link:label id="lab_skwd_EverestReinsuranceCoMember_documentation_en-US" xlink:label="lab_skwd_EverestReinsuranceCoMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Everest Reinsurance Co</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_EverestReinsuranceCoMember" xlink:href="skwd-20221231.xsd#skwd_EverestReinsuranceCoMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_EverestReinsuranceCoMember" xlink:to="lab_skwd_EverestReinsuranceCoMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_AgencyAgreementMember_118c12b0-e4b6-41af-b80d-e013be2290e4_terseLabel_en-US" xlink:label="lab_skwd_AgencyAgreementMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Agency agreement</link:label>
    <link:label id="lab_skwd_AgencyAgreementMember_label_en-US" xlink:label="lab_skwd_AgencyAgreementMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Agency Agreement [Member]</link:label>
    <link:label id="lab_skwd_AgencyAgreementMember_documentation_en-US" xlink:label="lab_skwd_AgencyAgreementMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Agency Agreement</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_AgencyAgreementMember" xlink:href="skwd-20221231.xsd#skwd_AgencyAgreementMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_AgencyAgreementMember" xlink:to="lab_skwd_AgencyAgreementMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CededCreditRiskReinsurerDomain_69acf1fa-589f-461e-89b5-3050931739c7_terseLabel_en-US" xlink:label="lab_us-gaap_CededCreditRiskReinsurerDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurer, Name [Domain]</link:label>
    <link:label id="lab_us-gaap_CededCreditRiskReinsurerDomain_label_en-US" xlink:label="lab_us-gaap_CededCreditRiskReinsurerDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurer, Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CededCreditRiskReinsurerDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CededCreditRiskReinsurerDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CededCreditRiskReinsurerDomain" xlink:to="lab_us-gaap_CededCreditRiskReinsurerDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFour_243bd578-2d14-41a1-81e1-8b726e7ab7ff_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFour" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">2026</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFour_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFour" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Finite-Lived Intangible Asset, Expected Amortization, Year Four</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFour" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFour"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFour" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFour" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InsuranceCommissions_1990031a-0b1b-4e71-8c7d-3d2fb216060a_terseLabel_en-US" xlink:label="lab_us-gaap_InsuranceCommissions" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross written commissions</link:label>
    <link:label id="lab_us-gaap_InsuranceCommissions_label_en-US" xlink:label="lab_us-gaap_InsuranceCommissions" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Insurance Commissions</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InsuranceCommissions" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_InsuranceCommissions"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InsuranceCommissions" xlink:to="lab_us-gaap_InsuranceCommissions" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatutoryAccountingPracticesDisclosureTextBlock_b57c8508-fa6b-4fc8-98ca-b98b4e74af01_terseLabel_en-US" xlink:label="lab_us-gaap_StatutoryAccountingPracticesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statutory Accounting Principles</link:label>
    <link:label id="lab_us-gaap_StatutoryAccountingPracticesDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_StatutoryAccountingPracticesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statutory Accounting Practices Disclosure [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatutoryAccountingPracticesDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StatutoryAccountingPracticesDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatutoryAccountingPracticesDisclosureTextBlock" xlink:to="lab_us-gaap_StatutoryAccountingPracticesDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable_ed725f53-f738-476c-a8a6-623b9d764a44_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment Income [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment Income [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:to="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_TitleOfIndividualAxis_297e5216-938a-4495-a3de-818e13e95a48_terseLabel_en-US" xlink:label="lab_srt_TitleOfIndividualAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Title of Individual [Axis]</link:label>
    <link:label id="lab_srt_TitleOfIndividualAxis_label_en-US" xlink:label="lab_srt_TitleOfIndividualAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Title of Individual [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_TitleOfIndividualAxis" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_TitleOfIndividualAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_TitleOfIndividualAxis" xlink:to="lab_srt_TitleOfIndividualAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DeferredIncomeTaxExpenseBenefitTemporaryDifferences_8247e152-bd1e-4a6d-87d4-a48ad07827df_terseLabel_en-US" xlink:label="lab_skwd_DeferredIncomeTaxExpenseBenefitTemporaryDifferences" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred tax expense related to temporary differences</link:label>
    <link:label id="lab_skwd_DeferredIncomeTaxExpenseBenefitTemporaryDifferences_label_en-US" xlink:label="lab_skwd_DeferredIncomeTaxExpenseBenefitTemporaryDifferences" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Income Tax Expense (Benefit), Temporary Differences</link:label>
    <link:label id="lab_skwd_DeferredIncomeTaxExpenseBenefitTemporaryDifferences_documentation_en-US" xlink:label="lab_skwd_DeferredIncomeTaxExpenseBenefitTemporaryDifferences" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Income Tax Expense (Benefit), Temporary Differences</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DeferredIncomeTaxExpenseBenefitTemporaryDifferences" xlink:href="skwd-20221231.xsd#skwd_DeferredIncomeTaxExpenseBenefitTemporaryDifferences"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DeferredIncomeTaxExpenseBenefitTemporaryDifferences" xlink:to="lab_skwd_DeferredIncomeTaxExpenseBenefitTemporaryDifferences" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod_ae1e79a0-0126-43df-bcdf-0e52bfe2b61b_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Granted (in shares)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Grants in Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_FixedMaturitiesHeldToMaturityMember_afd2ff23-4af0-4956-8e1a-224b9b5700ba_terseLabel_en-US" xlink:label="lab_skwd_FixedMaturitiesHeldToMaturityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fixed maturity securities, held to maturity:</link:label>
    <link:label id="lab_skwd_FixedMaturitiesHeldToMaturityMember_label_en-US" xlink:label="lab_skwd_FixedMaturitiesHeldToMaturityMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fixed Maturities, Held-To-Maturity [Member]</link:label>
    <link:label id="lab_skwd_FixedMaturitiesHeldToMaturityMember_documentation_en-US" xlink:label="lab_skwd_FixedMaturitiesHeldToMaturityMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fixed Maturities, Held-To-Maturity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_FixedMaturitiesHeldToMaturityMember" xlink:href="skwd-20221231.xsd#skwd_FixedMaturitiesHeldToMaturityMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_FixedMaturitiesHeldToMaturityMember" xlink:to="lab_skwd_FixedMaturitiesHeldToMaturityMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperations_217012fd-9be5-4d18-85ae-c8d5b50ce9af_totalLabel_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperations" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total income tax expense</link:label>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperations_label_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperations" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Effective Income Tax Rate Reconciliation, Percent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectiveIncomeTaxRateContinuingOperations" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EffectiveIncomeTaxRateContinuingOperations"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectiveIncomeTaxRateContinuingOperations" xlink:to="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperations" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ArenaSOPLPMember_db292d7c-74af-4e77-9756-45af9677b94d_terseLabel_en-US" xlink:label="lab_skwd_ArenaSOPLPMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Arena SOP LP units</link:label>
    <link:label id="lab_skwd_ArenaSOPLPMember_label_en-US" xlink:label="lab_skwd_ArenaSOPLPMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Arena SOP LP [Member]</link:label>
    <link:label id="lab_skwd_ArenaSOPLPMember_documentation_en-US" xlink:label="lab_skwd_ArenaSOPLPMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Arena SOP LP</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ArenaSOPLPMember" xlink:href="skwd-20221231.xsd#skwd_ArenaSOPLPMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ArenaSOPLPMember" xlink:to="lab_skwd_ArenaSOPLPMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConcentrationRiskByBenchmarkAxis_1d4b60aa-2e5e-4cef-8c01-254ddaf797c5_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskByBenchmarkAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Concentration Risk Benchmark [Axis]</link:label>
    <link:label id="lab_us-gaap_ConcentrationRiskByBenchmarkAxis_label_en-US" xlink:label="lab_us-gaap_ConcentrationRiskByBenchmarkAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Concentration Risk Benchmark [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConcentrationRiskByBenchmarkAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ConcentrationRiskByBenchmarkAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConcentrationRiskByBenchmarkAxis" xlink:to="lab_us-gaap_ConcentrationRiskByBenchmarkAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_UseOfEstimates_892bab06-3e72-4602-9d26-c8a5fb99c0db_terseLabel_en-US" xlink:label="lab_us-gaap_UseOfEstimates" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Use of Estimates</link:label>
    <link:label id="lab_us-gaap_UseOfEstimates_label_en-US" xlink:label="lab_us-gaap_UseOfEstimates" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Use of Estimates, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_UseOfEstimates" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_UseOfEstimates"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_UseOfEstimates" xlink:to="lab_us-gaap_UseOfEstimates" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AssumedPremiumsEarned_5e716a9f-d206-4249-a9bf-9a209d6dc6e3_terseLabel_en-US" xlink:label="lab_us-gaap_AssumedPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Assumed premiums</link:label>
    <link:label id="lab_us-gaap_AssumedPremiumsEarned_label_en-US" xlink:label="lab_us-gaap_AssumedPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Assumed Premiums Earned</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssumedPremiumsEarned" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AssumedPremiumsEarned"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssumedPremiumsEarned" xlink:to="lab_us-gaap_AssumedPremiumsEarned" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsAndJointVenturesAbstract_1172605a-b29f-42b2-b953-662aaaf42574_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsAndJointVenturesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Method Investments and Joint Ventures [Abstract]</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsAndJointVenturesAbstract_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsAndJointVenturesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Method Investments and Joint Ventures [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentsAndJointVenturesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EquityMethodInvestmentsAndJointVenturesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentsAndJointVenturesAbstract" xlink:to="lab_us-gaap_EquityMethodInvestmentsAndJointVenturesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsCumulativePaidClaimsAndAllocatedClaimAdjustmentExpenseNet_4b821cba-5a87-4126-b55e-c05f832f1a4b_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsCumulativePaidClaimsAndAllocatedClaimAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cumulative net paid loss and LAE from the table below</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsCumulativePaidClaimsAndAllocatedClaimAdjustmentExpenseNet_dd48bb38-ee74-48d7-a517-c2a90289777e_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsCumulativePaidClaimsAndAllocatedClaimAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cumulative net paid loss and LAE</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsCumulativePaidClaimsAndAllocatedClaimAdjustmentExpenseNet_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsCumulativePaidClaimsAndAllocatedClaimAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Cumulative Paid Claims and Allocated Claim Adjustment Expense, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsCumulativePaidClaimsAndAllocatedClaimAdjustmentExpenseNet" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortdurationInsuranceContractsCumulativePaidClaimsAndAllocatedClaimAdjustmentExpenseNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsCumulativePaidClaimsAndAllocatedClaimAdjustmentExpenseNet" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsCumulativePaidClaimsAndAllocatedClaimAdjustmentExpenseNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConcentrationRiskPercentage1_c002c9c4-7066-41e6-b454-3a3d4122a453_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskPercentage1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Concentration risk, percentage</link:label>
    <link:label id="lab_us-gaap_ConcentrationRiskPercentage1_label_en-US" xlink:label="lab_us-gaap_ConcentrationRiskPercentage1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Concentration Risk, Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConcentrationRiskPercentage1" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ConcentrationRiskPercentage1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConcentrationRiskPercentage1" xlink:to="lab_us-gaap_ConcentrationRiskPercentage1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PrincipalOwnerMember_8fa0c381-c628-4f8a-a106-8c45e04f0bd3_terseLabel_en-US" xlink:label="lab_us-gaap_PrincipalOwnerMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Principal Owner</link:label>
    <link:label id="lab_us-gaap_PrincipalOwnerMember_label_en-US" xlink:label="lab_us-gaap_PrincipalOwnerMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Principal Owner [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PrincipalOwnerMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PrincipalOwnerMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PrincipalOwnerMember" xlink:to="lab_us-gaap_PrincipalOwnerMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceAccountingPolicy_e3c1b27a-6ca6-43a9-9e1d-4ee746483c98_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceAccountingPolicy" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance</link:label>
    <link:label id="lab_us-gaap_ReinsuranceAccountingPolicy_label_en-US" xlink:label="lab_us-gaap_ReinsuranceAccountingPolicy" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Accounting Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceAccountingPolicy" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ReinsuranceAccountingPolicy"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceAccountingPolicy" xlink:to="lab_us-gaap_ReinsuranceAccountingPolicy" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities_fbe4a500-3507-4117-97bd-beefe3e8e320_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accounts payable and accrued liabilities</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Increase (Decrease) in Accounts Payable and Accrued Liabilities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities" xlink:to="lab_us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxDisclosureTextBlock_83c5a5f5-a3d3-404e-86fd-26e61839f33c_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Income Taxes</link:label>
    <link:label id="lab_us-gaap_IncomeTaxDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_IncomeTaxDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Income Tax Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncomeTaxDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxDisclosureTextBlock" xlink:to="lab_us-gaap_IncomeTaxDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CreditFacilityDomain_5da59a6b-2bcc-47bb-8b2a-dbcf25af3656_terseLabel_en-US" xlink:label="lab_us-gaap_CreditFacilityDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Credit Facility [Domain]</link:label>
    <link:label id="lab_us-gaap_CreditFacilityDomain_label_en-US" xlink:label="lab_us-gaap_CreditFacilityDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Credit Facility [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CreditFacilityDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CreditFacilityDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CreditFacilityDomain" xlink:to="lab_us-gaap_CreditFacilityDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwill_088e042c-868c-4923-bc11-31d878b32fc7_terseLabel_en-US" xlink:label="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Intangible assets, gross balance</link:label>
    <link:label id="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwill_label_en-US" xlink:label="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Intangible Assets, Gross (Excluding Goodwill)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IntangibleAssetsGrossExcludingGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IntangibleAssetsGrossExcludingGoodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IntangibleAssetsGrossExcludingGoodwill" xlink:to="lab_us-gaap_IntangibleAssetsGrossExcludingGoodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReceivableFromShareholdersOrAffiliatesForIssuanceOfCapitalStock_49d5f53b-dd50-44a2-b42a-2b94b1cd8c4b_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_ReceivableFromShareholdersOrAffiliatesForIssuanceOfCapitalStock" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stock notes receivable</link:label>
    <link:label id="lab_us-gaap_ReceivableFromShareholdersOrAffiliatesForIssuanceOfCapitalStock_label_en-US" xlink:label="lab_us-gaap_ReceivableFromShareholdersOrAffiliatesForIssuanceOfCapitalStock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Receivable from Shareholders or Affiliates for Issuance of Capital Stock</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReceivableFromShareholdersOrAffiliatesForIssuanceOfCapitalStock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ReceivableFromShareholdersOrAffiliatesForIssuanceOfCapitalStock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReceivableFromShareholdersOrAffiliatesForIssuanceOfCapitalStock" xlink:to="lab_us-gaap_ReceivableFromShareholdersOrAffiliatesForIssuanceOfCapitalStock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareBasic_086c5c35-aacd-457e-9c4c-4bc08d31eda8_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareBasic" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Basic earnings per share (in dollar per share)</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareBasic_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareBasic" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Earnings Per Share, Basic</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareBasic" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EarningsPerShareBasic"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareBasic" xlink:to="lab_us-gaap_EarningsPerShareBasic" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardRequisiteServicePeriod1_2dcfffcf-1d84-4b2a-8ebd-54a3661f3c5a_verboseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardRequisiteServicePeriod1" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Requisite service period</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardRequisiteServicePeriod1_3b6be5e8-6fb8-46d8-a793-518658745f54_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardRequisiteServicePeriod1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Requisite Service Period</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardRequisiteServicePeriod1_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardRequisiteServicePeriod1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Award Requisite Service Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardRequisiteServicePeriod1" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardRequisiteServicePeriod1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardRequisiteServicePeriod1" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardRequisiteServicePeriod1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfEquityMethodInvestmentsTable_82d6fe37-2f25-4369-a0f9-9db0e8de40f1_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfEquityMethodInvestmentsTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Equity Method Investments [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfEquityMethodInvestmentsTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfEquityMethodInvestmentsTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Equity Method Investments [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfEquityMethodInvestmentsTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfEquityMethodInvestmentsTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfEquityMethodInvestmentsTable" xlink:to="lab_us-gaap_ScheduleOfEquityMethodInvestmentsTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NewAccountingPronouncementsOrChangeInAccountingPrincipleTable_2c8a2b09-0213-45bd-9f03-3193b86e1a4c_terseLabel_en-US" xlink:label="lab_us-gaap_NewAccountingPronouncementsOrChangeInAccountingPrincipleTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accounting Standards Update and Change in Accounting Principle [Table]</link:label>
    <link:label id="lab_us-gaap_NewAccountingPronouncementsOrChangeInAccountingPrincipleTable_label_en-US" xlink:label="lab_us-gaap_NewAccountingPronouncementsOrChangeInAccountingPrincipleTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accounting Standards Update and Change in Accounting Principle [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NewAccountingPronouncementsOrChangeInAccountingPrincipleTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NewAccountingPronouncementsOrChangeInAccountingPrincipleTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NewAccountingPronouncementsOrChangeInAccountingPrincipleTable" xlink:to="lab_us-gaap_NewAccountingPronouncementsOrChangeInAccountingPrincipleTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InsuranceDisclosureTextBlock_61c38770-80c2-42b3-9865-7995f3f27c4c_verboseLabel_en-US" xlink:label="lab_us-gaap_InsuranceDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statutory Accounting Principles</link:label>
    <link:label id="lab_us-gaap_InsuranceDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_InsuranceDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Insurance Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InsuranceDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_InsuranceDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InsuranceDisclosureTextBlock" xlink:to="lab_us-gaap_InsuranceDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestAfterAllowanceForCreditLoss_98eee527-2b1e-44a4-a42e-0e376d9a359f_verboseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestAfterAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Amortized cost</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestAfterAllowanceForCreditLoss_2e614f92-0309-41fe-ac45-ae686154f764_totalLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestAfterAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross Amortized Cost</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestAfterAllowanceForCreditLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestAfterAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Amortized Cost, Excluding Accrued Interest, after Allowance for Credit Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestAfterAllowanceForCreditLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestAfterAllowanceForCreditLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestAfterAllowanceForCreditLoss" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestAfterAllowanceForCreditLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTable_483a7a15-3901-4543-9ac0-46ba247f88ff_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Accounts, Notes, Loans and Financing Receivable [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Accounts, Notes, Loans and Financing Receivable [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTable" xlink:to="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis_3cbb3d78-82f0-4c2c-a589-10a1a871cae5_terseLabel_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Indefinite-Lived Intangible Assets [Axis]</link:label>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis_label_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Indefinite-Lived Intangible Assets [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis" xlink:to="lab_us-gaap_IndefiniteLivedIntangibleAssetsByMajorClassAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AllowanceForUncollectiblePremiumsReceivableMember_dc73759b-e2dd-43c3-8620-f23c95323fab_terseLabel_en-US" xlink:label="lab_us-gaap_AllowanceForUncollectiblePremiumsReceivableMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Allowance for Uncollectible Premiums Receivable</link:label>
    <link:label id="lab_us-gaap_AllowanceForUncollectiblePremiumsReceivableMember_label_en-US" xlink:label="lab_us-gaap_AllowanceForUncollectiblePremiumsReceivableMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-09, Allowance, Uncollectible Premium Receivable [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AllowanceForUncollectiblePremiumsReceivableMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AllowanceForUncollectiblePremiumsReceivableMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AllowanceForUncollectiblePremiumsReceivableMember" xlink:to="lab_us-gaap_AllowanceForUncollectiblePremiumsReceivableMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost_ea6edda7-781e-445b-9464-1193a93466ee_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Due after five years through ten years</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Amortized Cost, Maturity, Allocated and Single Maturity Date, after Year 5 Through 10</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsAmortizedCost" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CondensedIncomeStatementTable_40fca2fd-ad5b-4efb-9e28-8fe3495260ec_terseLabel_en-US" xlink:label="lab_srt_CondensedIncomeStatementTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Condensed Income Statement [Table]</link:label>
    <link:label id="lab_srt_CondensedIncomeStatementTable_label_en-US" xlink:label="lab_srt_CondensedIncomeStatementTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Condensed Income Statement [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_CondensedIncomeStatementTable" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_CondensedIncomeStatementTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_CondensedIncomeStatementTable" xlink:to="lab_srt_CondensedIncomeStatementTable" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_OwnershipDomain_54c91a80-5049-4b7e-89f8-a0ec0d027cd3_terseLabel_en-US" xlink:label="lab_srt_OwnershipDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ownership [Domain]</link:label>
    <link:label id="lab_srt_OwnershipDomain_label_en-US" xlink:label="lab_srt_OwnershipDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ownership [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_OwnershipDomain" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_OwnershipDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_OwnershipDomain" xlink:to="lab_srt_OwnershipDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_WestaimHIIGLPAffiliatesMember_0ce4bb96-ae7b-4793-b448-46932a63eedb_terseLabel_en-US" xlink:label="lab_skwd_WestaimHIIGLPAffiliatesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Westaim HIIG LP Affiliates</link:label>
    <link:label id="lab_skwd_WestaimHIIGLPAffiliatesMember_label_en-US" xlink:label="lab_skwd_WestaimHIIGLPAffiliatesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Westaim HIIG LP Affiliates [Member]</link:label>
    <link:label id="lab_skwd_WestaimHIIGLPAffiliatesMember_documentation_en-US" xlink:label="lab_skwd_WestaimHIIGLPAffiliatesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Westaim HIIG LP Affiliates</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_WestaimHIIGLPAffiliatesMember" xlink:href="skwd-20221231.xsd#skwd_WestaimHIIGLPAffiliatesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_WestaimHIIGLPAffiliatesMember" xlink:to="lab_skwd_WestaimHIIGLPAffiliatesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ReinsuranceRecoveriesUnderTheLPT_a042c670-a90e-45bd-a900-9e69f7fce241_terseLabel_en-US" xlink:label="lab_skwd_ReinsuranceRecoveriesUnderTheLPT" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance recoveries under the LPT</link:label>
    <link:label id="lab_skwd_ReinsuranceRecoveriesUnderTheLPT_label_en-US" xlink:label="lab_skwd_ReinsuranceRecoveriesUnderTheLPT" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Recoveries Under The LPT</link:label>
    <link:label id="lab_skwd_ReinsuranceRecoveriesUnderTheLPT_documentation_en-US" xlink:label="lab_skwd_ReinsuranceRecoveriesUnderTheLPT" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Recoveries Under The LPT</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ReinsuranceRecoveriesUnderTheLPT" xlink:href="skwd-20221231.xsd#skwd_ReinsuranceRecoveriesUnderTheLPT"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ReinsuranceRecoveriesUnderTheLPT" xlink:to="lab_skwd_ReinsuranceRecoveriesUnderTheLPT" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityInteractiveDataCurrent_9ff5561f-4da2-402b-bd8d-d52fab2527f1_terseLabel_en-US" xlink:label="lab_dei_EntityInteractiveDataCurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Interactive Data Current</link:label>
    <link:label id="lab_dei_EntityInteractiveDataCurrent_label_en-US" xlink:label="lab_dei_EntityInteractiveDataCurrent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Interactive Data Current</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityInteractiveDataCurrent" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityInteractiveDataCurrent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityInteractiveDataCurrent" xlink:to="lab_dei_EntityInteractiveDataCurrent" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_IncrementalCommonSharesAttributableToDilutiveEffectOfConversionOfPerformanceAwards_6d2adf47-2316-42f4-82f0-a1318f0ffdd6_terseLabel_en-US" xlink:label="lab_skwd_IncrementalCommonSharesAttributableToDilutiveEffectOfConversionOfPerformanceAwards" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Performance awards (contingently issuable) (in shares)</link:label>
    <link:label id="lab_skwd_IncrementalCommonSharesAttributableToDilutiveEffectOfConversionOfPerformanceAwards_label_en-US" xlink:label="lab_skwd_IncrementalCommonSharesAttributableToDilutiveEffectOfConversionOfPerformanceAwards" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Incremental Common Shares Attributable to Dilutive Effect of Conversion of Performance Awards</link:label>
    <link:label id="lab_skwd_IncrementalCommonSharesAttributableToDilutiveEffectOfConversionOfPerformanceAwards_documentation_en-US" xlink:label="lab_skwd_IncrementalCommonSharesAttributableToDilutiveEffectOfConversionOfPerformanceAwards" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Incremental Common Shares Attributable to Dilutive Effect of Conversion of Performance Awards</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_IncrementalCommonSharesAttributableToDilutiveEffectOfConversionOfPerformanceAwards" xlink:href="skwd-20221231.xsd#skwd_IncrementalCommonSharesAttributableToDilutiveEffectOfConversionOfPerformanceAwards"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_IncrementalCommonSharesAttributableToDilutiveEffectOfConversionOfPerformanceAwards" xlink:to="lab_skwd_IncrementalCommonSharesAttributableToDilutiveEffectOfConversionOfPerformanceAwards" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CededPremiumsEarned_b6aac772-e224-4abd-95c3-750fab06816a_negatedLabel_en-US" xlink:label="lab_us-gaap_CededPremiumsEarned" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ceded premiums</link:label>
    <link:label id="lab_us-gaap_CededPremiumsEarned_1dd4f0ad-c78c-4991-a252-538a0192cf4c_terseLabel_en-US" xlink:label="lab_us-gaap_CededPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance premiums ceded</link:label>
    <link:label id="lab_us-gaap_CededPremiumsEarned_62b43cb4-0d9c-4964-9c5e-78302f714e6e_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_CededPremiumsEarned" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance premiums ceded</link:label>
    <link:label id="lab_us-gaap_CededPremiumsEarned_label_en-US" xlink:label="lab_us-gaap_CededPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ceded Premiums Earned</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CededPremiumsEarned" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CededPremiumsEarned"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CededPremiumsEarned" xlink:to="lab_us-gaap_CededPremiumsEarned" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfPropertyPlantAndEquipmentTable_932cccb9-11ee-4d07-b8fc-acc96535b1bf_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfPropertyPlantAndEquipmentTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Property, Plant and Equipment [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfPropertyPlantAndEquipmentTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfPropertyPlantAndEquipmentTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Property, Plant and Equipment [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfPropertyPlantAndEquipmentTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfPropertyPlantAndEquipmentTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfPropertyPlantAndEquipmentTable" xlink:to="lab_us-gaap_ScheduleOfPropertyPlantAndEquipmentTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInOperatingCapitalAbstract_8bab56ee-668f-4f8b-8da7-e8478429b731_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInOperatingCapitalAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Changes in operating assets and liabilities:</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInOperatingCapitalAbstract_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInOperatingCapitalAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Increase (Decrease) in Operating Capital [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInOperatingCapitalAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInOperatingCapitalAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInOperatingCapitalAbstract" xlink:to="lab_us-gaap_IncreaseDecreaseInOperatingCapitalAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncrementalCommonSharesAttributableToContingentlyIssuableShares_96c01a8e-1401-43b0-b46b-9347ae9a1403_verboseLabel_en-US" xlink:label="lab_us-gaap_IncrementalCommonSharesAttributableToContingentlyIssuableShares" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Contingently issuable instruments (treasury stock method) (in shares)</link:label>
    <link:label id="lab_us-gaap_IncrementalCommonSharesAttributableToContingentlyIssuableShares_label_en-US" xlink:label="lab_us-gaap_IncrementalCommonSharesAttributableToContingentlyIssuableShares" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Incremental Common Shares Attributable to Dilutive Effect of Contingently Issuable Shares</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncrementalCommonSharesAttributableToContingentlyIssuableShares" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncrementalCommonSharesAttributableToContingentlyIssuableShares"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncrementalCommonSharesAttributableToContingentlyIssuableShares" xlink:to="lab_us-gaap_IncrementalCommonSharesAttributableToContingentlyIssuableShares" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PortionAtFairValueFairValueDisclosureMember_24647134-91a7-4cc6-aef0-9683bc80c9e6_terseLabel_en-US" xlink:label="lab_us-gaap_PortionAtFairValueFairValueDisclosureMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Portion at Fair Value Measurement</link:label>
    <link:label id="lab_us-gaap_PortionAtFairValueFairValueDisclosureMember_label_en-US" xlink:label="lab_us-gaap_PortionAtFairValueFairValueDisclosureMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Portion at Fair Value Measurement [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PortionAtFairValueFairValueDisclosureMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PortionAtFairValueFairValueDisclosureMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PortionAtFairValueFairValueDisclosureMember" xlink:to="lab_us-gaap_PortionAtFairValueFairValueDisclosureMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_SMA2Member_598e803d-2f5b-4741-8248-71694e1a1a5a_terseLabel_en-US" xlink:label="lab_skwd_SMA2Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SMA2</link:label>
    <link:label id="lab_skwd_SMA2Member_label_en-US" xlink:label="lab_skwd_SMA2Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SMA2 [Member]</link:label>
    <link:label id="lab_skwd_SMA2Member_documentation_en-US" xlink:label="lab_skwd_SMA2Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SMA2</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_SMA2Member" xlink:href="skwd-20221231.xsd#skwd_SMA2Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_SMA2Member" xlink:to="lab_skwd_SMA2Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfShortTermInvestments_c50a3198-24b5-4d6f-8d82-22c2a54938fa_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfShortTermInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Change in short-term investments</link:label>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfShortTermInvestments_label_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfShortTermInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Proceeds from Sale of Short-Term Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromSaleOfShortTermInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ProceedsFromSaleOfShortTermInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromSaleOfShortTermInvestments" xlink:to="lab_us-gaap_ProceedsFromSaleOfShortTermInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfEmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsTextBlock_9443d651-69a8-46f8-9f19-816509969bea_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfEmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Share-Based Compensation Expense</link:label>
    <link:label id="lab_us-gaap_ScheduleOfEmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfEmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Payment Arrangement, Expensed and Capitalized, Amount [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfEmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfEmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfEmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsTextBlock" xlink:to="lab_us-gaap_ScheduleOfEmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent_dd3fc2b7-d315-4311-a93a-1368180d5a30_totalLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total other comprehensive loss</link:label>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent_8791dde0-c7a3-4be0-8b01-d23bd373b829_terseLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other comprehensive loss, net of tax</link:label>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent_label_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other Comprehensive Income (Loss), Net of Tax, Portion Attributable to Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent" xlink:to="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_GulfCapitalBankMember_632c20cb-8414-4994-b031-41ec5639efd7_terseLabel_en-US" xlink:label="lab_skwd_GulfCapitalBankMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gulf Capital Bank</link:label>
    <link:label id="lab_skwd_GulfCapitalBankMember_label_en-US" xlink:label="lab_skwd_GulfCapitalBankMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gulf Capital Bank [Member]</link:label>
    <link:label id="lab_skwd_GulfCapitalBankMember_documentation_en-US" xlink:label="lab_skwd_GulfCapitalBankMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gulf Capital Bank</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_GulfCapitalBankMember" xlink:href="skwd-20221231.xsd#skwd_GulfCapitalBankMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_GulfCapitalBankMember" xlink:to="lab_skwd_GulfCapitalBankMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodValueShareBasedCompensation_63f7316f-5b6f-4ae3-b18e-8e2053ed506f_terseLabel_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodValueShareBasedCompensation" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Employee equity transactions</link:label>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodValueShareBasedCompensation_label_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodValueShareBasedCompensation" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Shares Issued, Value, Share-Based Payment Arrangement, after Forfeiture</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockIssuedDuringPeriodValueShareBasedCompensation" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StockIssuedDuringPeriodValueShareBasedCompensation"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockIssuedDuringPeriodValueShareBasedCompensation" xlink:to="lab_us-gaap_StockIssuedDuringPeriodValueShareBasedCompensation" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxPolicyTextBlock_1b742a44-58df-4ed0-92ca-f7636a8cb93a_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Income Taxes</link:label>
    <link:label id="lab_us-gaap_IncomeTaxPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_IncomeTaxPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Income Tax, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncomeTaxPolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxPolicyTextBlock" xlink:to="lab_us-gaap_IncomeTaxPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesCost_809b3b66-d6ec-4bb9-8662-75c3c0b5b2b4_terseLabel_en-US" xlink:label="lab_us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cost</link:label>
    <link:label id="lab_us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesCost_label_en-US" xlink:label="lab_us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-15, Insurance Companies, Summary of Investments, Other than Investments in Related Parties, Cost</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesCost" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesCost"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesCost" xlink:to="lab_us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesCost" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_JuniorSubordinatedNotesDue2036CapitalSecuritiesMember_a50c73ff-2fc7-4369-9c3f-54e2e5d0126d_terseLabel_en-US" xlink:label="lab_skwd_JuniorSubordinatedNotesDue2036CapitalSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Junior Subordinated Notes Due 2036, Capital Securities</link:label>
    <link:label id="lab_skwd_JuniorSubordinatedNotesDue2036CapitalSecuritiesMember_label_en-US" xlink:label="lab_skwd_JuniorSubordinatedNotesDue2036CapitalSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Junior Subordinated Notes Due 2036, Capital Securities [Member]</link:label>
    <link:label id="lab_skwd_JuniorSubordinatedNotesDue2036CapitalSecuritiesMember_documentation_en-US" xlink:label="lab_skwd_JuniorSubordinatedNotesDue2036CapitalSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Junior Subordinated Notes Due 2036, Capital Securities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_JuniorSubordinatedNotesDue2036CapitalSecuritiesMember" xlink:href="skwd-20221231.xsd#skwd_JuniorSubordinatedNotesDue2036CapitalSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_JuniorSubordinatedNotesDue2036CapitalSecuritiesMember" xlink:to="lab_skwd_JuniorSubordinatedNotesDue2036CapitalSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RetainedEarningsAccumulatedDeficit_942686e9-a648-4071-89bb-e0f66f379d94_terseLabel_en-US" xlink:label="lab_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accumulated deficit</link:label>
    <link:label id="lab_us-gaap_RetainedEarningsAccumulatedDeficit_label_en-US" xlink:label="lab_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Retained Earnings (Accumulated Deficit)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RetainedEarningsAccumulatedDeficit"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:to="lab_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost_5faeba34-f294-4bee-bf24-ce7724119fe3_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Due after ten years</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Amortized Cost, Maturity, Allocated and Single Maturity Date, after Year 10</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfFiniteLivedIntangibleAssetsTable_7e628e5f-e8fd-4053-823f-4dc5afb1735b_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfFiniteLivedIntangibleAssetsTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Finite-Lived Intangible Assets [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfFiniteLivedIntangibleAssetsTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfFiniteLivedIntangibleAssetsTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Finite-Lived Intangible Assets [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfFiniteLivedIntangibleAssetsTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfFiniteLivedIntangibleAssetsTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfFiniteLivedIntangibleAssetsTable" xlink:to="lab_us-gaap_ScheduleOfFiniteLivedIntangibleAssetsTable" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ScenarioUnspecifiedDomain_90431896-460a-41bd-ab4c-3fa314240da7_terseLabel_en-US" xlink:label="lab_srt_ScenarioUnspecifiedDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Scenario [Domain]</link:label>
    <link:label id="lab_srt_ScenarioUnspecifiedDomain_label_en-US" xlink:label="lab_srt_ScenarioUnspecifiedDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Scenario [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ScenarioUnspecifiedDomain" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_ScenarioUnspecifiedDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ScenarioUnspecifiedDomain" xlink:to="lab_srt_ScenarioUnspecifiedDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TrademarksMember_2f2f508a-623e-4c56-a73e-df4b39492bf7_terseLabel_en-US" xlink:label="lab_us-gaap_TrademarksMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Trademarks</link:label>
    <link:label id="lab_us-gaap_TrademarksMember_label_en-US" xlink:label="lab_us-gaap_TrademarksMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Trademarks [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TrademarksMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_TrademarksMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TrademarksMember" xlink:to="lab_us-gaap_TrademarksMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_UniversaBlackSwanProtectionProtocolLIVLPMember_36835386-5bf9-4e29-ae10-454e87d7b24e_verboseLabel_en-US" xlink:label="lab_skwd_UniversaBlackSwanProtectionProtocolLIVLPMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Universa Black Swan</link:label>
    <link:label id="lab_skwd_UniversaBlackSwanProtectionProtocolLIVLPMember_3fd5f468-6cab-440d-a534-0171cdabeb26_terseLabel_en-US" xlink:label="lab_skwd_UniversaBlackSwanProtectionProtocolLIVLPMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Universa Black Swan LP units</link:label>
    <link:label id="lab_skwd_UniversaBlackSwanProtectionProtocolLIVLPMember_label_en-US" xlink:label="lab_skwd_UniversaBlackSwanProtectionProtocolLIVLPMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Universa Black Swan Protection Protocol LIV L.P. [Member]</link:label>
    <link:label id="lab_skwd_UniversaBlackSwanProtectionProtocolLIVLPMember_documentation_en-US" xlink:label="lab_skwd_UniversaBlackSwanProtectionProtocolLIVLPMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Universa Black Swan Protection Protocol LIV L.P.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_UniversaBlackSwanProtectionProtocolLIVLPMember" xlink:href="skwd-20221231.xsd#skwd_UniversaBlackSwanProtectionProtocolLIVLPMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_UniversaBlackSwanProtectionProtocolLIVLPMember" xlink:to="lab_skwd_UniversaBlackSwanProtectionProtocolLIVLPMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RelatedPartyTransactionsDisclosureTextBlock_c2791762-aecb-452d-a857-a60f5ef50d84_terseLabel_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Related Party Transactions</link:label>
    <link:label id="lab_us-gaap_RelatedPartyTransactionsDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Related Party Transactions Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RelatedPartyTransactionsDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RelatedPartyTransactionsDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RelatedPartyTransactionsDisclosureTextBlock" xlink:to="lab_us-gaap_RelatedPartyTransactionsDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_RelatedPartyTransactionShares_c2f84cc2-2cff-4d0f-ae3e-d484499d8c6d_terseLabel_en-US" xlink:label="lab_skwd_RelatedPartyTransactionShares" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Related party transaction, shares</link:label>
    <link:label id="lab_skwd_RelatedPartyTransactionShares_label_en-US" xlink:label="lab_skwd_RelatedPartyTransactionShares" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Related Party Transaction, Shares</link:label>
    <link:label id="lab_skwd_RelatedPartyTransactionShares_documentation_en-US" xlink:label="lab_skwd_RelatedPartyTransactionShares" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Related Party Transaction, Shares</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RelatedPartyTransactionShares" xlink:href="skwd-20221231.xsd#skwd_RelatedPartyTransactionShares"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_RelatedPartyTransactionShares" xlink:to="lab_skwd_RelatedPartyTransactionShares" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months_6ec852a6-3582-4a8f-9b02-a92e7194e7b4_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Less than 12 Months</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Continuous Unrealized Loss Position, Less than 12 Months</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentFiscalYearFocus_7d48e4be-e8e8-4c9e-bb3e-28467bdb3d10_terseLabel_en-US" xlink:label="lab_dei_DocumentFiscalYearFocus" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Document Fiscal Year Focus</link:label>
    <link:label id="lab_dei_DocumentFiscalYearFocus_label_en-US" xlink:label="lab_dei_DocumentFiscalYearFocus" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Document Fiscal Year Focus</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentFiscalYearFocus" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_DocumentFiscalYearFocus"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentFiscalYearFocus" xlink:to="lab_dei_DocumentFiscalYearFocus" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseTableTextBlock_06712676-55c8-43c5-baf1-29ad9a78ce9a_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Finite-Lived Intangible Assets Amortization Expense</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseTableTextBlock_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Finite-Lived Intangible Assets Amortization Expense [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseTableTextBlock" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract_527eed5c-5626-4f0b-aab5-7b70b76676f3_terseLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash flows from operating activities:</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net Cash Provided by (Used in) Operating Activities [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:to="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLoss_ebee1d67-23b6-4f32-93ae-6901dc858ce2_negatedTotalLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTotalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLoss_label_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Unrealized Loss Position, Accumulated Loss</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLoss_documentation_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Unrealized Loss Position, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLoss" xlink:href="skwd-20221231.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLoss" xlink:to="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentOther_15a08a91-5beb-4601-aecc-3ca7b5cda615_terseLabel_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentOther" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Property, equipment and other, gross</link:label>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentOther_label_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentOther" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Property, Plant and Equipment, Other, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentOther" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PropertyPlantAndEquipmentOther"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentOther" xlink:to="lab_us-gaap_PropertyPlantAndEquipmentOther" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve_4c183b12-7534-4313-ad1a-1e3c3b7d7a1e_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Losses and loss adjustment expenses</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Increase (Decrease) in Liability for Claims and Claims Adjustment Expense Reserve</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve" xlink:to="lab_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueByFairValueHierarchyLevelAxis_9ebd8725-aae6-48df-86a8-4f9dd794fdd0_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueByFairValueHierarchyLevelAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value Hierarchy and NAV [Axis]</link:label>
    <link:label id="lab_us-gaap_FairValueByFairValueHierarchyLevelAxis_label_en-US" xlink:label="lab_us-gaap_FairValueByFairValueHierarchyLevelAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value Hierarchy and NAV [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueByFairValueHierarchyLevelAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FairValueByFairValueHierarchyLevelAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueByFairValueHierarchyLevelAxis" xlink:to="lab_us-gaap_FairValueByFairValueHierarchyLevelAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NewAccountingPronouncementsAndChangesInAccountingPrinciplesTextBlock_a318e97d-c7a4-426c-b11f-f5b00c8e06ea_terseLabel_en-US" xlink:label="lab_us-gaap_NewAccountingPronouncementsAndChangesInAccountingPrinciplesTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Recent Accounting Pronouncements</link:label>
    <link:label id="lab_us-gaap_NewAccountingPronouncementsAndChangesInAccountingPrinciplesTextBlock_label_en-US" xlink:label="lab_us-gaap_NewAccountingPronouncementsAndChangesInAccountingPrinciplesTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accounting Standards Update and Change in Accounting Principle [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NewAccountingPronouncementsAndChangesInAccountingPrinciplesTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NewAccountingPronouncementsAndChangesInAccountingPrinciplesTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NewAccountingPronouncementsAndChangesInAccountingPrinciplesTextBlock" xlink:to="lab_us-gaap_NewAccountingPronouncementsAndChangesInAccountingPrinciplesTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CurrentIncomeTaxExpenseBenefit_9cb707f7-55c1-416c-986f-9664dd0dd0ac_terseLabel_en-US" xlink:label="lab_us-gaap_CurrentIncomeTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Current income tax expense</link:label>
    <link:label id="lab_us-gaap_CurrentIncomeTaxExpenseBenefit_label_en-US" xlink:label="lab_us-gaap_CurrentIncomeTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Current Income Tax Expense (Benefit)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CurrentIncomeTaxExpenseBenefit" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CurrentIncomeTaxExpenseBenefit"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CurrentIncomeTaxExpenseBenefit" xlink:to="lab_us-gaap_CurrentIncomeTaxExpenseBenefit" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_EffectiveIncomeTaxRateReconciliationAdvantagedInvestmentsPercent_529857b2-358b-4ada-ba4e-75946e4e0eda_terseLabel_en-US" xlink:label="lab_skwd_EffectiveIncomeTaxRateReconciliationAdvantagedInvestmentsPercent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Tax advantaged investments</link:label>
    <link:label id="lab_skwd_EffectiveIncomeTaxRateReconciliationAdvantagedInvestmentsPercent_label_en-US" xlink:label="lab_skwd_EffectiveIncomeTaxRateReconciliationAdvantagedInvestmentsPercent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Effective Income Tax Rate Reconciliation, Advantaged Investments, Percent</link:label>
    <link:label id="lab_skwd_EffectiveIncomeTaxRateReconciliationAdvantagedInvestmentsPercent_documentation_en-US" xlink:label="lab_skwd_EffectiveIncomeTaxRateReconciliationAdvantagedInvestmentsPercent" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Effective Income Tax Rate Reconciliation, Advantaged Investments, Percent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_EffectiveIncomeTaxRateReconciliationAdvantagedInvestmentsPercent" xlink:href="skwd-20221231.xsd#skwd_EffectiveIncomeTaxRateReconciliationAdvantagedInvestmentsPercent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_EffectiveIncomeTaxRateReconciliationAdvantagedInvestmentsPercent" xlink:to="lab_skwd_EffectiveIncomeTaxRateReconciliationAdvantagedInvestmentsPercent" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_MaterialsSectorMember_7a87abe6-5f49-46a1-925e-16f01d4f56f6_terseLabel_en-US" xlink:label="lab_skwd_MaterialsSectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Materials</link:label>
    <link:label id="lab_skwd_MaterialsSectorMember_label_en-US" xlink:label="lab_skwd_MaterialsSectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Materials Sector [Member]</link:label>
    <link:label id="lab_skwd_MaterialsSectorMember_documentation_en-US" xlink:label="lab_skwd_MaterialsSectorMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Materials Sector</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_MaterialsSectorMember" xlink:href="skwd-20221231.xsd#skwd_MaterialsSectorMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_MaterialsSectorMember" xlink:to="lab_skwd_MaterialsSectorMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OperatingLeaseExpense_fbd8b02f-4500-435a-8bf0-d1dea39984be_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingLeaseExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total lease expense</link:label>
    <link:label id="lab_us-gaap_OperatingLeaseExpense_28fb3e51-0f59-4cc8-8f9b-ad2624b288a9_totalLabel_en-US" xlink:label="lab_us-gaap_OperatingLeaseExpense" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total lease expense</link:label>
    <link:label id="lab_us-gaap_OperatingLeaseExpense_label_en-US" xlink:label="lab_us-gaap_OperatingLeaseExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Operating Lease, Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OperatingLeaseExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OperatingLeaseExpense" xlink:to="lab_us-gaap_OperatingLeaseExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis_5def8076-4f4d-4e9e-a786-fa240ae0a620_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Method Investment, Nonconsolidated Investee [Axis]</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Method Investment, Nonconsolidated Investee [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis" xlink:to="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsRollForward_35d79b2e-56cb-46ea-870b-93b76f23a19f_terseLabel_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Indefinite-Lived</link:label>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsRollForward_label_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Indefinite-Lived Intangible Assets [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefiniteLivedIntangibleAssetsRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IndefiniteLivedIntangibleAssetsRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IndefiniteLivedIntangibleAssetsRollForward" xlink:to="lab_us-gaap_IndefiniteLivedIntangibleAssetsRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquity_320d37e1-cd08-48ed-ac87-2836f2e1371a_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquity" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Difference</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquity_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquity" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Method Investment, Difference Between Carrying Amount and Underlying Equity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquity" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquity"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquity" xlink:to="lab_us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquity" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredTaxAssetsTaxDeferredExpenseCompensationAndBenefitsShareBasedCompensationCost_6c9a8463-b8a5-486f-8a3d-f6786c1b6865_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsTaxDeferredExpenseCompensationAndBenefitsShareBasedCompensationCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stock options/awards</link:label>
    <link:label id="lab_us-gaap_DeferredTaxAssetsTaxDeferredExpenseCompensationAndBenefitsShareBasedCompensationCost_label_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsTaxDeferredExpenseCompensationAndBenefitsShareBasedCompensationCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Tax Assets, Tax Deferred Expense, Compensation and Benefits, Share-Based Compensation Cost</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxAssetsTaxDeferredExpenseCompensationAndBenefitsShareBasedCompensationCost" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DeferredTaxAssetsTaxDeferredExpenseCompensationAndBenefitsShareBasedCompensationCost"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredTaxAssetsTaxDeferredExpenseCompensationAndBenefitsShareBasedCompensationCost" xlink:to="lab_us-gaap_DeferredTaxAssetsTaxDeferredExpenseCompensationAndBenefitsShareBasedCompensationCost" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentsInAffiliatesSubsidiariesAssociatesAndJointVentures_920137b1-400f-4e0d-8cef-9758725c1e22_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentsInAffiliatesSubsidiariesAssociatesAndJointVentures" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment in subsidiaries</link:label>
    <link:label id="lab_us-gaap_InvestmentsInAffiliatesSubsidiariesAssociatesAndJointVentures_label_en-US" xlink:label="lab_us-gaap_InvestmentsInAffiliatesSubsidiariesAssociatesAndJointVentures" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investments in and Advance to Affiliates, Subsidiaries, Associates, and Joint Ventures</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentsInAffiliatesSubsidiariesAssociatesAndJointVentures" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_InvestmentsInAffiliatesSubsidiariesAssociatesAndJointVentures"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentsInAffiliatesSubsidiariesAssociatesAndJointVentures" xlink:to="lab_us-gaap_InvestmentsInAffiliatesSubsidiariesAssociatesAndJointVentures" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_Goodwill_a8fdd52a-1629-4351-a34a-08a196f9b4a3_terseLabel_en-US" xlink:label="lab_us-gaap_Goodwill" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Goodwill recognized</link:label>
    <link:label id="lab_us-gaap_Goodwill_e9060151-f50d-4449-8a16-b54185df69fe_netLabel_en-US" xlink:label="lab_us-gaap_Goodwill" xlink:role="http://www.xbrl.org/2009/role/netLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Goodwill, net balance</link:label>
    <link:label id="lab_us-gaap_Goodwill_label_en-US" xlink:label="lab_us-gaap_Goodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Goodwill</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Goodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_Goodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Goodwill" xlink:to="lab_us-gaap_Goodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TreasuryStockShares_c0663e89-dfbf-4fd9-b83a-6891dec3a074_terseLabel_en-US" xlink:label="lab_us-gaap_TreasuryStockShares" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Treasury stock (in shares)</link:label>
    <link:label id="lab_us-gaap_TreasuryStockShares_label_en-US" xlink:label="lab_us-gaap_TreasuryStockShares" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Treasury Stock, Shares</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TreasuryStockShares" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_TreasuryStockShares"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TreasuryStockShares" xlink:to="lab_us-gaap_TreasuryStockShares" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentByTypeAxis_e0d48ce4-ac70-449e-956d-566829ccf5ed_terseLabel_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentByTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long-Lived Tangible Asset [Axis]</link:label>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentByTypeAxis_label_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentByTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long-Lived Tangible Asset [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentByTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PropertyPlantAndEquipmentByTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentByTypeAxis" xlink:to="lab_us-gaap_PropertyPlantAndEquipmentByTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NotesPayable_1b796d2a-f2b2-4c16-bf4a-b343452056fc_terseLabel_en-US" xlink:label="lab_us-gaap_NotesPayable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Notes payable</link:label>
    <link:label id="lab_us-gaap_NotesPayable_label_en-US" xlink:label="lab_us-gaap_NotesPayable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Notes Payable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NotesPayable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NotesPayable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NotesPayable" xlink:to="lab_us-gaap_NotesPayable" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_TermLoanDueDecember2024Member_b1e294be-167d-4488-8826-ed97a00a5c17_terseLabel_en-US" xlink:label="lab_skwd_TermLoanDueDecember2024Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Term Loan, due December 2024</link:label>
    <link:label id="lab_skwd_TermLoanDueDecember2024Member_label_en-US" xlink:label="lab_skwd_TermLoanDueDecember2024Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Term Loan Due December 2024 [Member]</link:label>
    <link:label id="lab_skwd_TermLoanDueDecember2024Member_documentation_en-US" xlink:label="lab_skwd_TermLoanDueDecember2024Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Term Loan Due December 2024</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_TermLoanDueDecember2024Member" xlink:href="skwd-20221231.xsd#skwd_TermLoanDueDecember2024Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_TermLoanDueDecember2024Member" xlink:to="lab_skwd_TermLoanDueDecember2024Member" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ManagementServicesAgreementMember_2e2654ce-9465-4e12-9aba-56145786d43d_terseLabel_en-US" xlink:label="lab_skwd_ManagementServicesAgreementMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Management services agreement</link:label>
    <link:label id="lab_skwd_ManagementServicesAgreementMember_label_en-US" xlink:label="lab_skwd_ManagementServicesAgreementMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Management Services Agreement [Member]</link:label>
    <link:label id="lab_skwd_ManagementServicesAgreementMember_documentation_en-US" xlink:label="lab_skwd_ManagementServicesAgreementMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Management Services Agreement</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ManagementServicesAgreementMember" xlink:href="skwd-20221231.xsd#skwd_ManagementServicesAgreementMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ManagementServicesAgreementMember" xlink:to="lab_skwd_ManagementServicesAgreementMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsLiability_086c6d6e-bde0-4d2b-9b7f-1e229e5a7850_terseLabel_en-US" xlink:label="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsLiability" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Funds held for others</link:label>
    <link:label id="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsLiability_label_en-US" xlink:label="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsLiability" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Funds Held under Reinsurance Agreements, Liability</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FundsHeldUnderReinsuranceAgreementsLiability" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FundsHeldUnderReinsuranceAgreementsLiability"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FundsHeldUnderReinsuranceAgreementsLiability" xlink:to="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsLiability" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxExpenseBenefit_cab8d258-098d-46b9-b575-6c286dfd89a8_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Income tax expense</link:label>
    <link:label id="lab_us-gaap_IncomeTaxExpenseBenefit_45c8725d-18e0-4906-b1e8-374db43c84d8_totalLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total income tax expense</link:label>
    <link:label id="lab_us-gaap_IncomeTaxExpenseBenefit_0655b216-f4e3-4158-a2a0-36a277b7f9ab_verboseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Income tax benefit</link:label>
    <link:label id="lab_us-gaap_IncomeTaxExpenseBenefit_label_en-US" xlink:label="lab_us-gaap_IncomeTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Income Tax Expense (Benefit)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxExpenseBenefit" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncomeTaxExpenseBenefit"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxExpenseBenefit" xlink:to="lab_us-gaap_IncomeTaxExpenseBenefit" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredTaxAssetsValuationAllowance_7f2c2af8-50c4-4ea7-9481-408fa1ccfe9c_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsValuationAllowance" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Less valuation allowance</link:label>
    <link:label id="lab_us-gaap_DeferredTaxAssetsValuationAllowance_bb2e0509-3f49-4b26-8990-f7898a2e16b4_periodStartLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsValuationAllowance" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Balance at beginning of year</link:label>
    <link:label id="lab_us-gaap_DeferredTaxAssetsValuationAllowance_abe29915-194b-447e-97dc-32ebfe19817a_periodEndLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsValuationAllowance" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Balance at end of year</link:label>
    <link:label id="lab_us-gaap_DeferredTaxAssetsValuationAllowance_label_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsValuationAllowance" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Tax Assets, Valuation Allowance</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxAssetsValuationAllowance" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DeferredTaxAssetsValuationAllowance"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredTaxAssetsValuationAllowance" xlink:to="lab_us-gaap_DeferredTaxAssetsValuationAllowance" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts_cd282333-6386-4ca0-8518-cd7447554775_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred policy acquisition costs</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Increase (Decrease) in Deferred Policy Acquisition Costs</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts" xlink:to="lab_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityPublicFloat_6b4ed3ed-6c12-4127-866d-8ae79cf62783_terseLabel_en-US" xlink:label="lab_dei_EntityPublicFloat" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Public Float</link:label>
    <link:label id="lab_dei_EntityPublicFloat_label_en-US" xlink:label="lab_dei_EntityPublicFloat" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Public Float</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityPublicFloat" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityPublicFloat"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityPublicFloat" xlink:to="lab_dei_EntityPublicFloat" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_BostonIndemnityCompanyMember_feb6eba5-4cb7-434c-9d2d-89ecce6dedfb_terseLabel_en-US" xlink:label="lab_skwd_BostonIndemnityCompanyMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Boston Indemnity Company</link:label>
    <link:label id="lab_skwd_BostonIndemnityCompanyMember_label_en-US" xlink:label="lab_skwd_BostonIndemnityCompanyMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Boston Indemnity Company [Member]</link:label>
    <link:label id="lab_skwd_BostonIndemnityCompanyMember_documentation_en-US" xlink:label="lab_skwd_BostonIndemnityCompanyMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Boston Indemnity Company</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_BostonIndemnityCompanyMember" xlink:href="skwd-20221231.xsd#skwd_BostonIndemnityCompanyMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_BostonIndemnityCompanyMember" xlink:to="lab_skwd_BostonIndemnityCompanyMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiRealizedLoss_ac163167-3a0e-4bba-93c2-7cc2f73d4335_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiRealizedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity securities</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiRealizedLoss_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiRealizedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Securities, FV-NI, Realized Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesFvNiRealizedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EquitySecuritiesFvNiRealizedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesFvNiRealizedLoss" xlink:to="lab_us-gaap_EquitySecuritiesFvNiRealizedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccumulatedDepreciationDepletionAndAmortizationPropertyPlantAndEquipment_947f5a01-fad4-44ac-abc6-ce851b9b0a53_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_AccumulatedDepreciationDepletionAndAmortizationPropertyPlantAndEquipment" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accumulated depreciation</link:label>
    <link:label id="lab_us-gaap_AccumulatedDepreciationDepletionAndAmortizationPropertyPlantAndEquipment_label_en-US" xlink:label="lab_us-gaap_AccumulatedDepreciationDepletionAndAmortizationPropertyPlantAndEquipment" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accumulated Depreciation, Depletion and Amortization, Property, Plant, and Equipment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedDepreciationDepletionAndAmortizationPropertyPlantAndEquipment" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AccumulatedDepreciationDepletionAndAmortizationPropertyPlantAndEquipment"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccumulatedDepreciationDepletionAndAmortizationPropertyPlantAndEquipment" xlink:to="lab_us-gaap_AccumulatedDepreciationDepletionAndAmortizationPropertyPlantAndEquipment" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GroupPoliciesMember_5e77d2f1-faba-4d9a-bec3-d44ec069db15_terseLabel_en-US" xlink:label="lab_us-gaap_GroupPoliciesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Group Accident &amp; Health</link:label>
    <link:label id="lab_us-gaap_GroupPoliciesMember_label_en-US" xlink:label="lab_us-gaap_GroupPoliciesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Group Insurance Policy [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GroupPoliciesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_GroupPoliciesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GroupPoliciesMember" xlink:to="lab_us-gaap_GroupPoliciesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_CaptexBancsharesMember_9fad91dd-929d-412d-b653-2702cfb2e811_terseLabel_en-US" xlink:label="lab_skwd_CaptexBancsharesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Captex Bancshares</link:label>
    <link:label id="lab_skwd_CaptexBancsharesMember_label_en-US" xlink:label="lab_skwd_CaptexBancsharesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Captex Bancshares [Member]</link:label>
    <link:label id="lab_skwd_CaptexBancsharesMember_documentation_en-US" xlink:label="lab_skwd_CaptexBancsharesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Captex Bancshares</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_CaptexBancsharesMember" xlink:href="skwd-20221231.xsd#skwd_CaptexBancsharesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_CaptexBancsharesMember" xlink:to="lab_skwd_CaptexBancsharesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_Investments_2dc7513e-37fb-4d29-a785-b1e7310c3c71_totalLabel_en-US" xlink:label="lab_us-gaap_Investments" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total investments</link:label>
    <link:label id="lab_us-gaap_Investments_label_en-US" xlink:label="lab_us-gaap_Investments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Investments" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_Investments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Investments" xlink:to="lab_us-gaap_Investments" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesReportableDataLineItems_e8ff88bd-b360-45ec-8400-389069db51a5_terseLabel_en-US" xlink:label="lab_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesReportableDataLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-15, Insurance Companies, Summary of Investments, Other than Investments in Related Parties [Line Items]</link:label>
    <link:label id="lab_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesReportableDataLineItems_label_en-US" xlink:label="lab_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesReportableDataLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-15, Insurance Companies, Summary of Investments, Other than Investments in Related Parties [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesReportableDataLineItems" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesReportableDataLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesReportableDataLineItems" xlink:to="lab_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesReportableDataLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockValue_e3b7b94f-2cfc-47ab-8208-0fc2bbf9628e_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common stock, $0.01 par value, 168,000,000 shares authorized, 16,832,955 and 16,763,069 shares issued, respectively</link:label>
    <link:label id="lab_us-gaap_CommonStockValue_label_en-US" xlink:label="lab_us-gaap_CommonStockValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common Stock, Value, Issued</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CommonStockValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockValue" xlink:to="lab_us-gaap_CommonStockValue" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardStockNotesReceivableAmount_996a1a2f-e98a-477c-a0b5-34f87d79de15_terseLabel_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardStockNotesReceivableAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common stock notes receivable</link:label>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardStockNotesReceivableAmount_label_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardStockNotesReceivableAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Stock Notes Receivable, Amount</link:label>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardStockNotesReceivableAmount_documentation_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardStockNotesReceivableAmount" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Stock Notes Receivable, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardStockNotesReceivableAmount" xlink:href="skwd-20221231.xsd#skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardStockNotesReceivableAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardStockNotesReceivableAmount" xlink:to="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardStockNotesReceivableAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentNameDomain_78ae9ac6-2a66-4092-8eb6-d135c3f2703c_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Name [Domain]</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentNameDomain_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtInstrumentNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentNameDomain" xlink:to="lab_us-gaap_DebtInstrumentNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessAcquisitionAcquireeDomain_6eb8d009-422e-4a7b-8302-709fbad640fa_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionAcquireeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Business Acquisition, Acquiree [Domain]</link:label>
    <link:label id="lab_us-gaap_BusinessAcquisitionAcquireeDomain_label_en-US" xlink:label="lab_us-gaap_BusinessAcquisitionAcquireeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Business Acquisition, Acquiree [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessAcquisitionAcquireeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_BusinessAcquisitionAcquireeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessAcquisitionAcquireeDomain" xlink:to="lab_us-gaap_BusinessAcquisitionAcquireeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesOnPaidLossesGross_900a40c6-e408-428d-80d3-96c20dba6adb_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesOnPaidLossesGross" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Paid losses and loss adjustment expense ceded</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesOnPaidLossesGross_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesOnPaidLossesGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Recoverables on Paid Losses, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverablesOnPaidLossesGross" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ReinsuranceRecoverablesOnPaidLossesGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverablesOnPaidLossesGross" xlink:to="lab_us-gaap_ReinsuranceRecoverablesOnPaidLossesGross" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PreferredStockMember_d51b0d29-4715-4bfa-abd1-8d8962f63afe_netLabel_en-US" xlink:label="lab_us-gaap_PreferredStockMember" xlink:role="http://www.xbrl.org/2009/role/netLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred&#160; Stock</link:label>
    <link:label id="lab_us-gaap_PreferredStockMember_ed024ee4-6d65-4a2c-a4e5-d650bd9aa8b0_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total preferred stocks</link:label>
    <link:label id="lab_us-gaap_PreferredStockMember_cb17bb92-ff60-452e-8af2-dc9cd4ace691_verboseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred stocks</link:label>
    <link:label id="lab_us-gaap_PreferredStockMember_label_en-US" xlink:label="lab_us-gaap_PreferredStockMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred Stock [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PreferredStockMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PreferredStockMember" xlink:to="lab_us-gaap_PreferredStockMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock_3f72dafd-49b2-4bb9-8e6b-6fac7a228450_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Antidilutive Securities Excluded from Computation of Earnings Per Share</link:label>
    <link:label id="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Antidilutive Securities Excluded from Computation of Earnings Per Share [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock" xlink:to="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherIncome_6ed6db99-af81-43e5-b69c-d66683fa286b_terseLabel_en-US" xlink:label="lab_us-gaap_OtherIncome" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other income (loss)</link:label>
    <link:label id="lab_us-gaap_OtherIncome_label_en-US" xlink:label="lab_us-gaap_OtherIncome" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other Income</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherIncome" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OtherIncome"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherIncome" xlink:to="lab_us-gaap_OtherIncome" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_5b51ed8d-2634-4a7e-a255-987e1770a74a_periodStartLabel_en-US" xlink:label="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash and cash equivalents and restricted cash at beginning of year</link:label>
    <link:label id="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_d961c285-825e-40ba-8bf4-f404dd7b6939_periodEndLabel_en-US" xlink:label="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash and cash equivalents and restricted cash at end of year</link:label>
    <link:label id="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_label_en-US" xlink:label="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash, Cash Equivalents, Restricted Cash, and Restricted Cash Equivalents</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:to="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ExterminatorProMember_dc84132a-e60e-4366-9abe-7f7322843302_terseLabel_en-US" xlink:label="lab_skwd_ExterminatorProMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Exterminator Pro</link:label>
    <link:label id="lab_skwd_ExterminatorProMember_label_en-US" xlink:label="lab_skwd_ExterminatorProMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Exterminator Pro [Member]</link:label>
    <link:label id="lab_skwd_ExterminatorProMember_documentation_en-US" xlink:label="lab_skwd_ExterminatorProMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Exterminator Pro</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ExterminatorProMember" xlink:href="skwd-20221231.xsd#skwd_ExterminatorProMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ExterminatorProMember" xlink:to="lab_skwd_ExterminatorProMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceTableTextBlock_70bc20af-6b97-4e9b-adbd-be775fb865b6_terseLabel_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Premiums Written</link:label>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceTableTextBlock_a106299f-e906-4a12-9e8f-103aa02e6a7d_verboseLabel_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Effects of Reinsurance</link:label>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceTableTextBlock_label_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Effects of Reinsurance [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectsOfReinsuranceTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EffectsOfReinsuranceTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectsOfReinsuranceTableTextBlock" xlink:to="lab_us-gaap_EffectsOfReinsuranceTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_UnrealizedGainLossOnInvestmentsTableTextBlock_6ecd8090-9c30-48ae-8817-51c6234df30e_terseLabel_en-US" xlink:label="lab_us-gaap_UnrealizedGainLossOnInvestmentsTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Unrealized Gain (Loss) on Investments</link:label>
    <link:label id="lab_us-gaap_UnrealizedGainLossOnInvestmentsTableTextBlock_label_en-US" xlink:label="lab_us-gaap_UnrealizedGainLossOnInvestmentsTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unrealized Gain (Loss) on Investments [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_UnrealizedGainLossOnInvestmentsTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_UnrealizedGainLossOnInvestmentsTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_UnrealizedGainLossOnInvestmentsTableTextBlock" xlink:to="lab_us-gaap_UnrealizedGainLossOnInvestmentsTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SummaryOfValuationAllowanceTextBlock_f9dcd833-306e-456e-972c-9dc22f736315_terseLabel_en-US" xlink:label="lab_us-gaap_SummaryOfValuationAllowanceTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Summary of Valuation Allowance</link:label>
    <link:label id="lab_us-gaap_SummaryOfValuationAllowanceTextBlock_label_en-US" xlink:label="lab_us-gaap_SummaryOfValuationAllowanceTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Summary of Valuation Allowance [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SummaryOfValuationAllowanceTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SummaryOfValuationAllowanceTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SummaryOfValuationAllowanceTextBlock" xlink:to="lab_us-gaap_SummaryOfValuationAllowanceTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubordinatedDebt_a2024e4b-1c32-4133-a6e8-f1bcba4f267c_terseLabel_en-US" xlink:label="lab_us-gaap_SubordinatedDebt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subordinated debt, net of debt issuance costs</link:label>
    <link:label id="lab_us-gaap_SubordinatedDebt_label_en-US" xlink:label="lab_us-gaap_SubordinatedDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subordinated Debt</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubordinatedDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SubordinatedDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubordinatedDebt" xlink:to="lab_us-gaap_SubordinatedDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredTaxAssetsTaxDeferredExpenseReservesAndAccrualsLossReserves_3da06a49-2df5-42f8-80c8-052057ecc947_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsTaxDeferredExpenseReservesAndAccrualsLossReserves" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Losses and loss adjustment expenses</link:label>
    <link:label id="lab_us-gaap_DeferredTaxAssetsTaxDeferredExpenseReservesAndAccrualsLossReserves_label_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsTaxDeferredExpenseReservesAndAccrualsLossReserves" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Tax Assets, Tax Deferred Expense, Reserves and Accruals, Loss Reserves</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxAssetsTaxDeferredExpenseReservesAndAccrualsLossReserves" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DeferredTaxAssetsTaxDeferredExpenseReservesAndAccrualsLossReserves"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredTaxAssetsTaxDeferredExpenseReservesAndAccrualsLossReserves" xlink:to="lab_us-gaap_DeferredTaxAssetsTaxDeferredExpenseReservesAndAccrualsLossReserves" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition_186fc06d-f8be-4e73-8df9-571b10e0da0d_totalLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Unrealized Loss Position</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_AmendmentFlag_644c9b49-b1d6-4c9b-b9aa-952e5724f3c6_terseLabel_en-US" xlink:label="lab_dei_AmendmentFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Amendment Flag</link:label>
    <link:label id="lab_dei_AmendmentFlag_label_en-US" xlink:label="lab_dei_AmendmentFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Amendment Flag</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_AmendmentFlag" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_AmendmentFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_AmendmentFlag" xlink:to="lab_dei_AmendmentFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseRemainingLeaseTerm_15da1893-623c-4e1e-9ea1-a101015959ba_terseLabel_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseRemainingLeaseTerm" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Remaining lease term</link:label>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseRemainingLeaseTerm_label_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseRemainingLeaseTerm" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Lessee, Operating Lease, Remaining Lease Term</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeaseRemainingLeaseTerm" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LesseeOperatingLeaseRemainingLeaseTerm"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LesseeOperatingLeaseRemainingLeaseTerm" xlink:to="lab_us-gaap_LesseeOperatingLeaseRemainingLeaseTerm" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetUsefulLife_387f6d51-2f43-42d2-a311-a4e69dde11ac_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetUsefulLife" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Useful life</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetUsefulLife_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetUsefulLife" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Finite-Lived Intangible Asset, Useful Life</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetUsefulLife" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FiniteLivedIntangibleAssetUsefulLife"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetUsefulLife" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetUsefulLife" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentTypeAxis_4e7f905f-58fb-4c9b-85f0-df6be9f8f415_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment Type [Axis]</link:label>
    <link:label id="lab_us-gaap_InvestmentTypeAxis_label_en-US" xlink:label="lab_us-gaap_InvestmentTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_InvestmentTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentTypeAxis" xlink:to="lab_us-gaap_InvestmentTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodFairValue_6b90487d-c3e7-46bd-a0ee-eb4a6c666134_terseLabel_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Shares granted, value</link:label>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodFairValue_label_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Grants in Period, Fair Value</link:label>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodFairValue_documentation_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodFairValue" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Grants in Period, Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodFairValue" xlink:href="skwd-20221231.xsd#skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodFairValue" xlink:to="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ValuationAndQualifyingAccountsAbstract_6b6f6c6a-99b6-4dab-9b35-fb95e7efb268_terseLabel_en-US" xlink:label="lab_srt_ValuationAndQualifyingAccountsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-09, Valuation and Qualifying Accounts [Abstract]</link:label>
    <link:label id="lab_srt_ValuationAndQualifyingAccountsAbstract_label_en-US" xlink:label="lab_srt_ValuationAndQualifyingAccountsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-09, Valuation and Qualifying Accounts [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ValuationAndQualifyingAccountsAbstract" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_ValuationAndQualifyingAccountsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ValuationAndQualifyingAccountsAbstract" xlink:to="lab_srt_ValuationAndQualifyingAccountsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearFive_3fda0c44-459e-483e-90a7-8f9c4e54674d_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearFive" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Year 5</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearFive_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearFive" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Historical Claims Duration, Year Five</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearFive" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearFive"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearFive" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearFive" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillAcquiredDuringPeriod_7c7098c8-12d7-4d23-a03f-8f03d2848b08_terseLabel_en-US" xlink:label="lab_us-gaap_GoodwillAcquiredDuringPeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Additions</link:label>
    <link:label id="lab_us-gaap_GoodwillAcquiredDuringPeriod_label_en-US" xlink:label="lab_us-gaap_GoodwillAcquiredDuringPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Goodwill, Acquired During Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillAcquiredDuringPeriod" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_GoodwillAcquiredDuringPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillAcquiredDuringPeriod" xlink:to="lab_us-gaap_GoodwillAcquiredDuringPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax_c8906d7b-c8fe-416f-a031-75f0e348eee3_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross Unrealized Gains</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Accumulated Gross Unrealized Gain, before Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax" xlink:to="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_HSICMember_2d026578-4bcc-40a4-b16b-512fa6cf005a_terseLabel_en-US" xlink:label="lab_skwd_HSICMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">HSIC</link:label>
    <link:label id="lab_skwd_HSICMember_label_en-US" xlink:label="lab_skwd_HSICMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">HSIC [Member]</link:label>
    <link:label id="lab_skwd_HSICMember_documentation_en-US" xlink:label="lab_skwd_HSICMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">HSIC</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_HSICMember" xlink:href="skwd-20221231.xsd#skwd_HSICMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_HSICMember" xlink:to="lab_skwd_HSICMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ComponentsOfDeferredTaxAssetsAbstract_383202cc-be87-4e81-9bc8-c6423ef81234_terseLabel_en-US" xlink:label="lab_us-gaap_ComponentsOfDeferredTaxAssetsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred tax assets:</link:label>
    <link:label id="lab_us-gaap_ComponentsOfDeferredTaxAssetsAbstract_label_en-US" xlink:label="lab_us-gaap_ComponentsOfDeferredTaxAssetsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Components of Deferred Tax Assets [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ComponentsOfDeferredTaxAssetsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ComponentsOfDeferredTaxAssetsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ComponentsOfDeferredTaxAssetsAbstract" xlink:to="lab_us-gaap_ComponentsOfDeferredTaxAssetsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract_label_en-US" xlink:label="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Goodwill and Intangible Assets Disclosure [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract" xlink:to="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillAndIntangibleAssetsPolicyTextBlock_49faae4e-bbd0-49b6-b4df-d802ce894f23_terseLabel_en-US" xlink:label="lab_us-gaap_GoodwillAndIntangibleAssetsPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Goodwill and Intangible Assets</link:label>
    <link:label id="lab_us-gaap_GoodwillAndIntangibleAssetsPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_GoodwillAndIntangibleAssetsPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Goodwill and Intangible Assets, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillAndIntangibleAssetsPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_GoodwillAndIntangibleAssetsPolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillAndIntangibleAssetsPolicyTextBlock" xlink:to="lab_us-gaap_GoodwillAndIntangibleAssetsPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsurerConcentrationRiskMember_228a2043-43c5-4bdf-82b9-718b3fed3096_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsurerConcentrationRiskMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurer concentration risk</link:label>
    <link:label id="lab_us-gaap_ReinsurerConcentrationRiskMember_label_en-US" xlink:label="lab_us-gaap_ReinsurerConcentrationRiskMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurer Concentration Risk [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsurerConcentrationRiskMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ReinsurerConcentrationRiskMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsurerConcentrationRiskMember" xlink:to="lab_us-gaap_ReinsurerConcentrationRiskMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardPurchasePriceOfCommonStockPercent_31ea2986-38c5-432b-95cd-57bd145c409a_terseLabel_en-US" xlink:label="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardPurchasePriceOfCommonStockPercent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Purchase price of common stock, percent</link:label>
    <link:label id="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardPurchasePriceOfCommonStockPercent_label_en-US" xlink:label="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardPurchasePriceOfCommonStockPercent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Purchase Price of Common Stock, Percent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardPurchasePriceOfCommonStockPercent" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardPurchasePriceOfCommonStockPercent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardPurchasePriceOfCommonStockPercent" xlink:to="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardPurchasePriceOfCommonStockPercent" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract_0c01953f-fce4-452c-bfe7-fbef65e45eeb_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Paid, net of reinsurance, related to:</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Claims Paid [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LineOfCreditFacilityUnusedCapacityCommitmentFeePercentage_1c0484e2-ebf0-44d2-9704-66d9a36a2bb7_terseLabel_en-US" xlink:label="lab_us-gaap_LineOfCreditFacilityUnusedCapacityCommitmentFeePercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unused capacity, commitment fee percentage</link:label>
    <link:label id="lab_us-gaap_LineOfCreditFacilityUnusedCapacityCommitmentFeePercentage_label_en-US" xlink:label="lab_us-gaap_LineOfCreditFacilityUnusedCapacityCommitmentFeePercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Line of Credit Facility, Unused Capacity, Commitment Fee Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LineOfCreditFacilityUnusedCapacityCommitmentFeePercentage" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LineOfCreditFacilityUnusedCapacityCommitmentFeePercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LineOfCreditFacilityUnusedCapacityCommitmentFeePercentage" xlink:to="lab_us-gaap_LineOfCreditFacilityUnusedCapacityCommitmentFeePercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ShortTermInvestmentsAndCashMember_93c4b58d-c5f5-4364-838f-f74643b29d7e_terseLabel_en-US" xlink:label="lab_skwd_ShortTermInvestmentsAndCashMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-term investments and cash</link:label>
    <link:label id="lab_skwd_ShortTermInvestmentsAndCashMember_label_en-US" xlink:label="lab_skwd_ShortTermInvestmentsAndCashMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-term Investments And Cash [Member]</link:label>
    <link:label id="lab_skwd_ShortTermInvestmentsAndCashMember_documentation_en-US" xlink:label="lab_skwd_ShortTermInvestmentsAndCashMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-term Investments And Cash</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ShortTermInvestmentsAndCashMember" xlink:href="skwd-20221231.xsd#skwd_ShortTermInvestmentsAndCashMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ShortTermInvestmentsAndCashMember" xlink:to="lab_skwd_ShortTermInvestmentsAndCashMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_70577bec-51ea-4e5c-ab06-3f3bf28b84f3_verboseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fixed maturity securities, available for sale, at fair value (amortized cost of $662,616 and $452,478, respectively)</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_aaa59bb0-035d-4ddb-9dc3-08b13f864474_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fixed maturity securities, available-for-sale:</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_00709a55-7aa8-4903-9d39-0fa824c90058_totalLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair value total</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Excluding Accrued Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems_7e309913-a751-43fa-97f6-a861b4b951b3_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability for Claims and Claims Adjustment Expense [Line Items]</link:label>
    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems_label_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability for Claims and Claims Adjustment Expense [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems" xlink:to="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsAccidentYear2015Member_3e7d0755-2145-454c-9913-27574dfc7905_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsAccidentYear2015Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accident Year 2015</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsAccidentYear2015Member_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsAccidentYear2015Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Accident Year 2015 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsAccidentYear2015Member" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortdurationInsuranceContractsAccidentYear2015Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsAccidentYear2015Member" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsAccidentYear2015Member" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CounterpartyNameAxis_83d8b35f-ab86-4d0a-9fe5-069323ead0d5_terseLabel_en-US" xlink:label="lab_srt_CounterpartyNameAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Counterparty Name [Axis]</link:label>
    <link:label id="lab_srt_CounterpartyNameAxis_label_en-US" xlink:label="lab_srt_CounterpartyNameAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Counterparty Name [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_CounterpartyNameAxis" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_CounterpartyNameAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_CounterpartyNameAxis" xlink:to="lab_srt_CounterpartyNameAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfRelatedPartyTransactionsTableTextBlock_09d6f5e4-7cdd-413a-9b05-00dd340890b0_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfRelatedPartyTransactionsTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Related Party Transactions</link:label>
    <link:label id="lab_us-gaap_ScheduleOfRelatedPartyTransactionsTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfRelatedPartyTransactionsTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Related Party Transactions [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfRelatedPartyTransactionsTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfRelatedPartyTransactionsTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfRelatedPartyTransactionsTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfRelatedPartyTransactionsTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_MarketConditionAwardsMember_cf05ab25-46ea-4eaa-a5bc-9a3ee4216f2b_terseLabel_en-US" xlink:label="lab_skwd_MarketConditionAwardsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Market condition awards</link:label>
    <link:label id="lab_skwd_MarketConditionAwardsMember_label_en-US" xlink:label="lab_skwd_MarketConditionAwardsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Market Condition Awards [Member]</link:label>
    <link:label id="lab_skwd_MarketConditionAwardsMember_documentation_en-US" xlink:label="lab_skwd_MarketConditionAwardsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Market Condition Awards</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_MarketConditionAwardsMember" xlink:href="skwd-20221231.xsd#skwd_MarketConditionAwardsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_MarketConditionAwardsMember" xlink:to="lab_skwd_MarketConditionAwardsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ShareBasedPaymentArrangementReversalDueToForfeiture_ff7440b1-58bf-4194-9259-7610f3480a2b_terseLabel_en-US" xlink:label="lab_skwd_ShareBasedPaymentArrangementReversalDueToForfeiture" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Forfeitures</link:label>
    <link:label id="lab_skwd_ShareBasedPaymentArrangementReversalDueToForfeiture_label_en-US" xlink:label="lab_skwd_ShareBasedPaymentArrangementReversalDueToForfeiture" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Payment Arrangement, Reversal Due to Forfeiture</link:label>
    <link:label id="lab_skwd_ShareBasedPaymentArrangementReversalDueToForfeiture_documentation_en-US" xlink:label="lab_skwd_ShareBasedPaymentArrangementReversalDueToForfeiture" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Payment Arrangement, Reversal Due to Forfeiture</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ShareBasedPaymentArrangementReversalDueToForfeiture" xlink:href="skwd-20221231.xsd#skwd_ShareBasedPaymentArrangementReversalDueToForfeiture"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ShareBasedPaymentArrangementReversalDueToForfeiture" xlink:to="lab_skwd_ShareBasedPaymentArrangementReversalDueToForfeiture" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredTaxAssetsCapitalLossCarryforwards_796b997e-ac86-4f65-b99b-1abe5f5425ff_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsCapitalLossCarryforwards" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Capital loss carryfoward</link:label>
    <link:label id="lab_us-gaap_DeferredTaxAssetsCapitalLossCarryforwards_label_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsCapitalLossCarryforwards" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Tax Assets, Capital Loss Carryforwards</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxAssetsCapitalLossCarryforwards" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DeferredTaxAssetsCapitalLossCarryforwards"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredTaxAssetsCapitalLossCarryforwards" xlink:to="lab_us-gaap_DeferredTaxAssetsCapitalLossCarryforwards" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill_a0bc4e9f-1d31-46d2-875f-a47141d9e327_terseLabel_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Goodwill and intangible assets, net</link:label>
    <link:label id="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill_label_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Intangible Assets, Net (Including Goodwill)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IntangibleAssetsNetIncludingGoodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:to="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityIncorporationStateCountryCode_51aea3d8-f9c8-434f-948b-b994d5f2de29_terseLabel_en-US" xlink:label="lab_dei_EntityIncorporationStateCountryCode" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Incorporation, State or Country Code</link:label>
    <link:label id="lab_dei_EntityIncorporationStateCountryCode_label_en-US" xlink:label="lab_dei_EntityIncorporationStateCountryCode" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Incorporation, State or Country Code</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityIncorporationStateCountryCode" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityIncorporationStateCountryCode"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityIncorporationStateCountryCode" xlink:to="lab_dei_EntityIncorporationStateCountryCode" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherCommitmentsTableTextBlock_2025aac9-bcd3-47d9-9932-f8865acd0b53_terseLabel_en-US" xlink:label="lab_us-gaap_OtherCommitmentsTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other Commitments</link:label>
    <link:label id="lab_us-gaap_OtherCommitmentsTableTextBlock_label_en-US" xlink:label="lab_us-gaap_OtherCommitmentsTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other Commitments [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherCommitmentsTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OtherCommitmentsTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherCommitmentsTableTextBlock" xlink:to="lab_us-gaap_OtherCommitmentsTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OperatingLeasePayments_bc5492e4-bb1c-4121-bcc5-0f0d2ee1f3d9_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingLeasePayments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Operating cash outflows from operating leases</link:label>
    <link:label id="lab_us-gaap_OperatingLeasePayments_label_en-US" xlink:label="lab_us-gaap_OperatingLeasePayments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Operating Lease, Payments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeasePayments" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OperatingLeasePayments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OperatingLeasePayments" xlink:to="lab_us-gaap_OperatingLeasePayments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReclassificationsOfTemporaryToPermanentEquity_7f047f21-2f3b-4d42-82e2-04ff6ec4b365_terseLabel_en-US" xlink:label="lab_us-gaap_ReclassificationsOfTemporaryToPermanentEquity" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reclassification of temporary equity to stockholders&#8217; equity</link:label>
    <link:label id="lab_us-gaap_ReclassificationsOfTemporaryToPermanentEquity_label_en-US" xlink:label="lab_us-gaap_ReclassificationsOfTemporaryToPermanentEquity" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reclassifications of Temporary to Permanent Equity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReclassificationsOfTemporaryToPermanentEquity" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ReclassificationsOfTemporaryToPermanentEquity"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReclassificationsOfTemporaryToPermanentEquity" xlink:to="lab_us-gaap_ReclassificationsOfTemporaryToPermanentEquity" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TreasuryStockValue_c5bfb86a-5946-4a06-b5ee-1aabf4c1972a_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_TreasuryStockValue" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Treasury stock, $0.01 par value, 233,289 and 229,449 shares, respectively</link:label>
    <link:label id="lab_us-gaap_TreasuryStockValue_label_en-US" xlink:label="lab_us-gaap_TreasuryStockValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Treasury Stock, Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TreasuryStockValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_TreasuryStockValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TreasuryStockValue" xlink:to="lab_us-gaap_TreasuryStockValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatutoryAccountingPracticesStatutoryCapitalAndSurplusBalance_181718eb-6ea7-4c97-be6d-2a448aba8282_terseLabel_en-US" xlink:label="lab_us-gaap_StatutoryAccountingPracticesStatutoryCapitalAndSurplusBalance" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statutory capital and surplus</link:label>
    <link:label id="lab_us-gaap_StatutoryAccountingPracticesStatutoryCapitalAndSurplusBalance_label_en-US" xlink:label="lab_us-gaap_StatutoryAccountingPracticesStatutoryCapitalAndSurplusBalance" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statutory Accounting Practices, Statutory Capital and Surplus, Balance</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatutoryAccountingPracticesStatutoryCapitalAndSurplusBalance" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StatutoryAccountingPracticesStatutoryCapitalAndSurplusBalance"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatutoryAccountingPracticesStatutoryCapitalAndSurplusBalance" xlink:to="lab_us-gaap_StatutoryAccountingPracticesStatutoryCapitalAndSurplusBalance" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_GrossRealizedInvestmentLossesAbstract_dd7d8c6e-04e4-4adf-8be3-f23fa76a941a_terseLabel_en-US" xlink:label="lab_skwd_GrossRealizedInvestmentLossesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross realized losses</link:label>
    <link:label id="lab_skwd_GrossRealizedInvestmentLossesAbstract_label_en-US" xlink:label="lab_skwd_GrossRealizedInvestmentLossesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross Realized Investment Losses [Abstract]</link:label>
    <link:label id="lab_skwd_GrossRealizedInvestmentLossesAbstract_documentation_en-US" xlink:label="lab_skwd_GrossRealizedInvestmentLossesAbstract" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross Realized Investment Losses</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_GrossRealizedInvestmentLossesAbstract" xlink:href="skwd-20221231.xsd#skwd_GrossRealizedInvestmentLossesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_GrossRealizedInvestmentLossesAbstract" xlink:to="lab_skwd_GrossRealizedInvestmentLossesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GeneralLiabilityMember_6ae47268-044a-4dbf-8b70-dc133e3fa8e0_terseLabel_en-US" xlink:label="lab_us-gaap_GeneralLiabilityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">General Liability</link:label>
    <link:label id="lab_us-gaap_GeneralLiabilityMember_label_en-US" xlink:label="lab_us-gaap_GeneralLiabilityMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">General Liability [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GeneralLiabilityMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_GeneralLiabilityMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GeneralLiabilityMember" xlink:to="lab_us-gaap_GeneralLiabilityMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockSharesAuthorized_c18be4d0-9812-40f9-a7d2-232acfe5e877_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockSharesAuthorized" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common stock, shares authorized (in shares)</link:label>
    <link:label id="lab_us-gaap_CommonStockSharesAuthorized_label_en-US" xlink:label="lab_us-gaap_CommonStockSharesAuthorized" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common Stock, Shares Authorized</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockSharesAuthorized" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CommonStockSharesAuthorized"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockSharesAuthorized" xlink:to="lab_us-gaap_CommonStockSharesAuthorized" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommercialPortfolioSegmentMember_24ac4a9c-7743-4111-9dc3-5a5ae285cf90_terseLabel_en-US" xlink:label="lab_us-gaap_CommercialPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Commercial</link:label>
    <link:label id="lab_us-gaap_CommercialPortfolioSegmentMember_label_en-US" xlink:label="lab_us-gaap_CommercialPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Commercial Portfolio Segment [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommercialPortfolioSegmentMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CommercialPortfolioSegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommercialPortfolioSegmentMember" xlink:to="lab_us-gaap_CommercialPortfolioSegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_MaximumMember_9104d87f-7ad5-4bb4-97ae-a33dc0e558c7_terseLabel_en-US" xlink:label="lab_srt_MaximumMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Maximum</link:label>
    <link:label id="lab_srt_MaximumMember_label_en-US" xlink:label="lab_srt_MaximumMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Maximum [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_MaximumMember" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_MaximumMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_MaximumMember" xlink:to="lab_srt_MaximumMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_IncreaseDecreaseInDeferredCedingCommission_54d2fd06-7325-4131-bce1-56916ebd394b_terseLabel_en-US" xlink:label="lab_skwd_IncreaseDecreaseInDeferredCedingCommission" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred ceding commission</link:label>
    <link:label id="lab_skwd_IncreaseDecreaseInDeferredCedingCommission_label_en-US" xlink:label="lab_skwd_IncreaseDecreaseInDeferredCedingCommission" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Increase (Decrease) in Deferred Ceding Commission</link:label>
    <link:label id="lab_skwd_IncreaseDecreaseInDeferredCedingCommission_documentation_en-US" xlink:label="lab_skwd_IncreaseDecreaseInDeferredCedingCommission" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Increase (Decrease) in Deferred Ceding Commission</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_IncreaseDecreaseInDeferredCedingCommission" xlink:href="skwd-20221231.xsd#skwd_IncreaseDecreaseInDeferredCedingCommission"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_IncreaseDecreaseInDeferredCedingCommission" xlink:to="lab_skwd_IncreaseDecreaseInDeferredCedingCommission" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceTable_ac00fdd0-6b79-405e-a8ac-c2f3223b2033_terseLabel_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Effects of Reinsurance [Table]</link:label>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceTable_label_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Effects of Reinsurance [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectsOfReinsuranceTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EffectsOfReinsuranceTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectsOfReinsuranceTable" xlink:to="lab_us-gaap_EffectsOfReinsuranceTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CondensedFinancialInformationOfParentCompanyOnlyDisclosureTextBlock_f4cb0ac2-f5a7-4e31-80a4-9d88f05c332b_terseLabel_en-US" xlink:label="lab_us-gaap_CondensedFinancialInformationOfParentCompanyOnlyDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SCHEDULE II&#160;&#8212; CONDENSED FINANCIAL INFORMATION OF REGISTRANT</link:label>
    <link:label id="lab_us-gaap_CondensedFinancialInformationOfParentCompanyOnlyDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_CondensedFinancialInformationOfParentCompanyOnlyDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Condensed Financial Information of Parent Company Only Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CondensedFinancialInformationOfParentCompanyOnlyDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CondensedFinancialInformationOfParentCompanyOnlyDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CondensedFinancialInformationOfParentCompanyOnlyDisclosureTextBlock" xlink:to="lab_us-gaap_CondensedFinancialInformationOfParentCompanyOnlyDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CashAndCashEquivalentsAtCarryingValue_31e7619b-eef5-4645-9881-08438c2d27fb_terseLabel_en-US" xlink:label="lab_us-gaap_CashAndCashEquivalentsAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash and cash equivalents</link:label>
    <link:label id="lab_us-gaap_CashAndCashEquivalentsAtCarryingValue_label_en-US" xlink:label="lab_us-gaap_CashAndCashEquivalentsAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash and Cash Equivalents, at Carrying Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashAndCashEquivalentsAtCarryingValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CashAndCashEquivalentsAtCarryingValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CashAndCashEquivalentsAtCarryingValue" xlink:to="lab_us-gaap_CashAndCashEquivalentsAtCarryingValue" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CondensedCashFlowStatementTable_3379d22e-89e1-44a2-8827-0dd0c5b203d5_terseLabel_en-US" xlink:label="lab_srt_CondensedCashFlowStatementTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Condensed Cash Flow Statement [Table]</link:label>
    <link:label id="lab_srt_CondensedCashFlowStatementTable_label_en-US" xlink:label="lab_srt_CondensedCashFlowStatementTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Condensed Cash Flow Statement [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_CondensedCashFlowStatementTable" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_CondensedCashFlowStatementTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_CondensedCashFlowStatementTable" xlink:to="lab_srt_CondensedCashFlowStatementTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OperatingLeaseRightOfUseAssetStatementOfFinancialPositionExtensibleList_56236d0c-271e-412d-b317-36aaeb36eca3_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingLeaseRightOfUseAssetStatementOfFinancialPositionExtensibleList" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Operating Lease, Right-of-Use Asset, Statement of Financial Position [Extensible Enumeration]</link:label>
    <link:label id="lab_us-gaap_OperatingLeaseRightOfUseAssetStatementOfFinancialPositionExtensibleList_label_en-US" xlink:label="lab_us-gaap_OperatingLeaseRightOfUseAssetStatementOfFinancialPositionExtensibleList" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Operating Lease, Right-of-Use Asset, Statement of Financial Position [Extensible Enumeration]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseRightOfUseAssetStatementOfFinancialPositionExtensibleList" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OperatingLeaseRightOfUseAssetStatementOfFinancialPositionExtensibleList"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OperatingLeaseRightOfUseAssetStatementOfFinancialPositionExtensibleList" xlink:to="lab_us-gaap_OperatingLeaseRightOfUseAssetStatementOfFinancialPositionExtensibleList" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockholdersEquityNoteDisclosureTextBlock_03e0c537-f141-4225-aef3-3ddf264c66dd_terseLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquityNoteDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stockholders&#8217; Equity</link:label>
    <link:label id="lab_us-gaap_StockholdersEquityNoteDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_StockholdersEquityNoteDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stockholders' Equity Note Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquityNoteDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StockholdersEquityNoteDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockholdersEquityNoteDisclosureTextBlock" xlink:to="lab_us-gaap_StockholdersEquityNoteDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_LineOfCreditFacilityAccordionFeatureIncreaseLimit_f8125cd2-1edd-49cd-a5d3-07c1cb7836cc_terseLabel_en-US" xlink:label="lab_skwd_LineOfCreditFacilityAccordionFeatureIncreaseLimit" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accordion feature, increase limit</link:label>
    <link:label id="lab_skwd_LineOfCreditFacilityAccordionFeatureIncreaseLimit_label_en-US" xlink:label="lab_skwd_LineOfCreditFacilityAccordionFeatureIncreaseLimit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Line of Credit Facility, Accordion Feature, Increase Limit</link:label>
    <link:label id="lab_skwd_LineOfCreditFacilityAccordionFeatureIncreaseLimit_documentation_en-US" xlink:label="lab_skwd_LineOfCreditFacilityAccordionFeatureIncreaseLimit" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Line of Credit Facility, Accordion Feature, Increase Limit</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_LineOfCreditFacilityAccordionFeatureIncreaseLimit" xlink:href="skwd-20221231.xsd#skwd_LineOfCreditFacilityAccordionFeatureIncreaseLimit"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_LineOfCreditFacilityAccordionFeatureIncreaseLimit" xlink:to="lab_skwd_LineOfCreditFacilityAccordionFeatureIncreaseLimit" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_PaymentsToAcquireHeldToMaturitySecuritiesAndEquityMethodInvestments_5eaf3717-917c-4daa-8888-b788e90ac689_negatedTerseLabel_en-US" xlink:label="lab_skwd_PaymentsToAcquireHeldToMaturitySecuritiesAndEquityMethodInvestments" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Purchase of illiquid investments</link:label>
    <link:label id="lab_skwd_PaymentsToAcquireHeldToMaturitySecuritiesAndEquityMethodInvestments_label_en-US" xlink:label="lab_skwd_PaymentsToAcquireHeldToMaturitySecuritiesAndEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Payments to Acquire Held-to-Maturity Securities and Equity Method Investments</link:label>
    <link:label id="lab_skwd_PaymentsToAcquireHeldToMaturitySecuritiesAndEquityMethodInvestments_documentation_en-US" xlink:label="lab_skwd_PaymentsToAcquireHeldToMaturitySecuritiesAndEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Payments to Acquire Held-to-Maturity Securities and Equity Method Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_PaymentsToAcquireHeldToMaturitySecuritiesAndEquityMethodInvestments" xlink:href="skwd-20221231.xsd#skwd_PaymentsToAcquireHeldToMaturitySecuritiesAndEquityMethodInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_PaymentsToAcquireHeldToMaturitySecuritiesAndEquityMethodInvestments" xlink:to="lab_skwd_PaymentsToAcquireHeldToMaturitySecuritiesAndEquityMethodInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_MortgageLoansMember_4a91595b-0381-4228-9bf3-98c12a971325_terseLabel_en-US" xlink:label="lab_skwd_MortgageLoansMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Mortgage loans</link:label>
    <link:label id="lab_skwd_MortgageLoansMember_label_en-US" xlink:label="lab_skwd_MortgageLoansMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Mortgage Loans [Member]</link:label>
    <link:label id="lab_skwd_MortgageLoansMember_documentation_en-US" xlink:label="lab_skwd_MortgageLoansMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Mortgage Loans</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_MortgageLoansMember" xlink:href="skwd-20221231.xsd#skwd_MortgageLoansMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_MortgageLoansMember" xlink:to="lab_skwd_MortgageLoansMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt_a91a7367-d816-4cb7-92d5-11c3484c7763_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Purchase of fixed maturity securities, available for sale</link:label>
    <link:label id="lab_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt_label_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Payments to Acquire Debt Securities, Available-for-Sale</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt" xlink:to="lab_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIndefiniteLivedIntangibleAssets_f116b64d-fff2-4855-a88d-9e66ad900021_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIndefiniteLivedIntangibleAssets" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Purchase price for intangible assets</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIndefiniteLivedIntangibleAssets_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIndefiniteLivedIntangibleAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Indefinite-Lived Intangible Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIndefiniteLivedIntangibleAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIndefiniteLivedIntangibleAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIndefiniteLivedIntangibleAssets" xlink:to="lab_us-gaap_BusinessCombinationRecognizedIdentifiableAssetsAcquiredAndLiabilitiesAssumedIndefiniteLivedIntangibleAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_LegacyProgramsMember_a3058b04-6a37-44dc-acb2-d423e982772b_terseLabel_en-US" xlink:label="lab_skwd_LegacyProgramsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Legacy Programs</link:label>
    <link:label id="lab_skwd_LegacyProgramsMember_label_en-US" xlink:label="lab_skwd_LegacyProgramsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Legacy Programs [Member]</link:label>
    <link:label id="lab_skwd_LegacyProgramsMember_documentation_en-US" xlink:label="lab_skwd_LegacyProgramsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Legacy Programs</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_LegacyProgramsMember" xlink:href="skwd-20221231.xsd#skwd_LegacyProgramsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_LegacyProgramsMember" xlink:to="lab_skwd_LegacyProgramsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAccumulatedLoss_4c88c89d-fa82-4a0d-8084-8293c4ebf108_negatedTotalLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTotalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total</link:label>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAccumulatedLoss_label_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Held-to-Maturity, Unrealized Loss Position, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAccumulatedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAccumulatedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAccumulatedLoss" xlink:to="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAccumulatedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherLongTermInvestments_f521592f-9928-4358-a9ec-04927215c24b_terseLabel_en-US" xlink:label="lab_us-gaap_OtherLongTermInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other long-term investments</link:label>
    <link:label id="lab_us-gaap_OtherLongTermInvestments_label_en-US" xlink:label="lab_us-gaap_OtherLongTermInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other Long-Term Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherLongTermInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OtherLongTermInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherLongTermInvestments" xlink:to="lab_us-gaap_OtherLongTermInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost_b0b854e8-74f9-4046-ba68-84918af69aae_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Without single maturity date</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Maturity, without Single Maturity Date, Amortized Cost</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DeferredTaxAssetsOperatingLossCarryforwardsSubjectToExpirationTaxEffected_9562624e-6678-4f64-8922-491c67c2f1c1_terseLabel_en-US" xlink:label="lab_skwd_DeferredTaxAssetsOperatingLossCarryforwardsSubjectToExpirationTaxEffected" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred tax effected by expiration</link:label>
    <link:label id="lab_skwd_DeferredTaxAssetsOperatingLossCarryforwardsSubjectToExpirationTaxEffected_label_en-US" xlink:label="lab_skwd_DeferredTaxAssetsOperatingLossCarryforwardsSubjectToExpirationTaxEffected" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Tax Assets, Operating Loss Carryforwards, Subject to Expiration, Tax Effected</link:label>
    <link:label id="lab_skwd_DeferredTaxAssetsOperatingLossCarryforwardsSubjectToExpirationTaxEffected_documentation_en-US" xlink:label="lab_skwd_DeferredTaxAssetsOperatingLossCarryforwardsSubjectToExpirationTaxEffected" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Tax Assets, Operating Loss Carryforwards, Subject to Expiration, Tax Effected</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DeferredTaxAssetsOperatingLossCarryforwardsSubjectToExpirationTaxEffected" xlink:href="skwd-20221231.xsd#skwd_DeferredTaxAssetsOperatingLossCarryforwardsSubjectToExpirationTaxEffected"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DeferredTaxAssetsOperatingLossCarryforwardsSubjectToExpirationTaxEffected" xlink:to="lab_skwd_DeferredTaxAssetsOperatingLossCarryforwardsSubjectToExpirationTaxEffected" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_JVMMultiFamilyPremierFundIVLLCMember_cf4878cc-a7ed-4b89-8cce-dac4936cca6c_terseLabel_en-US" xlink:label="lab_skwd_JVMMultiFamilyPremierFundIVLLCMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">JVM Multi-Family Premier Fund IV</link:label>
    <link:label id="lab_skwd_JVMMultiFamilyPremierFundIVLLCMember_label_en-US" xlink:label="lab_skwd_JVMMultiFamilyPremierFundIVLLCMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">JVM Multi-Family Premier Fund IV, LLC [Member]</link:label>
    <link:label id="lab_skwd_JVMMultiFamilyPremierFundIVLLCMember_documentation_en-US" xlink:label="lab_skwd_JVMMultiFamilyPremierFundIVLLCMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">JVM Multi-Family Premier Fund IV, LLC</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_JVMMultiFamilyPremierFundIVLLCMember" xlink:href="skwd-20221231.xsd#skwd_JVMMultiFamilyPremierFundIVLLCMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_JVMMultiFamilyPremierFundIVLLCMember" xlink:to="lab_skwd_JVMMultiFamilyPremierFundIVLLCMember" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_Security12bTitle_eedc2b88-192e-460c-95cc-5f8e1469987f_terseLabel_en-US" xlink:label="lab_dei_Security12bTitle" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Title of 12(b) Security</link:label>
    <link:label id="lab_dei_Security12bTitle_label_en-US" xlink:label="lab_dei_Security12bTitle" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Title of 12(b) Security</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_Security12bTitle" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_Security12bTitle"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_Security12bTitle" xlink:to="lab_dei_Security12bTitle" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatutoryAccountingPracticesTable_6a6a361e-18a4-4a14-a278-340ee9ff3912_terseLabel_en-US" xlink:label="lab_us-gaap_StatutoryAccountingPracticesTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statutory Accounting Practices [Table]</link:label>
    <link:label id="lab_us-gaap_StatutoryAccountingPracticesTable_label_en-US" xlink:label="lab_us-gaap_StatutoryAccountingPracticesTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statutory Accounting Practices [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatutoryAccountingPracticesTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StatutoryAccountingPracticesTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatutoryAccountingPracticesTable" xlink:to="lab_us-gaap_StatutoryAccountingPracticesTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CededCreditRiskAxis_dce51625-f3cf-4f0b-b8d9-d9458af557e3_terseLabel_en-US" xlink:label="lab_us-gaap_CededCreditRiskAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurer, Name [Axis]</link:label>
    <link:label id="lab_us-gaap_CededCreditRiskAxis_label_en-US" xlink:label="lab_us-gaap_CededCreditRiskAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurer, Name [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CededCreditRiskAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CededCreditRiskAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CededCreditRiskAxis" xlink:to="lab_us-gaap_CededCreditRiskAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NotesPayableFairValueDisclosure_e6d6183b-a624-4c5b-ad42-d0ec57b19823_terseLabel_en-US" xlink:label="lab_us-gaap_NotesPayableFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Notes payable</link:label>
    <link:label id="lab_us-gaap_NotesPayableFairValueDisclosure_label_en-US" xlink:label="lab_us-gaap_NotesPayableFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Notes Payable, Fair Value Disclosure</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NotesPayableFairValueDisclosure" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NotesPayableFairValueDisclosure"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NotesPayableFairValueDisclosure" xlink:to="lab_us-gaap_NotesPayableFairValueDisclosure" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_NetUnrealizedLossesAndGainsOnInvestmentsAbstract_eb3fc492-3fca-45ad-8ff7-17dd10b2fde1_terseLabel_en-US" xlink:label="lab_skwd_NetUnrealizedLossesAndGainsOnInvestmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net unrealized (losses) gains on securities still held</link:label>
    <link:label id="lab_skwd_NetUnrealizedLossesAndGainsOnInvestmentsAbstract_label_en-US" xlink:label="lab_skwd_NetUnrealizedLossesAndGainsOnInvestmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net Unrealized Losses and Gains on Investments [Abstract]</link:label>
    <link:label id="lab_skwd_NetUnrealizedLossesAndGainsOnInvestmentsAbstract_documentation_en-US" xlink:label="lab_skwd_NetUnrealizedLossesAndGainsOnInvestmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net Unrealized Losses and Gains on Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_NetUnrealizedLossesAndGainsOnInvestmentsAbstract" xlink:href="skwd-20221231.xsd#skwd_NetUnrealizedLossesAndGainsOnInvestmentsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_NetUnrealizedLossesAndGainsOnInvestmentsAbstract" xlink:to="lab_skwd_NetUnrealizedLossesAndGainsOnInvestmentsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_SellingStockholdersMember_1234cf5e-0562-44d1-a872-213c213a1f13_terseLabel_en-US" xlink:label="lab_skwd_SellingStockholdersMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Selling Stockholders</link:label>
    <link:label id="lab_skwd_SellingStockholdersMember_label_en-US" xlink:label="lab_skwd_SellingStockholdersMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Selling Stockholders [Member]</link:label>
    <link:label id="lab_skwd_SellingStockholdersMember_documentation_en-US" xlink:label="lab_skwd_SellingStockholdersMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Selling Stockholders</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_SellingStockholdersMember" xlink:href="skwd-20221231.xsd#skwd_SellingStockholdersMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_SellingStockholdersMember" xlink:to="lab_skwd_SellingStockholdersMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubsequentEventLineItems_6980b3ef-358c-46a6-8eee-e9b8416e1992_terseLabel_en-US" xlink:label="lab_us-gaap_SubsequentEventLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subsequent Event [Line Items]</link:label>
    <link:label id="lab_us-gaap_SubsequentEventLineItems_label_en-US" xlink:label="lab_us-gaap_SubsequentEventLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subsequent Event [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsequentEventLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SubsequentEventLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsequentEventLineItems" xlink:to="lab_us-gaap_SubsequentEventLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseLossPortfolioTransferPeriodIncreaseDecrease_be7ba4b6-b53a-4850-a634-7e0828f31825_terseLabel_en-US" xlink:label="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseLossPortfolioTransferPeriodIncreaseDecrease" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Strengthening of reserves subject to the LPT</link:label>
    <link:label id="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseLossPortfolioTransferPeriodIncreaseDecrease_40e851d1-a28b-458d-aea5-91e3a7f0f526_negatedLabel_en-US" xlink:label="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseLossPortfolioTransferPeriodIncreaseDecrease" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Strengthening of reserves subject to the LPT</link:label>
    <link:label id="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseLossPortfolioTransferPeriodIncreaseDecrease_label_en-US" xlink:label="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseLossPortfolioTransferPeriodIncreaseDecrease" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability For Unpaid Claims And Claims Adjustment Expense, Loss Portfolio Transfer, Period Increase (Decrease)</link:label>
    <link:label id="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseLossPortfolioTransferPeriodIncreaseDecrease_documentation_en-US" xlink:label="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseLossPortfolioTransferPeriodIncreaseDecrease" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability For Unpaid Claims And Claims Adjustment Expense, Loss Portfolio Transfer, Period Increase (Decrease)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseLossPortfolioTransferPeriodIncreaseDecrease" xlink:href="skwd-20221231.xsd#skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseLossPortfolioTransferPeriodIncreaseDecrease"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseLossPortfolioTransferPeriodIncreaseDecrease" xlink:to="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseLossPortfolioTransferPeriodIncreaseDecrease" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesCarryingAmount_bef9ef54-c69d-4824-aadf-862882a11600_terseLabel_en-US" xlink:label="lab_us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesCarryingAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Amount on Balance Sheet</link:label>
    <link:label id="lab_us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesCarryingAmount_label_en-US" xlink:label="lab_us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesCarryingAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-15, Insurance Companies, Summary of Investments, Other than Investments in Related Parties, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesCarryingAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesCarryingAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesCarryingAmount" xlink:to="lab_us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesCarryingAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_e51d8b80-9449-4faf-af2f-e457b405fd33_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Less than 12 Months</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Continuous Unrealized Loss Position, Less than 12 Months, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain_10eb6b27-2757-4822-a3f7-5ce6d65301ca_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Method Investment, Nonconsolidated Investee [Domain]</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Method Investment, Nonconsolidated Investee [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain" xlink:to="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod_08a4e0ac-378c-4751-8ec7-26d2b130975e_terseLabel_en-US" xlink:label="lab_skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Useful life</link:label>
    <link:label id="lab_skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod_label_en-US" xlink:label="lab_skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Method Investment, Difference in Net Assets, Amortization Period</link:label>
    <link:label id="lab_skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod_documentation_en-US" xlink:label="lab_skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Method Investment, Difference in Net Assets, Amortization Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod" xlink:href="skwd-20221231.xsd#skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod" xlink:to="lab_skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock_69d59fda-dfca-4905-9fc7-560227ba5146_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Intangible Assets and Goodwill</link:label>
    <link:label id="lab_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Intangible Assets and Goodwill [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss_2bde0d6d-8804-4063-9288-d5a0d0c22c08_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">12 Months or More</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Continuous Unrealized Loss Position, 12 Months or Longer, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilitiesAndStockholdersEquityAbstract_234779c0-fcfb-44e9-afb9-bfa01c66d196_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilitiesAndStockholdersEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liabilities and stockholders' equity</link:label>
    <link:label id="lab_us-gaap_LiabilitiesAndStockholdersEquityAbstract_c040f21a-e098-4ae4-94ba-fdc3eeb47b6a_verboseLabel_en-US" xlink:label="lab_us-gaap_LiabilitiesAndStockholdersEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liabilities and Stockholders&#8217; Equity</link:label>
    <link:label id="lab_us-gaap_LiabilitiesAndStockholdersEquityAbstract_label_en-US" xlink:label="lab_us-gaap_LiabilitiesAndStockholdersEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liabilities and Equity [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesAndStockholdersEquityAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilitiesAndStockholdersEquityAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilitiesAndStockholdersEquityAbstract" xlink:to="lab_us-gaap_LiabilitiesAndStockholdersEquityAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EstimateOfFairValueFairValueDisclosureMember_dab8abfd-d9df-4f2c-9c9d-3c19b7e28097_terseLabel_en-US" xlink:label="lab_us-gaap_EstimateOfFairValueFairValueDisclosureMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair&#160; Value</link:label>
    <link:label id="lab_us-gaap_EstimateOfFairValueFairValueDisclosureMember_label_en-US" xlink:label="lab_us-gaap_EstimateOfFairValueFairValueDisclosureMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Estimate of Fair Value Measurement [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EstimateOfFairValueFairValueDisclosureMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EstimateOfFairValueFairValueDisclosureMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EstimateOfFairValueFairValueDisclosureMember" xlink:to="lab_us-gaap_EstimateOfFairValueFairValueDisclosureMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable_a966f273-3758-40f7-911b-65948e88a937_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value, Recurring and Nonrecurring [Table]</link:label>
    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value, Recurring and Nonrecurring [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable" xlink:to="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersUnearnedPremiums_2a3b3b6b-0e29-4dbb-a5d8-64c8182079c4_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersUnearnedPremiums" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unearned premiums</link:label>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersUnearnedPremiums_label_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersUnearnedPremiums" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-18, Supplemental Information, Property-Casualty Insurance Underwriters, Unearned Premium</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersUnearnedPremiums" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersUnearnedPremiums"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersUnearnedPremiums" xlink:to="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersUnearnedPremiums" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense_b823b4ef-329b-4a62-a17d-0b1a515606c3_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Current period</link:label>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Current Year Claims and Claims Adjustment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense" xlink:to="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeOrGroupOfInvesteesMember_f3beb6ea-d49e-4922-a5c0-f85b054a15fc_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeOrGroupOfInvesteesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Method Investment, Nonconsolidated Investee or Group of Investees</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeOrGroupOfInvesteesMember_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeOrGroupOfInvesteesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Method Investment, Nonconsolidated Investee or Group of Investees [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeOrGroupOfInvesteesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeOrGroupOfInvesteesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeOrGroupOfInvesteesMember" xlink:to="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeOrGroupOfInvesteesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_LossOnSaleOfOtherInvestments_717fea24-e991-4514-a766-5ecd63417c29_negatedTerseLabel_en-US" xlink:label="lab_skwd_LossOnSaleOfOtherInvestments" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other</link:label>
    <link:label id="lab_skwd_LossOnSaleOfOtherInvestments_label_en-US" xlink:label="lab_skwd_LossOnSaleOfOtherInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Loss on Sale of Other Investments</link:label>
    <link:label id="lab_skwd_LossOnSaleOfOtherInvestments_documentation_en-US" xlink:label="lab_skwd_LossOnSaleOfOtherInvestments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Loss on Sale of Other Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_LossOnSaleOfOtherInvestments" xlink:href="skwd-20221231.xsd#skwd_LossOnSaleOfOtherInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_LossOnSaleOfOtherInvestments" xlink:to="lab_skwd_LossOnSaleOfOtherInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiCost_3b959c01-291a-4b72-b5eb-e2735a1fec7d_totalLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiCost" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross Amortized Cost</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiCost_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Securities, FV-NI, Cost</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesFvNiCost" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EquitySecuritiesFvNiCost"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesFvNiCost" xlink:to="lab_us-gaap_EquitySecuritiesFvNiCost" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LoansReceivableFairValueDisclosure_b44436bd-8c46-4e5c-bdef-3881c0a84994_terseLabel_en-US" xlink:label="lab_us-gaap_LoansReceivableFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Mortgage loans</link:label>
    <link:label id="lab_us-gaap_LoansReceivableFairValueDisclosure_label_en-US" xlink:label="lab_us-gaap_LoansReceivableFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Loans Receivable, Fair Value Disclosure</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LoansReceivableFairValueDisclosure" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LoansReceivableFairValueDisclosure"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LoansReceivableFairValueDisclosure" xlink:to="lab_us-gaap_LoansReceivableFairValueDisclosure" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic_8a985e38-16a7-41a9-8fe2-c40fa3f96651_terseLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Basic weighted-average common shares (in shares)</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic_label_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Weighted Average Number of Shares Outstanding, Basic</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_WeightedAverageNumberOfSharesOutstandingBasic"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:to="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CashAndSecuritiesSegregatedUnderFederalAndOtherRegulations_617b059f-b63b-4340-8bd6-9ad4675add2f_terseLabel_en-US" xlink:label="lab_us-gaap_CashAndSecuritiesSegregatedUnderFederalAndOtherRegulations" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash and securities segregated under federal and other regulations</link:label>
    <link:label id="lab_us-gaap_CashAndSecuritiesSegregatedUnderFederalAndOtherRegulations_label_en-US" xlink:label="lab_us-gaap_CashAndSecuritiesSegregatedUnderFederalAndOtherRegulations" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash and Securities Segregated under Federal and Other Regulations</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashAndSecuritiesSegregatedUnderFederalAndOtherRegulations" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CashAndSecuritiesSegregatedUnderFederalAndOtherRegulations"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CashAndSecuritiesSegregatedUnderFederalAndOtherRegulations" xlink:to="lab_us-gaap_CashAndSecuritiesSegregatedUnderFederalAndOtherRegulations" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAfterAllowanceForCreditLoss_ed2d0239-5b5b-45c4-b508-96e370c955fb_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAfterAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fixed maturity securities, held-to-maturity</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAfterAllowanceForCreditLoss_efcde16c-5d79-4969-8e87-856bb98f3e19_totalLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAfterAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross Amortized Cost</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAfterAllowanceForCreditLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAfterAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Held-to-Maturity, Excluding Accrued Interest, after Allowance for Credit Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAfterAllowanceForCreditLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAfterAllowanceForCreditLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAfterAllowanceForCreditLoss" xlink:to="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAfterAllowanceForCreditLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityLineItems_305293fc-ba82-4119-afe7-8e44d2ef3c83_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Reconciliation of Claims Development to Liability [Line Items]</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityLineItems_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Reconciliation of Claims Development to Liability [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityLineItems" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinancialServicesSectorMember_5b9122da-73d1-4cab-ac53-af5335aec8b8_terseLabel_en-US" xlink:label="lab_us-gaap_FinancialServicesSectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Finance</link:label>
    <link:label id="lab_us-gaap_FinancialServicesSectorMember_label_en-US" xlink:label="lab_us-gaap_FinancialServicesSectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Financial Services Sector [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancialServicesSectorMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FinancialServicesSectorMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancialServicesSectorMember" xlink:to="lab_us-gaap_FinancialServicesSectorMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LossContingencyAccrualAtCarryingValue_59bfb791-286b-40fb-b110-943c084c7395_terseLabel_en-US" xlink:label="lab_us-gaap_LossContingencyAccrualAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Loss contingency accrual</link:label>
    <link:label id="lab_us-gaap_LossContingencyAccrualAtCarryingValue_label_en-US" xlink:label="lab_us-gaap_LossContingencyAccrualAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Loss Contingency Accrual</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LossContingencyAccrualAtCarryingValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LossContingencyAccrualAtCarryingValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LossContingencyAccrualAtCarryingValue" xlink:to="lab_us-gaap_LossContingencyAccrualAtCarryingValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense_109981dc-573a-46b4-930d-4fd96fec9a4f_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Prior years</link:label>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense_82dd02f7-812d-42a9-bcee-60d8348ca8bd_verboseLabel_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Prior year claims incurred, unfavorable (favorable) development</link:label>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Prior Year Claims and Claims Adjustment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:to="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset_4e8d09da-bb55-4bdc-8070-3afbbb450a06_terseLabel_en-US" xlink:label="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Market value of trust funds</link:label>
    <link:label id="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset_label_en-US" xlink:label="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Funds Held under Reinsurance Agreements, Asset</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FundsHeldUnderReinsuranceAgreementsAsset"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset" xlink:to="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage_45669aad-2ce8-4688-852e-c65cb16f8e52_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity method investments ownership percentage</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Method Investment, Ownership Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EquityMethodInvestmentOwnershipPercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:to="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CondensedBalanceSheetStatementsCaptionsLineItems_c875fdd3-e9f0-4a20-ba3a-92fc1022825c_terseLabel_en-US" xlink:label="lab_srt_CondensedBalanceSheetStatementsCaptionsLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Condensed Balance Sheet Statements, Captions [Line Items]</link:label>
    <link:label id="lab_srt_CondensedBalanceSheetStatementsCaptionsLineItems_label_en-US" xlink:label="lab_srt_CondensedBalanceSheetStatementsCaptionsLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Condensed Balance Sheet Statements, Captions [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_CondensedBalanceSheetStatementsCaptionsLineItems" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_CondensedBalanceSheetStatementsCaptionsLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_CondensedBalanceSheetStatementsCaptionsLineItems" xlink:to="lab_srt_CondensedBalanceSheetStatementsCaptionsLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GainLossOnDispositionOfAssets1_14a3c36a-672d-42a9-b76f-ade130121b61_terseLabel_en-US" xlink:label="lab_us-gaap_GainLossOnDispositionOfAssets1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gain on disposition of assets</link:label>
    <link:label id="lab_us-gaap_GainLossOnDispositionOfAssets1_label_en-US" xlink:label="lab_us-gaap_GainLossOnDispositionOfAssets1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gain (Loss) on Disposition of Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GainLossOnDispositionOfAssets1" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_GainLossOnDispositionOfAssets1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GainLossOnDispositionOfAssets1" xlink:to="lab_us-gaap_GainLossOnDispositionOfAssets1" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_TotalIntangibleAssetsRollForward_d167c5ed-71d2-41f9-85e2-73cd70f8fc7b_terseLabel_en-US" xlink:label="lab_skwd_TotalIntangibleAssetsRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total</link:label>
    <link:label id="lab_skwd_TotalIntangibleAssetsRollForward_label_en-US" xlink:label="lab_skwd_TotalIntangibleAssetsRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total Intangible Assets [Roll Forward]</link:label>
    <link:label id="lab_skwd_TotalIntangibleAssetsRollForward_documentation_en-US" xlink:label="lab_skwd_TotalIntangibleAssetsRollForward" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total Intangible Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_TotalIntangibleAssetsRollForward" xlink:href="skwd-20221231.xsd#skwd_TotalIntangibleAssetsRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_TotalIntangibleAssetsRollForward" xlink:to="lab_skwd_TotalIntangibleAssetsRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PreferredStockValue_9e9d5681-a2a6-43f2-a7b7-a60acc4a0820_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Series A preferred stock, $0.01 par value; 2,000,000 shares authorized, 1,969,660 and 1,970,124 shares issued and outstanding, respectively</link:label>
    <link:label id="lab_us-gaap_PreferredStockValue_label_en-US" xlink:label="lab_us-gaap_PreferredStockValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred Stock, Value, Issued</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PreferredStockValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PreferredStockValue" xlink:to="lab_us-gaap_PreferredStockValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentLineItems_2247c3a2-5a0f-4b9f-93d1-3fb9ef74c3ed_terseLabel_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Property, Plant and Equipment [Line Items]</link:label>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentLineItems_label_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Property, Plant and Equipment [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PropertyPlantAndEquipmentLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentLineItems" xlink:to="lab_us-gaap_PropertyPlantAndEquipmentLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfDebtTableTextBlock_435309e3-9aac-431c-a4af-4b2551995cae_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfDebtTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Summary of Notes Payable</link:label>
    <link:label id="lab_us-gaap_ScheduleOfDebtTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfDebtTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Debt [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfDebtTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfDebtTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfDebtTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfDebtTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityWellKnownSeasonedIssuer_a7aa2092-ea56-49b0-9fde-7dfc0424e5f6_terseLabel_en-US" xlink:label="lab_dei_EntityWellKnownSeasonedIssuer" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Well-known Seasoned Issuer</link:label>
    <link:label id="lab_dei_EntityWellKnownSeasonedIssuer_label_en-US" xlink:label="lab_dei_EntityWellKnownSeasonedIssuer" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Well-known Seasoned Issuer</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityWellKnownSeasonedIssuer" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityWellKnownSeasonedIssuer"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityWellKnownSeasonedIssuer" xlink:to="lab_dei_EntityWellKnownSeasonedIssuer" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsAccidentYear2013Member_7ee33cda-d1c4-477a-9d83-55ea7a50077b_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsAccidentYear2013Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accident Year 2013</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsAccidentYear2013Member_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsAccidentYear2013Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Accident Year 2013 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsAccidentYear2013Member" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortdurationInsuranceContractsAccidentYear2013Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsAccidentYear2013Member" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsAccidentYear2013Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentTable_c08d557a-bfa1-4854-ae17-906e0983dfb0_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Long-Term Debt Instruments [Table]</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentTable_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Long-Term Debt Instruments [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtInstrumentTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentTable" xlink:to="lab_us-gaap_DebtInstrumentTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LesseeLeasesPolicyTextBlock_af9b5e87-b65a-4599-88f8-ccd7dfbad0f4_terseLabel_en-US" xlink:label="lab_us-gaap_LesseeLeasesPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Leases</link:label>
    <link:label id="lab_us-gaap_LesseeLeasesPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_LesseeLeasesPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Lessee, Leases [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeLeasesPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LesseeLeasesPolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LesseeLeasesPolicyTextBlock" xlink:to="lab_us-gaap_LesseeLeasesPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtInstrumentFixedRatePeriodAxis_91bbcd60-f490-4067-993e-75cc364debcc_terseLabel_en-US" xlink:label="lab_skwd_DebtInstrumentFixedRatePeriodAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Interest Rage Range [Axis]</link:label>
    <link:label id="lab_skwd_DebtInstrumentFixedRatePeriodAxis_label_en-US" xlink:label="lab_skwd_DebtInstrumentFixedRatePeriodAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Fixed Rate, Period [Axis]</link:label>
    <link:label id="lab_skwd_DebtInstrumentFixedRatePeriodAxis_documentation_en-US" xlink:label="lab_skwd_DebtInstrumentFixedRatePeriodAxis" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Fixed Rate, Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtInstrumentFixedRatePeriodAxis" xlink:href="skwd-20221231.xsd#skwd_DebtInstrumentFixedRatePeriodAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtInstrumentFixedRatePeriodAxis" xlink:to="lab_skwd_DebtInstrumentFixedRatePeriodAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OperatingLeaseLiabilityStatementOfFinancialPositionExtensibleList_c4385dca-6067-4b1a-ac8f-ed07b16ec8d1_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingLeaseLiabilityStatementOfFinancialPositionExtensibleList" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Operating lease, liability, statement of financial position</link:label>
    <link:label id="lab_us-gaap_OperatingLeaseLiabilityStatementOfFinancialPositionExtensibleList_label_en-US" xlink:label="lab_us-gaap_OperatingLeaseLiabilityStatementOfFinancialPositionExtensibleList" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Operating Lease, Liability, Statement of Financial Position [Extensible Enumeration]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseLiabilityStatementOfFinancialPositionExtensibleList" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OperatingLeaseLiabilityStatementOfFinancialPositionExtensibleList"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OperatingLeaseLiabilityStatementOfFinancialPositionExtensibleList" xlink:to="lab_us-gaap_OperatingLeaseLiabilityStatementOfFinancialPositionExtensibleList" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueInputsLevel3Member_540ab2d0-5c16-4abd-a327-753c58df394d_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel3Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value, Inputs, Level 3</link:label>
    <link:label id="lab_us-gaap_FairValueInputsLevel3Member_label_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel3Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value, Inputs, Level 3 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueInputsLevel3Member" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FairValueInputsLevel3Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueInputsLevel3Member" xlink:to="lab_us-gaap_FairValueInputsLevel3Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments_cf41f011-ce03-4b4a-bea9-28f055e7a692_verboseLabel_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Loss before income tax expense</link:label>
    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments_label_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Income (Loss) from Continuing Operations before Equity Method Investments, Income Taxes, Noncontrolling Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments" xlink:to="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock_27104ae2-e8f2-4f11-9ceb-2093a3b2a5b8_terseLabel_en-US" xlink:label="lab_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stock Based Compensation</link:label>
    <link:label id="lab_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock_label_en-US" xlink:label="lab_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Payment Arrangement [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock" xlink:to="lab_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ExcessLiabilityMember_5f1edd3a-2db1-443a-8600-edc91d22b026_terseLabel_en-US" xlink:label="lab_skwd_ExcessLiabilityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Excess Liability</link:label>
    <link:label id="lab_skwd_ExcessLiabilityMember_label_en-US" xlink:label="lab_skwd_ExcessLiabilityMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Excess Liability [Member]</link:label>
    <link:label id="lab_skwd_ExcessLiabilityMember_documentation_en-US" xlink:label="lab_skwd_ExcessLiabilityMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Excess Liability</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ExcessLiabilityMember" xlink:href="skwd-20221231.xsd#skwd_ExcessLiabilityMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ExcessLiabilityMember" xlink:to="lab_skwd_ExcessLiabilityMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesFairValue_db7f68cf-4e14-454b-891e-5b9d96e88bb7_terseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fixed maturity securities, held-to-maturity:</link:label>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesFairValue_label_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Held-to-Maturity, Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_HeldToMaturitySecuritiesFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HeldToMaturitySecuritiesFairValue" xlink:to="lab_us-gaap_HeldToMaturitySecuritiesFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncrementalCommonSharesAttributableToConversionOfPreferredStock_ce30ab18-818f-4e83-b62a-96a0ac2052e6_terseLabel_en-US" xlink:label="lab_us-gaap_IncrementalCommonSharesAttributableToConversionOfPreferredStock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred shares (if converted method) (in shares)</link:label>
    <link:label id="lab_us-gaap_IncrementalCommonSharesAttributableToConversionOfPreferredStock_label_en-US" xlink:label="lab_us-gaap_IncrementalCommonSharesAttributableToConversionOfPreferredStock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Incremental Common Shares Attributable to Dilutive Effect of Conversion of Preferred Stock</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncrementalCommonSharesAttributableToConversionOfPreferredStock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncrementalCommonSharesAttributableToConversionOfPreferredStock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncrementalCommonSharesAttributableToConversionOfPreferredStock" xlink:to="lab_us-gaap_IncrementalCommonSharesAttributableToConversionOfPreferredStock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_SuretyMember_8527aa37-65c2-4cf9-9c74-920f5c046032_terseLabel_en-US" xlink:label="lab_skwd_SuretyMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Surety</link:label>
    <link:label id="lab_skwd_SuretyMember_label_en-US" xlink:label="lab_skwd_SuretyMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Surety [Member]</link:label>
    <link:label id="lab_skwd_SuretyMember_documentation_en-US" xlink:label="lab_skwd_SuretyMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Surety</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_SuretyMember" xlink:href="skwd-20221231.xsd#skwd_SuretyMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_SuretyMember" xlink:to="lab_skwd_SuretyMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_AgentRelationshipMember_5382b020-1551-4743-b2e5-04b5fc527f8e_terseLabel_en-US" xlink:label="lab_skwd_AgentRelationshipMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Agent Relationships</link:label>
    <link:label id="lab_skwd_AgentRelationshipMember_label_en-US" xlink:label="lab_skwd_AgentRelationshipMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Agent Relationship [Member]</link:label>
    <link:label id="lab_skwd_AgentRelationshipMember_documentation_en-US" xlink:label="lab_skwd_AgentRelationshipMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Agent Relationship</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_AgentRelationshipMember" xlink:href="skwd-20221231.xsd#skwd_AgentRelationshipMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_AgentRelationshipMember" xlink:to="lab_skwd_AgentRelationshipMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PreferredStockRedemptionPricePerShare_18ec2e5c-145a-4841-83e7-9e9bfc4103f2_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockRedemptionPricePerShare" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred stock, redemption price (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_PreferredStockRedemptionPricePerShare_label_en-US" xlink:label="lab_us-gaap_PreferredStockRedemptionPricePerShare" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred Stock, Redemption Price Per Share</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockRedemptionPricePerShare" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PreferredStockRedemptionPricePerShare"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PreferredStockRedemptionPricePerShare" xlink:to="lab_us-gaap_PreferredStockRedemptionPricePerShare" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumsWrittenNet_63857f58-c350-4631-861c-ee6cc54fd0a3_totalLabel_en-US" xlink:label="lab_us-gaap_PremiumsWrittenNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net premiums</link:label>
    <link:label id="lab_us-gaap_PremiumsWrittenNet_label_en-US" xlink:label="lab_us-gaap_PremiumsWrittenNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Premiums Written, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsWrittenNet" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PremiumsWrittenNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsWrittenNet" xlink:to="lab_us-gaap_PremiumsWrittenNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillWrittenOffRelatedToSaleOfBusinessUnit_fd894ec7-76de-4cf5-b3af-33f34c964e38_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_GoodwillWrittenOffRelatedToSaleOfBusinessUnit" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Disposals</link:label>
    <link:label id="lab_us-gaap_GoodwillWrittenOffRelatedToSaleOfBusinessUnit_label_en-US" xlink:label="lab_us-gaap_GoodwillWrittenOffRelatedToSaleOfBusinessUnit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Goodwill, Written off Related to Sale of Business Unit</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillWrittenOffRelatedToSaleOfBusinessUnit" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_GoodwillWrittenOffRelatedToSaleOfBusinessUnit"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillWrittenOffRelatedToSaleOfBusinessUnit" xlink:to="lab_us-gaap_GoodwillWrittenOffRelatedToSaleOfBusinessUnit" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentPeriodicPaymentInterest_c575ed89-926a-4426-bdc0-61c80aa1b5bd_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentPeriodicPaymentInterest" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Interest payments on term loan</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentPeriodicPaymentInterest_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentPeriodicPaymentInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Periodic Payment, Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentPeriodicPaymentInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtInstrumentPeriodicPaymentInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentPeriodicPaymentInterest" xlink:to="lab_us-gaap_DebtInstrumentPeriodicPaymentInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfDeferredTaxAssetsAndLiabilitiesTableTextBlock_a68d57fa-ad3f-4c0b-81d3-22d63b98e62a_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfDeferredTaxAssetsAndLiabilitiesTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Deferred Tax Assets and Liabilities</link:label>
    <link:label id="lab_us-gaap_ScheduleOfDeferredTaxAssetsAndLiabilitiesTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfDeferredTaxAssetsAndLiabilitiesTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Deferred Tax Assets and Liabilities [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfDeferredTaxAssetsAndLiabilitiesTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfDeferredTaxAssetsAndLiabilitiesTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfDeferredTaxAssetsAndLiabilitiesTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfDeferredTaxAssetsAndLiabilitiesTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RelatedPartyTransactionsByRelatedPartyAxis_8957e12f-604b-4e7c-ab04-20f214a0b3e9_terseLabel_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionsByRelatedPartyAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Related Party [Axis]</link:label>
    <link:label id="lab_us-gaap_RelatedPartyTransactionsByRelatedPartyAxis_label_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionsByRelatedPartyAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Related Party [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RelatedPartyTransactionsByRelatedPartyAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RelatedPartyTransactionsByRelatedPartyAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RelatedPartyTransactionsByRelatedPartyAxis" xlink:to="lab_us-gaap_RelatedPartyTransactionsByRelatedPartyAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillRollForward_20ed6839-ad90-4880-a273-632024c201bf_terseLabel_en-US" xlink:label="lab_us-gaap_GoodwillRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Goodwill [Roll Forward]</link:label>
    <link:label id="lab_us-gaap_GoodwillRollForward_label_en-US" xlink:label="lab_us-gaap_GoodwillRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Goodwill [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_GoodwillRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillRollForward" xlink:to="lab_us-gaap_GoodwillRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements_cc5227b7-02bb-464c-ad84-34a2b59f2f3b_terseLabel_en-US" xlink:label="lab_us-gaap_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restricted stock units (treasury stock method) (in shares)</link:label>
    <link:label id="lab_us-gaap_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements_label_en-US" xlink:label="lab_us-gaap_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Incremental Common Shares Attributable to Dilutive Effect of Share-Based Payment Arrangements</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements" xlink:to="lab_us-gaap_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ValuationAllowancesAndReservesTypeAxis_cd2a3a86-4e9f-47c9-87ac-ad4a4b3bedd9_terseLabel_en-US" xlink:label="lab_us-gaap_ValuationAllowancesAndReservesTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-09, Valuation Allowances and Reserves Type [Axis]</link:label>
    <link:label id="lab_us-gaap_ValuationAllowancesAndReservesTypeAxis_label_en-US" xlink:label="lab_us-gaap_ValuationAllowancesAndReservesTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-09, Valuation Allowances and Reserves Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ValuationAllowancesAndReservesTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ValuationAllowancesAndReservesTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ValuationAllowancesAndReservesTypeAxis" xlink:to="lab_us-gaap_ValuationAllowancesAndReservesTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OrganizationConsolidationAndPresentationOfFinancialStatementsAbstract_label_en-US" xlink:label="lab_us-gaap_OrganizationConsolidationAndPresentationOfFinancialStatementsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Organization, Consolidation and Presentation of Financial Statements [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OrganizationConsolidationAndPresentationOfFinancialStatementsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OrganizationConsolidationAndPresentationOfFinancialStatementsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OrganizationConsolidationAndPresentationOfFinancialStatementsAbstract" xlink:to="lab_us-gaap_OrganizationConsolidationAndPresentationOfFinancialStatementsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisposalGroupsIncludingDiscontinuedOperationsNameDomain_10306d75-81ba-4a59-99ad-e941b390cca6_terseLabel_en-US" xlink:label="lab_us-gaap_DisposalGroupsIncludingDiscontinuedOperationsNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Disposal Group Name [Domain]</link:label>
    <link:label id="lab_us-gaap_DisposalGroupsIncludingDiscontinuedOperationsNameDomain_label_en-US" xlink:label="lab_us-gaap_DisposalGroupsIncludingDiscontinuedOperationsNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Disposal Group Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisposalGroupsIncludingDiscontinuedOperationsNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DisposalGroupsIncludingDiscontinuedOperationsNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisposalGroupsIncludingDiscontinuedOperationsNameDomain" xlink:to="lab_us-gaap_DisposalGroupsIncludingDiscontinuedOperationsNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueInputsLevel2Member_1e618f37-b4a3-4672-a791-335b8df9866f_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel2Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value, Inputs, Level 2</link:label>
    <link:label id="lab_us-gaap_FairValueInputsLevel2Member_label_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel2Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value, Inputs, Level 2 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueInputsLevel2Member" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FairValueInputsLevel2Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueInputsLevel2Member" xlink:to="lab_us-gaap_FairValueInputsLevel2Member" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_CurrentFiscalYearEndDate_2eabca5c-c44e-4bf1-86e4-87a729a0fea8_terseLabel_en-US" xlink:label="lab_dei_CurrentFiscalYearEndDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Current Fiscal Year End Date</link:label>
    <link:label id="lab_dei_CurrentFiscalYearEndDate_label_en-US" xlink:label="lab_dei_CurrentFiscalYearEndDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Current Fiscal Year End Date</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_CurrentFiscalYearEndDate" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_CurrentFiscalYearEndDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_CurrentFiscalYearEndDate" xlink:to="lab_dei_CurrentFiscalYearEndDate" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PropertyLiabilityAndCasualtyInsuranceSegmentMember_836004f1-d7c3-492c-8286-3416f577d2e0_terseLabel_en-US" xlink:label="lab_us-gaap_PropertyLiabilityAndCasualtyInsuranceSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Property &amp; Casualty</link:label>
    <link:label id="lab_us-gaap_PropertyLiabilityAndCasualtyInsuranceSegmentMember_label_en-US" xlink:label="lab_us-gaap_PropertyLiabilityAndCasualtyInsuranceSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Property, Liability and Casualty Insurance Product Line [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyLiabilityAndCasualtyInsuranceSegmentMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PropertyLiabilityAndCasualtyInsuranceSegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PropertyLiabilityAndCasualtyInsuranceSegmentMember" xlink:to="lab_us-gaap_PropertyLiabilityAndCasualtyInsuranceSegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_RelatedPartyOwnershipInterest_e35bb8c7-18a8-43f8-9bf1-5fe9b11b97e6_terseLabel_en-US" xlink:label="lab_skwd_RelatedPartyOwnershipInterest" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Agreement, ownership interest</link:label>
    <link:label id="lab_skwd_RelatedPartyOwnershipInterest_label_en-US" xlink:label="lab_skwd_RelatedPartyOwnershipInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Related Party, Ownership Interest</link:label>
    <link:label id="lab_skwd_RelatedPartyOwnershipInterest_documentation_en-US" xlink:label="lab_skwd_RelatedPartyOwnershipInterest" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Related Party, Ownership Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RelatedPartyOwnershipInterest" xlink:href="skwd-20221231.xsd#skwd_RelatedPartyOwnershipInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_RelatedPartyOwnershipInterest" xlink:to="lab_skwd_RelatedPartyOwnershipInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IntangibleAssetsNetExcludingGoodwill_b25eaa09-77ae-4ea8-921c-37bc1fc129db_periodEndLabel_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross intangible assets, ending balance</link:label>
    <link:label id="lab_us-gaap_IntangibleAssetsNetExcludingGoodwill_label_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Intangible Assets, Net (Excluding Goodwill)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IntangibleAssetsNetExcludingGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IntangibleAssetsNetExcludingGoodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IntangibleAssetsNetExcludingGoodwill" xlink:to="lab_us-gaap_IntangibleAssetsNetExcludingGoodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsLineItems_72094dee-7757-44de-b0cd-c89dbc072b3d_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Finite-Lived Intangible Assets [Line Items]</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsLineItems_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Finite-Lived Intangible Assets [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FiniteLivedIntangibleAssetsLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsLineItems" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockholdersEquityNoteStockSplitConversionRatio1_2c60747d-7ac6-4b94-819c-878634544939_terseLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquityNoteStockSplitConversionRatio1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity conversion ratio</link:label>
    <link:label id="lab_us-gaap_StockholdersEquityNoteStockSplitConversionRatio1_label_en-US" xlink:label="lab_us-gaap_StockholdersEquityNoteStockSplitConversionRatio1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stockholders' Equity Note, Stock Split, Conversion Ratio</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquityNoteStockSplitConversionRatio1" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StockholdersEquityNoteStockSplitConversionRatio1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockholdersEquityNoteStockSplitConversionRatio1" xlink:to="lab_us-gaap_StockholdersEquityNoteStockSplitConversionRatio1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConcentrationRiskByTypeAxis_4a289344-7622-42e7-b69c-333c85216511_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskByTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Concentration Risk Type [Axis]</link:label>
    <link:label id="lab_us-gaap_ConcentrationRiskByTypeAxis_label_en-US" xlink:label="lab_us-gaap_ConcentrationRiskByTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Concentration Risk Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConcentrationRiskByTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ConcentrationRiskByTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConcentrationRiskByTypeAxis" xlink:to="lab_us-gaap_ConcentrationRiskByTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfOtherInvestments_fcfbb235-8962-4939-9a32-2e1642db6902_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfOtherInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Sale of other invested asset</link:label>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfOtherInvestments_label_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfOtherInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Proceeds from Sale of Other Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromSaleOfOtherInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ProceedsFromSaleOfOtherInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromSaleOfOtherInvestments" xlink:to="lab_us-gaap_ProceedsFromSaleOfOtherInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_RealizedInvestmentLosses_91c1d156-c46e-4614-b657-1f76ac88c0c2_negatedTotalLabel_en-US" xlink:label="lab_skwd_RealizedInvestmentLosses" xlink:role="http://www.xbrl.org/2009/role/negatedTotalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total</link:label>
    <link:label id="lab_skwd_RealizedInvestmentLosses_label_en-US" xlink:label="lab_skwd_RealizedInvestmentLosses" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Realized Investment Losses</link:label>
    <link:label id="lab_skwd_RealizedInvestmentLosses_documentation_en-US" xlink:label="lab_skwd_RealizedInvestmentLosses" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Realized Investment Losses</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RealizedInvestmentLosses" xlink:href="skwd-20221231.xsd#skwd_RealizedInvestmentLosses"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_RealizedInvestmentLosses" xlink:to="lab_skwd_RealizedInvestmentLosses" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReportingUnitDomain_57ad9bc7-a68c-4228-85e0-a3f333eebf1c_terseLabel_en-US" xlink:label="lab_us-gaap_ReportingUnitDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reporting Unit [Domain]</link:label>
    <link:label id="lab_us-gaap_ReportingUnitDomain_label_en-US" xlink:label="lab_us-gaap_ReportingUnitDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reporting Unit [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReportingUnitDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ReportingUnitDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReportingUnitDomain" xlink:to="lab_us-gaap_ReportingUnitDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtInstrumentFixedInterestRatePeriodTwoMember_2c8d9708-e86b-4232-ac7e-a6b8b509cc0e_terseLabel_en-US" xlink:label="lab_skwd_DebtInstrumentFixedInterestRatePeriodTwoMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Interest Rate, After Year 8</link:label>
    <link:label id="lab_skwd_DebtInstrumentFixedInterestRatePeriodTwoMember_label_en-US" xlink:label="lab_skwd_DebtInstrumentFixedInterestRatePeriodTwoMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Fixed Interest Rate, Period Two [Member]</link:label>
    <link:label id="lab_skwd_DebtInstrumentFixedInterestRatePeriodTwoMember_documentation_en-US" xlink:label="lab_skwd_DebtInstrumentFixedInterestRatePeriodTwoMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Fixed Interest Rate, Period Two</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtInstrumentFixedInterestRatePeriodTwoMember" xlink:href="skwd-20221231.xsd#skwd_DebtInstrumentFixedInterestRatePeriodTwoMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtInstrumentFixedInterestRatePeriodTwoMember" xlink:to="lab_skwd_DebtInstrumentFixedInterestRatePeriodTwoMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTextBlock_4b9ebf40-eb70-498f-b593-412bd9dc7570_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Accounts, Notes, Loans and Financing Receivable</link:label>
    <link:label id="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Accounts, Notes, Loans and Financing Receivable [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTextBlock" xlink:to="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_EquitySecuritiesFVNIAccumulatedUnrealizedLoss_29a99ab9-6793-413f-9939-aaf7b96e57a3_negatedTerseLabel_en-US" xlink:label="lab_skwd_EquitySecuritiesFVNIAccumulatedUnrealizedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross Unrealized Losses</link:label>
    <link:label id="lab_skwd_EquitySecuritiesFVNIAccumulatedUnrealizedLoss_label_en-US" xlink:label="lab_skwd_EquitySecuritiesFVNIAccumulatedUnrealizedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Securities, FV-NI, Accumulated Unrealized Loss</link:label>
    <link:label id="lab_skwd_EquitySecuritiesFVNIAccumulatedUnrealizedLoss_documentation_en-US" xlink:label="lab_skwd_EquitySecuritiesFVNIAccumulatedUnrealizedLoss" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Securities, FV-NI, Accumulated Unrealized Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_EquitySecuritiesFVNIAccumulatedUnrealizedLoss" xlink:href="skwd-20221231.xsd#skwd_EquitySecuritiesFVNIAccumulatedUnrealizedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_EquitySecuritiesFVNIAccumulatedUnrealizedLoss" xlink:to="lab_skwd_EquitySecuritiesFVNIAccumulatedUnrealizedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_d00910c2-35a3-469d-9a9f-6111b0ea106b_periodStartLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reserves for losses and LAE, beginning of period, net of reinsurance</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_32009765-5d39-4f4f-8b97-5a5e1d415ce4_periodEndLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net reserves for losses and LAE, end of period</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityExTransitionPeriod_6d0c1045-38ee-48a7-a93c-320b3b253d97_terseLabel_en-US" xlink:label="lab_dei_EntityExTransitionPeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Ex Transition Period</link:label>
    <link:label id="lab_dei_EntityExTransitionPeriod_label_en-US" xlink:label="lab_dei_EntityExTransitionPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Ex Transition Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityExTransitionPeriod" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityExTransitionPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityExTransitionPeriod" xlink:to="lab_dei_EntityExTransitionPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredTaxAssetsOperatingLossCarryforwardsSubjectToExpiration_3c8efe2d-2960-470f-9f2c-0d4c3d7cb221_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsOperatingLossCarryforwardsSubjectToExpiration" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred tax subject to expiration</link:label>
    <link:label id="lab_us-gaap_DeferredTaxAssetsOperatingLossCarryforwardsSubjectToExpiration_label_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsOperatingLossCarryforwardsSubjectToExpiration" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Tax Assets, Operating Loss Carryforwards, Subject to Expiration</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxAssetsOperatingLossCarryforwardsSubjectToExpiration" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DeferredTaxAssetsOperatingLossCarryforwardsSubjectToExpiration"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredTaxAssetsOperatingLossCarryforwardsSubjectToExpiration" xlink:to="lab_us-gaap_DeferredTaxAssetsOperatingLossCarryforwardsSubjectToExpiration" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGainLoss_5da9a291-f5c1-4307-ba77-3a2acd414254_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGainLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unrealized losses on investment in Westaim</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGainLoss_a8358fb7-2000-44a5-8564-0a06a80aa55c_verboseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGainLoss" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity securities</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGainLoss_d47b38f3-3d99-46b5-bedd-7b9e4aa5ab94_terseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGainLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unrealized losses on investment in Westaim</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGainLoss_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGainLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Securities, FV-NI, Unrealized Gain (Loss)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesFvNiUnrealizedGainLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EquitySecuritiesFvNiUnrealizedGainLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesFvNiUnrealizedGainLoss" xlink:to="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGainLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_FixedMaturitiesAvailableForSaleMember_074cc481-98af-4d57-9091-8063063093bf_terseLabel_en-US" xlink:label="lab_skwd_FixedMaturitiesAvailableForSaleMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fixed maturity securities, available for sale:</link:label>
    <link:label id="lab_skwd_FixedMaturitiesAvailableForSaleMember_label_en-US" xlink:label="lab_skwd_FixedMaturitiesAvailableForSaleMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fixed Maturities, Available-For-Sale [Member]</link:label>
    <link:label id="lab_skwd_FixedMaturitiesAvailableForSaleMember_documentation_en-US" xlink:label="lab_skwd_FixedMaturitiesAvailableForSaleMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fixed Maturities, Available-For-Sale</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_FixedMaturitiesAvailableForSaleMember" xlink:href="skwd-20221231.xsd#skwd_FixedMaturitiesAvailableForSaleMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_FixedMaturitiesAvailableForSaleMember" xlink:to="lab_skwd_FixedMaturitiesAvailableForSaleMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableCreditQualityIndicatorTableTextBlock_a0ff2bea-93e1-472c-8102-8a218e2dc6a2_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableCreditQualityIndicatorTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Recoverable, Credit Quality Indicator</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableCreditQualityIndicatorTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableCreditQualityIndicatorTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Recoverable, Credit Quality Indicator [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverableCreditQualityIndicatorTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ReinsuranceRecoverableCreditQualityIndicatorTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverableCreditQualityIndicatorTableTextBlock" xlink:to="lab_us-gaap_ReinsuranceRecoverableCreditQualityIndicatorTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceTextBlock_67546e45-a6b4-4914-bfdd-d27d7a541dc4_verboseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceTextBlock" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Premiums</link:label>
    <link:label id="lab_us-gaap_ReinsuranceTextBlock_dbc084e4-3f3c-4421-a1d2-9514a27f39e1_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance</link:label>
    <link:label id="lab_us-gaap_ReinsuranceTextBlock_label_en-US" xlink:label="lab_us-gaap_ReinsuranceTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ReinsuranceTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceTextBlock" xlink:to="lab_us-gaap_ReinsuranceTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OverAllotmentOptionMember_cd2c05d7-e983-4dd5-8dda-dd3fd950796b_terseLabel_en-US" xlink:label="lab_us-gaap_OverAllotmentOptionMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Over-Allotment Option</link:label>
    <link:label id="lab_us-gaap_OverAllotmentOptionMember_label_en-US" xlink:label="lab_us-gaap_OverAllotmentOptionMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Over-Allotment Option [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OverAllotmentOptionMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OverAllotmentOptionMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OverAllotmentOptionMember" xlink:to="lab_us-gaap_OverAllotmentOptionMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ImpairmentOfIntangibleAssetsIndefinitelivedExcludingGoodwill_f35f897a-2aa6-48db-b805-b45a671dbe51_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_ImpairmentOfIntangibleAssetsIndefinitelivedExcludingGoodwill" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Impairment</link:label>
    <link:label id="lab_us-gaap_ImpairmentOfIntangibleAssetsIndefinitelivedExcludingGoodwill_label_en-US" xlink:label="lab_us-gaap_ImpairmentOfIntangibleAssetsIndefinitelivedExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Impairment of Intangible Assets, Indefinite-Lived (Excluding Goodwill)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ImpairmentOfIntangibleAssetsIndefinitelivedExcludingGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ImpairmentOfIntangibleAssetsIndefinitelivedExcludingGoodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ImpairmentOfIntangibleAssetsIndefinitelivedExcludingGoodwill" xlink:to="lab_us-gaap_ImpairmentOfIntangibleAssetsIndefinitelivedExcludingGoodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract_96e282a1-7d21-4585-9f12-7a9803d8bb67_terseLabel_en-US" xlink:label="lab_us-gaap_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Assets</link:label>
    <link:label id="lab_us-gaap_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract_label_en-US" xlink:label="lab_us-gaap_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Financial Instruments, Financial Assets, Balance Sheet Groupings [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract" xlink:to="lab_us-gaap_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueDisclosuresAbstract_label_en-US" xlink:label="lab_us-gaap_FairValueDisclosuresAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value Disclosures [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueDisclosuresAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FairValueDisclosuresAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueDisclosuresAbstract" xlink:to="lab_us-gaap_FairValueDisclosuresAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_2fb950b2-5cb9-4aab-82e1-9e6e2b53bb47_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Losses and loss adjustment expenses</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Incurred Claims</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ReinsuranceRecoverableForLossPortfolioTransfer_67bf0f86-829e-48cd-8301-7695049f330e_terseLabel_en-US" xlink:label="lab_skwd_ReinsuranceRecoverableForLossPortfolioTransfer" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Loss portfolio transfer</link:label>
    <link:label id="lab_skwd_ReinsuranceRecoverableForLossPortfolioTransfer_label_en-US" xlink:label="lab_skwd_ReinsuranceRecoverableForLossPortfolioTransfer" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Recoverable For Loss Portfolio Transfer</link:label>
    <link:label id="lab_skwd_ReinsuranceRecoverableForLossPortfolioTransfer_documentation_en-US" xlink:label="lab_skwd_ReinsuranceRecoverableForLossPortfolioTransfer" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Recoverable For Loss Portfolio Transfer</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ReinsuranceRecoverableForLossPortfolioTransfer" xlink:href="skwd-20221231.xsd#skwd_ReinsuranceRecoverableForLossPortfolioTransfer"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ReinsuranceRecoverableForLossPortfolioTransfer" xlink:to="lab_skwd_ReinsuranceRecoverableForLossPortfolioTransfer" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ShortTailMonolineSpecialtyMember_7d65bcd5-88b3-4c37-be39-044ca3c5675b_terseLabel_en-US" xlink:label="lab_skwd_ShortTailMonolineSpecialtyMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short Tail/Monoline Specialty</link:label>
    <link:label id="lab_skwd_ShortTailMonolineSpecialtyMember_label_en-US" xlink:label="lab_skwd_ShortTailMonolineSpecialtyMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short Tail/Monoline Specialty [Member]</link:label>
    <link:label id="lab_skwd_ShortTailMonolineSpecialtyMember_documentation_en-US" xlink:label="lab_skwd_ShortTailMonolineSpecialtyMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short Tail/Monoline Specialty</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ShortTailMonolineSpecialtyMember" xlink:href="skwd-20221231.xsd#skwd_ShortTailMonolineSpecialtyMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ShortTailMonolineSpecialtyMember" xlink:to="lab_skwd_ShortTailMonolineSpecialtyMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CreditFacilityAxis_28844163-4eeb-44dc-b515-e3e230d02790_terseLabel_en-US" xlink:label="lab_us-gaap_CreditFacilityAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Credit Facility [Axis]</link:label>
    <link:label id="lab_us-gaap_CreditFacilityAxis_label_en-US" xlink:label="lab_us-gaap_CreditFacilityAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Credit Facility [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CreditFacilityAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CreditFacilityAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CreditFacilityAxis" xlink:to="lab_us-gaap_CreditFacilityAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ScheduleOfDepositAssetTableTextBlock_0f8488d9-85d1-4dc5-a7ef-1f4470a192ba_terseLabel_en-US" xlink:label="lab_skwd_ScheduleOfDepositAssetTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Deposit Assets</link:label>
    <link:label id="lab_skwd_ScheduleOfDepositAssetTableTextBlock_label_en-US" xlink:label="lab_skwd_ScheduleOfDepositAssetTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule Of Deposit Asset [Table Text Block]</link:label>
    <link:label id="lab_skwd_ScheduleOfDepositAssetTableTextBlock_documentation_en-US" xlink:label="lab_skwd_ScheduleOfDepositAssetTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule Of Deposit Asset</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ScheduleOfDepositAssetTableTextBlock" xlink:href="skwd-20221231.xsd#skwd_ScheduleOfDepositAssetTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ScheduleOfDepositAssetTableTextBlock" xlink:to="lab_skwd_ScheduleOfDepositAssetTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RelatedPartyTransactionAmountsOfTransaction_ce78f8a6-fa1d-4a3a-a5b6-73e9641a7c4c_terseLabel_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionAmountsOfTransaction" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Transaction amount during the period</link:label>
    <link:label id="lab_us-gaap_RelatedPartyTransactionAmountsOfTransaction_label_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionAmountsOfTransaction" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Related Party Transaction, Amounts of Transaction</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RelatedPartyTransactionAmountsOfTransaction" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RelatedPartyTransactionAmountsOfTransaction"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RelatedPartyTransactionAmountsOfTransaction" xlink:to="lab_us-gaap_RelatedPartyTransactionAmountsOfTransaction" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityAbstract_c7f4d1e5-d438-49f4-bcc3-001ec2fb75c1_terseLabel_en-US" xlink:label="lab_us-gaap_EquityAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stockholders' equity</link:label>
    <link:label id="lab_us-gaap_EquityAbstract_c05b287a-6889-4815-b498-2513d1518e97_verboseLabel_en-US" xlink:label="lab_us-gaap_EquityAbstract" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stockholders&#8217; Equity:</link:label>
    <link:label id="lab_us-gaap_EquityAbstract_label_en-US" xlink:label="lab_us-gaap_EquityAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EquityAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityAbstract" xlink:to="lab_us-gaap_EquityAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubsequentEventTable_cc8112d2-6575-4182-8650-a8887cc1b5e5_terseLabel_en-US" xlink:label="lab_us-gaap_SubsequentEventTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subsequent Event [Table]</link:label>
    <link:label id="lab_us-gaap_SubsequentEventTable_label_en-US" xlink:label="lab_us-gaap_SubsequentEventTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subsequent Event [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsequentEventTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SubsequentEventTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsequentEventTable" xlink:to="lab_us-gaap_SubsequentEventTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod_8e1dd322-2ebf-48b7-98c8-0cc11a0c5142_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Vested (in shares)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Vested in Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityTaxIdentificationNumber_18aaeefb-ce65-49ff-afa0-aa23c524aff4_terseLabel_en-US" xlink:label="lab_dei_EntityTaxIdentificationNumber" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Tax Identification Number</link:label>
    <link:label id="lab_dei_EntityTaxIdentificationNumber_label_en-US" xlink:label="lab_dei_EntityTaxIdentificationNumber" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Tax Identification Number</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityTaxIdentificationNumber" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityTaxIdentificationNumber"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityTaxIdentificationNumber" xlink:to="lab_dei_EntityTaxIdentificationNumber" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAuthorized_0ba6e9a3-47db-4abc-9bb4-a3a0a86c4dbf_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAuthorized" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Authorized target common shares (in shares)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAuthorized_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAuthorized" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Number of Shares Authorized</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAuthorized" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAuthorized"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAuthorized" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAuthorized" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi_d2070a74-9967-491d-971e-b2ef40d9f173_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity securities</link:label>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi_label_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Proceeds from Sale of Equity Securities, FV-NI</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi" xlink:to="lab_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_RelatedPartyTransactionConsiderationReceived_93412d9f-3bc0-49e8-af5c-cb5bc7505c01_terseLabel_en-US" xlink:label="lab_skwd_RelatedPartyTransactionConsiderationReceived" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Related party transaction, consideration received</link:label>
    <link:label id="lab_skwd_RelatedPartyTransactionConsiderationReceived_label_en-US" xlink:label="lab_skwd_RelatedPartyTransactionConsiderationReceived" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Related Party Transaction, Consideration Received</link:label>
    <link:label id="lab_skwd_RelatedPartyTransactionConsiderationReceived_documentation_en-US" xlink:label="lab_skwd_RelatedPartyTransactionConsiderationReceived" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Related Party Transaction, Consideration Received</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RelatedPartyTransactionConsiderationReceived" xlink:href="skwd-20221231.xsd#skwd_RelatedPartyTransactionConsiderationReceived"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_RelatedPartyTransactionConsiderationReceived" xlink:to="lab_skwd_RelatedPartyTransactionConsiderationReceived" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForFuturePolicyBenefitsAndUnpaidClaimsDisclosureTextBlock_68128053-e900-495a-95cd-af4dfa2ccee9_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForFuturePolicyBenefitsAndUnpaidClaimsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reserves for Losses and Loss Adjustment Expenses</link:label>
    <link:label id="lab_us-gaap_LiabilityForFuturePolicyBenefitsAndUnpaidClaimsDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_LiabilityForFuturePolicyBenefitsAndUnpaidClaimsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability for Future Policy Benefits and Unpaid Claims Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForFuturePolicyBenefitsAndUnpaidClaimsDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilityForFuturePolicyBenefitsAndUnpaidClaimsDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForFuturePolicyBenefitsAndUnpaidClaimsDisclosureTextBlock" xlink:to="lab_us-gaap_LiabilityForFuturePolicyBenefitsAndUnpaidClaimsDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_CommoditySectorMember_689bdbb3-bf39-47ee-9dd2-765d49004b35_terseLabel_en-US" xlink:label="lab_skwd_CommoditySectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Commodity</link:label>
    <link:label id="lab_skwd_CommoditySectorMember_label_en-US" xlink:label="lab_skwd_CommoditySectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Commodity Sector [Member]</link:label>
    <link:label id="lab_skwd_CommoditySectorMember_documentation_en-US" xlink:label="lab_skwd_CommoditySectorMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Commodity Sector</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_CommoditySectorMember" xlink:href="skwd-20221231.xsd#skwd_CommoditySectorMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_CommoditySectorMember" xlink:to="lab_skwd_CommoditySectorMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfNonvestedShareActivityTableTextBlock_358536c3-9d69-48d7-acaa-fc1eb106ebb5_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfNonvestedShareActivityTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Nonvested Share Activity</link:label>
    <link:label id="lab_us-gaap_ScheduleOfNonvestedShareActivityTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfNonvestedShareActivityTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Nonvested Share Activity [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfNonvestedShareActivityTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfNonvestedShareActivityTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfNonvestedShareActivityTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfNonvestedShareActivityTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherAggregatedInvestmentsMember_6202d553-ea53-446e-a260-06ec87f4b8ff_terseLabel_en-US" xlink:label="lab_us-gaap_OtherAggregatedInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other</link:label>
    <link:label id="lab_us-gaap_OtherAggregatedInvestmentsMember_label_en-US" xlink:label="lab_us-gaap_OtherAggregatedInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other Security Investments [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherAggregatedInvestmentsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OtherAggregatedInvestmentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherAggregatedInvestmentsMember" xlink:to="lab_us-gaap_OtherAggregatedInvestmentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ExitedLinesMember_36288c98-7cec-4bf0-b152-72f7476cc124_terseLabel_en-US" xlink:label="lab_skwd_ExitedLinesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Exited Lines</link:label>
    <link:label id="lab_skwd_ExitedLinesMember_label_en-US" xlink:label="lab_skwd_ExitedLinesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Exited Lines [Member]</link:label>
    <link:label id="lab_skwd_ExitedLinesMember_documentation_en-US" xlink:label="lab_skwd_ExitedLinesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Exited Lines</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ExitedLinesMember" xlink:href="skwd-20221231.xsd#skwd_ExitedLinesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ExitedLinesMember" xlink:to="lab_skwd_ExitedLinesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DowlingCapitalPartnersLPMember_c1069bf5-e57f-4f46-8f76-b5f469d4feb8_terseLabel_en-US" xlink:label="lab_skwd_DowlingCapitalPartnersLPMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Dowling Capital Partners LP units</link:label>
    <link:label id="lab_skwd_DowlingCapitalPartnersLPMember_label_en-US" xlink:label="lab_skwd_DowlingCapitalPartnersLPMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Dowling Capital Partners LP [Member]</link:label>
    <link:label id="lab_skwd_DowlingCapitalPartnersLPMember_documentation_en-US" xlink:label="lab_skwd_DowlingCapitalPartnersLPMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Dowling Capital Partners LP</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DowlingCapitalPartnersLPMember" xlink:href="skwd-20221231.xsd#skwd_DowlingCapitalPartnersLPMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DowlingCapitalPartnersLPMember" xlink:to="lab_skwd_DowlingCapitalPartnersLPMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_CommercialAutoLiabilityMember_60fc5bae-7a85-4040-a444-53d9fefd2c5f_terseLabel_en-US" xlink:label="lab_skwd_CommercialAutoLiabilityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Commercial Auto Liability</link:label>
    <link:label id="lab_skwd_CommercialAutoLiabilityMember_label_en-US" xlink:label="lab_skwd_CommercialAutoLiabilityMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Commercial Auto Liability [Member]</link:label>
    <link:label id="lab_skwd_CommercialAutoLiabilityMember_documentation_en-US" xlink:label="lab_skwd_CommercialAutoLiabilityMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Commercial Auto Liability</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_CommercialAutoLiabilityMember" xlink:href="skwd-20221231.xsd#skwd_CommercialAutoLiabilityMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_CommercialAutoLiabilityMember" xlink:to="lab_skwd_CommercialAutoLiabilityMember" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ConsolidatedEntitiesDomain_f938e2e8-035f-4c69-b2de-ed7591e3bb5d_terseLabel_en-US" xlink:label="lab_srt_ConsolidatedEntitiesDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Consolidated Entities [Domain]</link:label>
    <link:label id="lab_srt_ConsolidatedEntitiesDomain_label_en-US" xlink:label="lab_srt_ConsolidatedEntitiesDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Consolidated Entities [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ConsolidatedEntitiesDomain" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_ConsolidatedEntitiesDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ConsolidatedEntitiesDomain" xlink:to="lab_srt_ConsolidatedEntitiesDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInReinsurancePayables_25d910de-ea71-4bd3-af15-23734081c69c_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInReinsurancePayables" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance and premium payables</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInReinsurancePayables_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInReinsurancePayables" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Increase (Decrease) in Reinsurance Payables</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInReinsurancePayables" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInReinsurancePayables"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInReinsurancePayables" xlink:to="lab_us-gaap_IncreaseDecreaseInReinsurancePayables" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfEffectiveIncomeTaxRateReconciliationTableTextBlock_c269c444-6d3c-482f-8d7c-6176bfc37644_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfEffectiveIncomeTaxRateReconciliationTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Effective Income Tax Rate Reconciliation</link:label>
    <link:label id="lab_us-gaap_ScheduleOfEffectiveIncomeTaxRateReconciliationTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfEffectiveIncomeTaxRateReconciliationTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Effective Income Tax Rate Reconciliation [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfEffectiveIncomeTaxRateReconciliationTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfEffectiveIncomeTaxRateReconciliationTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfEffectiveIncomeTaxRateReconciliationTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfEffectiveIncomeTaxRateReconciliationTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_e1079a8e-0c96-45bf-91ab-d33ae98265c6_totalLabel_en-US" xlink:label="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net increase (decrease) in cash and cash equivalents and restricted cash</link:label>
    <link:label id="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_label_en-US" xlink:label="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash, Cash Equivalents, Restricted Cash, and Restricted Cash Equivalents, Period Increase (Decrease), Including Exchange Rate Effect</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect" xlink:to="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearOne_2eb33fa4-c927-45bc-9bf6-02d1e09f0080_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearOne" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Year 1</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearOne_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearOne" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Historical Claims Duration, Year One</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearOne" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearOne"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearOne" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearOne" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityCentralIndexKey_b0f58c22-a392-41d8-9d06-b15b58b9ecf5_terseLabel_en-US" xlink:label="lab_dei_EntityCentralIndexKey" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Central Index Key</link:label>
    <link:label id="lab_dei_EntityCentralIndexKey_label_en-US" xlink:label="lab_dei_EntityCentralIndexKey" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Central Index Key</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityCentralIndexKey" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityCentralIndexKey"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityCentralIndexKey" xlink:to="lab_dei_EntityCentralIndexKey" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AntidilutiveSecuritiesNameDomain_7c92d7a4-f62c-4373-a9f8-8bf9a5c0e4a1_terseLabel_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Antidilutive Securities, Name [Domain]</link:label>
    <link:label id="lab_us-gaap_AntidilutiveSecuritiesNameDomain_label_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Antidilutive Securities, Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AntidilutiveSecuritiesNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AntidilutiveSecuritiesNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AntidilutiveSecuritiesNameDomain" xlink:to="lab_us-gaap_AntidilutiveSecuritiesNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsFutureAmortizationExpenseAbstract_d8a5a78f-243d-4ce8-a1ab-e830fa49ea0b_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsFutureAmortizationExpenseAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Years Ending December 31,</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsFutureAmortizationExpenseAbstract_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsFutureAmortizationExpenseAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Finite-Lived Intangible Assets, Net, Amortization Expense, Fiscal Year Maturity [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsFutureAmortizationExpenseAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FiniteLivedIntangibleAssetsFutureAmortizationExpenseAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsFutureAmortizationExpenseAbstract" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsFutureAmortizationExpenseAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsAccidentYearAxis_11b10ce2-dfb2-4642-aa6b-55fa8b2fa6eb_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsAccidentYearAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Accident Year [Axis]</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsAccidentYearAxis_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsAccidentYearAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Accident Year [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsAccidentYearAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortdurationInsuranceContractsAccidentYearAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsAccidentYearAxis" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsAccidentYearAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_SECSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersDeferredCedingCommission_ad71ec3b-402b-432c-86d3-ec109cd0a497_terseLabel_en-US" xlink:label="lab_skwd_SECSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersDeferredCedingCommission" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred ceding commission</link:label>
    <link:label id="lab_skwd_SECSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersDeferredCedingCommission_label_en-US" xlink:label="lab_skwd_SECSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersDeferredCedingCommission" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-18, Supplemental Information, Property-Casualty Insurance Underwriters, Deferred Ceding Commission</link:label>
    <link:label id="lab_skwd_SECSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersDeferredCedingCommission_documentation_en-US" xlink:label="lab_skwd_SECSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersDeferredCedingCommission" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-18, Supplemental Information, Property-Casualty Insurance Underwriters, Deferred Ceding Commission</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_SECSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersDeferredCedingCommission" xlink:href="skwd-20221231.xsd#skwd_SECSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersDeferredCedingCommission"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_SECSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersDeferredCedingCommission" xlink:to="lab_skwd_SECSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersDeferredCedingCommission" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationLineItems_f0aef9c8-7bf4-4f21-8ae2-3e917662b70a_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationLineItems_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationLineItems" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis_f7074fe6-2ecd-49d9-8078-c4be3236b1d3_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Finite-Lived Intangible Assets by Major Class [Axis]</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Finite-Lived Intangible Assets by Major Class [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable_d77f2cb0-8800-471c-9ab0-26328ae6f288_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Share-Based Compensation Arrangements by Share-Based Payment Award [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Share-Based Compensation Arrangements by Share-Based Payment Award [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable" xlink:to="lab_us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConcentrationRiskCreditRisk_e8cb77c1-2af0-4bd3-a6ef-ca80a6727f32_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskCreditRisk" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Concentration of Credit Risk</link:label>
    <link:label id="lab_us-gaap_ConcentrationRiskCreditRisk_label_en-US" xlink:label="lab_us-gaap_ConcentrationRiskCreditRisk" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Concentration Risk, Credit Risk, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConcentrationRiskCreditRisk" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ConcentrationRiskCreditRisk"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConcentrationRiskCreditRisk" xlink:to="lab_us-gaap_ConcentrationRiskCreditRisk" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityDomain_e697f76f-4b13-4616-929a-cb676e6e755e_terseLabel_en-US" xlink:label="lab_dei_EntityDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity [Domain]</link:label>
    <link:label id="lab_dei_EntityDomain_label_en-US" xlink:label="lab_dei_EntityDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityDomain" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityDomain" xlink:to="lab_dei_EntityDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_CityAreaCode_e3e8f328-8272-479c-ac46-1d1f391a5a6d_terseLabel_en-US" xlink:label="lab_dei_CityAreaCode" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">City Area Code</link:label>
    <link:label id="lab_dei_CityAreaCode_label_en-US" xlink:label="lab_dei_CityAreaCode" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">City Area Code</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_CityAreaCode" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_CityAreaCode"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_CityAreaCode" xlink:to="lab_dei_CityAreaCode" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommercialAndIndustrialSectorMember_036ff19b-7bed-4423-bc64-d8a76009ba26_terseLabel_en-US" xlink:label="lab_us-gaap_CommercialAndIndustrialSectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Industrial</link:label>
    <link:label id="lab_us-gaap_CommercialAndIndustrialSectorMember_label_en-US" xlink:label="lab_us-gaap_CommercialAndIndustrialSectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Commercial and Industrial Sector [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommercialAndIndustrialSectorMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CommercialAndIndustrialSectorMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommercialAndIndustrialSectorMember" xlink:to="lab_us-gaap_CommercialAndIndustrialSectorMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AssetsAbstract_816727df-838c-47ae-b1ce-12dbff2272d1_terseLabel_en-US" xlink:label="lab_us-gaap_AssetsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Assets</link:label>
    <link:label id="lab_us-gaap_AssetsAbstract_label_en-US" xlink:label="lab_us-gaap_AssetsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Assets [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AssetsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssetsAbstract" xlink:to="lab_us-gaap_AssetsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubsidiarySaleOfStockAxis_26679075-a234-4371-bbef-a87c2eb35057_terseLabel_en-US" xlink:label="lab_us-gaap_SubsidiarySaleOfStockAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Sale of Stock [Axis]</link:label>
    <link:label id="lab_us-gaap_SubsidiarySaleOfStockAxis_label_en-US" xlink:label="lab_us-gaap_SubsidiarySaleOfStockAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Sale of Stock [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsidiarySaleOfStockAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SubsidiarySaleOfStockAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsidiarySaleOfStockAxis" xlink:to="lab_us-gaap_SubsidiarySaleOfStockAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredTaxLiabilitiesOtherComprehensiveIncome_274a70bd-d0b9-4810-91d2-85bab75fe524_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxLiabilitiesOtherComprehensiveIncome" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unrealized gains on investments</link:label>
    <link:label id="lab_us-gaap_DeferredTaxLiabilitiesOtherComprehensiveIncome_label_en-US" xlink:label="lab_us-gaap_DeferredTaxLiabilitiesOtherComprehensiveIncome" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Tax Liabilities, Other Comprehensive Income</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxLiabilitiesOtherComprehensiveIncome" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DeferredTaxLiabilitiesOtherComprehensiveIncome"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredTaxLiabilitiesOtherComprehensiveIncome" xlink:to="lab_us-gaap_DeferredTaxLiabilitiesOtherComprehensiveIncome" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentOtherTypesMember_4d62c936-45bd-4f61-8a19-c1b411d7ffe5_terseLabel_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentOtherTypesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other</link:label>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentOtherTypesMember_label_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentOtherTypesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Property, Plant and Equipment, Other Types [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentOtherTypesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PropertyPlantAndEquipmentOtherTypesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentOtherTypesMember" xlink:to="lab_us-gaap_PropertyPlantAndEquipmentOtherTypesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DepositContractsAssets_f31c068a-7f4a-4975-9192-768104806753_terseLabel_en-US" xlink:label="lab_us-gaap_DepositContractsAssets" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deposit asset</link:label>
    <link:label id="lab_us-gaap_DepositContractsAssets_label_en-US" xlink:label="lab_us-gaap_DepositContractsAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deposit Contracts, Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DepositContractsAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DepositContractsAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DepositContractsAssets" xlink:to="lab_us-gaap_DepositContractsAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerSharePolicyTextBlock_1eae2690-3c79-4fab-b710-a32f77c9a43f_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerSharePolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Earnings Per Share</link:label>
    <link:label id="lab_us-gaap_EarningsPerSharePolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_EarningsPerSharePolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Earnings Per Share, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerSharePolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EarningsPerSharePolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerSharePolicyTextBlock" xlink:to="lab_us-gaap_EarningsPerSharePolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensation_a4511980-903f-47cb-97d6-1485ef38c98b_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensation" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stock-based compensation expense</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensation_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensation" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Payment Arrangement, Noncash Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensation" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensation"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensation" xlink:to="lab_us-gaap_ShareBasedCompensation" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsToAcquireEquityMethodInvestments_8dc116e0-c614-4e49-a3fc-b5c2ec109994_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireEquityMethodInvestments" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment in direct and indirect loans</link:label>
    <link:label id="lab_us-gaap_PaymentsToAcquireEquityMethodInvestments_d26d19d3-2cd8-4b8d-a6f3-e121916db329_terseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Payment to acquire equity method investment</link:label>
    <link:label id="lab_us-gaap_PaymentsToAcquireEquityMethodInvestments_label_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Payments to Acquire Equity Method Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireEquityMethodInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PaymentsToAcquireEquityMethodInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsToAcquireEquityMethodInvestments" xlink:to="lab_us-gaap_PaymentsToAcquireEquityMethodInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentUnderlyingEquityInNetAssets_539097ff-e46a-4a86-9800-b9cfc3c5fa25_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentUnderlyingEquityInNetAssets" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Underlying equity</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentUnderlyingEquityInNetAssets_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentUnderlyingEquityInNetAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Method Investment, Underlying Equity in Net Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentUnderlyingEquityInNetAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EquityMethodInvestmentUnderlyingEquityInNetAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentUnderlyingEquityInNetAssets" xlink:to="lab_us-gaap_EquityMethodInvestmentUnderlyingEquityInNetAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_VariableRateAxis_baaa0994-4d47-4fe9-9c83-bc98fcb9dac2_terseLabel_en-US" xlink:label="lab_us-gaap_VariableRateAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Variable Rate [Axis]</link:label>
    <link:label id="lab_us-gaap_VariableRateAxis_label_en-US" xlink:label="lab_us-gaap_VariableRateAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Variable Rate [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_VariableRateAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_VariableRateAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_VariableRateAxis" xlink:to="lab_us-gaap_VariableRateAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment_a444c5bc-9d6a-419c-8fc8-cd54a974a81c_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Purchase of property and equipment</link:label>
    <link:label id="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment_label_en-US" xlink:label="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Payments to Acquire Property, Plant, and Equipment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PaymentsToAcquirePropertyPlantAndEquipment"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment" xlink:to="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseNextTwelveMonths_7ca32d6f-9b4b-495c-ab15-548ce701ca55_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseNextTwelveMonths" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">2023</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseNextTwelveMonths_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseNextTwelveMonths" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Finite-Lived Intangible Asset, Expected Amortization, Year One</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseNextTwelveMonths" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseNextTwelveMonths"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseNextTwelveMonths" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseNextTwelveMonths" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock_46da7d41-e05f-47ca-ae51-6bbbe8a08861_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Earnings Per Share, Basic and Diluted</link:label>
    <link:label id="lab_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Earnings Per Share, Basic and Diluted [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss_cd4b6dd3-c403-4331-b922-c5519e1b9d22_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fixed maturity securities, available-for sale</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Realized Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_UnearnedPremiums_48e7c691-39dd-4896-a874-4838bd6a725d_terseLabel_en-US" xlink:label="lab_us-gaap_UnearnedPremiums" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unearned premiums</link:label>
    <link:label id="lab_us-gaap_UnearnedPremiums_label_en-US" xlink:label="lab_us-gaap_UnearnedPremiums" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unearned Premiums</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_UnearnedPremiums" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_UnearnedPremiums"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_UnearnedPremiums" xlink:to="lab_us-gaap_UnearnedPremiums" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_SkywardSpecialtyInsuranceGroupMember_4c3dce16-f1d8-4109-b219-12cf47d6d2ec_terseLabel_en-US" xlink:label="lab_skwd_SkywardSpecialtyInsuranceGroupMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Skyward Specialty Insurance Group</link:label>
    <link:label id="lab_skwd_SkywardSpecialtyInsuranceGroupMember_label_en-US" xlink:label="lab_skwd_SkywardSpecialtyInsuranceGroupMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Skyward Specialty Insurance Group [Member]</link:label>
    <link:label id="lab_skwd_SkywardSpecialtyInsuranceGroupMember_documentation_en-US" xlink:label="lab_skwd_SkywardSpecialtyInsuranceGroupMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Skyward Specialty Insurance Group</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_SkywardSpecialtyInsuranceGroupMember" xlink:href="skwd-20221231.xsd#skwd_SkywardSpecialtyInsuranceGroupMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_SkywardSpecialtyInsuranceGroupMember" xlink:to="lab_skwd_SkywardSpecialtyInsuranceGroupMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxExpenseBenefitContinuingOperationsIncomeTaxReconciliationAbstract_38815e88-b486-421e-a9bc-bb743654abe8_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxExpenseBenefitContinuingOperationsIncomeTaxReconciliationAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Amount</link:label>
    <link:label id="lab_us-gaap_IncomeTaxExpenseBenefitContinuingOperationsIncomeTaxReconciliationAbstract_label_en-US" xlink:label="lab_us-gaap_IncomeTaxExpenseBenefitContinuingOperationsIncomeTaxReconciliationAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Income Tax Expense (Benefit), Effective Income Tax Rate Reconciliation, Amount [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxExpenseBenefitContinuingOperationsIncomeTaxReconciliationAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncomeTaxExpenseBenefitContinuingOperationsIncomeTaxReconciliationAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxExpenseBenefitContinuingOperationsIncomeTaxReconciliationAbstract" xlink:to="lab_us-gaap_IncomeTaxExpenseBenefitContinuingOperationsIncomeTaxReconciliationAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue_6eda62ce-29dd-4102-af28-537ee714a764_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Due in less than one year</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Fair Value, Maturity, Allocated and Single Maturity Date, Year One</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_ea8a42b3-3b0d-459a-b666-7f9adcbbef1c_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Increase (Decrease) in Stockholders' Equity [Roll Forward]</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Increase (Decrease) in Stockholders' Equity [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInStockholdersEquityRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:to="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue_0768a7f9-d389-4876-b0ae-aab309546d56_totalLabel_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total future minimum operating lease payments</link:label>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue_label_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Lessee, Operating Lease, Liability, to be Paid</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue" xlink:to="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatutoryAccountingPracticesStatutoryNetIncomeAmount_ff334887-dcab-422b-b0db-eb4d781f569a_terseLabel_en-US" xlink:label="lab_us-gaap_StatutoryAccountingPracticesStatutoryNetIncomeAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statutory net income (loss)</link:label>
    <link:label id="lab_us-gaap_StatutoryAccountingPracticesStatutoryNetIncomeAmount_label_en-US" xlink:label="lab_us-gaap_StatutoryAccountingPracticesStatutoryNetIncomeAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statutory Accounting Practices, Statutory Net Income Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatutoryAccountingPracticesStatutoryNetIncomeAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StatutoryAccountingPracticesStatutoryNetIncomeAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatutoryAccountingPracticesStatutoryNetIncomeAmount" xlink:to="lab_us-gaap_StatutoryAccountingPracticesStatutoryNetIncomeAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableMember_917d7c4b-ae20-4b1a-b29a-740940a55751_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance recoverable including reinsurance premium paid</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableMember_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Recoverable Including Reinsurance Premium Paid [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverableMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ReinsuranceRecoverableMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverableMember" xlink:to="lab_us-gaap_ReinsuranceRecoverableMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesTradingAndEquitySecuritiesFvNiAbstract_b21f27fc-82bc-4324-932f-1eb405c14398_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesTradingAndEquitySecuritiesFvNiAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total equity securities</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesTradingAndEquitySecuritiesFvNiAbstract_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesTradingAndEquitySecuritiesFvNiAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Trading, and Equity Securities, FV-NI [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesTradingAndEquitySecuritiesFvNiAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesTradingAndEquitySecuritiesFvNiAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesTradingAndEquitySecuritiesFvNiAbstract" xlink:to="lab_us-gaap_DebtSecuritiesTradingAndEquitySecuritiesFvNiAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressPostalZipCode_4b3c6a29-24b4-4ed3-b9f8-95b3eb614af6_terseLabel_en-US" xlink:label="lab_dei_EntityAddressPostalZipCode" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Address, Postal Zip Code</link:label>
    <link:label id="lab_dei_EntityAddressPostalZipCode_label_en-US" xlink:label="lab_dei_EntityAddressPostalZipCode" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Address, Postal Zip Code</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressPostalZipCode" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityAddressPostalZipCode"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityAddressPostalZipCode" xlink:to="lab_dei_EntityAddressPostalZipCode" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SuretySegmentMember_1b545a2c-b2b4-4709-aa3c-43c74ee731d3_terseLabel_en-US" xlink:label="lab_us-gaap_SuretySegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Surety</link:label>
    <link:label id="lab_us-gaap_SuretySegmentMember_label_en-US" xlink:label="lab_us-gaap_SuretySegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Surety Product Line [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SuretySegmentMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SuretySegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SuretySegmentMember" xlink:to="lab_us-gaap_SuretySegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_FixedMaturitySecuritiesAvailableForSaleMember_c80f99db-2ed3-4481-a8c4-4b1366426906_terseLabel_en-US" xlink:label="lab_skwd_FixedMaturitySecuritiesAvailableForSaleMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fixed maturity securities, available-for sale</link:label>
    <link:label id="lab_skwd_FixedMaturitySecuritiesAvailableForSaleMember_label_en-US" xlink:label="lab_skwd_FixedMaturitySecuritiesAvailableForSaleMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fixed Maturity Securities, Available-for-sale [Member]</link:label>
    <link:label id="lab_skwd_FixedMaturitySecuritiesAvailableForSaleMember_documentation_en-US" xlink:label="lab_skwd_FixedMaturitySecuritiesAvailableForSaleMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fixed Maturity Securities, Available-for-sale</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_FixedMaturitySecuritiesAvailableForSaleMember" xlink:href="skwd-20221231.xsd#skwd_FixedMaturitySecuritiesAvailableForSaleMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_FixedMaturitySecuritiesAvailableForSaleMember" xlink:to="lab_skwd_FixedMaturitySecuritiesAvailableForSaleMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingGain_931faef6-0f8d-40f3-b2dd-a5f1668bc3ed_terseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingGain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross Unrealized Gains</link:label>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingGain_label_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingGain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Held-to-Maturity, Accumulated Unrecognized Gain</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingGain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingGain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingGain" xlink:to="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingGain" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_CommercialAutoPhysicalDamageMember_29f02911-0dc8-4ef7-8322-288e0538d9aa_terseLabel_en-US" xlink:label="lab_skwd_CommercialAutoPhysicalDamageMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Commercial Auto Physical Damage</link:label>
    <link:label id="lab_skwd_CommercialAutoPhysicalDamageMember_label_en-US" xlink:label="lab_skwd_CommercialAutoPhysicalDamageMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Commercial Auto Physical Damage [Member]</link:label>
    <link:label id="lab_skwd_CommercialAutoPhysicalDamageMember_documentation_en-US" xlink:label="lab_skwd_CommercialAutoPhysicalDamageMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Commercial Auto Physical Damage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_CommercialAutoPhysicalDamageMember" xlink:href="skwd-20221231.xsd#skwd_CommercialAutoPhysicalDamageMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_CommercialAutoPhysicalDamageMember" xlink:to="lab_skwd_CommercialAutoPhysicalDamageMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortDurationInsuranceContractsAccidentYear2017Member_e5ca4856-2a07-49ad-a9ef-544d8c3b4490_terseLabel_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractsAccidentYear2017Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accident Year 2017</link:label>
    <link:label id="lab_us-gaap_ShortDurationInsuranceContractsAccidentYear2017Member_label_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractsAccidentYear2017Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Accident Year 2017 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortDurationInsuranceContractsAccidentYear2017Member" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortDurationInsuranceContractsAccidentYear2017Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortDurationInsuranceContractsAccidentYear2017Member" xlink:to="lab_us-gaap_ShortDurationInsuranceContractsAccidentYear2017Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionFairValue_dd07c765-e608-4a9f-a04a-04ca0ea289b9_totalLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionFairValue" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total</link:label>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionFairValue_label_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Held-to-Maturity, Unrealized Loss Position, Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionFairValue" xlink:to="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RelatedPartyTransactionExpensesFromTransactionsWithRelatedParty_42e83d62-fb8c-481b-93a6-f3ca1b9fdc3e_terseLabel_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionExpensesFromTransactionsWithRelatedParty" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Expenses from related party transactions</link:label>
    <link:label id="lab_us-gaap_RelatedPartyTransactionExpensesFromTransactionsWithRelatedParty_label_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionExpensesFromTransactionsWithRelatedParty" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Related Party Transaction, Expenses from Transactions with Related Party</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RelatedPartyTransactionExpensesFromTransactionsWithRelatedParty" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RelatedPartyTransactionExpensesFromTransactionsWithRelatedParty"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RelatedPartyTransactionExpensesFromTransactionsWithRelatedParty" xlink:to="lab_us-gaap_RelatedPartyTransactionExpensesFromTransactionsWithRelatedParty" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity_9f17998c-6b15-47fc-82a4-0c94a009fa37_terseLabel_en-US" xlink:label="lab_us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Maximum borrowing capacity</link:label>
    <link:label id="lab_us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity_label_en-US" xlink:label="lab_us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Line of Credit Facility, Maximum Borrowing Capacity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity" xlink:to="lab_us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxDisclosureAbstract_label_en-US" xlink:label="lab_us-gaap_IncomeTaxDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Income Tax Disclosure [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxDisclosureAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncomeTaxDisclosureAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxDisclosureAbstract" xlink:to="lab_us-gaap_IncomeTaxDisclosureAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredTaxLiabilitiesPropertyPlantAndEquipment_df79527a-4963-4653-9464-bb0ebc5b6c81_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxLiabilitiesPropertyPlantAndEquipment" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Depreciation</link:label>
    <link:label id="lab_us-gaap_DeferredTaxLiabilitiesPropertyPlantAndEquipment_label_en-US" xlink:label="lab_us-gaap_DeferredTaxLiabilitiesPropertyPlantAndEquipment" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Tax Liabilities, Property, Plant and Equipment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxLiabilitiesPropertyPlantAndEquipment" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DeferredTaxLiabilitiesPropertyPlantAndEquipment"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredTaxLiabilitiesPropertyPlantAndEquipment" xlink:to="lab_us-gaap_DeferredTaxLiabilitiesPropertyPlantAndEquipment" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsScheduleOfHistoricalClaimsDurationTableTextBlock_049b87b4-3f5a-4084-b72a-6de4acad53c3_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsScheduleOfHistoricalClaimsDurationTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Historical Claims Duration</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsScheduleOfHistoricalClaimsDurationTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsScheduleOfHistoricalClaimsDurationTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Schedule of Historical Claims Duration [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsScheduleOfHistoricalClaimsDurationTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortdurationInsuranceContractsScheduleOfHistoricalClaimsDurationTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsScheduleOfHistoricalClaimsDurationTableTextBlock" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsScheduleOfHistoricalClaimsDurationTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ValuationAllowancesAndReservesDeductions_cb2ecc40-4743-41b9-9581-5a32fd304fb4_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_ValuationAllowancesAndReservesDeductions" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Amounts written off</link:label>
    <link:label id="lab_us-gaap_ValuationAllowancesAndReservesDeductions_label_en-US" xlink:label="lab_us-gaap_ValuationAllowancesAndReservesDeductions" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-09, Valuation Allowances and Reserves, Deduction</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ValuationAllowancesAndReservesDeductions" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ValuationAllowancesAndReservesDeductions"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ValuationAllowancesAndReservesDeductions" xlink:to="lab_us-gaap_ValuationAllowancesAndReservesDeductions" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsForProceedsFromOtherInvestingActivities_8b892b07-3ee1-4a32-a13b-6cef5e86c681_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsForProceedsFromOtherInvestingActivities" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other, net</link:label>
    <link:label id="lab_us-gaap_PaymentsForProceedsFromOtherInvestingActivities_label_en-US" xlink:label="lab_us-gaap_PaymentsForProceedsFromOtherInvestingActivities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Payments for (Proceeds from) Other Investing Activities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsForProceedsFromOtherInvestingActivities" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PaymentsForProceedsFromOtherInvestingActivities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsForProceedsFromOtherInvestingActivities" xlink:to="lab_us-gaap_PaymentsForProceedsFromOtherInvestingActivities" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_RangeMember_da8d0057-7363-4691-9dc9-2c817e7a3076_terseLabel_en-US" xlink:label="lab_srt_RangeMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statistical Measurement [Domain]</link:label>
    <link:label id="lab_srt_RangeMember_label_en-US" xlink:label="lab_srt_RangeMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statistical Measurement [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_RangeMember" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_RangeMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_RangeMember" xlink:to="lab_srt_RangeMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain_a7bfd7a1-0754-4511-bcd3-3efff878fef8_terseLabel_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Indefinite-Lived Intangible Assets, Major Class Name [Domain]</link:label>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain_label_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Indefinite-Lived Intangible Assets, Major Class Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:to="lab_us-gaap_IndefiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearSix_e08a87d3-e390-408d-835e-c475e49c8791_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearSix" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Year 6</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearSix_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearSix" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Historical Claims Duration, Year Six</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearSix" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearSix"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearSix" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearSix" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_LossPortfolioTransferMember_0d47cbd8-5636-406d-99f7-6b0056c55971_terseLabel_en-US" xlink:label="lab_skwd_LossPortfolioTransferMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Loss Portfolio transfer</link:label>
    <link:label id="lab_skwd_LossPortfolioTransferMember_label_en-US" xlink:label="lab_skwd_LossPortfolioTransferMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Loss Portfolio transfer [Member]</link:label>
    <link:label id="lab_skwd_LossPortfolioTransferMember_documentation_en-US" xlink:label="lab_skwd_LossPortfolioTransferMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Loss Portfolio transfer</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_LossPortfolioTransferMember" xlink:href="skwd-20221231.xsd#skwd_LossPortfolioTransferMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_LossPortfolioTransferMember" xlink:to="lab_skwd_LossPortfolioTransferMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_IndirectLoansAndLoanCollateralMember_d97f94dd-1de7-4341-a287-3e59851b26eb_verboseLabel_en-US" xlink:label="lab_skwd_IndirectLoansAndLoanCollateralMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Indirect loans</link:label>
    <link:label id="lab_skwd_IndirectLoansAndLoanCollateralMember_932aa111-191d-4a25-b659-d884e85832d6_terseLabel_en-US" xlink:label="lab_skwd_IndirectLoansAndLoanCollateralMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment in indirect loans and loan collateral</link:label>
    <link:label id="lab_skwd_IndirectLoansAndLoanCollateralMember_label_en-US" xlink:label="lab_skwd_IndirectLoansAndLoanCollateralMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Indirect Loans and Loan Collateral [Member]</link:label>
    <link:label id="lab_skwd_IndirectLoansAndLoanCollateralMember_documentation_en-US" xlink:label="lab_skwd_IndirectLoansAndLoanCollateralMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Indirect Loans and Loan Collateral</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_IndirectLoansAndLoanCollateralMember" xlink:href="skwd-20221231.xsd#skwd_IndirectLoansAndLoanCollateralMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_IndirectLoansAndLoanCollateralMember" xlink:to="lab_skwd_IndirectLoansAndLoanCollateralMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities_0d1c5181-1ca9-4e7b-b5c1-c71cc035c46e_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Sales and maturities of investment securities</link:label>
    <link:label id="lab_us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities_label_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Proceeds from Sale and Maturity of Marketable Securities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities" xlink:to="lab_us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract_label_en-US" xlink:label="lab_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Payment Arrangement [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract" xlink:to="lab_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetIncomeLoss_45c0555e-7f8c-4266-b332-a6c5ffde596f_totalLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net income</link:label>
    <link:label id="lab_us-gaap_NetIncomeLoss_772f67b1-5eb7-43d9-9a42-c84abfad81f2_terseLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net income</link:label>
    <link:label id="lab_us-gaap_NetIncomeLoss_label_en-US" xlink:label="lab_us-gaap_NetIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net Income (Loss) Attributable to Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetIncomeLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetIncomeLoss" xlink:to="lab_us-gaap_NetIncomeLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue_69257cbb-aa76-4c65-bd8d-3e8cf752752a_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Due after one year through five years</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Fair Value, Maturity, Allocated and Single Maturity Date, after Year One Through Five</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CumulativeEffectPeriodOfAdoptionAxis_8595b547-591e-4b62-98d3-c0cee55ae2ed_terseLabel_en-US" xlink:label="lab_srt_CumulativeEffectPeriodOfAdoptionAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cumulative Effect, Period of Adoption [Axis]</link:label>
    <link:label id="lab_srt_CumulativeEffectPeriodOfAdoptionAxis_label_en-US" xlink:label="lab_srt_CumulativeEffectPeriodOfAdoptionAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cumulative Effect, Period of Adoption [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_CumulativeEffectPeriodOfAdoptionAxis" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_CumulativeEffectPeriodOfAdoptionAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_CumulativeEffectPeriodOfAdoptionAxis" xlink:to="lab_srt_CumulativeEffectPeriodOfAdoptionAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubsequentEventTypeAxis_7302337d-61ad-459e-af8f-4ba69655d2d3_terseLabel_en-US" xlink:label="lab_us-gaap_SubsequentEventTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subsequent Event Type [Axis]</link:label>
    <link:label id="lab_us-gaap_SubsequentEventTypeAxis_label_en-US" xlink:label="lab_us-gaap_SubsequentEventTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subsequent Event Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsequentEventTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SubsequentEventTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsequentEventTypeAxis" xlink:to="lab_us-gaap_SubsequentEventTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_UnderwritingAcquisitionAndInsuranceExpensesTextBlock_471b3664-0cb5-436d-b92c-394d6a75e500_terseLabel_en-US" xlink:label="lab_skwd_UnderwritingAcquisitionAndInsuranceExpensesTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Underwriting, Acquisition and Insurance Expenses</link:label>
    <link:label id="lab_skwd_UnderwritingAcquisitionAndInsuranceExpensesTextBlock_label_en-US" xlink:label="lab_skwd_UnderwritingAcquisitionAndInsuranceExpensesTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Underwriting, Acquisition and Insurance Expenses [Text Block]</link:label>
    <link:label id="lab_skwd_UnderwritingAcquisitionAndInsuranceExpensesTextBlock_documentation_en-US" xlink:label="lab_skwd_UnderwritingAcquisitionAndInsuranceExpensesTextBlock" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Underwriting, Acquisition and Insurance Expenses</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_UnderwritingAcquisitionAndInsuranceExpensesTextBlock" xlink:href="skwd-20221231.xsd#skwd_UnderwritingAcquisitionAndInsuranceExpensesTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_UnderwritingAcquisitionAndInsuranceExpensesTextBlock" xlink:to="lab_skwd_UnderwritingAcquisitionAndInsuranceExpensesTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_StatementScenarioAxis_569b02e7-5626-4bbe-b8c9-9a7151400f09_terseLabel_en-US" xlink:label="lab_srt_StatementScenarioAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Scenario [Axis]</link:label>
    <link:label id="lab_srt_StatementScenarioAxis_label_en-US" xlink:label="lab_srt_StatementScenarioAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Scenario [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_StatementScenarioAxis" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_StatementScenarioAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_StatementScenarioAxis" xlink:to="lab_srt_StatementScenarioAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract_6c2e7147-97d9-4e98-a6ff-9aeca678cc8f_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AssetsFairValueDisclosure_0aafaf78-8e76-4a6c-bbfe-2ed9b9e2e52c_totalLabel_en-US" xlink:label="lab_us-gaap_AssetsFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total assets measured at fair value</link:label>
    <link:label id="lab_us-gaap_AssetsFairValueDisclosure_label_en-US" xlink:label="lab_us-gaap_AssetsFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Assets, Fair Value Disclosure</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetsFairValueDisclosure" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AssetsFairValueDisclosure"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssetsFairValueDisclosure" xlink:to="lab_us-gaap_AssetsFairValueDisclosure" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationTable_8a706d68-67ff-479b-a362-264a0425add4_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Historical Claims Duration [Table]</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationTable_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Historical Claims Duration [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationTable" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LesseeOperatingLeasesTextBlock_55ef476c-aa04-4b90-8d8e-eeb945d08a9d_terseLabel_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeasesTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Leases</link:label>
    <link:label id="lab_us-gaap_LesseeOperatingLeasesTextBlock_label_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeasesTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Lessee, Operating Leases [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeasesTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LesseeOperatingLeasesTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LesseeOperatingLeasesTextBlock" xlink:to="lab_us-gaap_LesseeOperatingLeasesTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PlanNameAxis_fbc8e38e-4f0d-4ca2-b296-185abb463244_terseLabel_en-US" xlink:label="lab_us-gaap_PlanNameAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Plan Name [Axis]</link:label>
    <link:label id="lab_us-gaap_PlanNameAxis_label_en-US" xlink:label="lab_us-gaap_PlanNameAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Plan Name [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PlanNameAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PlanNameAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PlanNameAxis" xlink:to="lab_us-gaap_PlanNameAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ContractWithCustomerAssetNet_3f9e9ad3-72eb-4935-9c26-0661121e6f01_terseLabel_en-US" xlink:label="lab_us-gaap_ContractWithCustomerAssetNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Contract asset</link:label>
    <link:label id="lab_us-gaap_ContractWithCustomerAssetNet_label_en-US" xlink:label="lab_us-gaap_ContractWithCustomerAssetNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Contract with Customer, Asset, after Allowance for Credit Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ContractWithCustomerAssetNet" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ContractWithCustomerAssetNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ContractWithCustomerAssetNet" xlink:to="lab_us-gaap_ContractWithCustomerAssetNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPremiumsWritten_499c00cb-0f1f-4960-81db-1039d79debd5_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net premiums written</link:label>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPremiumsWritten_label_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-18, Supplemental Information, Property-Casualty Insurance Underwriters, Premium Written</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPremiumsWritten" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPremiumsWritten"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPremiumsWritten" xlink:to="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPremiumsWritten" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_RandallQuilterRQBermudaSACLtdMember_02274134-4a12-4885-84ed-28f00d4cf98b_terseLabel_en-US" xlink:label="lab_skwd_RandallQuilterRQBermudaSACLtdMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Randall &amp; Quilter (R&amp;Q Bermuda (SAC) Ltd)</link:label>
    <link:label id="lab_skwd_RandallQuilterRQBermudaSACLtdMember_label_en-US" xlink:label="lab_skwd_RandallQuilterRQBermudaSACLtdMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Randall &amp; Quilter (R&amp;Q Bermuda (SAC) Ltd) [Member]</link:label>
    <link:label id="lab_skwd_RandallQuilterRQBermudaSACLtdMember_documentation_en-US" xlink:label="lab_skwd_RandallQuilterRQBermudaSACLtdMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Randall &amp; Quilter (R&amp;Q Bermuda (SAC) Ltd)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RandallQuilterRQBermudaSACLtdMember" xlink:href="skwd-20221231.xsd#skwd_RandallQuilterRQBermudaSACLtdMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_RandallQuilterRQBermudaSACLtdMember" xlink:to="lab_skwd_RandallQuilterRQBermudaSACLtdMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAwardedForfeited_77ed93d5-9f4e-4686-949a-e1fed2c3b14c_terseLabel_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAwardedForfeited" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stock notes receivable, stock awards forfeited (in shares)</link:label>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAwardedForfeited_label_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAwardedForfeited" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Number of Shares Awarded, Forfeited</link:label>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAwardedForfeited_documentation_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAwardedForfeited" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Number of Shares Awarded, Forfeited</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAwardedForfeited" xlink:href="skwd-20221231.xsd#skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAwardedForfeited"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAwardedForfeited" xlink:to="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAwardedForfeited" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NumberOfOperatingSegments_b03c8641-02f5-4d66-863e-0a45396acd8c_terseLabel_en-US" xlink:label="lab_us-gaap_NumberOfOperatingSegments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Number of operating segments</link:label>
    <link:label id="lab_us-gaap_NumberOfOperatingSegments_label_en-US" xlink:label="lab_us-gaap_NumberOfOperatingSegments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Number of Operating Segments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NumberOfOperatingSegments" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NumberOfOperatingSegments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NumberOfOperatingSegments" xlink:to="lab_us-gaap_NumberOfOperatingSegments" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_JVMPreferredEquityFundLLCMember_a5582ddc-ba63-47fa-9f22-b8de0f58548e_terseLabel_en-US" xlink:label="lab_skwd_JVMPreferredEquityFundLLCMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">JVM Preferred Equity Fund, LLC</link:label>
    <link:label id="lab_skwd_JVMPreferredEquityFundLLCMember_label_en-US" xlink:label="lab_skwd_JVMPreferredEquityFundLLCMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">JVM Preferred Equity Fund, LLC [Member]</link:label>
    <link:label id="lab_skwd_JVMPreferredEquityFundLLCMember_documentation_en-US" xlink:label="lab_skwd_JVMPreferredEquityFundLLCMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">JVM Preferred Equity Fund, LLC</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_JVMPreferredEquityFundLLCMember" xlink:href="skwd-20221231.xsd#skwd_JVMPreferredEquityFundLLCMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_JVMPreferredEquityFundLLCMember" xlink:to="lab_skwd_JVMPreferredEquityFundLLCMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPaidClaimsAndClaimsAdjustmentExpense_c6cbbc29-dc9b-47b8-ba06-e0a7954b1c0f_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPaidClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Paid claims and claim adjustment expenses</link:label>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPaidClaimsAndClaimsAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPaidClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-18, Supplemental Information, Property-Casualty Insurance Underwriters, Paid Claim and Claim Adjustment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPaidClaimsAndClaimsAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPaidClaimsAndClaimsAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPaidClaimsAndClaimsAdjustmentExpense" xlink:to="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPaidClaimsAndClaimsAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementOfCashFlowsAbstract_label_en-US" xlink:label="lab_us-gaap_StatementOfCashFlowsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statement of Cash Flows [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementOfCashFlowsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StatementOfCashFlowsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementOfCashFlowsAbstract" xlink:to="lab_us-gaap_StatementOfCashFlowsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueInputsLevel1Member_4d7ab65a-ea32-4f9d-8341-a2c22a1be426_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel1Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value, Inputs, Level 1</link:label>
    <link:label id="lab_us-gaap_FairValueInputsLevel1Member_label_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel1Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value, Inputs, Level 1 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueInputsLevel1Member" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FairValueInputsLevel1Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueInputsLevel1Member" xlink:to="lab_us-gaap_FairValueInputsLevel1Member" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ConsumerDiscretionarySectorMember_e8ca0dec-fe41-4ff9-98c0-abd9ae8b4cc8_terseLabel_en-US" xlink:label="lab_skwd_ConsumerDiscretionarySectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Consumer discretionary</link:label>
    <link:label id="lab_skwd_ConsumerDiscretionarySectorMember_label_en-US" xlink:label="lab_skwd_ConsumerDiscretionarySectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Consumer Discretionary Sector [Member]</link:label>
    <link:label id="lab_skwd_ConsumerDiscretionarySectorMember_documentation_en-US" xlink:label="lab_skwd_ConsumerDiscretionarySectorMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Consumer Discretionary Sector</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ConsumerDiscretionarySectorMember" xlink:href="skwd-20221231.xsd#skwd_ConsumerDiscretionarySectorMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ConsumerDiscretionarySectorMember" xlink:to="lab_skwd_ConsumerDiscretionarySectorMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsAccidentYear2014Member_5f4cf469-42e3-4cd1-a679-95f9c59197b8_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsAccidentYear2014Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accident Year 2014</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsAccidentYear2014Member_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsAccidentYear2014Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Accident Year 2014 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsAccidentYear2014Member" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortdurationInsuranceContractsAccidentYear2014Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsAccidentYear2014Member" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsAccidentYear2014Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NewAccountingPronouncementsOrChangeInAccountingPrincipleLineItems_2efd0fbc-9643-4c7c-b9f3-e4dc6c05da9d_terseLabel_en-US" xlink:label="lab_us-gaap_NewAccountingPronouncementsOrChangeInAccountingPrincipleLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">New Accounting Pronouncements or Change in Accounting Principle [Line Items]</link:label>
    <link:label id="lab_us-gaap_NewAccountingPronouncementsOrChangeInAccountingPrincipleLineItems_label_en-US" xlink:label="lab_us-gaap_NewAccountingPronouncementsOrChangeInAccountingPrincipleLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">New Accounting Pronouncements or Change in Accounting Principle [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NewAccountingPronouncementsOrChangeInAccountingPrincipleLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NewAccountingPronouncementsOrChangeInAccountingPrincipleLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NewAccountingPronouncementsOrChangeInAccountingPrincipleLineItems" xlink:to="lab_us-gaap_NewAccountingPronouncementsOrChangeInAccountingPrincipleLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities_76394701-4b73-4c82-b889-cdff3f54ad43_totalLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net cash provided by operating activities</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net Cash Provided by (Used in) Operating Activities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetCashProvidedByUsedInOperatingActivities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities" xlink:to="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccountsNotesAndLoansReceivableLineItems_dea52c07-10c5-445f-bccb-d651a64a44af_terseLabel_en-US" xlink:label="lab_us-gaap_AccountsNotesAndLoansReceivableLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accounts, Notes, Loans and Financing Receivable [Line Items]</link:label>
    <link:label id="lab_us-gaap_AccountsNotesAndLoansReceivableLineItems_label_en-US" xlink:label="lab_us-gaap_AccountsNotesAndLoansReceivableLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accounts, Notes, Loans and Financing Receivable [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccountsNotesAndLoansReceivableLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AccountsNotesAndLoansReceivableLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccountsNotesAndLoansReceivableLineItems" xlink:to="lab_us-gaap_AccountsNotesAndLoansReceivableLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTableTextBlock_0db2a8fb-c94c-4a6b-8586-fa834b6fc32f_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Short-Duration Insurance Contracts</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Claims Development [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTableTextBlock" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RelatedPartyTransactionDomain_e78e93ff-3912-44f0-8fe9-59c0efbf9b05_terseLabel_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Related Party Transaction [Domain]</link:label>
    <link:label id="lab_us-gaap_RelatedPartyTransactionDomain_label_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Related Party Transaction [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RelatedPartyTransactionDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RelatedPartyTransactionDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RelatedPartyTransactionDomain" xlink:to="lab_us-gaap_RelatedPartyTransactionDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems_db63f55b-9179-407b-b7f4-8144cb691346_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Equity Method Investments [Line Items]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems_label_en-US" xlink:label="lab_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Equity Method Investments [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfEquityMethodInvestmentsLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems" xlink:to="lab_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReceivablesAbstract_label_en-US" xlink:label="lab_us-gaap_ReceivablesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Receivables [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReceivablesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ReceivablesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReceivablesAbstract" xlink:to="lab_us-gaap_ReceivablesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentAnnualReport_892da127-3832-4194-9be1-72191a7e270e_terseLabel_en-US" xlink:label="lab_dei_DocumentAnnualReport" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Document Annual Report</link:label>
    <link:label id="lab_dei_DocumentAnnualReport_label_en-US" xlink:label="lab_dei_DocumentAnnualReport" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Document Annual Report</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentAnnualReport" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_DocumentAnnualReport"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentAnnualReport" xlink:to="lab_dei_DocumentAnnualReport" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_LegalEntityAxis_53e52ec8-c8ef-41ab-854d-f0607bdfcc47_terseLabel_en-US" xlink:label="lab_dei_LegalEntityAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Legal Entity [Axis]</link:label>
    <link:label id="lab_dei_LegalEntityAxis_label_en-US" xlink:label="lab_dei_LegalEntityAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Legal Entity [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_LegalEntityAxis" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_LegalEntityAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_LegalEntityAxis" xlink:to="lab_dei_LegalEntityAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LoansNotesTradeAndOtherReceivablesDisclosureTextBlock_b19b5c1d-90d8-4016-a793-d5d12b88b54a_terseLabel_en-US" xlink:label="lab_us-gaap_LoansNotesTradeAndOtherReceivablesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Mortgage Loans</link:label>
    <link:label id="lab_us-gaap_LoansNotesTradeAndOtherReceivablesDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_LoansNotesTradeAndOtherReceivablesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Loans, Notes, Trade and Other Receivables Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LoansNotesTradeAndOtherReceivablesDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LoansNotesTradeAndOtherReceivablesDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LoansNotesTradeAndOtherReceivablesDisclosureTextBlock" xlink:to="lab_us-gaap_LoansNotesTradeAndOtherReceivablesDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember_6006047a-6d0e-4555-af3d-49f951080e6c_terseLabel_en-US" xlink:label="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SUA fee income</link:label>
    <link:label id="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember_label_en-US" xlink:label="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Managing General Insurance Agent And Broker, Fee Icome [Member]</link:label>
    <link:label id="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember_documentation_en-US" xlink:label="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Managing General Insurance Agent And Broker, Fee Icome</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember" xlink:href="skwd-20221231.xsd#skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember" xlink:to="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerFeeIcomeMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PreferredStockConvertibleConversionPrice_e8561658-be0f-4c8a-b15a-d8f8b0773e53_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockConvertibleConversionPrice" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred stock, convertible, conversion price (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_PreferredStockConvertibleConversionPrice_label_en-US" xlink:label="lab_us-gaap_PreferredStockConvertibleConversionPrice" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred Stock, Convertible, Conversion Price</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockConvertibleConversionPrice" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PreferredStockConvertibleConversionPrice"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PreferredStockConvertibleConversionPrice" xlink:to="lab_us-gaap_PreferredStockConvertibleConversionPrice" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss_08ffe774-e5b6-4a9f-82e5-0576f75eff04_negatedTerseLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">12 Months or More</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss_label_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Continuous Unrealized Loss Position, 12 Months or Longer, Accumulated Loss</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss_documentation_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Continuous Unrealized Loss Position, 12 Months or Longer, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:href="skwd-20221231.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:to="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProfessionalLiabilityInsuranceMember_ad4d64bf-a192-4eec-934b-bc109b18a45a_terseLabel_en-US" xlink:label="lab_us-gaap_ProfessionalLiabilityInsuranceMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Professional Liability</link:label>
    <link:label id="lab_us-gaap_ProfessionalLiabilityInsuranceMember_label_en-US" xlink:label="lab_us-gaap_ProfessionalLiabilityInsuranceMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Professional Liability Insurance [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProfessionalLiabilityInsuranceMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ProfessionalLiabilityInsuranceMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProfessionalLiabilityInsuranceMember" xlink:to="lab_us-gaap_ProfessionalLiabilityInsuranceMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1_22558629-4283-4aa0-bcef-fe177d6fc072_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Prior years</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Claims Paid, Prior Years</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesIndustryMember_4fffa4e4-43f8-457b-ba16-13af7ad95010_terseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesIndustryMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Industry Sector [Domain]</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesIndustryMember_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesIndustryMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Industry Sector [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesIndustryMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EquitySecuritiesIndustryMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesIndustryMember" xlink:to="lab_us-gaap_EquitySecuritiesIndustryMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAbstract_fcba6304-9682-4611-9e2c-438a3b827de4_terseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Held-to-maturity, fair value</link:label>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAbstract_label_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Held-to-Maturity, Continuous Unrealized Loss Position [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAbstract" xlink:to="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesFinancedReturnedAmount_d86be5d9-3663-4cbe-94d2-e47996bc8e68_terseLabel_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesFinancedReturnedAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stock notes receivable, stock awards returned</link:label>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesFinancedReturnedAmount_label_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesFinancedReturnedAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Number of Shares Financed, Returned, Amount</link:label>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesFinancedReturnedAmount_documentation_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesFinancedReturnedAmount" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Number of Shares Financed, Returned, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesFinancedReturnedAmount" xlink:href="skwd-20221231.xsd#skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesFinancedReturnedAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesFinancedReturnedAmount" xlink:to="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesFinancedReturnedAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentTextBlock_9eed2feb-91dd-4771-8675-ac2706322cfd_terseLabel_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Property, Plant and Equipment</link:label>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentTextBlock_label_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Property, Plant and Equipment [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PropertyPlantAndEquipmentTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentTextBlock" xlink:to="lab_us-gaap_PropertyPlantAndEquipmentTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PreferredStockSharesIssued_3cb850c3-5669-4b3f-acf9-32764b3dc92c_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockSharesIssued" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred stock, shares issued (in shares)</link:label>
    <link:label id="lab_us-gaap_PreferredStockSharesIssued_label_en-US" xlink:label="lab_us-gaap_PreferredStockSharesIssued" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred Stock, Shares Issued</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockSharesIssued" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PreferredStockSharesIssued"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PreferredStockSharesIssued" xlink:to="lab_us-gaap_PreferredStockSharesIssued" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesBeforeReclassificationAdjustmentsTax_9de0f7c6-32e5-4a14-b620-8c9b69e5ca7b_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesBeforeReclassificationAdjustmentsTax" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred income taxes</link:label>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesBeforeReclassificationAdjustmentsTax_label_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesBeforeReclassificationAdjustmentsTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">OCI, Debt Securities, Available-for-Sale, Gain (Loss), before Adjustment, Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesBeforeReclassificationAdjustmentsTax" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesBeforeReclassificationAdjustmentsTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesBeforeReclassificationAdjustmentsTax" xlink:to="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesBeforeReclassificationAdjustmentsTax" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward_31da8fee-e1ab-4405-a322-96fcf6a91def_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Number&#160;of Common&#160;Shares</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Nonvested, Number of Shares [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConcentrationRiskBenchmarkDomain_850afee8-9b82-4603-b562-ff6135c022f8_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskBenchmarkDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Concentration Risk Benchmark [Domain]</link:label>
    <link:label id="lab_us-gaap_ConcentrationRiskBenchmarkDomain_label_en-US" xlink:label="lab_us-gaap_ConcentrationRiskBenchmarkDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Concentration Risk Benchmark [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConcentrationRiskBenchmarkDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ConcentrationRiskBenchmarkDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConcentrationRiskBenchmarkDomain" xlink:to="lab_us-gaap_ConcentrationRiskBenchmarkDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromEquityMethodInvestmentDividendsOrDistributionsReturnOfCapital_b86b8350-fc19-459f-85b2-2e77656ca3d6_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromEquityMethodInvestmentDividendsOrDistributionsReturnOfCapital" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Distributions from equity method investments</link:label>
    <link:label id="lab_us-gaap_ProceedsFromEquityMethodInvestmentDividendsOrDistributionsReturnOfCapital_label_en-US" xlink:label="lab_us-gaap_ProceedsFromEquityMethodInvestmentDividendsOrDistributionsReturnOfCapital" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Proceeds from Equity Method Investment, Distribution, Return of Capital</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromEquityMethodInvestmentDividendsOrDistributionsReturnOfCapital" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ProceedsFromEquityMethodInvestmentDividendsOrDistributionsReturnOfCapital"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromEquityMethodInvestmentDividendsOrDistributionsReturnOfCapital" xlink:to="lab_us-gaap_ProceedsFromEquityMethodInvestmentDividendsOrDistributionsReturnOfCapital" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_InvestmentInBankHoldingCompanyMember_a4aebb32-b9c0-4cb4-a0da-ab91f5eb928b_terseLabel_en-US" xlink:label="lab_skwd_InvestmentInBankHoldingCompanyMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment in Bank Holding Company</link:label>
    <link:label id="lab_skwd_InvestmentInBankHoldingCompanyMember_label_en-US" xlink:label="lab_skwd_InvestmentInBankHoldingCompanyMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment in Bank Holding Company [Member]</link:label>
    <link:label id="lab_skwd_InvestmentInBankHoldingCompanyMember_documentation_en-US" xlink:label="lab_skwd_InvestmentInBankHoldingCompanyMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment in Bank Holding Company</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_InvestmentInBankHoldingCompanyMember" xlink:href="skwd-20221231.xsd#skwd_InvestmentInBankHoldingCompanyMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_InvestmentInBankHoldingCompanyMember" xlink:to="lab_skwd_InvestmentInBankHoldingCompanyMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_cdd6b5c3-c97e-44bc-ad05-cd129de33c8b_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Less than 12 Months</link:label>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_label_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Held-to-Maturity, Continuous Unrealized Loss Position, Less than 12 Months, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:to="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtDisclosureTextBlock_09dfc31e-daad-46f1-90bc-dbd807b54608_terseLabel_en-US" xlink:label="lab_us-gaap_DebtDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subordinated Debt</link:label>
    <link:label id="lab_us-gaap_DebtDisclosureTextBlock_2b8ce5cd-a678-4913-b043-2848b8339859_verboseLabel_en-US" xlink:label="lab_us-gaap_DebtDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Notes Payable</link:label>
    <link:label id="lab_us-gaap_DebtDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_DebtDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtDisclosureTextBlock" xlink:to="lab_us-gaap_DebtDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ProductsAndServicesDomain_1e01714c-3248-497b-b7ee-d78a03ab07a4_terseLabel_en-US" xlink:label="lab_srt_ProductsAndServicesDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Product and Service [Domain]</link:label>
    <link:label id="lab_srt_ProductsAndServicesDomain_label_en-US" xlink:label="lab_srt_ProductsAndServicesDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Product and Service [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ProductsAndServicesDomain" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_ProductsAndServicesDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ProductsAndServicesDomain" xlink:to="lab_srt_ProductsAndServicesDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityShellCompany_f4c33be2-1035-40c2-94cd-501eb6083209_terseLabel_en-US" xlink:label="lab_dei_EntityShellCompany" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Shell Company</link:label>
    <link:label id="lab_dei_EntityShellCompany_label_en-US" xlink:label="lab_dei_EntityShellCompany" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Shell Company</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityShellCompany" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityShellCompany"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityShellCompany" xlink:to="lab_dei_EntityShellCompany" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRetentionPolicyTableTextBlock_d1f1a39f-14d6-41f5-b796-93d8d298a159_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRetentionPolicyTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Retention</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRetentionPolicyTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRetentionPolicyTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Retention [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRetentionPolicyTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ReinsuranceRetentionPolicyTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRetentionPolicyTableTextBlock" xlink:to="lab_us-gaap_ReinsuranceRetentionPolicyTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DirectPremiumsEarned_b6d4e01f-e066-402d-a6e6-443887c5299c_terseLabel_en-US" xlink:label="lab_us-gaap_DirectPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Direct premiums</link:label>
    <link:label id="lab_us-gaap_DirectPremiumsEarned_label_en-US" xlink:label="lab_us-gaap_DirectPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Direct Premiums Earned</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DirectPremiumsEarned" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DirectPremiumsEarned"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DirectPremiumsEarned" xlink:to="lab_us-gaap_DirectPremiumsEarned" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentIncomeTextBlock_85c7c019-da5b-43c8-bea4-f4ad7974ce03_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentIncomeTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment Income</link:label>
    <link:label id="lab_us-gaap_InvestmentIncomeTextBlock_label_en-US" xlink:label="lab_us-gaap_InvestmentIncomeTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment Income [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentIncomeTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_InvestmentIncomeTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentIncomeTextBlock" xlink:to="lab_us-gaap_InvestmentIncomeTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConcentrationRiskTable_2e3a5a38-5bdb-4a3e-acd6-fc0723c63ebc_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Concentration Risk [Table]</link:label>
    <link:label id="lab_us-gaap_ConcentrationRiskTable_label_en-US" xlink:label="lab_us-gaap_ConcentrationRiskTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Concentration Risk [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConcentrationRiskTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ConcentrationRiskTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConcentrationRiskTable" xlink:to="lab_us-gaap_ConcentrationRiskTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueNextTwelveMonths_e58adde1-62f9-4681-b671-a1278026dc57_terseLabel_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueNextTwelveMonths" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">2023</link:label>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueNextTwelveMonths_label_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueNextTwelveMonths" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Lessee, Operating Lease, Liability, to be Paid, Year One</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueNextTwelveMonths" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueNextTwelveMonths"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueNextTwelveMonths" xlink:to="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueNextTwelveMonths" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableforSaleUnrealizedLossPositionAbstract_c9147929-b2b1-45c2-9efc-f4f03217ca70_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableforSaleUnrealizedLossPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Available for sale, fair value</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableforSaleUnrealizedLossPositionAbstract_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableforSaleUnrealizedLossPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Unrealized Loss Position [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableforSaleUnrealizedLossPositionAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableforSaleUnrealizedLossPositionAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableforSaleUnrealizedLossPositionAbstract" xlink:to="lab_us-gaap_DebtSecuritiesAvailableforSaleUnrealizedLossPositionAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinancialInstrumentAxis_86cc4810-aec8-400c-9c60-5cec11b0c0b4_terseLabel_en-US" xlink:label="lab_us-gaap_FinancialInstrumentAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Financial Instrument [Axis]</link:label>
    <link:label id="lab_us-gaap_FinancialInstrumentAxis_label_en-US" xlink:label="lab_us-gaap_FinancialInstrumentAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Financial Instrument [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancialInstrumentAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FinancialInstrumentAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancialInstrumentAxis" xlink:to="lab_us-gaap_FinancialInstrumentAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ComponentsOfDeferredTaxLiabilitiesAbstract_37b7d15b-050a-4360-a6a9-060a93ae175f_terseLabel_en-US" xlink:label="lab_us-gaap_ComponentsOfDeferredTaxLiabilitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred tax liabilities:</link:label>
    <link:label id="lab_us-gaap_ComponentsOfDeferredTaxLiabilitiesAbstract_label_en-US" xlink:label="lab_us-gaap_ComponentsOfDeferredTaxLiabilitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Components of Deferred Tax Liabilities [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ComponentsOfDeferredTaxLiabilitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ComponentsOfDeferredTaxLiabilitiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ComponentsOfDeferredTaxLiabilitiesAbstract" xlink:to="lab_us-gaap_ComponentsOfDeferredTaxLiabilitiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ValuationAllowancesAndReservesDomain_30998a00-1ef0-4726-8e27-df41bf8cecf2_terseLabel_en-US" xlink:label="lab_us-gaap_ValuationAllowancesAndReservesDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-09, Valuation Allowances and Reserves [Domain]</link:label>
    <link:label id="lab_us-gaap_ValuationAllowancesAndReservesDomain_label_en-US" xlink:label="lab_us-gaap_ValuationAllowancesAndReservesDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-09, Valuation Allowances and Reserves [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ValuationAllowancesAndReservesDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ValuationAllowancesAndReservesDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ValuationAllowancesAndReservesDomain" xlink:to="lab_us-gaap_ValuationAllowancesAndReservesDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_AffiliatedEntityMember_eb961287-0a21-4ccd-ac9e-b50a0c1d68ee_terseLabel_en-US" xlink:label="lab_srt_AffiliatedEntityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Affiliated entity</link:label>
    <link:label id="lab_srt_AffiliatedEntityMember_label_en-US" xlink:label="lab_srt_AffiliatedEntityMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Affiliated Entity [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_AffiliatedEntityMember" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_AffiliatedEntityMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_AffiliatedEntityMember" xlink:to="lab_srt_AffiliatedEntityMember" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersAbstract_label_en-US" xlink:label="lab_srt_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-18, Supplemental Information, Property-Casualty Insurance Underwriters [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersAbstract" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersAbstract" xlink:to="lab_srt_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_OtherSectorsMember_4f0e72eb-c3dc-4e4e-b2a9-26584bb7c60f_terseLabel_en-US" xlink:label="lab_skwd_OtherSectorsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other</link:label>
    <link:label id="lab_skwd_OtherSectorsMember_label_en-US" xlink:label="lab_skwd_OtherSectorsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other Sectors [Member]</link:label>
    <link:label id="lab_skwd_OtherSectorsMember_documentation_en-US" xlink:label="lab_skwd_OtherSectorsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other Sectors</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_OtherSectorsMember" xlink:href="skwd-20221231.xsd#skwd_OtherSectorsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_OtherSectorsMember" xlink:to="lab_skwd_OtherSectorsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubsequentEventMember_8bf07313-dc64-4620-a540-c977ebd0f8ed_terseLabel_en-US" xlink:label="lab_us-gaap_SubsequentEventMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subsequent event</link:label>
    <link:label id="lab_us-gaap_SubsequentEventMember_label_en-US" xlink:label="lab_us-gaap_SubsequentEventMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subsequent Event [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsequentEventMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SubsequentEventMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsequentEventMember" xlink:to="lab_us-gaap_SubsequentEventMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_EquitySecuritiesFVNIAccumulatedUnrealizedGain_161c461d-1be4-4654-a9b7-d7cec0a917f2_terseLabel_en-US" xlink:label="lab_skwd_EquitySecuritiesFVNIAccumulatedUnrealizedGain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross Unrealized Gains</link:label>
    <link:label id="lab_skwd_EquitySecuritiesFVNIAccumulatedUnrealizedGain_label_en-US" xlink:label="lab_skwd_EquitySecuritiesFVNIAccumulatedUnrealizedGain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Securities, FV-NI, Accumulated Unrealized Gain</link:label>
    <link:label id="lab_skwd_EquitySecuritiesFVNIAccumulatedUnrealizedGain_documentation_en-US" xlink:label="lab_skwd_EquitySecuritiesFVNIAccumulatedUnrealizedGain" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Securities, FV-NI, Accumulated Unrealized Gain</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_EquitySecuritiesFVNIAccumulatedUnrealizedGain" xlink:href="skwd-20221231.xsd#skwd_EquitySecuritiesFVNIAccumulatedUnrealizedGain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_EquitySecuritiesFVNIAccumulatedUnrealizedGain" xlink:to="lab_skwd_EquitySecuritiesFVNIAccumulatedUnrealizedGain" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentPeriodEndDate_01e2b16e-b69e-484b-b8d8-ff61e74df012_terseLabel_en-US" xlink:label="lab_dei_DocumentPeriodEndDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Document Period End Date</link:label>
    <link:label id="lab_dei_DocumentPeriodEndDate_label_en-US" xlink:label="lab_dei_DocumentPeriodEndDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Document Period End Date</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentPeriodEndDate" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_DocumentPeriodEndDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentPeriodEndDate" xlink:to="lab_dei_DocumentPeriodEndDate" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ShareBasedPaymentArrangementExpenseGross_36366dd8-1c5e-4ddb-8074-4e6a6b46a80c_terseLabel_en-US" xlink:label="lab_skwd_ShareBasedPaymentArrangementExpenseGross" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stock-based compensation expense</link:label>
    <link:label id="lab_skwd_ShareBasedPaymentArrangementExpenseGross_label_en-US" xlink:label="lab_skwd_ShareBasedPaymentArrangementExpenseGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Payment Arrangement, Expense, Gross</link:label>
    <link:label id="lab_skwd_ShareBasedPaymentArrangementExpenseGross_documentation_en-US" xlink:label="lab_skwd_ShareBasedPaymentArrangementExpenseGross" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Payment Arrangement, Expense, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ShareBasedPaymentArrangementExpenseGross" xlink:href="skwd-20221231.xsd#skwd_ShareBasedPaymentArrangementExpenseGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ShareBasedPaymentArrangementExpenseGross" xlink:to="lab_skwd_ShareBasedPaymentArrangementExpenseGross" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DeferredCedingCommission_bf27a8ae-9091-4556-b0c0-c0e0c2b23acd_terseLabel_en-US" xlink:label="lab_skwd_DeferredCedingCommission" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred ceding commission</link:label>
    <link:label id="lab_skwd_DeferredCedingCommission_label_en-US" xlink:label="lab_skwd_DeferredCedingCommission" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Ceding Commission</link:label>
    <link:label id="lab_skwd_DeferredCedingCommission_documentation_en-US" xlink:label="lab_skwd_DeferredCedingCommission" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Ceding Commission</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DeferredCedingCommission" xlink:href="skwd-20221231.xsd#skwd_DeferredCedingCommission"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DeferredCedingCommission" xlink:to="lab_skwd_DeferredCedingCommission" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_SECSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersCededUnearnedPremium_0a475b0c-065b-4ab2-949d-d013fc0f73f2_terseLabel_en-US" xlink:label="lab_skwd_SECSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersCededUnearnedPremium" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ceded unearned premium</link:label>
    <link:label id="lab_skwd_SECSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersCededUnearnedPremium_label_en-US" xlink:label="lab_skwd_SECSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersCededUnearnedPremium" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-18, Supplemental Information, Property-Casualty Insurance Underwriters, Ceded Unearned Premium</link:label>
    <link:label id="lab_skwd_SECSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersCededUnearnedPremium_documentation_en-US" xlink:label="lab_skwd_SECSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersCededUnearnedPremium" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-18, Supplemental Information, Property-Casualty Insurance Underwriters, Ceded Unearned Premium</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_SECSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersCededUnearnedPremium" xlink:href="skwd-20221231.xsd#skwd_SECSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersCededUnearnedPremium"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_SECSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersCededUnearnedPremium" xlink:to="lab_skwd_SECSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersCededUnearnedPremium" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock_c9b6d4aa-663d-4336-babd-b2146943a49c_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Accumulated Other Comprehensive Income (Loss)</link:label>
    <link:label id="lab_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Accumulated Other Comprehensive Income (Loss) [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_Assets_c215ac01-d174-4c9a-aa03-bbc78fb57b48_totalLabel_en-US" xlink:label="lab_us-gaap_Assets" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total assets</link:label>
    <link:label id="lab_us-gaap_Assets_label_en-US" xlink:label="lab_us-gaap_Assets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Assets" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_Assets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Assets" xlink:to="lab_us-gaap_Assets" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearFour_33733ae2-d35e-40e6-8344-e587e33372bf_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearFour" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Year 4</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearFour_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearFour" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Historical Claims Duration, Year Four</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearFour" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearFour"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearFour" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearFour" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareAbstract_05bb85df-325b-48ee-aec1-fed8a955275f_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Per share data:</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareAbstract_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Earnings Per Share [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EarningsPerShareAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareAbstract" xlink:to="lab_us-gaap_EarningsPerShareAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardPayoutPercentage_09bc68d9-8ba2-44d4-9170-fc7d0ca10f04_terseLabel_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardPayoutPercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Award Payout Range</link:label>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardPayoutPercentage_label_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardPayoutPercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Award Payout, Percentage</link:label>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardPayoutPercentage_documentation_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardPayoutPercentage" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Award Payout, Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardPayoutPercentage" xlink:href="skwd-20221231.xsd#skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardPayoutPercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardPayoutPercentage" xlink:to="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardPayoutPercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis_bb5eb9a0-e600-4e20-84af-5f74fcc65b78_terseLabel_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Antidilutive Securities [Axis]</link:label>
    <link:label id="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis_label_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Antidilutive Securities [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis" xlink:to="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PerformanceSharesMember_8f52a8cc-364a-4fd2-bd97-0b4ef7ea0dd9_terseLabel_en-US" xlink:label="lab_us-gaap_PerformanceSharesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Performance condition awards</link:label>
    <link:label id="lab_us-gaap_PerformanceSharesMember_label_en-US" xlink:label="lab_us-gaap_PerformanceSharesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Performance Shares [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PerformanceSharesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PerformanceSharesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PerformanceSharesMember" xlink:to="lab_us-gaap_PerformanceSharesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PreferredStockLiquidationPreference_8f138231-8e3c-453e-9750-085c9a07bf13_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockLiquidationPreference" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred stock, liquidation preference (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_PreferredStockLiquidationPreference_label_en-US" xlink:label="lab_us-gaap_PreferredStockLiquidationPreference" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred Stock, Liquidation Preference Per Share</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockLiquidationPreference" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PreferredStockLiquidationPreference"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PreferredStockLiquidationPreference" xlink:to="lab_us-gaap_PreferredStockLiquidationPreference" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFive_2b9ffa7d-b734-48de-861f-6f753dcb6ad1_terseLabel_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFive" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">2027</link:label>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFive_label_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFive" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Lessee, Operating Lease, Liability, to be Paid, Year Five</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFive" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFive"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFive" xlink:to="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFive" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumsWrittenGross_0f20ea67-ae46-46fe-9f65-a010a137e2c3_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsWrittenGross" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Direct and assumed premiums written</link:label>
    <link:label id="lab_us-gaap_PremiumsWrittenGross_label_en-US" xlink:label="lab_us-gaap_PremiumsWrittenGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Premiums Written, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsWrittenGross" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PremiumsWrittenGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsWrittenGross" xlink:to="lab_us-gaap_PremiumsWrittenGross" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AssetBackedSecuritiesMember_93caf3fa-1c23-44c4-aea0-820da3ed2748_terseLabel_en-US" xlink:label="lab_us-gaap_AssetBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Asset-backed securities</link:label>
    <link:label id="lab_us-gaap_AssetBackedSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_AssetBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Asset-Backed Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetBackedSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AssetBackedSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssetBackedSecuritiesMember" xlink:to="lab_us-gaap_AssetBackedSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_bb99cf77-ce1f-4029-8e85-433812eca137_totalLabel_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Income before income taxes</link:label>
    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_label_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Income (Loss) from Continuing Operations before Income Taxes, Noncontrolling Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:to="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MortgageLoansInProcessOfForeclosureAmount_b6490ce7-0e52-4e27-81de-2e6cc6a66c15_terseLabel_en-US" xlink:label="lab_us-gaap_MortgageLoansInProcessOfForeclosureAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Mortgage loans in foreclosure</link:label>
    <link:label id="lab_us-gaap_MortgageLoansInProcessOfForeclosureAmount_label_en-US" xlink:label="lab_us-gaap_MortgageLoansInProcessOfForeclosureAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Mortgage Loans in Process of Foreclosure, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MortgageLoansInProcessOfForeclosureAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_MortgageLoansInProcessOfForeclosureAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MortgageLoansInProcessOfForeclosureAmount" xlink:to="lab_us-gaap_MortgageLoansInProcessOfForeclosureAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareTextBlock_b9f2dd09-047b-4920-bc4e-9a8db659c547_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Earnings Per Share</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareTextBlock_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Earnings Per Share [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EarningsPerShareTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareTextBlock" xlink:to="lab_us-gaap_EarningsPerShareTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredTaxLiabilitiesOther_b56cd6b1-22a1-4268-8ace-d711e9cacaee_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxLiabilitiesOther" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other</link:label>
    <link:label id="lab_us-gaap_DeferredTaxLiabilitiesOther_label_en-US" xlink:label="lab_us-gaap_DeferredTaxLiabilitiesOther" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Tax Liabilities, Other</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxLiabilitiesOther" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DeferredTaxLiabilitiesOther"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredTaxLiabilitiesOther" xlink:to="lab_us-gaap_DeferredTaxLiabilitiesOther" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_adab4ffe-29f3-49b7-aee7-9a79a59c82ae_negatedPeriodStartLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:role="http://www.xbrl.org/2009/role/negatedPeriodStartLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Less: reinsurance recoverable on unpaid claims, beginning of period</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_891ff35f-bccb-48d1-9c7c-e514620876a3_periodEndLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Plus: reinsurance recoverable on unpaid claims, end of period</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_d62c3cbb-e75e-431f-b81a-07cbcda2938e_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total reinsurance recoverable on unpaid claims</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Recoverable for Unpaid Claims and Claims Adjustments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:to="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillGross_b7006c79-2fff-4071-a413-238a7f028aaa_verboseLabel_en-US" xlink:label="lab_us-gaap_GoodwillGross" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Goodwill, gross balance</link:label>
    <link:label id="lab_us-gaap_GoodwillGross_label_en-US" xlink:label="lab_us-gaap_GoodwillGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Goodwill, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillGross" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_GoodwillGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillGross" xlink:to="lab_us-gaap_GoodwillGross" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_IntangibleAssetDisposals_32ae213f-d662-4110-817c-ff906c3e9cf0_negatedTerseLabel_en-US" xlink:label="lab_skwd_IntangibleAssetDisposals" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Disposals</link:label>
    <link:label id="lab_skwd_IntangibleAssetDisposals_label_en-US" xlink:label="lab_skwd_IntangibleAssetDisposals" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Intangible Asset, Disposals</link:label>
    <link:label id="lab_skwd_IntangibleAssetDisposals_documentation_en-US" xlink:label="lab_skwd_IntangibleAssetDisposals" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Intangible Asset, Disposals</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_IntangibleAssetDisposals" xlink:href="skwd-20221231.xsd#skwd_IntangibleAssetDisposals"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_IntangibleAssetDisposals" xlink:to="lab_skwd_IntangibleAssetDisposals" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CashAndCashEquivalentsPolicyTextBlock_be810c39-d85f-4234-8716-02d7f33fe834_terseLabel_en-US" xlink:label="lab_us-gaap_CashAndCashEquivalentsPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash and Cash Equivalents</link:label>
    <link:label id="lab_us-gaap_CashAndCashEquivalentsPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_CashAndCashEquivalentsPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash and Cash Equivalents, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashAndCashEquivalentsPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CashAndCashEquivalentsPolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CashAndCashEquivalentsPolicyTextBlock" xlink:to="lab_us-gaap_CashAndCashEquivalentsPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortTermInvestmentsMember_c5aa4ccf-9692-48a4-a80f-907213b61e1a_terseLabel_en-US" xlink:label="lab_us-gaap_ShortTermInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-term investments</link:label>
    <link:label id="lab_us-gaap_ShortTermInvestmentsMember_label_en-US" xlink:label="lab_us-gaap_ShortTermInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Term Investments [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortTermInvestmentsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortTermInvestmentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortTermInvestmentsMember" xlink:to="lab_us-gaap_ShortTermInvestmentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain_1a5ce44f-3f47-4479-bb62-1de48958b021_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Award Type [Domain]</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Award Type [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_GrossRealizedInvestmentGainsAbstract_7c98a233-ed30-407e-9ffa-5394e9e10a27_terseLabel_en-US" xlink:label="lab_skwd_GrossRealizedInvestmentGainsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross realized gains</link:label>
    <link:label id="lab_skwd_GrossRealizedInvestmentGainsAbstract_label_en-US" xlink:label="lab_skwd_GrossRealizedInvestmentGainsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross Realized Investment Gains [Abstract]</link:label>
    <link:label id="lab_skwd_GrossRealizedInvestmentGainsAbstract_documentation_en-US" xlink:label="lab_skwd_GrossRealizedInvestmentGainsAbstract" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross Realized Investment Gains</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_GrossRealizedInvestmentGainsAbstract" xlink:href="skwd-20221231.xsd#skwd_GrossRealizedInvestmentGainsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_GrossRealizedInvestmentGainsAbstract" xlink:to="lab_skwd_GrossRealizedInvestmentGainsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded_181d3718-2514-4224-9a47-3495eded2671_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ceded losses and LAE incurred</link:label>
    <link:label id="lab_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded_label_en-US" xlink:label="lab_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Policyholder Benefits and Claims Incurred, Ceded</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded" xlink:to="lab_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquityAbstract_78364c43-d782-4355-b9d4-1ba65b555efc_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Method Investment, Difference Between Carrying Amount and Underlying Equity [Abstract]</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquityAbstract_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Method Investment, Difference Between Carrying Amount and Underlying Equity [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquityAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquityAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquityAbstract" xlink:to="lab_us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquityAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_AegisSuretyMember_a5ddd2cb-dd57-4b33-b4ea-6326ecc90f4a_terseLabel_en-US" xlink:label="lab_skwd_AegisSuretyMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Aegis Surety</link:label>
    <link:label id="lab_skwd_AegisSuretyMember_label_en-US" xlink:label="lab_skwd_AegisSuretyMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Aegis Surety [Member]</link:label>
    <link:label id="lab_skwd_AegisSuretyMember_documentation_en-US" xlink:label="lab_skwd_AegisSuretyMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Aegis Surety</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_AegisSuretyMember" xlink:href="skwd-20221231.xsd#skwd_AegisSuretyMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_AegisSuretyMember" xlink:to="lab_skwd_AegisSuretyMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MortgagesMember_93242143-8b5a-4246-a343-7c86213f8f7b_terseLabel_en-US" xlink:label="lab_us-gaap_MortgagesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Mortgage loans</link:label>
    <link:label id="lab_us-gaap_MortgagesMember_label_en-US" xlink:label="lab_us-gaap_MortgagesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Mortgages [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MortgagesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_MortgagesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MortgagesMember" xlink:to="lab_us-gaap_MortgagesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InsuranceAbstract_label_en-US" xlink:label="lab_us-gaap_InsuranceAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Insurance [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InsuranceAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_InsuranceAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InsuranceAbstract" xlink:to="lab_us-gaap_InsuranceAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SoftwareDevelopmentMember_8aaa6227-9e97-44d2-aad1-3973d2086abb_terseLabel_en-US" xlink:label="lab_us-gaap_SoftwareDevelopmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Software</link:label>
    <link:label id="lab_us-gaap_SoftwareDevelopmentMember_label_en-US" xlink:label="lab_us-gaap_SoftwareDevelopmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Software Development [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SoftwareDevelopmentMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SoftwareDevelopmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SoftwareDevelopmentMember" xlink:to="lab_us-gaap_SoftwareDevelopmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet_fd304010-835e-4234-a990-cf1f4211f5ca_terseLabel_en-US" xlink:label="lab_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Mortgage loans</link:label>
    <link:label id="lab_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet_label_en-US" xlink:label="lab_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Mortgage Loans on Real Estate, Commercial and Consumer, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet" xlink:to="lab_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2022Member_8ee34027-22dd-4c20-9ca9-ef940b47d57b_terseLabel_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2022Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accident Year 2022</link:label>
    <link:label id="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2022Member_label_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2022Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contract, Accident Year 2022 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortDurationInsuranceContractAccidentYear2022Member" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortDurationInsuranceContractAccidentYear2022Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortDurationInsuranceContractAccidentYear2022Member" xlink:to="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2022Member" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet_8043ff62-1442-48f8-aa20-7f1fed520de8_totalLabel_en-US" xlink:label="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total incurred, net of reinsurance</link:label>
    <link:label id="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet_label_en-US" xlink:label="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability For Unpaid Claims And Claims Adjustment Expense, Incurred Claims, Net</link:label>
    <link:label id="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet_documentation_en-US" xlink:label="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability For Unpaid Claims And Claims Adjustment Expense, Incurred Claims, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet" xlink:href="skwd-20221231.xsd#skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet" xlink:to="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressCityOrTown_75ac6300-fabc-43fc-b0c6-984405c5a130_terseLabel_en-US" xlink:label="lab_dei_EntityAddressCityOrTown" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Address, City or Town</link:label>
    <link:label id="lab_dei_EntityAddressCityOrTown_label_en-US" xlink:label="lab_dei_EntityAddressCityOrTown" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Address, City or Town</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressCityOrTown" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityAddressCityOrTown"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityAddressCityOrTown" xlink:to="lab_dei_EntityAddressCityOrTown" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax_92f4de05-478d-4db9-837d-de7eeddd3e45_terseLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net change in unrealized losses on investments, net of tax</link:label>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax_label_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">OCI, Debt Securities, Available-for-Sale, Gain (Loss), before Adjustment, after Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax" xlink:to="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CondensedIncomeStatementsCaptionsLineItems_b9bfffc2-c89f-4be5-8a82-4b7b79749de6_terseLabel_en-US" xlink:label="lab_srt_CondensedIncomeStatementsCaptionsLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Condensed Income Statements, Captions [Line Items]</link:label>
    <link:label id="lab_srt_CondensedIncomeStatementsCaptionsLineItems_label_en-US" xlink:label="lab_srt_CondensedIncomeStatementsCaptionsLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Condensed Income Statements, Captions [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_CondensedIncomeStatementsCaptionsLineItems" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_CondensedIncomeStatementsCaptionsLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_CondensedIncomeStatementsCaptionsLineItems" xlink:to="lab_srt_CondensedIncomeStatementsCaptionsLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LongTermDebtTerm_bc2a9102-86ca-4fee-93f3-56393a3b2bb4_terseLabel_en-US" xlink:label="lab_us-gaap_LongTermDebtTerm" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt term</link:label>
    <link:label id="lab_us-gaap_LongTermDebtTerm_label_en-US" xlink:label="lab_us-gaap_LongTermDebtTerm" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long-Term Debt, Term</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtTerm" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LongTermDebtTerm"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LongTermDebtTerm" xlink:to="lab_us-gaap_LongTermDebtTerm" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsIncurredButNotReportedIbnrClaimsLiabilityNet_63f8e28e-6686-433b-9077-72a5092ba7e4_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsIncurredButNotReportedIbnrClaimsLiabilityNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Incurred but Not Reported (IBNR) Claims Liability, Net</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsIncurredButNotReportedIbnrClaimsLiabilityNet_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsIncurredButNotReportedIbnrClaimsLiabilityNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Incurred but Not Reported (IBNR) Claims Liability, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsIncurredButNotReportedIbnrClaimsLiabilityNet" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortdurationInsuranceContractsIncurredButNotReportedIbnrClaimsLiabilityNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsIncurredButNotReportedIbnrClaimsLiabilityNet" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsIncurredButNotReportedIbnrClaimsLiabilityNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesByIndustryAxis_af226da5-34ed-42c8-81b2-a2d62ed8830e_terseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesByIndustryAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Industry Sector [Axis]</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesByIndustryAxis_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesByIndustryAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Industry Sector [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesByIndustryAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EquitySecuritiesByIndustryAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesByIndustryAxis" xlink:to="lab_us-gaap_EquitySecuritiesByIndustryAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesFinancedAndAwardedReturnedAndForfeited_c08cfdaf-5068-4f3e-882b-c1c04f7a50e3_terseLabel_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesFinancedAndAwardedReturnedAndForfeited" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Shares forfeited (in shares)</link:label>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesFinancedAndAwardedReturnedAndForfeited_label_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesFinancedAndAwardedReturnedAndForfeited" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Number of Shares Financed And Awarded, Returned and Forfeited</link:label>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesFinancedAndAwardedReturnedAndForfeited_documentation_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesFinancedAndAwardedReturnedAndForfeited" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Number of Shares Financed And Awarded, Returned and Forfeited</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesFinancedAndAwardedReturnedAndForfeited" xlink:href="skwd-20221231.xsd#skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesFinancedAndAwardedReturnedAndForfeited"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesFinancedAndAwardedReturnedAndForfeited" xlink:to="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesFinancedAndAwardedReturnedAndForfeited" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementOfFinancialPositionAbstract_label_en-US" xlink:label="lab_us-gaap_StatementOfFinancialPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statement of Financial Position [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementOfFinancialPositionAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StatementOfFinancialPositionAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementOfFinancialPositionAbstract" xlink:to="lab_us-gaap_StatementOfFinancialPositionAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CreditRatingAMBestDomain_4d8d502e-df5a-49cc-ab4f-e997b336efac_terseLabel_en-US" xlink:label="lab_srt_CreditRatingAMBestDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Credit Rating, AM Best [Domain]</link:label>
    <link:label id="lab_srt_CreditRatingAMBestDomain_label_en-US" xlink:label="lab_srt_CreditRatingAMBestDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Credit Rating, AM Best [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_CreditRatingAMBestDomain" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_CreditRatingAMBestDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_CreditRatingAMBestDomain" xlink:to="lab_srt_CreditRatingAMBestDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ClaimsDevelopmentLineItems_271ec925-d4f9-4ddb-a566-27c2745a7d95_terseLabel_en-US" xlink:label="lab_us-gaap_ClaimsDevelopmentLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Claims Development [Line Items]</link:label>
    <link:label id="lab_us-gaap_ClaimsDevelopmentLineItems_label_en-US" xlink:label="lab_us-gaap_ClaimsDevelopmentLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Claims Development [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ClaimsDevelopmentLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ClaimsDevelopmentLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ClaimsDevelopmentLineItems" xlink:to="lab_us-gaap_ClaimsDevelopmentLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredFinanceCostsNet_bc5826db-7ec8-4ec9-9f72-0bf2a4460adb_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_DeferredFinanceCostsNet" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Less: Debt issuance costs</link:label>
    <link:label id="lab_us-gaap_DeferredFinanceCostsNet_91365947-1e78-4f9d-873c-371bdd861a45_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredFinanceCostsNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Less: Debt issuance costs</link:label>
    <link:label id="lab_us-gaap_DeferredFinanceCostsNet_label_en-US" xlink:label="lab_us-gaap_DeferredFinanceCostsNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Issuance Costs, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredFinanceCostsNet" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DeferredFinanceCostsNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredFinanceCostsNet" xlink:to="lab_us-gaap_DeferredFinanceCostsNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredPolicyAcquisitionCosts_3b2029fa-074d-48c8-a9ec-c6a7642e1e19_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredPolicyAcquisitionCosts" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred policy acquisition costs</link:label>
    <link:label id="lab_us-gaap_DeferredPolicyAcquisitionCosts_label_en-US" xlink:label="lab_us-gaap_DeferredPolicyAcquisitionCosts" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Policy Acquisition Cost</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredPolicyAcquisitionCosts" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DeferredPolicyAcquisitionCosts"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredPolicyAcquisitionCosts" xlink:to="lab_us-gaap_DeferredPolicyAcquisitionCosts" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_AuditorName_08d739c6-2992-4bdf-a522-f0bbb11a2ab3_terseLabel_en-US" xlink:label="lab_dei_AuditorName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Auditor Name</link:label>
    <link:label id="lab_dei_AuditorName_label_en-US" xlink:label="lab_dei_AuditorName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Auditor Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_AuditorName" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_AuditorName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_AuditorName" xlink:to="lab_dei_AuditorName" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OperatingLossCarryforwards_e2eeffa8-1f2f-41a0-b09d-1376e8f5c021_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingLossCarryforwards" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Operating loss carryforwards</link:label>
    <link:label id="lab_us-gaap_OperatingLossCarryforwards_label_en-US" xlink:label="lab_us-gaap_OperatingLossCarryforwards" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Operating Loss Carryforwards</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLossCarryforwards" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OperatingLossCarryforwards"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OperatingLossCarryforwards" xlink:to="lab_us-gaap_OperatingLossCarryforwards" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_WorkersCompensationInsuranceMember_7f7e155a-b661-46e4-a226-2da01763c431_terseLabel_en-US" xlink:label="lab_us-gaap_WorkersCompensationInsuranceMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Workers&#8217; Compensation</link:label>
    <link:label id="lab_us-gaap_WorkersCompensationInsuranceMember_label_en-US" xlink:label="lab_us-gaap_WorkersCompensationInsuranceMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Workers' Compensation Insurance [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WorkersCompensationInsuranceMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_WorkersCompensationInsuranceMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_WorkersCompensationInsuranceMember" xlink:to="lab_us-gaap_WorkersCompensationInsuranceMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_UndistributedEarningsLossAllocatedToParticipatingSecuritiesBasic_62b9cb99-6632-439b-a85b-669e301b23e0_terseLabel_en-US" xlink:label="lab_us-gaap_UndistributedEarningsLossAllocatedToParticipatingSecuritiesBasic" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net income attributable to participating securities</link:label>
    <link:label id="lab_us-gaap_UndistributedEarningsLossAllocatedToParticipatingSecuritiesBasic_fb3c4194-0014-45bd-8111-503cbc676ee5_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_UndistributedEarningsLossAllocatedToParticipatingSecuritiesBasic" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Less: Undistributed income allocated to participating securities</link:label>
    <link:label id="lab_us-gaap_UndistributedEarningsLossAllocatedToParticipatingSecuritiesBasic_6211b764-d44a-4184-a948-b3624d25bbed_verboseLabel_en-US" xlink:label="lab_us-gaap_UndistributedEarningsLossAllocatedToParticipatingSecuritiesBasic" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Add back: Undistributed income allocated to participating securities</link:label>
    <link:label id="lab_us-gaap_UndistributedEarningsLossAllocatedToParticipatingSecuritiesBasic_label_en-US" xlink:label="lab_us-gaap_UndistributedEarningsLossAllocatedToParticipatingSecuritiesBasic" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Undistributed Earnings (Loss) Allocated to Participating Securities, Basic</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_UndistributedEarningsLossAllocatedToParticipatingSecuritiesBasic" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_UndistributedEarningsLossAllocatedToParticipatingSecuritiesBasic"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_UndistributedEarningsLossAllocatedToParticipatingSecuritiesBasic" xlink:to="lab_us-gaap_UndistributedEarningsLossAllocatedToParticipatingSecuritiesBasic" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquipmentMember_db4fdd8a-7ae6-4815-bb56-cab2c440c1ca_terseLabel_en-US" xlink:label="lab_us-gaap_EquipmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equipment</link:label>
    <link:label id="lab_us-gaap_EquipmentMember_label_en-US" xlink:label="lab_us-gaap_EquipmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equipment [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquipmentMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EquipmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquipmentMember" xlink:to="lab_us-gaap_EquipmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RestrictedCashAndCashEquivalents_682c2173-a1f0-4d0c-a023-6175b7dd2821_terseLabel_en-US" xlink:label="lab_us-gaap_RestrictedCashAndCashEquivalents" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restricted cash</link:label>
    <link:label id="lab_us-gaap_RestrictedCashAndCashEquivalents_label_en-US" xlink:label="lab_us-gaap_RestrictedCashAndCashEquivalents" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restricted Cash and Cash Equivalents</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestrictedCashAndCashEquivalents" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RestrictedCashAndCashEquivalents"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RestrictedCashAndCashEquivalents" xlink:to="lab_us-gaap_RestrictedCashAndCashEquivalents" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RestrictedStockUnitsRSUMember_c6f39f8e-c5b9-44bf-bced-91fb97a9af42_terseLabel_en-US" xlink:label="lab_us-gaap_RestrictedStockUnitsRSUMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restricted share and stock unit awards</link:label>
    <link:label id="lab_us-gaap_RestrictedStockUnitsRSUMember_label_en-US" xlink:label="lab_us-gaap_RestrictedStockUnitsRSUMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restricted Stock Units (RSUs) [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestrictedStockUnitsRSUMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RestrictedStockUnitsRSUMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RestrictedStockUnitsRSUMember" xlink:to="lab_us-gaap_RestrictedStockUnitsRSUMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfComplianceWithRegulatoryCapitalRequirementsUnderBankingRegulationsTextBlock_3f417da6-5ee9-41e8-a9ed-0e142450a6fa_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfComplianceWithRegulatoryCapitalRequirementsUnderBankingRegulationsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Compliance with Regulatory Capital Requirements under Banking Regulations</link:label>
    <link:label id="lab_us-gaap_ScheduleOfComplianceWithRegulatoryCapitalRequirementsUnderBankingRegulationsTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfComplianceWithRegulatoryCapitalRequirementsUnderBankingRegulationsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Compliance with Regulatory Capital Requirements under Banking Regulations [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfComplianceWithRegulatoryCapitalRequirementsUnderBankingRegulationsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfComplianceWithRegulatoryCapitalRequirementsUnderBankingRegulationsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfComplianceWithRegulatoryCapitalRequirementsUnderBankingRegulationsTextBlock" xlink:to="lab_us-gaap_ScheduleOfComplianceWithRegulatoryCapitalRequirementsUnderBankingRegulationsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CashAndCashEquivalentsFairValueDisclosure_1090adb2-548c-4ad3-bd71-4dd9bff06153_terseLabel_en-US" xlink:label="lab_us-gaap_CashAndCashEquivalentsFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash and cash equivalents</link:label>
    <link:label id="lab_us-gaap_CashAndCashEquivalentsFairValueDisclosure_label_en-US" xlink:label="lab_us-gaap_CashAndCashEquivalentsFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash and Cash Equivalents, Fair Value Disclosure</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashAndCashEquivalentsFairValueDisclosure" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CashAndCashEquivalentsFairValueDisclosure"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CashAndCashEquivalentsFairValueDisclosure" xlink:to="lab_us-gaap_CashAndCashEquivalentsFairValueDisclosure" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ParentCompanyMember_b7d399ad-35c8-4d5c-8bc6-4739e03950d4_terseLabel_en-US" xlink:label="lab_srt_ParentCompanyMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Parent Company</link:label>
    <link:label id="lab_srt_ParentCompanyMember_label_en-US" xlink:label="lab_srt_ParentCompanyMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Parent Company [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ParentCompanyMember" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_ParentCompanyMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ParentCompanyMember" xlink:to="lab_srt_ParentCompanyMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LondonInterbankOfferedRateLIBORMember_ff263846-9401-4cc0-9f14-35a9373e8bff_terseLabel_en-US" xlink:label="lab_us-gaap_LondonInterbankOfferedRateLIBORMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">London Interbank Offered Rate (LIBOR)</link:label>
    <link:label id="lab_us-gaap_LondonInterbankOfferedRateLIBORMember_label_en-US" xlink:label="lab_us-gaap_LondonInterbankOfferedRateLIBORMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">London Interbank Offered Rate (LIBOR) [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LondonInterbankOfferedRateLIBORMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LondonInterbankOfferedRateLIBORMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LondonInterbankOfferedRateLIBORMember" xlink:to="lab_us-gaap_LondonInterbankOfferedRateLIBORMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_BrewerLaneVenturesFundIILPMember_1589271d-a1b2-4d6e-b4d7-a538d35e89f7_terseLabel_en-US" xlink:label="lab_skwd_BrewerLaneVenturesFundIILPMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Brewer Lane Ventures Fund II LP units</link:label>
    <link:label id="lab_skwd_BrewerLaneVenturesFundIILPMember_label_en-US" xlink:label="lab_skwd_BrewerLaneVenturesFundIILPMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Brewer Lane Ventures Fund II, L.P. [Member]</link:label>
    <link:label id="lab_skwd_BrewerLaneVenturesFundIILPMember_documentation_en-US" xlink:label="lab_skwd_BrewerLaneVenturesFundIILPMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Brewer Lane Ventures Fund II, L.P.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_BrewerLaneVenturesFundIILPMember" xlink:href="skwd-20221231.xsd#skwd_BrewerLaneVenturesFundIILPMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_BrewerLaneVenturesFundIILPMember" xlink:to="lab_skwd_BrewerLaneVenturesFundIILPMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubsequentEventsAbstract_label_en-US" xlink:label="lab_us-gaap_SubsequentEventsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subsequent Events [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsequentEventsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SubsequentEventsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsequentEventsAbstract" xlink:to="lab_us-gaap_SubsequentEventsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_Revenues_6e4c5b90-a398-4a78-aca9-ac99d2494e35_totalLabel_en-US" xlink:label="lab_us-gaap_Revenues" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total revenues</link:label>
    <link:label id="lab_us-gaap_Revenues_label_en-US" xlink:label="lab_us-gaap_Revenues" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Revenues</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Revenues" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_Revenues"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Revenues" xlink:to="lab_us-gaap_Revenues" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_AMBestAPlusRatingMember_c39099d2-fb63-4eb3-8161-71c92c09de58_terseLabel_en-US" xlink:label="lab_srt_AMBestAPlusRatingMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">A+</link:label>
    <link:label id="lab_srt_AMBestAPlusRatingMember_label_en-US" xlink:label="lab_srt_AMBestAPlusRatingMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">AM Best, A+ Rating [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_AMBestAPlusRatingMember" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_AMBestAPlusRatingMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_AMBestAPlusRatingMember" xlink:to="lab_srt_AMBestAPlusRatingMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerNumberOfPositions_d395a0a6-73de-438a-b3cd-d7389ccb0d09_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerNumberOfPositions" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unrealized loss position aged over 12 months, number of positions</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerNumberOfPositions_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerNumberOfPositions" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Continuous Unrealized Loss Position, 12 Months or Longer, Number of Positions</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerNumberOfPositions" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerNumberOfPositions"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerNumberOfPositions" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerNumberOfPositions" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperations_250fe5cd-3625-4f0c-bc7b-e9a9a5e9b239_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperations" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net income</link:label>
    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperations_label_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperations" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Income (Loss) from Continuing Operations, Net of Tax, Attributable to Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossFromContinuingOperations" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncomeLossFromContinuingOperations"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeLossFromContinuingOperations" xlink:to="lab_us-gaap_IncomeLossFromContinuingOperations" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_GrossInvestmentIncomeExpenseOperating_a3939a1f-7d18-476c-93df-2b04395317cd_terseLabel_en-US" xlink:label="lab_skwd_GrossInvestmentIncomeExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total investment income</link:label>
    <link:label id="lab_skwd_GrossInvestmentIncomeExpenseOperating_label_en-US" xlink:label="lab_skwd_GrossInvestmentIncomeExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross Investment Income (Expense), Operating</link:label>
    <link:label id="lab_skwd_GrossInvestmentIncomeExpenseOperating_documentation_en-US" xlink:label="lab_skwd_GrossInvestmentIncomeExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross Investment Income (Expense), Operating</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_GrossInvestmentIncomeExpenseOperating" xlink:href="skwd-20221231.xsd#skwd_GrossInvestmentIncomeExpenseOperating"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_GrossInvestmentIncomeExpenseOperating" xlink:to="lab_skwd_GrossInvestmentIncomeExpenseOperating" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger_a50430ac-e33c-4754-b440-e842e61aa5ff_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">12 Months or More</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Continuous Unrealized Loss Position, 12 Months or Longer</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AmortizationOfIntangibleAssets_bf069570-47e9-474f-823d-4777a5750470_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_AmortizationOfIntangibleAssets" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Amortization</link:label>
    <link:label id="lab_us-gaap_AmortizationOfIntangibleAssets_ef37f1c3-0f3a-4cd8-826f-638b62e265f2_verboseLabel_en-US" xlink:label="lab_us-gaap_AmortizationOfIntangibleAssets" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Amortization expense</link:label>
    <link:label id="lab_us-gaap_AmortizationOfIntangibleAssets_label_en-US" xlink:label="lab_us-gaap_AmortizationOfIntangibleAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Amortization of Intangible Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AmortizationOfIntangibleAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AmortizationOfIntangibleAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AmortizationOfIntangibleAssets" xlink:to="lab_us-gaap_AmortizationOfIntangibleAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfGoodwillTextBlock_2ad13362-1b8c-4735-b329-80e4b1f2cc90_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfGoodwillTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Goodwill</link:label>
    <link:label id="lab_us-gaap_ScheduleOfGoodwillTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfGoodwillTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Goodwill [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfGoodwillTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfGoodwillTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfGoodwillTextBlock" xlink:to="lab_us-gaap_ScheduleOfGoodwillTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InterestPaidNet_34960ec5-f24b-4d46-8ed3-1e7bf7d673c6_terseLabel_en-US" xlink:label="lab_us-gaap_InterestPaidNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash paid for interest</link:label>
    <link:label id="lab_us-gaap_InterestPaidNet_label_en-US" xlink:label="lab_us-gaap_InterestPaidNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Interest Paid, Excluding Capitalized Interest, Operating Activities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestPaidNet" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_InterestPaidNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InterestPaidNet" xlink:to="lab_us-gaap_InterestPaidNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearThree_25fa60b3-dd3a-4dc4-b42c-8bf80ba7baaf_terseLabel_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearThree" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">2025</link:label>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearThree_label_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearThree" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Lessee, Operating Lease, Liability, to be Paid, Year Three</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearThree" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearThree"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearThree" xlink:to="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearThree" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_PaymentsForContributionsToSubsidiaries_c2ca4b17-be90-471b-944c-fae101371fbe_negatedTerseLabel_en-US" xlink:label="lab_skwd_PaymentsForContributionsToSubsidiaries" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Capital contribution to subsidiaries</link:label>
    <link:label id="lab_skwd_PaymentsForContributionsToSubsidiaries_label_en-US" xlink:label="lab_skwd_PaymentsForContributionsToSubsidiaries" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Payments For Contributions To Subsidiaries</link:label>
    <link:label id="lab_skwd_PaymentsForContributionsToSubsidiaries_documentation_en-US" xlink:label="lab_skwd_PaymentsForContributionsToSubsidiaries" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Payments For Contributions To Subsidiaries</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_PaymentsForContributionsToSubsidiaries" xlink:href="skwd-20221231.xsd#skwd_PaymentsForContributionsToSubsidiaries"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_PaymentsForContributionsToSubsidiaries" xlink:to="lab_skwd_PaymentsForContributionsToSubsidiaries" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating_2aa01b3a-7dc5-42cd-be69-6935ebf34391_terseLabel_en-US" xlink:label="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Underwriting, acquisition and insurance expenses</link:label>
    <link:label id="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating_b3d779c3-cf20-438b-af78-47cae8e70170_totalLabel_en-US" xlink:label="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total underwriting, acquisition and insurance expenses</link:label>
    <link:label id="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating_label_en-US" xlink:label="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Policy Acquisition Costs, Amortization Expense And Other Cost And Expense, Operating</link:label>
    <link:label id="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating_documentation_en-US" xlink:label="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Policy Acquisition Costs, Amortization Expense And Other Cost And Expense, Operating</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating" xlink:href="skwd-20221231.xsd#skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating" xlink:to="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_EnergySectorMember_a9e1a464-69da-401e-83a9-d9df1f7cb416_terseLabel_en-US" xlink:label="lab_skwd_EnergySectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Energy</link:label>
    <link:label id="lab_skwd_EnergySectorMember_label_en-US" xlink:label="lab_skwd_EnergySectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Energy Sector [Member]</link:label>
    <link:label id="lab_skwd_EnergySectorMember_documentation_en-US" xlink:label="lab_skwd_EnergySectorMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Energy Sector</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_EnergySectorMember" xlink:href="skwd-20221231.xsd#skwd_EnergySectorMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_EnergySectorMember" xlink:to="lab_skwd_EnergySectorMember" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_SupplementalScheduleOfReinsurancePremiumsForInsuranceCompaniesAbstract_label_en-US" xlink:label="lab_srt_SupplementalScheduleOfReinsurancePremiumsForInsuranceCompaniesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-17, Insurance Companies, Reinsurance [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_SupplementalScheduleOfReinsurancePremiumsForInsuranceCompaniesAbstract" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_SupplementalScheduleOfReinsurancePremiumsForInsuranceCompaniesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_SupplementalScheduleOfReinsurancePremiumsForInsuranceCompaniesAbstract" xlink:to="lab_srt_SupplementalScheduleOfReinsurancePremiumsForInsuranceCompaniesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_BICMember_ed8720f2-13dc-4086-b76c-8b237bc90eb7_terseLabel_en-US" xlink:label="lab_skwd_BICMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">BIC</link:label>
    <link:label id="lab_skwd_BICMember_label_en-US" xlink:label="lab_skwd_BICMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">BIC [Member]</link:label>
    <link:label id="lab_skwd_BICMember_documentation_en-US" xlink:label="lab_skwd_BICMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">BIC</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_BICMember" xlink:href="skwd-20221231.xsd#skwd_BICMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_BICMember" xlink:to="lab_skwd_BICMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PropertyInsuranceProductLineMember_a3584412-b24d-45a4-8813-405a09e43ea2_terseLabel_en-US" xlink:label="lab_us-gaap_PropertyInsuranceProductLineMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Property</link:label>
    <link:label id="lab_us-gaap_PropertyInsuranceProductLineMember_label_en-US" xlink:label="lab_us-gaap_PropertyInsuranceProductLineMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Property Insurance [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyInsuranceProductLineMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PropertyInsuranceProductLineMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PropertyInsuranceProductLineMember" xlink:to="lab_us-gaap_PropertyInsuranceProductLineMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConcentrationRiskTypeDomain_12537dc8-da6f-44d0-a2af-c07e7fd285cd_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskTypeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Concentration Risk Type [Domain]</link:label>
    <link:label id="lab_us-gaap_ConcentrationRiskTypeDomain_label_en-US" xlink:label="lab_us-gaap_ConcentrationRiskTypeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Concentration Risk Type [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConcentrationRiskTypeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ConcentrationRiskTypeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConcentrationRiskTypeDomain" xlink:to="lab_us-gaap_ConcentrationRiskTypeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_RepurchaseAgreementCounterpartyNameDomain_cddeb911-fee8-459b-8b66-ba082d183f0a_terseLabel_en-US" xlink:label="lab_srt_RepurchaseAgreementCounterpartyNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Counterparty Name [Domain]</link:label>
    <link:label id="lab_srt_RepurchaseAgreementCounterpartyNameDomain_label_en-US" xlink:label="lab_srt_RepurchaseAgreementCounterpartyNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Counterparty Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_RepurchaseAgreementCounterpartyNameDomain" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_RepurchaseAgreementCounterpartyNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_RepurchaseAgreementCounterpartyNameDomain" xlink:to="lab_srt_RepurchaseAgreementCounterpartyNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TreasuryStockMember_2ff6b87f-4eaa-4c4f-a59c-e1ebaa66398b_terseLabel_en-US" xlink:label="lab_us-gaap_TreasuryStockMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Treasury Stock</link:label>
    <link:label id="lab_us-gaap_TreasuryStockMember_label_en-US" xlink:label="lab_us-gaap_TreasuryStockMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Treasury Stock [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TreasuryStockMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_TreasuryStockMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TreasuryStockMember" xlink:to="lab_us-gaap_TreasuryStockMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockholdersEquity_027bab5e-cd16-4455-a50d-78ba2a8fbbaf_totalLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total stockholders' equity</link:label>
    <link:label id="lab_us-gaap_StockholdersEquity_8a144e43-2022-4bf4-a1f9-88a70d66221a_periodStartLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stockholders' equity beginning balance</link:label>
    <link:label id="lab_us-gaap_StockholdersEquity_ce3d13e0-e074-41a3-93ef-1fb7e8ee2b9f_periodEndLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stockholders' equity ending balance</link:label>
    <link:label id="lab_us-gaap_StockholdersEquity_e5f24e1e-c25c-449e-abe7-a471a20c9c3c_terseLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stockholders&#8217; equity</link:label>
    <link:label id="lab_us-gaap_StockholdersEquity_label_en-US" xlink:label="lab_us-gaap_StockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stockholders' Equity Attributable to Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquity" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StockholdersEquity"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockholdersEquity" xlink:to="lab_us-gaap_StockholdersEquity" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_RealizedInvestmentGains_29e144db-c82b-44ad-b9d3-beb3183b4305_totalLabel_en-US" xlink:label="lab_skwd_RealizedInvestmentGains" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total</link:label>
    <link:label id="lab_skwd_RealizedInvestmentGains_label_en-US" xlink:label="lab_skwd_RealizedInvestmentGains" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Realized Investment Gains</link:label>
    <link:label id="lab_skwd_RealizedInvestmentGains_documentation_en-US" xlink:label="lab_skwd_RealizedInvestmentGains" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Realized Investment Gains</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RealizedInvestmentGains" xlink:href="skwd-20221231.xsd#skwd_RealizedInvestmentGains"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_RealizedInvestmentGains" xlink:to="lab_skwd_RealizedInvestmentGains" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_DirectorMember_d9b6eb27-a3ee-49b9-92b6-e4e876fc3e02_terseLabel_en-US" xlink:label="lab_srt_DirectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Director</link:label>
    <link:label id="lab_srt_DirectorMember_label_en-US" xlink:label="lab_srt_DirectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Director [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_DirectorMember" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_DirectorMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_DirectorMember" xlink:to="lab_srt_DirectorMember" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CondensedBalanceSheetStatementTable_779fda46-e83c-4ad1-91c1-9df6b0abfe7d_terseLabel_en-US" xlink:label="lab_srt_CondensedBalanceSheetStatementTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Condensed Balance Sheet Statement [Table]</link:label>
    <link:label id="lab_srt_CondensedBalanceSheetStatementTable_label_en-US" xlink:label="lab_srt_CondensedBalanceSheetStatementTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Condensed Balance Sheet Statement [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_CondensedBalanceSheetStatementTable" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_CondensedBalanceSheetStatementTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_CondensedBalanceSheetStatementTable" xlink:to="lab_srt_CondensedBalanceSheetStatementTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeituresWeightedAverageGrantDateFairValue_26f51e1e-b68f-4e47-ac60-d68abba27f51_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeituresWeightedAverageGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Forfeited (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeituresWeightedAverageGrantDateFairValue_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeituresWeightedAverageGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Forfeitures, Weighted Average Grant Date Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeituresWeightedAverageGrantDateFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeituresWeightedAverageGrantDateFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeituresWeightedAverageGrantDateFairValue" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeituresWeightedAverageGrantDateFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinancingReceivablePortfolioSegmentDomain_22368dc5-5ea2-48b4-9cb2-ce81f08037f9_terseLabel_en-US" xlink:label="lab_us-gaap_FinancingReceivablePortfolioSegmentDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Financing Receivable Portfolio Segment [Domain]</link:label>
    <link:label id="lab_us-gaap_FinancingReceivablePortfolioSegmentDomain_label_en-US" xlink:label="lab_us-gaap_FinancingReceivablePortfolioSegmentDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Financing Receivable Portfolio Segment [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancingReceivablePortfolioSegmentDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FinancingReceivablePortfolioSegmentDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancingReceivablePortfolioSegmentDomain" xlink:to="lab_us-gaap_FinancingReceivablePortfolioSegmentDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesFinancedReturned_94efaf0a-dc54-4a6f-b24a-bee1866e266a_terseLabel_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesFinancedReturned" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stock notes receivable, stock awards returned (in shares)</link:label>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesFinancedReturned_label_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesFinancedReturned" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Number of Shares Financed, Returned</link:label>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesFinancedReturned_documentation_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesFinancedReturned" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Number of Shares Financed, Returned</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesFinancedReturned" xlink:href="skwd-20221231.xsd#skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesFinancedReturned"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesFinancedReturned" xlink:to="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesFinancedReturned" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatutoryAccountingPracticesLineItems_25b9921d-f9d4-4237-94c2-60a7448f843c_terseLabel_en-US" xlink:label="lab_us-gaap_StatutoryAccountingPracticesLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statutory Accounting Practices [Line Items]</link:label>
    <link:label id="lab_us-gaap_StatutoryAccountingPracticesLineItems_label_en-US" xlink:label="lab_us-gaap_StatutoryAccountingPracticesLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statutory Accounting Practices [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatutoryAccountingPracticesLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StatutoryAccountingPracticesLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatutoryAccountingPracticesLineItems" xlink:to="lab_us-gaap_StatutoryAccountingPracticesLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredTaxAssetsOther_5731bef5-e72b-4402-9f9a-fee3a8a21b96_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsOther" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other</link:label>
    <link:label id="lab_us-gaap_DeferredTaxAssetsOther_label_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsOther" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Tax Assets, Other</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxAssetsOther" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DeferredTaxAssetsOther"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredTaxAssetsOther" xlink:to="lab_us-gaap_DeferredTaxAssetsOther" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommercialMortgageBackedSecuritiesMember_aa6b259b-a74e-4e9b-b97f-de4ed8d1d5dd_terseLabel_en-US" xlink:label="lab_us-gaap_CommercialMortgageBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Commercial mortgage-backed securities</link:label>
    <link:label id="lab_us-gaap_CommercialMortgageBackedSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_CommercialMortgageBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Commercial Mortgage-Backed Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommercialMortgageBackedSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CommercialMortgageBackedSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommercialMortgageBackedSecuritiesMember" xlink:to="lab_us-gaap_CommercialMortgageBackedSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SaleOfStockNumberOfSharesIssuedInTransaction_478d05ed-e641-4f09-b6d5-7ccdb8491e4a_terseLabel_en-US" xlink:label="lab_us-gaap_SaleOfStockNumberOfSharesIssuedInTransaction" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Sale of stock, number of shares issued (in shares)</link:label>
    <link:label id="lab_us-gaap_SaleOfStockNumberOfSharesIssuedInTransaction_label_en-US" xlink:label="lab_us-gaap_SaleOfStockNumberOfSharesIssuedInTransaction" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Sale of Stock, Number of Shares Issued in Transaction</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SaleOfStockNumberOfSharesIssuedInTransaction" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SaleOfStockNumberOfSharesIssuedInTransaction"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SaleOfStockNumberOfSharesIssuedInTransaction" xlink:to="lab_us-gaap_SaleOfStockNumberOfSharesIssuedInTransaction" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger_3bb993f9-a577-4f12-818a-5e1fcd05bb5c_terseLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">12 Months or More</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger_label_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Continuous Unrealized Loss Position, 12 Months or Longer</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger_documentation_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Continuous Unrealized Loss Position, 12 Months or Longer</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:href="skwd-20221231.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:to="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization_114d0d6a-ceed-46d0-934a-5409ec51d07f_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accumulated amortization</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Finite-Lived Intangible Assets, Accumulated Amortization</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearThree_8674ce92-9569-4717-b959-031bcac37f4f_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearThree" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">2025</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearThree_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearThree" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Finite-Lived Intangible Asset, Expected Amortization, Year Three</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearThree" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearThree"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearThree" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearThree" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2021Member_2f8356e2-53d9-4533-9357-9841100b16b4_terseLabel_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2021Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accident Year 2021</link:label>
    <link:label id="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2021Member_label_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2021Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contract, Accident Year 2021 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortDurationInsuranceContractAccidentYear2021Member" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortDurationInsuranceContractAccidentYear2021Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortDurationInsuranceContractAccidentYear2021Member" xlink:to="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2021Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt_66f96381-50d0-4a5c-a533-9e274c035029_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fixed maturity securities, available-for sale</link:label>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt_label_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Proceeds from Sale of Debt Securities, Available-for-Sale</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt" xlink:to="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccidentAndHealthInsuranceSegmentMember_cd14a669-aa5d-49fe-976c-b50ad131dff4_terseLabel_en-US" xlink:label="lab_us-gaap_AccidentAndHealthInsuranceSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accident &amp; Health</link:label>
    <link:label id="lab_us-gaap_AccidentAndHealthInsuranceSegmentMember_label_en-US" xlink:label="lab_us-gaap_AccidentAndHealthInsuranceSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accident and Health Insurance Product Line [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccidentAndHealthInsuranceSegmentMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AccidentAndHealthInsuranceSegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccidentAndHealthInsuranceSegmentMember" xlink:to="lab_us-gaap_AccidentAndHealthInsuranceSegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RetainedEarningsMember_7af421e8-2cd6-411f-883d-22ad8fa50dcb_terseLabel_en-US" xlink:label="lab_us-gaap_RetainedEarningsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accumulated Deficit</link:label>
    <link:label id="lab_us-gaap_RetainedEarningsMember_label_en-US" xlink:label="lab_us-gaap_RetainedEarningsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Retained Earnings [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RetainedEarningsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RetainedEarningsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RetainedEarningsMember" xlink:to="lab_us-gaap_RetainedEarningsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_RISCOMMember_3cb509e3-d4aa-46b9-887e-89ed994636d3_terseLabel_en-US" xlink:label="lab_skwd_RISCOMMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">RISCOM</link:label>
    <link:label id="lab_skwd_RISCOMMember_label_en-US" xlink:label="lab_skwd_RISCOMMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">RISCOM [Member]</link:label>
    <link:label id="lab_skwd_RISCOMMember_documentation_en-US" xlink:label="lab_skwd_RISCOMMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">RISCOM</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RISCOMMember" xlink:href="skwd-20221231.xsd#skwd_RISCOMMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_RISCOMMember" xlink:to="lab_skwd_RISCOMMember" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_SupplementalScheduleOfReinsurancePremiumsForInsuranceCompaniesTextBlock_8eb8127f-b139-44ab-8441-afae6f0f9ba5_terseLabel_en-US" xlink:label="lab_srt_SupplementalScheduleOfReinsurancePremiumsForInsuranceCompaniesTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SCHEDULE IV&#160;&#8212; REINSURANCE</link:label>
    <link:label id="lab_srt_SupplementalScheduleOfReinsurancePremiumsForInsuranceCompaniesTextBlock_label_en-US" xlink:label="lab_srt_SupplementalScheduleOfReinsurancePremiumsForInsuranceCompaniesTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-17, Insurance Companies, Reinsurance [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_SupplementalScheduleOfReinsurancePremiumsForInsuranceCompaniesTextBlock" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_SupplementalScheduleOfReinsurancePremiumsForInsuranceCompaniesTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_SupplementalScheduleOfReinsurancePremiumsForInsuranceCompaniesTextBlock" xlink:to="lab_srt_SupplementalScheduleOfReinsurancePremiumsForInsuranceCompaniesTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CondensedCashFlowStatementsCaptionsLineItems_7384eb09-4c00-4b9e-bac1-10473f1463ad_terseLabel_en-US" xlink:label="lab_srt_CondensedCashFlowStatementsCaptionsLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Condensed Cash Flow Statements, Captions [Line Items]</link:label>
    <link:label id="lab_srt_CondensedCashFlowStatementsCaptionsLineItems_label_en-US" xlink:label="lab_srt_CondensedCashFlowStatementsCaptionsLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Condensed Cash Flow Statements, Captions [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_CondensedCashFlowStatementsCaptionsLineItems" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_CondensedCashFlowStatementsCaptionsLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_CondensedCashFlowStatementsCaptionsLineItems" xlink:to="lab_srt_CondensedCashFlowStatementsCaptionsLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LeaseCost_4e290ed0-74cf-4983-80fb-60860fde35f5_terseLabel_en-US" xlink:label="lab_us-gaap_LeaseCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Operating lease expense</link:label>
    <link:label id="lab_us-gaap_LeaseCost_label_en-US" xlink:label="lab_us-gaap_LeaseCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Lease, Cost</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LeaseCost" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LeaseCost"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LeaseCost" xlink:to="lab_us-gaap_LeaseCost" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockMember_47d59dea-2802-4b60-9c25-50cac421d55b_netLabel_en-US" xlink:label="lab_us-gaap_CommonStockMember" xlink:role="http://www.xbrl.org/2009/role/netLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common Stock</link:label>
    <link:label id="lab_us-gaap_CommonStockMember_57e88f26-7b61-4a63-93cc-c8ed33e93c40_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total common stocks</link:label>
    <link:label id="lab_us-gaap_CommonStockMember_e5c5a90a-8987-4ab5-9e10-0969b7952376_verboseLabel_en-US" xlink:label="lab_us-gaap_CommonStockMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common stocks</link:label>
    <link:label id="lab_us-gaap_CommonStockMember_label_en-US" xlink:label="lab_us-gaap_CommonStockMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common Stock [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CommonStockMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockMember" xlink:to="lab_us-gaap_CommonStockMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumsReceivableAtCarryingValue_8c5b25f8-0890-43ea-a7b0-d06ade709de9_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsReceivableAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Premiums receivable</link:label>
    <link:label id="lab_us-gaap_PremiumsReceivableAtCarryingValue_label_en-US" xlink:label="lab_us-gaap_PremiumsReceivableAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Premiums Receivable, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsReceivableAtCarryingValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PremiumsReceivableAtCarryingValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsReceivableAtCarryingValue" xlink:to="lab_us-gaap_PremiumsReceivableAtCarryingValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LeaseCostTableTextBlock_4402a9e3-164c-4214-a4f1-b6844f1b1120_terseLabel_en-US" xlink:label="lab_us-gaap_LeaseCostTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Lease, Cost</link:label>
    <link:label id="lab_us-gaap_LeaseCostTableTextBlock_label_en-US" xlink:label="lab_us-gaap_LeaseCostTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Lease, Cost [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LeaseCostTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LeaseCostTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LeaseCostTableTextBlock" xlink:to="lab_us-gaap_LeaseCostTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BusinessCombinationContingentConsiderationLiability_108f4edf-e048-4897-9415-62e706e144d4_terseLabel_en-US" xlink:label="lab_us-gaap_BusinessCombinationContingentConsiderationLiability" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Earn-out payments to former owners</link:label>
    <link:label id="lab_us-gaap_BusinessCombinationContingentConsiderationLiability_label_en-US" xlink:label="lab_us-gaap_BusinessCombinationContingentConsiderationLiability" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Business Combination, Contingent Consideration, Liability</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BusinessCombinationContingentConsiderationLiability" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_BusinessCombinationContingentConsiderationLiability"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BusinessCombinationContingentConsiderationLiability" xlink:to="lab_us-gaap_BusinessCombinationContingentConsiderationLiability" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months_5720f579-8d9f-49cc-b25f-03af71187552_terseLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Less than 12 Months</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months_label_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Continuous Unrealized Loss Position, Less than 12 Months</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months_documentation_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Continuous Unrealized Loss Position, Less than 12 Months</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months" xlink:href="skwd-20221231.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months" xlink:to="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementTable_30c8c440-c8fa-4648-bdd3-255ba3c1dced_terseLabel_en-US" xlink:label="lab_us-gaap_StatementTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statement [Table]</link:label>
    <link:label id="lab_us-gaap_StatementTable_label_en-US" xlink:label="lab_us-gaap_StatementTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statement [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StatementTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementTable" xlink:to="lab_us-gaap_StatementTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue_0f08d595-e214-43a2-8ac8-af881673ded7_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Vested (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Vested in Period, Weighted Average Grant Date Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_JuniorSubordinatedNotesDue2036Member_9d9227cb-c1dd-43b1-91aa-e4e75e13a2d0_terseLabel_en-US" xlink:label="lab_skwd_JuniorSubordinatedNotesDue2036Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Junior Subordinated Notes Due 2036</link:label>
    <link:label id="lab_skwd_JuniorSubordinatedNotesDue2036Member_label_en-US" xlink:label="lab_skwd_JuniorSubordinatedNotesDue2036Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Junior Subordinated Notes Due 2036 [Member]</link:label>
    <link:label id="lab_skwd_JuniorSubordinatedNotesDue2036Member_documentation_en-US" xlink:label="lab_skwd_JuniorSubordinatedNotesDue2036Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Junior Subordinated Notes Due 2036</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_JuniorSubordinatedNotesDue2036Member" xlink:href="skwd-20221231.xsd#skwd_JuniorSubordinatedNotesDue2036Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_JuniorSubordinatedNotesDue2036Member" xlink:to="lab_skwd_JuniorSubordinatedNotesDue2036Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LetterOfCreditMember_f0875a61-67c9-44ad-9669-2daabf4d5888_terseLabel_en-US" xlink:label="lab_us-gaap_LetterOfCreditMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Letter of Credit</link:label>
    <link:label id="lab_us-gaap_LetterOfCreditMember_label_en-US" xlink:label="lab_us-gaap_LetterOfCreditMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Letter of Credit [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LetterOfCreditMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LetterOfCreditMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LetterOfCreditMember" xlink:to="lab_us-gaap_LetterOfCreditMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredTaxLiabilitiesInvestments_c476552f-7877-492a-b7a7-c7cdd08498a4_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxLiabilitiesInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investments</link:label>
    <link:label id="lab_us-gaap_DeferredTaxLiabilitiesInvestments_label_en-US" xlink:label="lab_us-gaap_DeferredTaxLiabilitiesInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Tax Liabilities, Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxLiabilitiesInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DeferredTaxLiabilitiesInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredTaxLiabilitiesInvestments" xlink:to="lab_us-gaap_DeferredTaxLiabilitiesInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_RestrictedCashFairValueDisclosure_b058cbd5-4f5c-4742-b974-20004e310706_terseLabel_en-US" xlink:label="lab_skwd_RestrictedCashFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restricted cash</link:label>
    <link:label id="lab_skwd_RestrictedCashFairValueDisclosure_label_en-US" xlink:label="lab_skwd_RestrictedCashFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restricted Cash, Fair Value Disclosure</link:label>
    <link:label id="lab_skwd_RestrictedCashFairValueDisclosure_documentation_en-US" xlink:label="lab_skwd_RestrictedCashFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restricted Cash, Fair Value Disclosure</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RestrictedCashFairValueDisclosure" xlink:href="skwd-20221231.xsd#skwd_RestrictedCashFairValueDisclosure"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_RestrictedCashFairValueDisclosure" xlink:to="lab_skwd_RestrictedCashFairValueDisclosure" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DefinedContributionPlanCostRecognized_79fbc743-3e0d-4f05-9106-80da78434bd8_terseLabel_en-US" xlink:label="lab_us-gaap_DefinedContributionPlanCostRecognized" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">401(k) matching contributions</link:label>
    <link:label id="lab_us-gaap_DefinedContributionPlanCostRecognized_label_en-US" xlink:label="lab_us-gaap_DefinedContributionPlanCostRecognized" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Defined Contribution Plan, Cost</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DefinedContributionPlanCostRecognized" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DefinedContributionPlanCostRecognized"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DefinedContributionPlanCostRecognized" xlink:to="lab_us-gaap_DefinedContributionPlanCostRecognized" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_RangeAxis_f1d0bd6b-56db-4de8-8195-d346b3ab137d_terseLabel_en-US" xlink:label="lab_srt_RangeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statistical Measurement [Axis]</link:label>
    <link:label id="lab_srt_RangeAxis_label_en-US" xlink:label="lab_srt_RangeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statistical Measurement [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_RangeAxis" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_RangeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_RangeAxis" xlink:to="lab_srt_RangeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiRealizedGain_f839ada1-8171-44b9-9680-5fd42ac5788b_terseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiRealizedGain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity securities</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiRealizedGain_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiRealizedGain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Securities, FV-NI, Realized Gain</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesFvNiRealizedGain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EquitySecuritiesFvNiRealizedGain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesFvNiRealizedGain" xlink:to="lab_us-gaap_EquitySecuritiesFvNiRealizedGain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill_54caa1d9-74b1-4584-9937-b91c2babe3a3_periodStartLabel_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Beginning balance</link:label>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill_bcc51b7c-790a-415a-b0af-7140bda79978_periodEndLabel_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ending balance</link:label>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill_label_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Indefinite-Lived Intangible Assets (Excluding Goodwill)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill" xlink:to="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RelatedPartyTransactionAxis_356edec5-2c42-4185-abd9-d097c2b71f40_terseLabel_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Related Party Transaction [Axis]</link:label>
    <link:label id="lab_us-gaap_RelatedPartyTransactionAxis_label_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Related Party Transaction [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RelatedPartyTransactionAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RelatedPartyTransactionAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RelatedPartyTransactionAxis" xlink:to="lab_us-gaap_RelatedPartyTransactionAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LeaseholdImprovementsMember_80584ad1-4efc-4ff1-9e9f-7adb167840f0_terseLabel_en-US" xlink:label="lab_us-gaap_LeaseholdImprovementsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Leasehold improvements</link:label>
    <link:label id="lab_us-gaap_LeaseholdImprovementsMember_label_en-US" xlink:label="lab_us-gaap_LeaseholdImprovementsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Leasehold Improvements [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LeaseholdImprovementsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LeaseholdImprovementsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LeaseholdImprovementsMember" xlink:to="lab_us-gaap_LeaseholdImprovementsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis_09ef255f-fd50-4f04-bef8-a92c3595ed24_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Disposal Group Name [Axis]</link:label>
    <link:label id="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis_label_en-US" xlink:label="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Disposal Group Name [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis" xlink:to="lab_us-gaap_IncomeStatementBalanceSheetAndAdditionalDisclosuresByDisposalGroupsIncludingDiscontinuedOperationsAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_FiniteLivedIntangibleAssetDisposals_275ad2bd-720f-4085-a566-704c1e09e25f_negatedTerseLabel_en-US" xlink:label="lab_skwd_FiniteLivedIntangibleAssetDisposals" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Disposals</link:label>
    <link:label id="lab_skwd_FiniteLivedIntangibleAssetDisposals_label_en-US" xlink:label="lab_skwd_FiniteLivedIntangibleAssetDisposals" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Finite-Lived Intangible Asset, Disposals</link:label>
    <link:label id="lab_skwd_FiniteLivedIntangibleAssetDisposals_documentation_en-US" xlink:label="lab_skwd_FiniteLivedIntangibleAssetDisposals" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Finite-Lived Intangible Asset, Disposals</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_FiniteLivedIntangibleAssetDisposals" xlink:href="skwd-20221231.xsd#skwd_FiniteLivedIntangibleAssetDisposals"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_FiniteLivedIntangibleAssetDisposals" xlink:to="lab_skwd_FiniteLivedIntangibleAssetDisposals" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementEquityComponentsAxis_a3d4ee10-76f2-4af0-8cfc-d28cd0b4adba_terseLabel_en-US" xlink:label="lab_us-gaap_StatementEquityComponentsAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Components [Axis]</link:label>
    <link:label id="lab_us-gaap_StatementEquityComponentsAxis_label_en-US" xlink:label="lab_us-gaap_StatementEquityComponentsAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Components [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementEquityComponentsAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StatementEquityComponentsAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementEquityComponentsAxis" xlink:to="lab_us-gaap_StatementEquityComponentsAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember_4b610cb8-0f7e-4519-8137-1cf984514204_terseLabel_en-US" xlink:label="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SUA commission revenue</link:label>
    <link:label id="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember_label_en-US" xlink:label="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Managing General Insurance Agent And Broker, Commission Revenue [Member]</link:label>
    <link:label id="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember_documentation_en-US" xlink:label="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Managing General Insurance Agent And Broker, Commission Revenue</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember" xlink:href="skwd-20221231.xsd#skwd_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember" xlink:to="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsAccidentYearDomain_5bce36c8-c832-4a75-9422-9a0bf50b6f5e_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsAccidentYearDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Accident Year [Domain]</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsAccidentYearDomain_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsAccidentYearDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Accident Year [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsAccidentYearDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortdurationInsuranceContractsAccidentYearDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsAccidentYearDomain" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsAccidentYearDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersNetInvestmentIncome_f0769d8c-1edf-4d0a-b316-88fbda98f1ac_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersNetInvestmentIncome" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net investment income</link:label>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersNetInvestmentIncome_label_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersNetInvestmentIncome" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-18, Supplemental Information, Property-Casualty Insurance Underwriters, Net Investment Income</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersNetInvestmentIncome" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersNetInvestmentIncome"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersNetInvestmentIncome" xlink:to="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersNetInvestmentIncome" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueLiabilitiesMeasuredOnRecurringBasisSubordinatedDebtObligations_c622f8bb-0179-4b05-be4c-3b9f07308abf_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueLiabilitiesMeasuredOnRecurringBasisSubordinatedDebtObligations" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subordinated debt</link:label>
    <link:label id="lab_us-gaap_FairValueLiabilitiesMeasuredOnRecurringBasisSubordinatedDebtObligations_label_en-US" xlink:label="lab_us-gaap_FairValueLiabilitiesMeasuredOnRecurringBasisSubordinatedDebtObligations" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subordinated Debt Obligations, Fair Value Disclosure</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueLiabilitiesMeasuredOnRecurringBasisSubordinatedDebtObligations" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FairValueLiabilitiesMeasuredOnRecurringBasisSubordinatedDebtObligations"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueLiabilitiesMeasuredOnRecurringBasisSubordinatedDebtObligations" xlink:to="lab_us-gaap_FairValueLiabilitiesMeasuredOnRecurringBasisSubordinatedDebtObligations" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentHoldingsScheduleOfInvestmentsTextBlock_d718da90-a0fd-40d1-9109-39b70a04358a_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentHoldingsScheduleOfInvestmentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investments</link:label>
    <link:label id="lab_us-gaap_InvestmentHoldingsScheduleOfInvestmentsTextBlock_label_en-US" xlink:label="lab_us-gaap_InvestmentHoldingsScheduleOfInvestmentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment Holdings, Schedule of Investments [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentHoldingsScheduleOfInvestmentsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_InvestmentHoldingsScheduleOfInvestmentsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentHoldingsScheduleOfInvestmentsTextBlock" xlink:to="lab_us-gaap_InvestmentHoldingsScheduleOfInvestmentsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementLineItems_a0d3018e-e8a4-4c65-b1c5-4492c41bfba9_terseLabel_en-US" xlink:label="lab_us-gaap_StatementLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statement [Line Items]</link:label>
    <link:label id="lab_us-gaap_StatementLineItems_label_en-US" xlink:label="lab_us-gaap_StatementLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statement [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StatementLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementLineItems" xlink:to="lab_us-gaap_StatementLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber_a10e9a9a-39d9-4028-a0a0-429ad5036b85_periodStartLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Non-vested, beginning period (in shares)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber_be138390-97fd-4e6b-a48d-74bac768f6d0_periodEndLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Non-vested, ending period (in shares)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Nonvested, Number</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_VariableRateDomain_b5099575-f727-4d25-88d4-a6e4c1d37560_terseLabel_en-US" xlink:label="lab_us-gaap_VariableRateDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Variable Rate [Domain]</link:label>
    <link:label id="lab_us-gaap_VariableRateDomain_label_en-US" xlink:label="lab_us-gaap_VariableRateDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Variable Rate [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_VariableRateDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_VariableRateDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_VariableRateDomain" xlink:to="lab_us-gaap_VariableRateDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract_43f4a7c1-0d68-4ee7-8ed2-df35f22d96f7_terseLabel_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other comprehensive loss:</link:label>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract_label_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accumulated Other Comprehensive Income (Loss), Net of Tax [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract" xlink:to="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceLineItems_c6616b59-b292-4123-b89b-44e1d9033560_terseLabel_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Effects of Reinsurance [Line Items]</link:label>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceLineItems_label_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Effects of Reinsurance [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectsOfReinsuranceLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EffectsOfReinsuranceLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectsOfReinsuranceLineItems" xlink:to="lab_us-gaap_EffectsOfReinsuranceLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PreferredStockConvertibleSharesIssuable_877d03ea-3d50-4204-8c64-21c8e91e65d6_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockConvertibleSharesIssuable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common shares upon conversion of preferred shares (in shares)</link:label>
    <link:label id="lab_us-gaap_PreferredStockConvertibleSharesIssuable_label_en-US" xlink:label="lab_us-gaap_PreferredStockConvertibleSharesIssuable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred Stock, Convertible, Shares Issuable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockConvertibleSharesIssuable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PreferredStockConvertibleSharesIssuable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PreferredStockConvertibleSharesIssuable" xlink:to="lab_us-gaap_PreferredStockConvertibleSharesIssuable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsGross_47915d89-ec94-48ff-b1e0-ed26bbd82abc_periodStartLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsGross" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross, beginning balance</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsGross_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Finite-Lived Intangible Assets, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsGross" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FiniteLivedIntangibleAssetsGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsGross" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsGross" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2019Member_985cafa8-14ed-4644-9eec-7d5fb4fd591a_terseLabel_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2019Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accident Year 2019</link:label>
    <link:label id="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2019Member_label_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2019Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contract, Accident Year 2019 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortDurationInsuranceContractAccidentYear2019Member" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortDurationInsuranceContractAccidentYear2019Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortDurationInsuranceContractAccidentYear2019Member" xlink:to="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2019Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InsuranceCommissionsAndFees_555d33d7-352a-4685-ae5e-5e5f98df6619_terseLabel_en-US" xlink:label="lab_us-gaap_InsuranceCommissionsAndFees" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Commission and fee income</link:label>
    <link:label id="lab_us-gaap_InsuranceCommissionsAndFees_label_en-US" xlink:label="lab_us-gaap_InsuranceCommissionsAndFees" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Insurance Commissions and Fees</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InsuranceCommissionsAndFees" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_InsuranceCommissionsAndFees"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InsuranceCommissionsAndFees" xlink:to="lab_us-gaap_InsuranceCommissionsAndFees" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AssumedPremiumsWritten_28d5c6bb-5245-4c21-a47f-53713c9f355b_terseLabel_en-US" xlink:label="lab_us-gaap_AssumedPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Assumed premiums</link:label>
    <link:label id="lab_us-gaap_AssumedPremiumsWritten_label_en-US" xlink:label="lab_us-gaap_AssumedPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Assumed Premiums Written</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssumedPremiumsWritten" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AssumedPremiumsWritten"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssumedPremiumsWritten" xlink:to="lab_us-gaap_AssumedPremiumsWritten" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OperatingLeaseRightOfUseAsset_b8b905e6-2fea-4d23-846c-e56b9231b9aa_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingLeaseRightOfUseAsset" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Operating lease right-of-use assets</link:label>
    <link:label id="lab_us-gaap_OperatingLeaseRightOfUseAsset_label_en-US" xlink:label="lab_us-gaap_OperatingLeaseRightOfUseAsset" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Operating Lease, Right-of-Use Asset</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseRightOfUseAsset" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OperatingLeaseRightOfUseAsset"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OperatingLeaseRightOfUseAsset" xlink:to="lab_us-gaap_OperatingLeaseRightOfUseAsset" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax_53700c92-d48d-40ba-b8dd-15d530435e8e_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross Unrealized Losses</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Accumulated Gross Unrealized Loss, before Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax" xlink:to="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember_144f6d08-e46b-4c64-b862-5256d46b756d_terseLabel_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accumulated Other Comprehensive Income</link:label>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember_label_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">AOCI Attributable to Parent [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AccumulatedOtherComprehensiveIncomeMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:to="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SecSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersPriorYearClaimAndClaimAdjustmentExpense_82c4b6b1-2eb2-48ae-86b9-0d003a161986_terseLabel_en-US" xlink:label="lab_us-gaap_SecSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersPriorYearClaimAndClaimAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Losses and loss adjustment expenses (prior years)</link:label>
    <link:label id="lab_us-gaap_SecSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersPriorYearClaimAndClaimAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_SecSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersPriorYearClaimAndClaimAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-18, Supplemental Information, Property-Casualty Insurance Underwriters, Prior Year Claim and Claim Adjustment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SecSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersPriorYearClaimAndClaimAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SecSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersPriorYearClaimAndClaimAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SecSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersPriorYearClaimAndClaimAdjustmentExpense" xlink:to="lab_us-gaap_SecSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersPriorYearClaimAndClaimAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinancingReceivablePortfolioSegmentAxis_61666f6a-e6e6-4ca5-af80-bd0cc19c3677_terseLabel_en-US" xlink:label="lab_us-gaap_FinancingReceivablePortfolioSegmentAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Financing Receivable Portfolio Segment [Axis]</link:label>
    <link:label id="lab_us-gaap_FinancingReceivablePortfolioSegmentAxis_label_en-US" xlink:label="lab_us-gaap_FinancingReceivablePortfolioSegmentAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Financing Receivable Portfolio Segment [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancingReceivablePortfolioSegmentAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FinancingReceivablePortfolioSegmentAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancingReceivablePortfolioSegmentAxis" xlink:to="lab_us-gaap_FinancingReceivablePortfolioSegmentAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_AuditorFirmId_58c3691f-48eb-404b-b29c-77061b6be514_terseLabel_en-US" xlink:label="lab_dei_AuditorFirmId" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Auditor Firm ID</link:label>
    <link:label id="lab_dei_AuditorFirmId_label_en-US" xlink:label="lab_dei_AuditorFirmId" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Auditor Firm ID</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_AuditorFirmId" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_AuditorFirmId"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_AuditorFirmId" xlink:to="lab_dei_AuditorFirmId" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumReceivableAllowanceForCreditLossTableTextBlock_0c5036c9-bcf8-4bb7-99c0-025df66e96fe_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumReceivableAllowanceForCreditLossTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Premium Receivable, Allowance for Credit Loss</link:label>
    <link:label id="lab_us-gaap_PremiumReceivableAllowanceForCreditLossTableTextBlock_label_en-US" xlink:label="lab_us-gaap_PremiumReceivableAllowanceForCreditLossTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Premium Receivable, Allowance for Credit Loss [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumReceivableAllowanceForCreditLossTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PremiumReceivableAllowanceForCreditLossTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumReceivableAllowanceForCreditLossTableTextBlock" xlink:to="lab_us-gaap_PremiumReceivableAllowanceForCreditLossTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentTransitionReport_232c57c3-694e-480b-97e9-edaffc40d5fc_terseLabel_en-US" xlink:label="lab_dei_DocumentTransitionReport" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Document Transition Report</link:label>
    <link:label id="lab_dei_DocumentTransitionReport_label_en-US" xlink:label="lab_dei_DocumentTransitionReport" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Document Transition Report</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentTransitionReport" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_DocumentTransitionReport"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentTransitionReport" xlink:to="lab_dei_DocumentTransitionReport" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_LocalPhoneNumber_2ee6cf88-014e-4fa9-a27a-49e4acbc3e93_terseLabel_en-US" xlink:label="lab_dei_LocalPhoneNumber" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Local Phone Number</link:label>
    <link:label id="lab_dei_LocalPhoneNumber_label_en-US" xlink:label="lab_dei_LocalPhoneNumber" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Local Phone Number</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_LocalPhoneNumber" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_LocalPhoneNumber"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_LocalPhoneNumber" xlink:to="lab_dei_LocalPhoneNumber" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_MortgageLoansOnRealEstatePrincipalAmountPercentageOfPropertyAppraisalValue_d6ab40dc-87df-4c96-afbe-3b32d4787f98_terseLabel_en-US" xlink:label="lab_skwd_MortgageLoansOnRealEstatePrincipalAmountPercentageOfPropertyAppraisalValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Percentage of property appraisal value</link:label>
    <link:label id="lab_skwd_MortgageLoansOnRealEstatePrincipalAmountPercentageOfPropertyAppraisalValue_label_en-US" xlink:label="lab_skwd_MortgageLoansOnRealEstatePrincipalAmountPercentageOfPropertyAppraisalValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Mortgage Loans on Real Estate, Principal Amount, Percentage of Property Appraisal Value</link:label>
    <link:label id="lab_skwd_MortgageLoansOnRealEstatePrincipalAmountPercentageOfPropertyAppraisalValue_documentation_en-US" xlink:label="lab_skwd_MortgageLoansOnRealEstatePrincipalAmountPercentageOfPropertyAppraisalValue" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Mortgage Loans on Real Estate, Principal Amount, Percentage of Property Appraisal Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_MortgageLoansOnRealEstatePrincipalAmountPercentageOfPropertyAppraisalValue" xlink:href="skwd-20221231.xsd#skwd_MortgageLoansOnRealEstatePrincipalAmountPercentageOfPropertyAppraisalValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_MortgageLoansOnRealEstatePrincipalAmountPercentageOfPropertyAppraisalValue" xlink:to="lab_skwd_MortgageLoansOnRealEstatePrincipalAmountPercentageOfPropertyAppraisalValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherCostAndExpenseOperating_751ed26a-c051-48c8-b53d-ce4c1a70349c_terseLabel_en-US" xlink:label="lab_us-gaap_OtherCostAndExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other operating and general expenses</link:label>
    <link:label id="lab_us-gaap_OtherCostAndExpenseOperating_label_en-US" xlink:label="lab_us-gaap_OtherCostAndExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other Cost and Expense, Operating</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherCostAndExpenseOperating" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OtherCostAndExpenseOperating"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherCostAndExpenseOperating" xlink:to="lab_us-gaap_OtherCostAndExpenseOperating" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NewAccountingPronouncementsPolicyPolicyTextBlock_98c754d4-323d-4375-be4f-2f2381b14b2b_terseLabel_en-US" xlink:label="lab_us-gaap_NewAccountingPronouncementsPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Recent Accounting Standards Not Yet Adopted</link:label>
    <link:label id="lab_us-gaap_NewAccountingPronouncementsPolicyPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_NewAccountingPronouncementsPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">New Accounting Pronouncements, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NewAccountingPronouncementsPolicyPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NewAccountingPronouncementsPolicyPolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NewAccountingPronouncementsPolicyPolicyTextBlock" xlink:to="lab_us-gaap_NewAccountingPronouncementsPolicyPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumsPercentageAssumedToNet_4ea9eefc-0b3c-4096-8d17-2e13b9919ba9_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsPercentageAssumedToNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Percentage of amount assumed to net</link:label>
    <link:label id="lab_us-gaap_PremiumsPercentageAssumedToNet_label_en-US" xlink:label="lab_us-gaap_PremiumsPercentageAssumedToNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-17, Insurance Companies, Reinsurance, Premium, Percentage Assumed to Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsPercentageAssumedToNet" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PremiumsPercentageAssumedToNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsPercentageAssumedToNet" xlink:to="lab_us-gaap_PremiumsPercentageAssumedToNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustmentAbstract_d52d3410-e17c-4c28-9dfb-dd8c0456c4ea_terseLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustmentAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Denominator</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustmentAbstract_label_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustmentAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Weighted Average Number of Shares Outstanding, Diluted, Adjustment [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustmentAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustmentAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustmentAbstract" xlink:to="lab_us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustmentAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillAndIntangibleAssetImpairment_4f19c2b5-b658-492f-95a0-830d95b54e93_terseLabel_en-US" xlink:label="lab_us-gaap_GoodwillAndIntangibleAssetImpairment" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Impairment charges</link:label>
    <link:label id="lab_us-gaap_GoodwillAndIntangibleAssetImpairment_label_en-US" xlink:label="lab_us-gaap_GoodwillAndIntangibleAssetImpairment" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Goodwill and Intangible Asset Impairment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillAndIntangibleAssetImpairment" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_GoodwillAndIntangibleAssetImpairment"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillAndIntangibleAssetImpairment" xlink:to="lab_us-gaap_GoodwillAndIntangibleAssetImpairment" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IndefinitelivedIntangibleAssetsAcquired_87557059-81eb-4a68-925c-57db8a83005a_terseLabel_en-US" xlink:label="lab_us-gaap_IndefinitelivedIntangibleAssetsAcquired" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Additions</link:label>
    <link:label id="lab_us-gaap_IndefinitelivedIntangibleAssetsAcquired_label_en-US" xlink:label="lab_us-gaap_IndefinitelivedIntangibleAssetsAcquired" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Indefinite-Lived Intangible Assets Acquired</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefinitelivedIntangibleAssetsAcquired" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IndefinitelivedIntangibleAssetsAcquired"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IndefinitelivedIntangibleAssetsAcquired" xlink:to="lab_us-gaap_IndefinitelivedIntangibleAssetsAcquired" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract_2c119ab0-312a-4437-b339-5767c04f3a14_terseLabel_en-US" xlink:label="lab_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Adjustments to reconcile net income to net cash provided by (used in) operating activities:</link:label>
    <link:label id="lab_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract_label_en-US" xlink:label="lab_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Adjustments to Reconcile Net Income (Loss) to Cash Provided by (Used in) Operating Activities [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract" xlink:to="lab_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivitiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock_b8205fdb-ac11-49a6-aa9b-07a93ecfb162_terseLabel_en-US" xlink:label="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Goodwill and Intangible Assets</link:label>
    <link:label id="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Goodwill and Intangible Assets Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock" xlink:to="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_JVMFundsLLCMember_36fe133b-f49c-45bc-98b3-9999baa10eba_terseLabel_en-US" xlink:label="lab_skwd_JVMFundsLLCMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">JVM Funds LLC units</link:label>
    <link:label id="lab_skwd_JVMFundsLLCMember_label_en-US" xlink:label="lab_skwd_JVMFundsLLCMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">JVM Funds LLC [Member]</link:label>
    <link:label id="lab_skwd_JVMFundsLLCMember_documentation_en-US" xlink:label="lab_skwd_JVMFundsLLCMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">JVM Funds LLC</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_JVMFundsLLCMember" xlink:href="skwd-20221231.xsd#skwd_JVMFundsLLCMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_JVMFundsLLCMember" xlink:to="lab_skwd_JVMFundsLLCMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentPolicyTextBlock_fbb9514d-4354-49ba-8bd0-2185884ae4d3_terseLabel_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Property and Equipment</link:label>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Property, Plant and Equipment, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PropertyPlantAndEquipmentPolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentPolicyTextBlock" xlink:to="lab_us-gaap_PropertyPlantAndEquipmentPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PreferredStockParOrStatedValuePerShare_fe7eaef0-d58b-448a-8bc8-2bdc475e7c6f_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockParOrStatedValuePerShare" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred stock, par value (in USD per share)</link:label>
    <link:label id="lab_us-gaap_PreferredStockParOrStatedValuePerShare_label_en-US" xlink:label="lab_us-gaap_PreferredStockParOrStatedValuePerShare" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred Stock, Par or Stated Value Per Share</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockParOrStatedValuePerShare" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PreferredStockParOrStatedValuePerShare"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PreferredStockParOrStatedValuePerShare" xlink:to="lab_us-gaap_PreferredStockParOrStatedValuePerShare" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFour_a3e834b8-ff7e-4978-8008-0ecb5633edfa_terseLabel_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFour" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">2026</link:label>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFour_label_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFour" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Lessee, Operating Lease, Liability, to be Paid, Year Four</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFour" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFour"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFour" xlink:to="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFour" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeStatementAbstract_label_en-US" xlink:label="lab_us-gaap_IncomeStatementAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Income Statement [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeStatementAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncomeStatementAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeStatementAbstract" xlink:to="lab_us-gaap_IncomeStatementAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AdditionalPaidInCapitalMember_7b769600-6792-447d-a348-65f6c8e18e5c_terseLabel_en-US" xlink:label="lab_us-gaap_AdditionalPaidInCapitalMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Additional Paid-In Capital</link:label>
    <link:label id="lab_us-gaap_AdditionalPaidInCapitalMember_label_en-US" xlink:label="lab_us-gaap_AdditionalPaidInCapitalMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Additional Paid-in Capital [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdditionalPaidInCapitalMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AdditionalPaidInCapitalMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AdditionalPaidInCapitalMember" xlink:to="lab_us-gaap_AdditionalPaidInCapitalMember" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentFiscalPeriodFocus_ead8eea9-6517-4e71-bc58-b706de91d4aa_terseLabel_en-US" xlink:label="lab_dei_DocumentFiscalPeriodFocus" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Document Fiscal Period Focus</link:label>
    <link:label id="lab_dei_DocumentFiscalPeriodFocus_label_en-US" xlink:label="lab_dei_DocumentFiscalPeriodFocus" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Document Fiscal Period Focus</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentFiscalPeriodFocus" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_DocumentFiscalPeriodFocus"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentFiscalPeriodFocus" xlink:to="lab_dei_DocumentFiscalPeriodFocus" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss_ae7b9836-48a7-4fb8-9549-27bab20a5542_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">12 Months or More</link:label>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss_label_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Held-to-Maturity, Continuous Unrealized Loss Position, 12 Months or Longer, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:to="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfEquityMethodInvestments_26544a9d-8a6d-438d-8365-8e209cbb4773_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Proceeds from sale of equity method investment</link:label>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfEquityMethodInvestments_label_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Proceeds from Sale of Equity Method Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromSaleOfEquityMethodInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ProceedsFromSaleOfEquityMethodInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromSaleOfEquityMethodInvestments" xlink:to="lab_us-gaap_ProceedsFromSaleOfEquityMethodInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_4abf346d-e983-4cff-ac8a-44698e2dc4d8_terseLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Diluted weighted-average common shares (in shares)</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_84b5c549-934b-4cf0-b1bd-69ae4882b444_totalLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Diluted weighted-average common share equivalents (in shares)</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_label_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Weighted Average Number of Shares Outstanding, Diluted</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:to="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent_5f29601f-462f-4f21-8056-5b0b61c891b9_terseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity securities, at fair value</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Securities, FV-NI</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent" xlink:to="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems_7ec48649-6fb9-4a17-ba98-208f23ab0d89_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale [Line Items]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems_label_en-US" xlink:label="lab_us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems" xlink:to="lab_us-gaap_ScheduleOfAvailableForSaleSecuritiesLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearThree_665a345a-5cbb-4078-ba3d-fc84e51af62f_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearThree" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Year 3</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearThree_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearThree" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Historical Claims Duration, Year Three</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearThree" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearThree"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearThree" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearThree" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CarryingReportedAmountFairValueDisclosureMember_753a9b12-4874-44fd-a083-e428a0c7363d_terseLabel_en-US" xlink:label="lab_us-gaap_CarryingReportedAmountFairValueDisclosureMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Carrying&#160; Value</link:label>
    <link:label id="lab_us-gaap_CarryingReportedAmountFairValueDisclosureMember_label_en-US" xlink:label="lab_us-gaap_CarryingReportedAmountFairValueDisclosureMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reported Value Measurement [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CarryingReportedAmountFairValueDisclosureMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CarryingReportedAmountFairValueDisclosureMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CarryingReportedAmountFairValueDisclosureMember" xlink:to="lab_us-gaap_CarryingReportedAmountFairValueDisclosureMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ShortDurationInsuranceContractsHistoricalClaimsDurationYear10AndOlder_10c65526-d029-4d40-8003-1757a7c6e62b_terseLabel_en-US" xlink:label="lab_skwd_ShortDurationInsuranceContractsHistoricalClaimsDurationYear10AndOlder" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Year 10</link:label>
    <link:label id="lab_skwd_ShortDurationInsuranceContractsHistoricalClaimsDurationYear10AndOlder_label_en-US" xlink:label="lab_skwd_ShortDurationInsuranceContractsHistoricalClaimsDurationYear10AndOlder" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Historical Claims Duration, Year 10 And Older</link:label>
    <link:label id="lab_skwd_ShortDurationInsuranceContractsHistoricalClaimsDurationYear10AndOlder_documentation_en-US" xlink:label="lab_skwd_ShortDurationInsuranceContractsHistoricalClaimsDurationYear10AndOlder" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Historical Claims Duration, Year 10 And Older</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ShortDurationInsuranceContractsHistoricalClaimsDurationYear10AndOlder" xlink:href="skwd-20221231.xsd#skwd_ShortDurationInsuranceContractsHistoricalClaimsDurationYear10AndOlder"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ShortDurationInsuranceContractsHistoricalClaimsDurationYear10AndOlder" xlink:to="lab_skwd_ShortDurationInsuranceContractsHistoricalClaimsDurationYear10AndOlder" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardStockNotesReceivableInterestRatePercentage_409898bd-ee0a-4ffa-bde3-f5b71ef658f3_terseLabel_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardStockNotesReceivableInterestRatePercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stock notes receivable interest, percent</link:label>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardStockNotesReceivableInterestRatePercentage_label_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardStockNotesReceivableInterestRatePercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Stock Notes Receivable, Interest Rate, Percentage</link:label>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardStockNotesReceivableInterestRatePercentage_documentation_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardStockNotesReceivableInterestRatePercentage" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Stock Notes Receivable, Interest Rate, Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardStockNotesReceivableInterestRatePercentage" xlink:href="skwd-20221231.xsd#skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardStockNotesReceivableInterestRatePercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardStockNotesReceivableInterestRatePercentage" xlink:to="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardStockNotesReceivableInterestRatePercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DirectAndAssumedPremiumsProductAndServiceBenchmarkMember_feb899b2-c603-41fd-8824-478f24140132_terseLabel_en-US" xlink:label="lab_skwd_DirectAndAssumedPremiumsProductAndServiceBenchmarkMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Direct and assumed premiums, business line benchmark</link:label>
    <link:label id="lab_skwd_DirectAndAssumedPremiumsProductAndServiceBenchmarkMember_label_en-US" xlink:label="lab_skwd_DirectAndAssumedPremiumsProductAndServiceBenchmarkMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Direct And Assumed Premiums, Product And Service Benchmark [Member]</link:label>
    <link:label id="lab_skwd_DirectAndAssumedPremiumsProductAndServiceBenchmarkMember_documentation_en-US" xlink:label="lab_skwd_DirectAndAssumedPremiumsProductAndServiceBenchmarkMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Direct And Assumed Premiums, Product And Service Benchmark</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DirectAndAssumedPremiumsProductAndServiceBenchmarkMember" xlink:href="skwd-20221231.xsd#skwd_DirectAndAssumedPremiumsProductAndServiceBenchmarkMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DirectAndAssumedPremiumsProductAndServiceBenchmarkMember" xlink:to="lab_skwd_DirectAndAssumedPremiumsProductAndServiceBenchmarkMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodWeightedAverageGrantDateFairValue_22077240-c0ff-4aa0-91a7-0e75e46245f3_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodWeightedAverageGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Granted (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodWeightedAverageGrantDateFairValue_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodWeightedAverageGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Grants in Period, Weighted Average Grant Date Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodWeightedAverageGrantDateFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodWeightedAverageGrantDateFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodWeightedAverageGrantDateFairValue" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodWeightedAverageGrantDateFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RealizedInvestmentGainsLosses_4160f55b-8494-45a4-9fd6-a89a0b20edcb_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_RealizedInvestmentGainsLosses" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net realized losses (gains)</link:label>
    <link:label id="lab_us-gaap_RealizedInvestmentGainsLosses_label_en-US" xlink:label="lab_us-gaap_RealizedInvestmentGainsLosses" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Realized Investment Gains (Losses)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RealizedInvestmentGainsLosses" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RealizedInvestmentGainsLosses"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RealizedInvestmentGainsLosses" xlink:to="lab_us-gaap_RealizedInvestmentGainsLosses" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock_2dbd3152-fe20-41d7-beb9-02bb02eca397_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Fair Value, Assets and Liabilities Measured on Recurring Basis</link:label>
    <link:label id="lab_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Fair Value, Assets and Liabilities Measured on Recurring Basis [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_380de409-2ba6-446b-a185-2312c1cbee73_negatedTerseLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Less than 12 Months</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_label_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Continuous Unrealized Loss Position, Less than 12 Months, Accumulated Loss</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_documentation_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Continuous Unrealized Loss Position, Less than 12 Months, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:href="skwd-20221231.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:to="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinancialLiabilitiesFairValueDisclosureAbstract_96de5b4f-953b-4c14-bbdb-f61c9192dc2e_terseLabel_en-US" xlink:label="lab_us-gaap_FinancialLiabilitiesFairValueDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liabilities:</link:label>
    <link:label id="lab_us-gaap_FinancialLiabilitiesFairValueDisclosureAbstract_label_en-US" xlink:label="lab_us-gaap_FinancialLiabilitiesFairValueDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Financial Liabilities Fair Value Disclosure [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancialLiabilitiesFairValueDisclosureAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FinancialLiabilitiesFairValueDisclosureAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancialLiabilitiesFairValueDisclosureAbstract" xlink:to="lab_us-gaap_FinancialLiabilitiesFairValueDisclosureAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LimitedPartnerMember_4e068f41-65f1-4abf-9464-d1ddc946a0d3_terseLabel_en-US" xlink:label="lab_us-gaap_LimitedPartnerMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Limited partner</link:label>
    <link:label id="lab_us-gaap_LimitedPartnerMember_label_en-US" xlink:label="lab_us-gaap_LimitedPartnerMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Limited Partner [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LimitedPartnerMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LimitedPartnerMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LimitedPartnerMember" xlink:to="lab_us-gaap_LimitedPartnerMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortTermLeaseCost_b1320a54-c051-44ef-9019-85c70d2fbbf8_terseLabel_en-US" xlink:label="lab_us-gaap_ShortTermLeaseCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-term lease expense</link:label>
    <link:label id="lab_us-gaap_ShortTermLeaseCost_label_en-US" xlink:label="lab_us-gaap_ShortTermLeaseCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Term Lease, Cost</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortTermLeaseCost" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortTermLeaseCost"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortTermLeaseCost" xlink:to="lab_us-gaap_ShortTermLeaseCost" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PreferredStockSharesAuthorized_a1926916-7f19-459e-bc71-8274c85160d3_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockSharesAuthorized" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred stock, shares authorized (in shares)</link:label>
    <link:label id="lab_us-gaap_PreferredStockSharesAuthorized_label_en-US" xlink:label="lab_us-gaap_PreferredStockSharesAuthorized" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred Stock, Shares Authorized</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockSharesAuthorized" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PreferredStockSharesAuthorized"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PreferredStockSharesAuthorized" xlink:to="lab_us-gaap_PreferredStockSharesAuthorized" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_AccidentAndHealthMember_a75cd098-c4be-493e-8219-03cde9f7f5e4_terseLabel_en-US" xlink:label="lab_skwd_AccidentAndHealthMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accident and Health</link:label>
    <link:label id="lab_skwd_AccidentAndHealthMember_label_en-US" xlink:label="lab_skwd_AccidentAndHealthMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accident and Health [Member]</link:label>
    <link:label id="lab_skwd_AccidentAndHealthMember_documentation_en-US" xlink:label="lab_skwd_AccidentAndHealthMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accident and Health</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_AccidentAndHealthMember" xlink:href="skwd-20221231.xsd#skwd_AccidentAndHealthMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_AccidentAndHealthMember" xlink:to="lab_skwd_AccidentAndHealthMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProductConcentrationRiskMember_66fda039-81a4-45e0-bfa1-24d18e48fa42_terseLabel_en-US" xlink:label="lab_us-gaap_ProductConcentrationRiskMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Product concentration risk</link:label>
    <link:label id="lab_us-gaap_ProductConcentrationRiskMember_label_en-US" xlink:label="lab_us-gaap_ProductConcentrationRiskMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Product Concentration Risk [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProductConcentrationRiskMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ProductConcentrationRiskMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProductConcentrationRiskMember" xlink:to="lab_us-gaap_ProductConcentrationRiskMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_EffectiveIncomeTaxRateReconciliationAdvantagedInvestmentsAmount_f3290f1e-e755-485b-9ca4-3aa0f5ba8540_terseLabel_en-US" xlink:label="lab_skwd_EffectiveIncomeTaxRateReconciliationAdvantagedInvestmentsAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Tax advantaged investments</link:label>
    <link:label id="lab_skwd_EffectiveIncomeTaxRateReconciliationAdvantagedInvestmentsAmount_label_en-US" xlink:label="lab_skwd_EffectiveIncomeTaxRateReconciliationAdvantagedInvestmentsAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Effective Income Tax Rate Reconciliation, Advantaged Investments, Amount</link:label>
    <link:label id="lab_skwd_EffectiveIncomeTaxRateReconciliationAdvantagedInvestmentsAmount_documentation_en-US" xlink:label="lab_skwd_EffectiveIncomeTaxRateReconciliationAdvantagedInvestmentsAmount" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Effective Income Tax Rate Reconciliation, Advantaged Investments, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_EffectiveIncomeTaxRateReconciliationAdvantagedInvestmentsAmount" xlink:href="skwd-20221231.xsd#skwd_EffectiveIncomeTaxRateReconciliationAdvantagedInvestmentsAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_EffectiveIncomeTaxRateReconciliationAdvantagedInvestmentsAmount" xlink:to="lab_skwd_EffectiveIncomeTaxRateReconciliationAdvantagedInvestmentsAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ImpairmentOfIntangibleAssetsFinitelived_870e236a-f886-4c6c-a40b-2eeaf4bc9958_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_ImpairmentOfIntangibleAssetsFinitelived" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Impairment</link:label>
    <link:label id="lab_us-gaap_ImpairmentOfIntangibleAssetsFinitelived_label_en-US" xlink:label="lab_us-gaap_ImpairmentOfIntangibleAssetsFinitelived" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Impairment of Intangible Assets, Finite-Lived</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ImpairmentOfIntangibleAssetsFinitelived" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ImpairmentOfIntangibleAssetsFinitelived"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ImpairmentOfIntangibleAssetsFinitelived" xlink:to="lab_us-gaap_ImpairmentOfIntangibleAssetsFinitelived" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock_33fd82ca-25ba-40c2-bdd2-e48ba5de2ff3_terseLabel_en-US" xlink:label="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Commitments and Contingencies</link:label>
    <link:label id="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Commitments and Contingencies Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CommitmentsAndContingenciesDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" xlink:to="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillImpairedAccumulatedImpairmentLoss_cc17c703-22c1-417e-8161-50bd48903937_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_GoodwillImpairedAccumulatedImpairmentLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accumulated impairment</link:label>
    <link:label id="lab_us-gaap_GoodwillImpairedAccumulatedImpairmentLoss_label_en-US" xlink:label="lab_us-gaap_GoodwillImpairedAccumulatedImpairmentLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Goodwill, Impaired, Accumulated Impairment Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillImpairedAccumulatedImpairmentLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_GoodwillImpairedAccumulatedImpairmentLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillImpairedAccumulatedImpairmentLoss" xlink:to="lab_us-gaap_GoodwillImpairedAccumulatedImpairmentLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic_c5fa4d64-d212-4de4-9c44-85fb7dfa55bd_totalLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net income attributable to common shareholders</link:label>
    <link:label id="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic_5394527d-d218-4019-9486-d86f0acc2df6_terseLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net income attributable to common shareholders</link:label>
    <link:label id="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic_label_en-US" xlink:label="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net Income (Loss) Available to Common Stockholders, Basic</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic" xlink:to="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsTextBlock_0407d652-1406-4826-aa68-110b8a50762b_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Carrying Value of Equity Method Investments</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsTextBlock_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Method Investments [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EquityMethodInvestmentsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentsTextBlock" xlink:to="lab_us-gaap_EquityMethodInvestmentsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockSharesIssued_7c79387d-8e3f-4780-bdad-6ff51c700ee4_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockSharesIssued" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common stock, shares issued (in shares)</link:label>
    <link:label id="lab_us-gaap_CommonStockSharesIssued_label_en-US" xlink:label="lab_us-gaap_CommonStockSharesIssued" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common Stock, Shares, Issued</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockSharesIssued" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CommonStockSharesIssued"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockSharesIssued" xlink:to="lab_us-gaap_CommonStockSharesIssued" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestments_5b24c731-ac5e-42ce-8695-8592333baa47_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Recorded investment balance</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestments_cedc1e37-4641-4c41-a138-540217712a0b_verboseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Carrying Value</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestments_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Method Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EquityMethodInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestments" xlink:to="lab_us-gaap_EquityMethodInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConcentrationRiskLineItems_84a23e8e-ef2f-4565-9bfd-15b050086f47_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Concentration Risk [Line Items]</link:label>
    <link:label id="lab_us-gaap_ConcentrationRiskLineItems_label_en-US" xlink:label="lab_us-gaap_ConcentrationRiskLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Concentration Risk [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConcentrationRiskLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ConcentrationRiskLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConcentrationRiskLineItems" xlink:to="lab_us-gaap_ConcentrationRiskLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_A2022LongTermIncentivePlanMember_9e23da53-d224-44f4-9bcc-a5986f482abd_terseLabel_en-US" xlink:label="lab_skwd_A2022LongTermIncentivePlanMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">2022 Long-Term Incentive Plan</link:label>
    <link:label id="lab_skwd_A2022LongTermIncentivePlanMember_label_en-US" xlink:label="lab_skwd_A2022LongTermIncentivePlanMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">2022 Long-Term Incentive Plan [Member]</link:label>
    <link:label id="lab_skwd_A2022LongTermIncentivePlanMember_documentation_en-US" xlink:label="lab_skwd_A2022LongTermIncentivePlanMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">2022 Long-Term Incentive Plan</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_A2022LongTermIncentivePlanMember" xlink:href="skwd-20221231.xsd#skwd_A2022LongTermIncentivePlanMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_A2022LongTermIncentivePlanMember" xlink:to="lab_skwd_A2022LongTermIncentivePlanMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock_8e31896a-6c05-498e-8286-419039015dd1_terseLabel_en-US" xlink:label="lab_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Trading, and Equity Securities, FV-NI</link:label>
    <link:label id="lab_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock_label_en-US" xlink:label="lab_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Trading, and Equity Securities, FV-NI [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock" xlink:to="lab_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisLineItems_7e916c65-23c9-4039-9248-501f700edc00_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]</link:label>
    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisLineItems_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisLineItems" xlink:to="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities_d52b1c53-f09a-4bf4-a188-7edc06b811df_totalLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net cash used in investing activities</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net Cash Provided by (Used in) Investing Activities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetCashProvidedByUsedInInvestingActivities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:to="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentFaceAmount_49bcf29a-e547-4a63-97e2-92136da5d75e_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentFaceAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Face amount</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentFaceAmount_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentFaceAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Face Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentFaceAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtInstrumentFaceAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentFaceAmount" xlink:to="lab_us-gaap_DebtInstrumentFaceAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentPolicyTextBlock_44b378c2-c931-4da6-bf21-799f81e1b9cf_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investments</link:label>
    <link:label id="lab_us-gaap_InvestmentPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_InvestmentPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_InvestmentPolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentPolicyTextBlock" xlink:to="lab_us-gaap_InvestmentPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_AuditInformationAbstract_label_en-US" xlink:label="lab_skwd_AuditInformationAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Audit Information [Abstract]</link:label>
    <link:label id="lab_skwd_AuditInformationAbstract_documentation_en-US" xlink:label="lab_skwd_AuditInformationAbstract" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Audit Information</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_AuditInformationAbstract" xlink:href="skwd-20221231.xsd#skwd_AuditInformationAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_AuditInformationAbstract" xlink:to="lab_skwd_AuditInformationAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ComprehensiveIncomeNetOfTax_8a3cd0a2-d271-483a-9deb-5277bfeec68e_totalLabel_en-US" xlink:label="lab_us-gaap_ComprehensiveIncomeNetOfTax" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Comprehensive (loss) income</link:label>
    <link:label id="lab_us-gaap_ComprehensiveIncomeNetOfTax_label_en-US" xlink:label="lab_us-gaap_ComprehensiveIncomeNetOfTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Comprehensive Income (Loss), Net of Tax, Attributable to Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ComprehensiveIncomeNetOfTax" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ComprehensiveIncomeNetOfTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ComprehensiveIncomeNetOfTax" xlink:to="lab_us-gaap_ComprehensiveIncomeNetOfTax" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2020Member_b8ac5dc2-846b-4e96-9346-3e574515d68d_terseLabel_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2020Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accident Year 2020</link:label>
    <link:label id="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2020Member_label_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2020Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contract, Accident Year 2020 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortDurationInsuranceContractAccidentYear2020Member" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortDurationInsuranceContractAccidentYear2020Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortDurationInsuranceContractAccidentYear2020Member" xlink:to="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2020Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredTaxLiabilitiesDeferredExpenseDeferredPolicyAcquisitionCost_cc005051-d2e5-4be8-af45-d42c3850d9c4_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxLiabilitiesDeferredExpenseDeferredPolicyAcquisitionCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred policy acquisition costs</link:label>
    <link:label id="lab_us-gaap_DeferredTaxLiabilitiesDeferredExpenseDeferredPolicyAcquisitionCost_label_en-US" xlink:label="lab_us-gaap_DeferredTaxLiabilitiesDeferredExpenseDeferredPolicyAcquisitionCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Tax Liabilities, Deferred Expense, Deferred Policy Acquisition Cost</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxLiabilitiesDeferredExpenseDeferredPolicyAcquisitionCost" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DeferredTaxLiabilitiesDeferredExpenseDeferredPolicyAcquisitionCost"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredTaxLiabilitiesDeferredExpenseDeferredPolicyAcquisitionCost" xlink:to="lab_us-gaap_DeferredTaxLiabilitiesDeferredExpenseDeferredPolicyAcquisitionCost" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_RetailPortfolioSegmentMember_749985e5-84cc-4aeb-a264-0394f4becf94_terseLabel_en-US" xlink:label="lab_skwd_RetailPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Retail</link:label>
    <link:label id="lab_skwd_RetailPortfolioSegmentMember_label_en-US" xlink:label="lab_skwd_RetailPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Retail Portfolio Segment [Member]</link:label>
    <link:label id="lab_skwd_RetailPortfolioSegmentMember_documentation_en-US" xlink:label="lab_skwd_RetailPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Retail Portfolio Segment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RetailPortfolioSegmentMember" xlink:href="skwd-20221231.xsd#skwd_RetailPortfolioSegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_RetailPortfolioSegmentMember" xlink:to="lab_skwd_RetailPortfolioSegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTableTextBlock_03adc46e-a55f-44b6-9e9b-b035122710f7_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reconciliation of Claims Development to Liability</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Reconciliation of Claims Development to Liability [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTableTextBlock" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesTextBlock_da931efb-a523-40f0-b6dd-11d80f612292_terseLabel_en-US" xlink:label="lab_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SCHEDULE I&#160;&#8212; SUMMARY OF INVESTMENTS&#160;&#8212; OTHER THAN IN RELATED PARTIES</link:label>
    <link:label id="lab_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesTextBlock_label_en-US" xlink:label="lab_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-15, Insurance Companies, Summary of Investments, Other than Investments in Related Parties [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesTextBlock" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesTextBlock" xlink:to="lab_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityCurrentReportingStatus_74e5249e-2273-44d9-8c0f-f73be2829ca0_terseLabel_en-US" xlink:label="lab_dei_EntityCurrentReportingStatus" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Current Reporting Status</link:label>
    <link:label id="lab_dei_EntityCurrentReportingStatus_label_en-US" xlink:label="lab_dei_EntityCurrentReportingStatus" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Current Reporting Status</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityCurrentReportingStatus" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityCurrentReportingStatus"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityCurrentReportingStatus" xlink:to="lab_dei_EntityCurrentReportingStatus" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CondensedFinancialInformationOfParentCompanyOnlyDisclosureAbstract_label_en-US" xlink:label="lab_srt_CondensedFinancialInformationOfParentCompanyOnlyDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Condensed Financial Information Disclosure [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_CondensedFinancialInformationOfParentCompanyOnlyDisclosureAbstract" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_CondensedFinancialInformationOfParentCompanyOnlyDisclosureAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_CondensedFinancialInformationOfParentCompanyOnlyDisclosureAbstract" xlink:to="lab_srt_CondensedFinancialInformationOfParentCompanyOnlyDisclosureAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ScheduleOfSupplementalInformationForPropertyCasualtyInsuranceUnderwritersTextBlock_15d9ec4e-4642-4062-a88c-62b1e90976aa_terseLabel_en-US" xlink:label="lab_srt_ScheduleOfSupplementalInformationForPropertyCasualtyInsuranceUnderwritersTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SCHEDULE VI&#160;&#8212; SUPPLEMENTAL INFORMATION CONCERNING PROPERTY-CASUALTY INSURANCE OPERATIONS</link:label>
    <link:label id="lab_srt_ScheduleOfSupplementalInformationForPropertyCasualtyInsuranceUnderwritersTextBlock_label_en-US" xlink:label="lab_srt_ScheduleOfSupplementalInformationForPropertyCasualtyInsuranceUnderwritersTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-18, Supplemental Information, Property-Casualty Insurance Underwriters [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ScheduleOfSupplementalInformationForPropertyCasualtyInsuranceUnderwritersTextBlock" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_ScheduleOfSupplementalInformationForPropertyCasualtyInsuranceUnderwritersTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ScheduleOfSupplementalInformationForPropertyCasualtyInsuranceUnderwritersTextBlock" xlink:to="lab_srt_ScheduleOfSupplementalInformationForPropertyCasualtyInsuranceUnderwritersTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ArenaSpecialOpportunitiesFundLPMember_f2b8358a-2340-4972-b003-d5f903c80d4b_terseLabel_en-US" xlink:label="lab_skwd_ArenaSpecialOpportunitiesFundLPMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Arena Special Opportunities Fund, LP units</link:label>
    <link:label id="lab_skwd_ArenaSpecialOpportunitiesFundLPMember_label_en-US" xlink:label="lab_skwd_ArenaSpecialOpportunitiesFundLPMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Arena Special Opportunities Fund, LP [Member]</link:label>
    <link:label id="lab_skwd_ArenaSpecialOpportunitiesFundLPMember_documentation_en-US" xlink:label="lab_skwd_ArenaSpecialOpportunitiesFundLPMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Arena Special Opportunities Fund, LP</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ArenaSpecialOpportunitiesFundLPMember" xlink:href="skwd-20221231.xsd#skwd_ArenaSpecialOpportunitiesFundLPMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ArenaSpecialOpportunitiesFundLPMember" xlink:to="lab_skwd_ArenaSpecialOpportunitiesFundLPMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisaggregationOfRevenueTable_0d120633-8eb7-4be4-8c79-23c61613d379_terseLabel_en-US" xlink:label="lab_us-gaap_DisaggregationOfRevenueTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Disaggregation of Revenue [Table]</link:label>
    <link:label id="lab_us-gaap_DisaggregationOfRevenueTable_label_en-US" xlink:label="lab_us-gaap_DisaggregationOfRevenueTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Disaggregation of Revenue [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisaggregationOfRevenueTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DisaggregationOfRevenueTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisaggregationOfRevenueTable" xlink:to="lab_us-gaap_DisaggregationOfRevenueTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseOpeningBalanceAdjustments_c6440df0-da9c-4a2d-9786-2c906246e0fa_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseOpeningBalanceAdjustments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability for unpaid claims and claims adjustment</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseOpeningBalanceAdjustments_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseOpeningBalanceAdjustments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Adjustments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseOpeningBalanceAdjustments" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseOpeningBalanceAdjustments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseOpeningBalanceAdjustments" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseOpeningBalanceAdjustments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationAtFederalStatutoryIncomeTaxRate_0726db63-4c12-47b6-b297-836e6a3fe407_terseLabel_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationAtFederalStatutoryIncomeTaxRate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Income tax expense at federal statutory rate</link:label>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationAtFederalStatutoryIncomeTaxRate_label_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationAtFederalStatutoryIncomeTaxRate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Effective Income Tax Rate Reconciliation, at Federal Statutory Income Tax Rate, Percent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectiveIncomeTaxRateReconciliationAtFederalStatutoryIncomeTaxRate" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EffectiveIncomeTaxRateReconciliationAtFederalStatutoryIncomeTaxRate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectiveIncomeTaxRateReconciliationAtFederalStatutoryIncomeTaxRate" xlink:to="lab_us-gaap_EffectiveIncomeTaxRateReconciliationAtFederalStatutoryIncomeTaxRate" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThanTwelveMonthsFairValue_111e3776-f618-4296-804f-3580f935e19d_terseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThanTwelveMonthsFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Less than 12 Months</link:label>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThanTwelveMonthsFairValue_label_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThanTwelveMonthsFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Held-to-Maturity, Continuous Unrealized Loss Position, Less than 12 Months, Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThanTwelveMonthsFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThanTwelveMonthsFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThanTwelveMonthsFairValue" xlink:to="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThanTwelveMonthsFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease_ace4e6bc-ad82-4986-a4d3-01a9e51d8747_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reserves for losses and LAE, increase (decrease)</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Period Increase (Decrease)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ValuationAllowancesAndReservesChargedToCostAndExpense_e2dd0de9-9492-487a-98b4-4dd6ceccf705_terseLabel_en-US" xlink:label="lab_us-gaap_ValuationAllowancesAndReservesChargedToCostAndExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Charged to costs and expenses</link:label>
    <link:label id="lab_us-gaap_ValuationAllowancesAndReservesChargedToCostAndExpense_label_en-US" xlink:label="lab_us-gaap_ValuationAllowancesAndReservesChargedToCostAndExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-09, Valuation Allowances and Reserves, Additions, Charge to Cost and Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ValuationAllowancesAndReservesChargedToCostAndExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ValuationAllowancesAndReservesChargedToCostAndExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ValuationAllowancesAndReservesChargedToCostAndExpense" xlink:to="lab_us-gaap_ValuationAllowancesAndReservesChargedToCostAndExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ProceedsFromDistributionsFromConsolidatedEntities_e28482fa-a300-4620-8716-2d3256926835_terseLabel_en-US" xlink:label="lab_skwd_ProceedsFromDistributionsFromConsolidatedEntities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Distributions from investment in subsidiaries</link:label>
    <link:label id="lab_skwd_ProceedsFromDistributionsFromConsolidatedEntities_label_en-US" xlink:label="lab_skwd_ProceedsFromDistributionsFromConsolidatedEntities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Proceeds From Distributions From Consolidated Entities</link:label>
    <link:label id="lab_skwd_ProceedsFromDistributionsFromConsolidatedEntities_documentation_en-US" xlink:label="lab_skwd_ProceedsFromDistributionsFromConsolidatedEntities" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Proceeds From Distributions From Consolidated Entities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ProceedsFromDistributionsFromConsolidatedEntities" xlink:href="skwd-20221231.xsd#skwd_ProceedsFromDistributionsFromConsolidatedEntities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ProceedsFromDistributionsFromConsolidatedEntities" xlink:to="lab_skwd_ProceedsFromDistributionsFromConsolidatedEntities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IPOMember_c908882f-73f9-4393-87ed-d40b3a8ef680_terseLabel_en-US" xlink:label="lab_us-gaap_IPOMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">IPO</link:label>
    <link:label id="lab_us-gaap_IPOMember_label_en-US" xlink:label="lab_us-gaap_IPOMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">IPO [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IPOMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IPOMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IPOMember" xlink:to="lab_us-gaap_IPOMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInFundsHeldUnderReinsuranceAgreements_f7bd157b-8495-4b1f-ac3c-4e475eaf2502_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInFundsHeldUnderReinsuranceAgreements" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Funds held for others</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInFundsHeldUnderReinsuranceAgreements_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInFundsHeldUnderReinsuranceAgreements" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Increase (Decrease) in Funds Held under Reinsurance Agreements</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInFundsHeldUnderReinsuranceAgreements" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInFundsHeldUnderReinsuranceAgreements"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInFundsHeldUnderReinsuranceAgreements" xlink:to="lab_us-gaap_IncreaseDecreaseInFundsHeldUnderReinsuranceAgreements" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentNet_0b677e1c-9630-4819-917c-25912d728dcb_totalLabel_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total</link:label>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentNet_label_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Property, Plant and Equipment, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentNet" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PropertyPlantAndEquipmentNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentNet" xlink:to="lab_us-gaap_PropertyPlantAndEquipmentNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock_45a3f7aa-8e4a-415e-91fa-8127169c1ae9_terseLabel_en-US" xlink:label="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Basis of Presentation</link:label>
    <link:label id="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Basis of Accounting, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_BasisOfAccountingPolicyPolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:to="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilitiesAbstract_a5a09b58-1ad0-4478-9b43-5c0006a1e362_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liabilities:</link:label>
    <link:label id="lab_us-gaap_LiabilitiesAbstract_label_en-US" xlink:label="lab_us-gaap_LiabilitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liabilities [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilitiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilitiesAbstract" xlink:to="lab_us-gaap_LiabilitiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_TreasuryStockParValue_5ea48315-8638-43f4-bd5b-f6bbce875244_terseLabel_en-US" xlink:label="lab_skwd_TreasuryStockParValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Treasury stock, par value (in USD per share)</link:label>
    <link:label id="lab_skwd_TreasuryStockParValue_label_en-US" xlink:label="lab_skwd_TreasuryStockParValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Treasury Stock, Par Value</link:label>
    <link:label id="lab_skwd_TreasuryStockParValue_documentation_en-US" xlink:label="lab_skwd_TreasuryStockParValue" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Treasury Stock, Par Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_TreasuryStockParValue" xlink:href="skwd-20221231.xsd#skwd_TreasuryStockParValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_TreasuryStockParValue" xlink:to="lab_skwd_TreasuryStockParValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PreferredStockDividendsAndOtherAdjustmentsAbstract_5b13a53b-a142-4487-9112-d9f9b4e18072_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockDividendsAndOtherAdjustmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Numerator</link:label>
    <link:label id="lab_us-gaap_PreferredStockDividendsAndOtherAdjustmentsAbstract_label_en-US" xlink:label="lab_us-gaap_PreferredStockDividendsAndOtherAdjustmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Preferred Stock Dividends and Other Adjustments [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockDividendsAndOtherAdjustmentsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PreferredStockDividendsAndOtherAdjustmentsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PreferredStockDividendsAndOtherAdjustmentsAbstract" xlink:to="lab_us-gaap_PreferredStockDividendsAndOtherAdjustmentsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DeferredTaxAssetsValuationAllowanceAbstract_a4dbe4cd-793e-46b6-aa70-47b6a3f7cb88_terseLabel_en-US" xlink:label="lab_skwd_DeferredTaxAssetsValuationAllowanceAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Tax Assets, Valuation Allowance [Abstract]</link:label>
    <link:label id="lab_skwd_DeferredTaxAssetsValuationAllowanceAbstract_label_en-US" xlink:label="lab_skwd_DeferredTaxAssetsValuationAllowanceAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Tax Assets, Valuation Allowance [Abstract]</link:label>
    <link:label id="lab_skwd_DeferredTaxAssetsValuationAllowanceAbstract_documentation_en-US" xlink:label="lab_skwd_DeferredTaxAssetsValuationAllowanceAbstract" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Tax Assets, Valuation Allowance</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DeferredTaxAssetsValuationAllowanceAbstract" xlink:href="skwd-20221231.xsd#skwd_DeferredTaxAssetsValuationAllowanceAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DeferredTaxAssetsValuationAllowanceAbstract" xlink:to="lab_skwd_DeferredTaxAssetsValuationAllowanceAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_MultiFamilyPortfolioSegmentMember_41406b8c-fc6b-4bd8-92cd-d1e00a94494c_terseLabel_en-US" xlink:label="lab_skwd_MultiFamilyPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Multi-family</link:label>
    <link:label id="lab_skwd_MultiFamilyPortfolioSegmentMember_label_en-US" xlink:label="lab_skwd_MultiFamilyPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Multi-Family Portfolio Segment [Member]</link:label>
    <link:label id="lab_skwd_MultiFamilyPortfolioSegmentMember_documentation_en-US" xlink:label="lab_skwd_MultiFamilyPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Multi-Family Portfolio Segment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_MultiFamilyPortfolioSegmentMember" xlink:href="skwd-20221231.xsd#skwd_MultiFamilyPortfolioSegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_MultiFamilyPortfolioSegmentMember" xlink:to="lab_skwd_MultiFamilyPortfolioSegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AllowanceForDoubtfulAccountsPremiumsAndOtherReceivables_5f161522-829b-4659-ac7f-6c474f44f715_terseLabel_en-US" xlink:label="lab_us-gaap_AllowanceForDoubtfulAccountsPremiumsAndOtherReceivables" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Allowance for doubtful accounts</link:label>
    <link:label id="lab_us-gaap_AllowanceForDoubtfulAccountsPremiumsAndOtherReceivables_label_en-US" xlink:label="lab_us-gaap_AllowanceForDoubtfulAccountsPremiumsAndOtherReceivables" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Allowance for Doubtful Accounts, Premiums and Other Receivables</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AllowanceForDoubtfulAccountsPremiumsAndOtherReceivables" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AllowanceForDoubtfulAccountsPremiumsAndOtherReceivables"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AllowanceForDoubtfulAccountsPremiumsAndOtherReceivables" xlink:to="lab_us-gaap_AllowanceForDoubtfulAccountsPremiumsAndOtherReceivables" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DepreciationAmortizationAndAccretionNet_120c8039-1ee7-46d8-9b53-f5cbbf9be919_terseLabel_en-US" xlink:label="lab_us-gaap_DepreciationAmortizationAndAccretionNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Depreciation and amortization expense</link:label>
    <link:label id="lab_us-gaap_DepreciationAmortizationAndAccretionNet_label_en-US" xlink:label="lab_us-gaap_DepreciationAmortizationAndAccretionNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Depreciation, Amortization and Accretion, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DepreciationAmortizationAndAccretionNet" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DepreciationAmortizationAndAccretionNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DepreciationAmortizationAndAccretionNet" xlink:to="lab_us-gaap_DepreciationAmortizationAndAccretionNet" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CreditRatingAMBestAxis_755ec540-d865-4071-8480-c6cb5df8b949_terseLabel_en-US" xlink:label="lab_srt_CreditRatingAMBestAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Credit Rating, AM Best [Axis]</link:label>
    <link:label id="lab_srt_CreditRatingAMBestAxis_label_en-US" xlink:label="lab_srt_CreditRatingAMBestAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Credit Rating, AM Best [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_CreditRatingAMBestAxis" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_CreditRatingAMBestAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_CreditRatingAMBestAxis" xlink:to="lab_srt_CreditRatingAMBestAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleofFiniteLivedIntangibleAssetsFutureAmortizationExpenseTableTextBlock_fa1053d1-9790-42b0-a6a0-bb565f22ebd0_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleofFiniteLivedIntangibleAssetsFutureAmortizationExpenseTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Finite-Lived Intangible Assets, Future Amortization Expense</link:label>
    <link:label id="lab_us-gaap_ScheduleofFiniteLivedIntangibleAssetsFutureAmortizationExpenseTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleofFiniteLivedIntangibleAssetsFutureAmortizationExpenseTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Finite-Lived Intangible Assets, Future Amortization Expense [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleofFiniteLivedIntangibleAssetsFutureAmortizationExpenseTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleofFiniteLivedIntangibleAssetsFutureAmortizationExpenseTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleofFiniteLivedIntangibleAssetsFutureAmortizationExpenseTableTextBlock" xlink:to="lab_us-gaap_ScheduleofFiniteLivedIntangibleAssetsFutureAmortizationExpenseTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_TitleOfIndividualWithRelationshipToEntityDomain_79a0aa5e-245b-41bb-b45e-a114243cf56c_terseLabel_en-US" xlink:label="lab_srt_TitleOfIndividualWithRelationshipToEntityDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Title of Individual [Domain]</link:label>
    <link:label id="lab_srt_TitleOfIndividualWithRelationshipToEntityDomain_label_en-US" xlink:label="lab_srt_TitleOfIndividualWithRelationshipToEntityDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Title of Individual [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_TitleOfIndividualWithRelationshipToEntityDomain" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_TitleOfIndividualWithRelationshipToEntityDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_TitleOfIndividualWithRelationshipToEntityDomain" xlink:to="lab_srt_TitleOfIndividualWithRelationshipToEntityDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_RevolvingLineOfCreditDueDecember2024Member_dc133d2a-81fd-4e6b-afa6-cf69d7031a6c_terseLabel_en-US" xlink:label="lab_skwd_RevolvingLineOfCreditDueDecember2024Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Revolving Line of Credit, due December 2024</link:label>
    <link:label id="lab_skwd_RevolvingLineOfCreditDueDecember2024Member_label_en-US" xlink:label="lab_skwd_RevolvingLineOfCreditDueDecember2024Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Revolving Line Of Credit Due December 2024 [Member]</link:label>
    <link:label id="lab_skwd_RevolvingLineOfCreditDueDecember2024Member_documentation_en-US" xlink:label="lab_skwd_RevolvingLineOfCreditDueDecember2024Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Revolving Line Of Credit Due December 2024</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RevolvingLineOfCreditDueDecember2024Member" xlink:href="skwd-20221231.xsd#skwd_RevolvingLineOfCreditDueDecember2024Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_RevolvingLineOfCreditDueDecember2024Member" xlink:to="lab_skwd_RevolvingLineOfCreditDueDecember2024Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod_dc8f6c11-fc2c-46d8-9738-cac21fdd2e18_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Forfeited (in shares)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Forfeited in Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LongTermDebt_9ce5f35f-c9c5-4470-807c-4b60488676c2_totalLabel_en-US" xlink:label="lab_us-gaap_LongTermDebt" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subordinated debt, net of debt issuance costs</link:label>
    <link:label id="lab_us-gaap_LongTermDebt_80c2b4ce-2787-42a4-849f-c39ebd8fc776_terseLabel_en-US" xlink:label="lab_us-gaap_LongTermDebt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long-term debt</link:label>
    <link:label id="lab_us-gaap_LongTermDebt_label_en-US" xlink:label="lab_us-gaap_LongTermDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long-Term Debt</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LongTermDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LongTermDebt" xlink:to="lab_us-gaap_LongTermDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_IICMember_e11b611c-0622-487d-a814-bb032b79b151_terseLabel_en-US" xlink:label="lab_skwd_IICMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">IIC</link:label>
    <link:label id="lab_skwd_IICMember_label_en-US" xlink:label="lab_skwd_IICMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">IIC [Member]</link:label>
    <link:label id="lab_skwd_IICMember_documentation_en-US" xlink:label="lab_skwd_IICMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">IIC</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_IICMember" xlink:href="skwd-20221231.xsd#skwd_IICMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_IICMember" xlink:to="lab_skwd_IICMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SaleOfStockPricePerShare_7484f66e-57c5-450d-baf9-bff498fe2b06_terseLabel_en-US" xlink:label="lab_us-gaap_SaleOfStockPricePerShare" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Sale of stock, price per share (usd per share)</link:label>
    <link:label id="lab_us-gaap_SaleOfStockPricePerShare_label_en-US" xlink:label="lab_us-gaap_SaleOfStockPricePerShare" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Sale of Stock, Price Per Share</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SaleOfStockPricePerShare" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SaleOfStockPricePerShare"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SaleOfStockPricePerShare" xlink:to="lab_us-gaap_SaleOfStockPricePerShare" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortDurationInsuranceContractsAccidentYear2018Member_e71ff613-314d-41df-a2d0-61d504a6df52_terseLabel_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractsAccidentYear2018Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accident Year 2018</link:label>
    <link:label id="lab_us-gaap_ShortDurationInsuranceContractsAccidentYear2018Member_label_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractsAccidentYear2018Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Accident Year 2018 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortDurationInsuranceContractsAccidentYear2018Member" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortDurationInsuranceContractsAccidentYear2018Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortDurationInsuranceContractsAccidentYear2018Member" xlink:to="lab_us-gaap_ShortDurationInsuranceContractsAccidentYear2018Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfRelatedPartyTransactionsByRelatedPartyTable_2df9acbf-5a50-4e37-b8a1-f029d910c5a6_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfRelatedPartyTransactionsByRelatedPartyTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Related Party Transactions, by Related Party [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfRelatedPartyTransactionsByRelatedPartyTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfRelatedPartyTransactionsByRelatedPartyTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Related Party Transactions, by Related Party [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfRelatedPartyTransactionsByRelatedPartyTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfRelatedPartyTransactionsByRelatedPartyTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfRelatedPartyTransactionsByRelatedPartyTable" xlink:to="lab_us-gaap_ScheduleOfRelatedPartyTransactionsByRelatedPartyTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax_79910d1d-3342-4f98-9c48-fe6323740699_terseLabel_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accumulated other comprehensive (loss) income</link:label>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax_label_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Accumulated Other Comprehensive Income (Loss), Net of Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax" xlink:to="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CashAndCashEquivalentsRestrictedCashAndCashEquivalentsPolicy_14f75280-c6f6-4923-a50e-97d8eb389f7c_terseLabel_en-US" xlink:label="lab_us-gaap_CashAndCashEquivalentsRestrictedCashAndCashEquivalentsPolicy" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Restricted Cash</link:label>
    <link:label id="lab_us-gaap_CashAndCashEquivalentsRestrictedCashAndCashEquivalentsPolicy_label_en-US" xlink:label="lab_us-gaap_CashAndCashEquivalentsRestrictedCashAndCashEquivalentsPolicy" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash and Cash Equivalents, Restricted Cash and Cash Equivalents, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashAndCashEquivalentsRestrictedCashAndCashEquivalentsPolicy" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CashAndCashEquivalentsRestrictedCashAndCashEquivalentsPolicy"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CashAndCashEquivalentsRestrictedCashAndCashEquivalentsPolicy" xlink:to="lab_us-gaap_CashAndCashEquivalentsRestrictedCashAndCashEquivalentsPolicy" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RegulatoryCapitalRequirementsUnderBankingRegulationsTextBlock_ba3060e5-aacf-4064-b40f-fa3d9f1568eb_terseLabel_en-US" xlink:label="lab_us-gaap_RegulatoryCapitalRequirementsUnderBankingRegulationsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Regulatory Matters</link:label>
    <link:label id="lab_us-gaap_RegulatoryCapitalRequirementsUnderBankingRegulationsTextBlock_label_en-US" xlink:label="lab_us-gaap_RegulatoryCapitalRequirementsUnderBankingRegulationsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Regulatory Capital Requirements under Banking Regulations [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RegulatoryCapitalRequirementsUnderBankingRegulationsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RegulatoryCapitalRequirementsUnderBankingRegulationsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RegulatoryCapitalRequirementsUnderBankingRegulationsTextBlock" xlink:to="lab_us-gaap_RegulatoryCapitalRequirementsUnderBankingRegulationsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntitySmallBusiness_a190827f-774e-479c-9b10-c0a78c739d76_terseLabel_en-US" xlink:label="lab_dei_EntitySmallBusiness" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Small Business</link:label>
    <link:label id="lab_dei_EntitySmallBusiness_label_en-US" xlink:label="lab_dei_EntitySmallBusiness" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Small Business</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntitySmallBusiness" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntitySmallBusiness"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntitySmallBusiness" xlink:to="lab_dei_EntitySmallBusiness" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueByMeasurementBasisAxis_2be4e18c-0552-499a-8821-7009a03acd07_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueByMeasurementBasisAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Measurement Basis [Axis]</link:label>
    <link:label id="lab_us-gaap_FairValueByMeasurementBasisAxis_label_en-US" xlink:label="lab_us-gaap_FairValueByMeasurementBasisAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Measurement Basis [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueByMeasurementBasisAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FairValueByMeasurementBasisAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueByMeasurementBasisAxis" xlink:to="lab_us-gaap_FairValueByMeasurementBasisAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod_e00e1ee8-6c82-435d-b662-c4085678b20d_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Shares issued in period (in shares)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Shares Issued in Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RevenuesAbstract_494a3c47-3f0f-4ddb-a28a-6443649391c5_terseLabel_en-US" xlink:label="lab_us-gaap_RevenuesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Revenues:</link:label>
    <link:label id="lab_us-gaap_RevenuesAbstract_label_en-US" xlink:label="lab_us-gaap_RevenuesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Revenues [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RevenuesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RevenuesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RevenuesAbstract" xlink:to="lab_us-gaap_RevenuesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsNet_98959271-750e-4969-bf14-21b97fa8a61d_periodEndLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsNet" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net, ending balance</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsNet_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Finite-Lived Intangible Assets, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsNet" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FiniteLivedIntangibleAssetsNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsNet" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_UnpaidPolicyClaimsAndClaimsAdjustmentExpensePolicy_faf51735-416c-4a87-8a6b-8dea4e705b44_terseLabel_en-US" xlink:label="lab_us-gaap_UnpaidPolicyClaimsAndClaimsAdjustmentExpensePolicy" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reserves for losses and loss adjustment expenses</link:label>
    <link:label id="lab_us-gaap_UnpaidPolicyClaimsAndClaimsAdjustmentExpensePolicy_label_en-US" xlink:label="lab_us-gaap_UnpaidPolicyClaimsAndClaimsAdjustmentExpensePolicy" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unpaid Policy Claims and Claims Adjustment Expense, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_UnpaidPolicyClaimsAndClaimsAdjustmentExpensePolicy" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_UnpaidPolicyClaimsAndClaimsAdjustmentExpensePolicy"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_UnpaidPolicyClaimsAndClaimsAdjustmentExpensePolicy" xlink:to="lab_us-gaap_UnpaidPolicyClaimsAndClaimsAdjustmentExpensePolicy" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SignificantAccountingPoliciesTextBlock_22e7f6bf-f552-4a25-9611-9658ee8c3c66_terseLabel_en-US" xlink:label="lab_us-gaap_SignificantAccountingPoliciesTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Summary of Significant Accounting Policies</link:label>
    <link:label id="lab_us-gaap_SignificantAccountingPoliciesTextBlock_label_en-US" xlink:label="lab_us-gaap_SignificantAccountingPoliciesTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Significant Accounting Policies [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SignificantAccountingPoliciesTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SignificantAccountingPoliciesTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SignificantAccountingPoliciesTextBlock" xlink:to="lab_us-gaap_SignificantAccountingPoliciesTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumsEarnedNet_002e12cc-dc0a-4c68-90a1-962919d74acc_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsEarnedNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net earned premiums</link:label>
    <link:label id="lab_us-gaap_PremiumsEarnedNet_93d385e4-744d-4f88-a8ae-99535f9f7f9c_totalLabel_en-US" xlink:label="lab_us-gaap_PremiumsEarnedNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net earned premium</link:label>
    <link:label id="lab_us-gaap_PremiumsEarnedNet_91f65436-3344-4796-8f82-8e6fa9e9842b_verboseLabel_en-US" xlink:label="lab_us-gaap_PremiumsEarnedNet" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net earned premium</link:label>
    <link:label id="lab_us-gaap_PremiumsEarnedNet_label_en-US" xlink:label="lab_us-gaap_PremiumsEarnedNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Premiums Earned, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsEarnedNet" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PremiumsEarnedNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsEarnedNet" xlink:to="lab_us-gaap_PremiumsEarnedNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumsWrittenGrossAbstract_932cc660-0cbc-4149-877c-8c8695038a54_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsWrittenGrossAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Written</link:label>
    <link:label id="lab_us-gaap_PremiumsWrittenGrossAbstract_label_en-US" xlink:label="lab_us-gaap_PremiumsWrittenGrossAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Premiums Written, Gross [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsWrittenGrossAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PremiumsWrittenGrossAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsWrittenGrossAbstract" xlink:to="lab_us-gaap_PremiumsWrittenGrossAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsAndTax_a83c1fec-bad4-4661-af6e-64f21ab3f845_terseLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsAndTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fixed maturity securities</link:label>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsAndTax_label_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsAndTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">OCI, Debt Securities, Available-for-Sale, Gain (Loss), before Adjustment and Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsAndTax" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsAndTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsAndTax" xlink:to="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsAndTax" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MovementInValuationAllowancesAndReservesRollForward_c2ddf616-0d8f-4b6a-91b3-b92d684e0798_terseLabel_en-US" xlink:label="lab_us-gaap_MovementInValuationAllowancesAndReservesRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-09, Movement in Valuation Allowances and Reserves [Roll Forward]</link:label>
    <link:label id="lab_us-gaap_MovementInValuationAllowancesAndReservesRollForward_label_en-US" xlink:label="lab_us-gaap_MovementInValuationAllowancesAndReservesRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-09, Movement in Valuation Allowances and Reserves [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MovementInValuationAllowancesAndReservesRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_MovementInValuationAllowancesAndReservesRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MovementInValuationAllowancesAndReservesRollForward" xlink:to="lab_us-gaap_MovementInValuationAllowancesAndReservesRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentDisclosureTextBlock_64992c6d-dc1a-40e3-a98e-0fc2de42a869_terseLabel_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Property and Equipment</link:label>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Property, Plant and Equipment Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PropertyPlantAndEquipmentDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentDisclosureTextBlock" xlink:to="lab_us-gaap_PropertyPlantAndEquipmentDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNetNotSeparatelyPresented_4c37234d-afb0-4b73-a15a-465ad1a019d3_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNetNotSeparatelyPresented" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net reserves for loss and LAE before 2018</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNetNotSeparatelyPresented_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNetNotSeparatelyPresented" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net, Not Separately Presented</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNetNotSeparatelyPresented" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNetNotSeparatelyPresented"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNetNotSeparatelyPresented" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNetNotSeparatelyPresented" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubordinatedDebtMember_7e8a6948-6194-43ed-816f-0c6dcbcb73dd_terseLabel_en-US" xlink:label="lab_us-gaap_SubordinatedDebtMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subordinated Debt</link:label>
    <link:label id="lab_us-gaap_SubordinatedDebtMember_label_en-US" xlink:label="lab_us-gaap_SubordinatedDebtMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Subordinated Debt [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubordinatedDebtMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SubordinatedDebtMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubordinatedDebtMember" xlink:to="lab_us-gaap_SubordinatedDebtMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentTypeDomain_3403448b-ada6-438f-a5df-6600253bb69f_terseLabel_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentTypeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long-Lived Tangible Asset [Domain]</link:label>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentTypeDomain_label_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentTypeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long-Lived Tangible Asset [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentTypeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PropertyPlantAndEquipmentTypeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentTypeDomain" xlink:to="lab_us-gaap_PropertyPlantAndEquipmentTypeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ConsolidatedEntitiesAxis_34569fe4-0166-4547-a34c-c9061e9ee110_terseLabel_en-US" xlink:label="lab_srt_ConsolidatedEntitiesAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Consolidated Entities [Axis]</link:label>
    <link:label id="lab_srt_ConsolidatedEntitiesAxis_label_en-US" xlink:label="lab_srt_ConsolidatedEntitiesAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Consolidated Entities [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ConsolidatedEntitiesAxis" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_ConsolidatedEntitiesAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ConsolidatedEntitiesAxis" xlink:to="lab_srt_ConsolidatedEntitiesAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentLineItems_6105c21d-7fd1-4242-98fd-5e74bf9b8fe2_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument [Line Items]</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentLineItems_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtInstrumentLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentLineItems" xlink:to="lab_us-gaap_DebtInstrumentLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReportingUnitAxis_545ea674-8f33-4b2b-847f-1cd3699ce79b_terseLabel_en-US" xlink:label="lab_us-gaap_ReportingUnitAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reporting Unit [Axis]</link:label>
    <link:label id="lab_us-gaap_ReportingUnitAxis_label_en-US" xlink:label="lab_us-gaap_ReportingUnitAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reporting Unit [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReportingUnitAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ReportingUnitAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReportingUnitAxis" xlink:to="lab_us-gaap_ReportingUnitAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock_1f378187-21a5-4615-aab9-d2383e6c1c7b_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ceded Credit Risk</link:label>
    <link:label id="lab_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ceded Credit Risk [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock" xlink:to="lab_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OperatingLeaseLiability_f96ff76f-f9f7-4ae5-8a80-f9cebf14c58b_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingLeaseLiability" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Operating lease liabilities</link:label>
    <link:label id="lab_us-gaap_OperatingLeaseLiability_label_en-US" xlink:label="lab_us-gaap_OperatingLeaseLiability" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Operating Lease, Liability</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseLiability" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OperatingLeaseLiability"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OperatingLeaseLiability" xlink:to="lab_us-gaap_OperatingLeaseLiability" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_IntangibleAssetsAcquired_01cd3fd9-a7c6-47c9-bd83-a6b07322e827_terseLabel_en-US" xlink:label="lab_skwd_IntangibleAssetsAcquired" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Additions</link:label>
    <link:label id="lab_skwd_IntangibleAssetsAcquired_label_en-US" xlink:label="lab_skwd_IntangibleAssetsAcquired" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Intangible Assets Acquired</link:label>
    <link:label id="lab_skwd_IntangibleAssetsAcquired_documentation_en-US" xlink:label="lab_skwd_IntangibleAssetsAcquired" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Intangible Assets Acquired</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_IntangibleAssetsAcquired" xlink:href="skwd-20221231.xsd#skwd_IntangibleAssetsAcquired"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_IntangibleAssetsAcquired" xlink:to="lab_skwd_IntangibleAssetsAcquired" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses_5b9f5b95-bf55-47b1-86fc-234c18154d13_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance recoverable, net of premium payables</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses_f95ec842-e19c-4e3f-8bbb-972b126b67f5_totalLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance recoverables</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Recoverable for Paid and Unpaid Claims and Claims Adjustments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses" xlink:to="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ValuationAllowancesAndReservesBalance_0d52c254-1af1-4b30-bb49-e58a4c03316b_periodStartLabel_en-US" xlink:label="lab_us-gaap_ValuationAllowancesAndReservesBalance" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Balance at beginning of year</link:label>
    <link:label id="lab_us-gaap_ValuationAllowancesAndReservesBalance_0c1ef0cc-1502-4a78-b196-c8fe4241f283_periodEndLabel_en-US" xlink:label="lab_us-gaap_ValuationAllowancesAndReservesBalance" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Balance at end of year</link:label>
    <link:label id="lab_us-gaap_ValuationAllowancesAndReservesBalance_label_en-US" xlink:label="lab_us-gaap_ValuationAllowancesAndReservesBalance" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-09, Valuation Allowances and Reserves, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ValuationAllowancesAndReservesBalance" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ValuationAllowancesAndReservesBalance"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ValuationAllowancesAndReservesBalance" xlink:to="lab_us-gaap_ValuationAllowancesAndReservesBalance" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationOptionAndIncentivePlansPolicy_811ff805-35a6-4bfb-a5f6-d925312989e6_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationOptionAndIncentivePlansPolicy" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Stock Based Compensation</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationOptionAndIncentivePlansPolicy_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationOptionAndIncentivePlansPolicy" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Payment Arrangement [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationOptionAndIncentivePlansPolicy" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationOptionAndIncentivePlansPolicy"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationOptionAndIncentivePlansPolicy" xlink:to="lab_us-gaap_ShareBasedCompensationOptionAndIncentivePlansPolicy" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract_label_en-US" xlink:label="lab_us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investments, Debt and Equity Securities [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract" xlink:to="lab_us-gaap_InvestmentsDebtAndEquitySecuritiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearTwo_d3ca7750-57e5-43f5-ad57-505d987f171f_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearTwo" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">2024</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearTwo_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearTwo" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Finite-Lived Intangible Asset, Expected Amortization, Year Two</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearTwo" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearTwo"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearTwo" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearTwo" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersDeferredPolicyAcquisitionCosts_0f83daac-80e6-488d-a8ad-9ae6a86928a6_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersDeferredPolicyAcquisitionCosts" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred policy acquisition costs</link:label>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersDeferredPolicyAcquisitionCosts_label_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersDeferredPolicyAcquisitionCosts" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-18, Supplemental Information, Property-Casualty Insurance Underwriters, Deferred Policy Acquisition Cost</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersDeferredPolicyAcquisitionCosts" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersDeferredPolicyAcquisitionCosts"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersDeferredPolicyAcquisitionCosts" xlink:to="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersDeferredPolicyAcquisitionCosts" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SaleOfStockConsiderationReceivedOnTransaction_f1f51e65-7d3c-485c-b370-643346cb647c_terseLabel_en-US" xlink:label="lab_us-gaap_SaleOfStockConsiderationReceivedOnTransaction" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Sale of stock, consideration</link:label>
    <link:label id="lab_us-gaap_SaleOfStockConsiderationReceivedOnTransaction_label_en-US" xlink:label="lab_us-gaap_SaleOfStockConsiderationReceivedOnTransaction" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Sale of Stock, Consideration Received on Transaction</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SaleOfStockConsiderationReceivedOnTransaction" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SaleOfStockConsiderationReceivedOnTransaction"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SaleOfStockConsiderationReceivedOnTransaction" xlink:to="lab_us-gaap_SaleOfStockConsiderationReceivedOnTransaction" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesAbstract_label_en-US" xlink:label="lab_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-15, Insurance Companies, Summary of Investments, Other than Investments in Related Parties [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesAbstract" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesAbstract" xlink:to="lab_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInOtherOperatingAssets_8adfc2c1-cf9a-47ef-b4b5-61c0f44f3501_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInOtherOperatingAssets" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other, net</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInOtherOperatingAssets_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInOtherOperatingAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Increase (Decrease) in Other Operating Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInOtherOperatingAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInOtherOperatingAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInOtherOperatingAssets" xlink:to="lab_us-gaap_IncreaseDecreaseInOtherOperatingAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_LandPortfolioSegmentMember_75f96790-7204-473f-9b97-78c6a6f81353_terseLabel_en-US" xlink:label="lab_skwd_LandPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Land</link:label>
    <link:label id="lab_skwd_LandPortfolioSegmentMember_label_en-US" xlink:label="lab_skwd_LandPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Land Portfolio Segment [Member]</link:label>
    <link:label id="lab_skwd_LandPortfolioSegmentMember_documentation_en-US" xlink:label="lab_skwd_LandPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Land Portfolio Segment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_LandPortfolioSegmentMember" xlink:href="skwd-20221231.xsd#skwd_LandPortfolioSegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_LandPortfolioSegmentMember" xlink:to="lab_skwd_LandPortfolioSegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock_52c3503e-68cf-42f4-9404-8392881e35ab_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investments Classified by Contractual Maturity Date</link:label>
    <link:label id="lab_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock_label_en-US" xlink:label="lab_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investments Classified by Contractual Maturity Date [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock" xlink:to="lab_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_AuditorLocation_2f1d54f9-40cc-4318-a297-c39904151604_terseLabel_en-US" xlink:label="lab_dei_AuditorLocation" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Auditor Location</link:label>
    <link:label id="lab_dei_AuditorLocation_label_en-US" xlink:label="lab_dei_AuditorLocation" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Auditor Location</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_AuditorLocation" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_AuditorLocation"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_AuditorLocation" xlink:to="lab_dei_AuditorLocation" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NatureOfOperations_8c389352-0218-4f62-856c-8406cd3ca868_terseLabel_en-US" xlink:label="lab_us-gaap_NatureOfOperations" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Nature of Operations</link:label>
    <link:label id="lab_us-gaap_NatureOfOperations_label_en-US" xlink:label="lab_us-gaap_NatureOfOperations" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Nature of Operations [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NatureOfOperations" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NatureOfOperations"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NatureOfOperations" xlink:to="lab_us-gaap_NatureOfOperations" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_NonCompetesMember_53696cf1-0d25-4810-911e-4c0fb888d677_terseLabel_en-US" xlink:label="lab_skwd_NonCompetesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Non-competes</link:label>
    <link:label id="lab_skwd_NonCompetesMember_label_en-US" xlink:label="lab_skwd_NonCompetesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Non-Competes [Member]</link:label>
    <link:label id="lab_skwd_NonCompetesMember_documentation_en-US" xlink:label="lab_skwd_NonCompetesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Non-Competes</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_NonCompetesMember" xlink:href="skwd-20221231.xsd#skwd_NonCompetesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_NonCompetesMember" xlink:to="lab_skwd_NonCompetesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityFilerCategory_1bc4f5a0-5b07-4acc-bc09-8ba3ac41bab1_terseLabel_en-US" xlink:label="lab_dei_EntityFilerCategory" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Filer Category</link:label>
    <link:label id="lab_dei_EntityFilerCategory_label_en-US" xlink:label="lab_dei_EntityFilerCategory" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Filer Category</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityFilerCategory" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityFilerCategory"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityFilerCategory" xlink:to="lab_dei_EntityFilerCategory" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract_e6b076f1-8a04-4d60-be12-2171151ff1c4_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total fixed maturity securities, held to maturity</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale and Held-to-Maturity, Fair Value to Amortized Cost, after Allowance for Credit Loss [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsurancePayable_735ec46a-88fa-4527-a7cb-988eba116693_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsurancePayable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance and premium payables</link:label>
    <link:label id="lab_us-gaap_ReinsurancePayable_label_en-US" xlink:label="lab_us-gaap_ReinsurancePayable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Payable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsurancePayable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ReinsurancePayable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsurancePayable" xlink:to="lab_us-gaap_ReinsurancePayable" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ProfessionalFeesAndReimbursementsMember_fd5b8223-74f4-4850-b816-f475b084c906_terseLabel_en-US" xlink:label="lab_skwd_ProfessionalFeesAndReimbursementsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Professional fees and reimbursements</link:label>
    <link:label id="lab_skwd_ProfessionalFeesAndReimbursementsMember_label_en-US" xlink:label="lab_skwd_ProfessionalFeesAndReimbursementsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Professional Fees And Reimbursements [Member]</link:label>
    <link:label id="lab_skwd_ProfessionalFeesAndReimbursementsMember_documentation_en-US" xlink:label="lab_skwd_ProfessionalFeesAndReimbursementsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Professional Fees And Reimbursements</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ProfessionalFeesAndReimbursementsMember" xlink:href="skwd-20221231.xsd#skwd_ProfessionalFeesAndReimbursementsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ProfessionalFeesAndReimbursementsMember" xlink:to="lab_skwd_ProfessionalFeesAndReimbursementsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AllocatedShareBasedCompensationExpense_84416c94-7b81-42b8-874c-778ee7b79429_totalLabel_en-US" xlink:label="lab_us-gaap_AllocatedShareBasedCompensationExpense" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total</link:label>
    <link:label id="lab_us-gaap_AllocatedShareBasedCompensationExpense_label_en-US" xlink:label="lab_us-gaap_AllocatedShareBasedCompensationExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Payment Arrangement, Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AllocatedShareBasedCompensationExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AllocatedShareBasedCompensationExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AllocatedShareBasedCompensationExpense" xlink:to="lab_us-gaap_AllocatedShareBasedCompensationExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_SecurityExchangeName_8c12db33-52a3-44db-9b63-6b4a74e420d8_terseLabel_en-US" xlink:label="lab_dei_SecurityExchangeName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Security Exchange Name</link:label>
    <link:label id="lab_dei_SecurityExchangeName_label_en-US" xlink:label="lab_dei_SecurityExchangeName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Security Exchange Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_SecurityExchangeName" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_SecurityExchangeName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_SecurityExchangeName" xlink:to="lab_dei_SecurityExchangeName" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LicenseMember_25f40788-42f4-4370-bac9-7e2e6dc6e1c2_terseLabel_en-US" xlink:label="lab_us-gaap_LicenseMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Licenses</link:label>
    <link:label id="lab_us-gaap_LicenseMember_label_en-US" xlink:label="lab_us-gaap_LicenseMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">License [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LicenseMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LicenseMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LicenseMember" xlink:to="lab_us-gaap_LicenseMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense_88a9d342-193a-49e5-8e3e-27f3f4eb7a95_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Amortization of policy acquisition costs</link:label>
    <link:label id="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense_label_en-US" xlink:label="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Policy Acquisition Costs, Amortization Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense" xlink:to="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract_1d17b7ce-faa6-4bc4-b432-918a9a059dc0_terseLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Held-to-maturity, gross unrealized losses</link:label>
    <link:label id="lab_skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract_label_en-US" xlink:label="lab_skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Held-to-Maturity, Continuous Unrealized Loss Position, Accumulated Loss [Abstract]</link:label>
    <link:label id="lab_skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract_documentation_en-US" xlink:label="lab_skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Held-to-Maturity, Continuous Unrealized Loss Position, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:href="skwd-20221231.xsd#skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:to="lab_skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AmortizationOfDeferredCharges_5ca36ac2-30d7-4e77-ba18-4f328849123c_verboseLabel_en-US" xlink:label="lab_us-gaap_AmortizationOfDeferredCharges" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Amortization expense</link:label>
    <link:label id="lab_us-gaap_AmortizationOfDeferredCharges_9d4341a9-648b-4c73-9b05-2c3bb33121f0_terseLabel_en-US" xlink:label="lab_us-gaap_AmortizationOfDeferredCharges" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Amortization</link:label>
    <link:label id="lab_us-gaap_AmortizationOfDeferredCharges_label_en-US" xlink:label="lab_us-gaap_AmortizationOfDeferredCharges" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Amortization of Deferred Charges</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AmortizationOfDeferredCharges" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AmortizationOfDeferredCharges"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AmortizationOfDeferredCharges" xlink:to="lab_us-gaap_AmortizationOfDeferredCharges" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract_7c568b80-89a8-4e59-9849-b1c9eb6ff63a_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total fixed maturity securities, available for sale</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Fair Value to Amortized Cost, after Allowance for Credit Loss [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax_5c6d8676-3310-4882-b5ba-4f463d5ce162_terseLabel_en-US" xlink:label="lab_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total commission and fee income</link:label>
    <link:label id="lab_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax_label_en-US" xlink:label="lab_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Revenue from Contract with Customer, Excluding Assessed Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax" xlink:to="lab_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinancialInstrumentsFinancialLiabilitiesBalanceSheetGroupingsAbstract_90254464-649a-4d62-8d3c-8c96885b94c6_terseLabel_en-US" xlink:label="lab_us-gaap_FinancialInstrumentsFinancialLiabilitiesBalanceSheetGroupingsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liabilities</link:label>
    <link:label id="lab_us-gaap_FinancialInstrumentsFinancialLiabilitiesBalanceSheetGroupingsAbstract_label_en-US" xlink:label="lab_us-gaap_FinancialInstrumentsFinancialLiabilitiesBalanceSheetGroupingsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Financial Instruments, Financial Liabilities, Balance Sheet Groupings [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancialInstrumentsFinancialLiabilitiesBalanceSheetGroupingsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FinancialInstrumentsFinancialLiabilitiesBalanceSheetGroupingsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancialInstrumentsFinancialLiabilitiesBalanceSheetGroupingsAbstract" xlink:to="lab_us-gaap_FinancialInstrumentsFinancialLiabilitiesBalanceSheetGroupingsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInPrepaidReinsurancePremiums_14cfe4e5-cd8a-438e-872d-438c81025f09_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInPrepaidReinsurancePremiums" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ceded unearned premium</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInPrepaidReinsurancePremiums_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInPrepaidReinsurancePremiums" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Increase (Decrease) in Prepaid Reinsurance Premiums</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInPrepaidReinsurancePremiums" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInPrepaidReinsurancePremiums"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInPrepaidReinsurancePremiums" xlink:to="lab_us-gaap_IncreaseDecreaseInPrepaidReinsurancePremiums" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ValuationAllowanceOfDeferredTaxAssetsMember_68abaf77-33c4-4639-8c37-c8de0cd63444_terseLabel_en-US" xlink:label="lab_us-gaap_ValuationAllowanceOfDeferredTaxAssetsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Valuation Allowance For Deferred Tax Assets</link:label>
    <link:label id="lab_us-gaap_ValuationAllowanceOfDeferredTaxAssetsMember_label_en-US" xlink:label="lab_us-gaap_ValuationAllowanceOfDeferredTaxAssetsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-09, Valuation Allowance, Deferred Tax Asset [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ValuationAllowanceOfDeferredTaxAssetsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ValuationAllowanceOfDeferredTaxAssetsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ValuationAllowanceOfDeferredTaxAssetsMember" xlink:to="lab_us-gaap_ValuationAllowanceOfDeferredTaxAssetsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtInstrumentFixedRatePeriodDomain_f7d93b8d-fc6e-4184-8ad4-c6c9f46ff7cd_terseLabel_en-US" xlink:label="lab_skwd_DebtInstrumentFixedRatePeriodDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Interest Rage Range [Domain]</link:label>
    <link:label id="lab_skwd_DebtInstrumentFixedRatePeriodDomain_label_en-US" xlink:label="lab_skwd_DebtInstrumentFixedRatePeriodDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Fixed Rate, Period [Domain]</link:label>
    <link:label id="lab_skwd_DebtInstrumentFixedRatePeriodDomain_documentation_en-US" xlink:label="lab_skwd_DebtInstrumentFixedRatePeriodDomain" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Instrument, Fixed Rate, Period [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtInstrumentFixedRatePeriodDomain" xlink:href="skwd-20221231.xsd#skwd_DebtInstrumentFixedRatePeriodDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtInstrumentFixedRatePeriodDomain" xlink:to="lab_skwd_DebtInstrumentFixedRatePeriodDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockCapitalSharesReservedForFutureIssuance_e8b7ee5f-1060-42a3-89c1-287f202c552d_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockCapitalSharesReservedForFutureIssuance" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common stock, reserved for future issuance (in shares)</link:label>
    <link:label id="lab_us-gaap_CommonStockCapitalSharesReservedForFutureIssuance_label_en-US" xlink:label="lab_us-gaap_CommonStockCapitalSharesReservedForFutureIssuance" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Common Stock, Capital Shares Reserved for Future Issuance</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockCapitalSharesReservedForFutureIssuance" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CommonStockCapitalSharesReservedForFutureIssuance"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockCapitalSharesReservedForFutureIssuance" xlink:to="lab_us-gaap_CommonStockCapitalSharesReservedForFutureIssuance" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_CoverAbstract_label_en-US" xlink:label="lab_dei_CoverAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cover [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_CoverAbstract" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_CoverAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_CoverAbstract" xlink:to="lab_dei_CoverAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityVoluntaryFilers_bc1f2e7d-d34a-44d9-ad11-93409b1e2569_terseLabel_en-US" xlink:label="lab_dei_EntityVoluntaryFilers" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Voluntary Filers</link:label>
    <link:label id="lab_dei_EntityVoluntaryFilers_label_en-US" xlink:label="lab_dei_EntityVoluntaryFilers" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Voluntary Filers</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityVoluntaryFilers" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityVoluntaryFilers"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityVoluntaryFilers" xlink:to="lab_dei_EntityVoluntaryFilers" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CapitalRequiredForCapitalAdequacy_835b8646-8cd8-4cfb-a68a-5ab4aa372588_terseLabel_en-US" xlink:label="lab_us-gaap_CapitalRequiredForCapitalAdequacy" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">RBC authorized control level</link:label>
    <link:label id="lab_us-gaap_CapitalRequiredForCapitalAdequacy_label_en-US" xlink:label="lab_us-gaap_CapitalRequiredForCapitalAdequacy" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Banking Regulation, Total Risk-Based Capital, Capital Adequacy, Minimum</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CapitalRequiredForCapitalAdequacy" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CapitalRequiredForCapitalAdequacy"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CapitalRequiredForCapitalAdequacy" xlink:to="lab_us-gaap_CapitalRequiredForCapitalAdequacy" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillImpairmentLoss_4a588fd3-ceaf-4bcd-8f2e-cc7717cdaa06_verboseLabel_en-US" xlink:label="lab_us-gaap_GoodwillImpairmentLoss" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Goodwill impairment</link:label>
    <link:label id="lab_us-gaap_GoodwillImpairmentLoss_0edbea40-ad4e-483e-9e2c-41aa6d295e86_terseLabel_en-US" xlink:label="lab_us-gaap_GoodwillImpairmentLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Impairment</link:label>
    <link:label id="lab_us-gaap_GoodwillImpairmentLoss_89355765-9c9f-45c6-b893-635f75cc73d5_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_GoodwillImpairmentLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Impairment</link:label>
    <link:label id="lab_us-gaap_GoodwillImpairmentLoss_label_en-US" xlink:label="lab_us-gaap_GoodwillImpairmentLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Goodwill, Impairment Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillImpairmentLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_GoodwillImpairmentLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillImpairmentLoss" xlink:to="lab_us-gaap_GoodwillImpairmentLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ArenaSOPIIMember_04c95703-3d13-4fde-ba2a-71d6a53f68fb_terseLabel_en-US" xlink:label="lab_skwd_ArenaSOPIIMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Arena SOP II</link:label>
    <link:label id="lab_skwd_ArenaSOPIIMember_label_en-US" xlink:label="lab_skwd_ArenaSOPIIMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Arena SOP II [Member]</link:label>
    <link:label id="lab_skwd_ArenaSOPIIMember_documentation_en-US" xlink:label="lab_skwd_ArenaSOPIIMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Arena SOP II</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ArenaSOPIIMember" xlink:href="skwd-20221231.xsd#skwd_ArenaSOPIIMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ArenaSOPIIMember" xlink:to="lab_skwd_ArenaSOPIIMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock_2c644a5b-03fb-48ee-9632-2f02b4cc2484_terseLabel_en-US" xlink:label="lab_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Underwriting, Acquisition and Insurance Expenses</link:label>
    <link:label id="lab_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock_label_en-US" xlink:label="lab_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule Of Underwriting, Acquisition and Insurance Expenses [Table Text Block]</link:label>
    <link:label id="lab_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock_documentation_en-US" xlink:label="lab_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule Of Underwriting, Acquisition and Insurance Expenses</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock" xlink:href="skwd-20221231.xsd#skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock" xlink:to="lab_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherAssets_31a78ef0-76f4-4ee1-81e3-48bec502ca62_terseLabel_en-US" xlink:label="lab_us-gaap_OtherAssets" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other assets</link:label>
    <link:label id="lab_us-gaap_OtherAssets_label_en-US" xlink:label="lab_us-gaap_OtherAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OtherAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherAssets" xlink:to="lab_us-gaap_OtherAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RevenueFromContractWithCustomerTextBlock_ddb504c4-1c1a-4cfa-981c-f1475391620d_terseLabel_en-US" xlink:label="lab_us-gaap_RevenueFromContractWithCustomerTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Revenue from Contract with Customer</link:label>
    <link:label id="lab_us-gaap_RevenueFromContractWithCustomerTextBlock_label_en-US" xlink:label="lab_us-gaap_RevenueFromContractWithCustomerTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Revenue from Contract with Customer [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RevenueFromContractWithCustomerTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RevenueFromContractWithCustomerTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RevenueFromContractWithCustomerTextBlock" xlink:to="lab_us-gaap_RevenueFromContractWithCustomerTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract_87c426a8-80f7-4c25-889b-8ae2aae75ed3_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Incurred, net of reinsurance, related to:</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Incurred Claims [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract_264d1bb8-1e76-4973-8b70-a96f4800d8d1_terseLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Available-for-sale and held-to-maturity, gross unrealized losses</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract_label_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Unrealized Loss Position, Accumulated Loss [Abstract]</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract_documentation_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Unrealized Loss Position, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract" xlink:href="skwd-20221231.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract" xlink:to="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_USGovernmentDebtSecuritiesMember_9e5ba07f-a060-403e-9ab2-00b530e6c492_terseLabel_en-US" xlink:label="lab_us-gaap_USGovernmentDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">U.S. government securities</link:label>
    <link:label id="lab_us-gaap_USGovernmentDebtSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_USGovernmentDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">US Government Debt Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_USGovernmentDebtSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_USGovernmentDebtSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_USGovernmentDebtSecuritiesMember" xlink:to="lab_us-gaap_USGovernmentDebtSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearTwo_6053d04d-a495-43ba-9dbf-cd4fb79c7a25_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearTwo" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Year 2</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearTwo_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearTwo" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Historical Claims Duration, Year Two</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearTwo" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearTwo"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearTwo" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearTwo" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentTypeCategorizationMember_20a45716-663c-4679-8866-073c804c3c62_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentTypeCategorizationMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investments [Domain]</link:label>
    <link:label id="lab_us-gaap_InvestmentTypeCategorizationMember_label_en-US" xlink:label="lab_us-gaap_InvestmentTypeCategorizationMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investments [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentTypeCategorizationMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_InvestmentTypeCategorizationMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentTypeCategorizationMember" xlink:to="lab_us-gaap_InvestmentTypeCategorizationMember" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentsIncorporatedByReferenceTextBlock_f2f7d0c5-0fb8-4cb2-846a-3aac41b927f2_terseLabel_en-US" xlink:label="lab_dei_DocumentsIncorporatedByReferenceTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Documents Incorporated by Reference</link:label>
    <link:label id="lab_dei_DocumentsIncorporatedByReferenceTextBlock_label_en-US" xlink:label="lab_dei_DocumentsIncorporatedByReferenceTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Documents Incorporated by Reference [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentsIncorporatedByReferenceTextBlock" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_DocumentsIncorporatedByReferenceTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentsIncorporatedByReferenceTextBlock" xlink:to="lab_dei_DocumentsIncorporatedByReferenceTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilitiesAndStockholdersEquity_3919b718-a4d8-4d32-bbff-290eabb06082_totalLabel_en-US" xlink:label="lab_us-gaap_LiabilitiesAndStockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total liabilities and stockholders' equity</link:label>
    <link:label id="lab_us-gaap_LiabilitiesAndStockholdersEquity_label_en-US" xlink:label="lab_us-gaap_LiabilitiesAndStockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liabilities and Equity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesAndStockholdersEquity" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilitiesAndStockholdersEquity"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilitiesAndStockholdersEquity" xlink:to="lab_us-gaap_LiabilitiesAndStockholdersEquity" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1_91c57719-093f-4cd9-a063-ef4ae767bd4e_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Current period</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Claims Paid, Current Year</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AllowanceForReinsuranceRecoverableMember_15eaf6ec-bf76-4dc5-8241-92f2b96777e7_terseLabel_en-US" xlink:label="lab_us-gaap_AllowanceForReinsuranceRecoverableMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Allowance for Uncollectible Reinsurance Recoverable</link:label>
    <link:label id="lab_us-gaap_AllowanceForReinsuranceRecoverableMember_label_en-US" xlink:label="lab_us-gaap_AllowanceForReinsuranceRecoverableMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-09, Allowance, Reinsurance Recoverable [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AllowanceForReinsuranceRecoverableMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AllowanceForReinsuranceRecoverableMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AllowanceForReinsuranceRecoverableMember" xlink:to="lab_us-gaap_AllowanceForReinsuranceRecoverableMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_EquityMethodInvestmentsUnfundedCommitment_2ed9d180-cf63-45ff-90bd-819877bb3bf9_terseLabel_en-US" xlink:label="lab_skwd_EquityMethodInvestmentsUnfundedCommitment" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Unfunded Commitment</link:label>
    <link:label id="lab_skwd_EquityMethodInvestmentsUnfundedCommitment_label_en-US" xlink:label="lab_skwd_EquityMethodInvestmentsUnfundedCommitment" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Method Investments, Unfunded Commitment</link:label>
    <link:label id="lab_skwd_EquityMethodInvestmentsUnfundedCommitment_documentation_en-US" xlink:label="lab_skwd_EquityMethodInvestmentsUnfundedCommitment" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Method Investments, Unfunded Commitment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_EquityMethodInvestmentsUnfundedCommitment" xlink:href="skwd-20221231.xsd#skwd_EquityMethodInvestmentsUnfundedCommitment"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_EquityMethodInvestmentsUnfundedCommitment" xlink:to="lab_skwd_EquityMethodInvestmentsUnfundedCommitment" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromIssuanceOfSharesUnderIncentiveAndShareBasedCompensationPlans_2854e2eb-4de0-4cb4-abea-ee7f0f9cd857_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromIssuanceOfSharesUnderIncentiveAndShareBasedCompensationPlans" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Employee share purchases</link:label>
    <link:label id="lab_us-gaap_ProceedsFromIssuanceOfSharesUnderIncentiveAndShareBasedCompensationPlans_label_en-US" xlink:label="lab_us-gaap_ProceedsFromIssuanceOfSharesUnderIncentiveAndShareBasedCompensationPlans" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Proceeds, Issuance of Shares, Share-Based Payment Arrangement, Excluding Option Exercised</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromIssuanceOfSharesUnderIncentiveAndShareBasedCompensationPlans" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ProceedsFromIssuanceOfSharesUnderIncentiveAndShareBasedCompensationPlans"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromIssuanceOfSharesUnderIncentiveAndShareBasedCompensationPlans" xlink:to="lab_us-gaap_ProceedsFromIssuanceOfSharesUnderIncentiveAndShareBasedCompensationPlans" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LongtermDebtTypeAxis_8b76814a-c656-48f7-8816-de300dac389d_terseLabel_en-US" xlink:label="lab_us-gaap_LongtermDebtTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long-Term Debt, Type [Axis]</link:label>
    <link:label id="lab_us-gaap_LongtermDebtTypeAxis_label_en-US" xlink:label="lab_us-gaap_LongtermDebtTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long-Term Debt, Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongtermDebtTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LongtermDebtTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LongtermDebtTypeAxis" xlink:to="lab_us-gaap_LongtermDebtTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentTable_712a596d-7a49-4f96-a4e6-be2f5524f8fc_terseLabel_en-US" xlink:label="lab_srt_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-17, Insurance Companies, Reinsurance [Table]</link:label>
    <link:label id="lab_srt_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentTable_label_en-US" xlink:label="lab_srt_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-17, Insurance Companies, Reinsurance [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentTable" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentTable" xlink:to="lab_srt_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredTaxAssetsGoodwillAndIntangibleAssets_3bd33055-0ab2-49e6-a0aa-447129e7ddf9_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsGoodwillAndIntangibleAssets" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Intangibles</link:label>
    <link:label id="lab_us-gaap_DeferredTaxAssetsGoodwillAndIntangibleAssets_label_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsGoodwillAndIntangibleAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Tax Assets, Goodwill and Intangible Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxAssetsGoodwillAndIntangibleAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DeferredTaxAssetsGoodwillAndIntangibleAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredTaxAssetsGoodwillAndIntangibleAssets" xlink:to="lab_us-gaap_DeferredTaxAssetsGoodwillAndIntangibleAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LimitedLiabilityCompanyLLCOrLimitedPartnershipLPManagingMemberOrGeneralPartnerOwnershipInterest_b8d608ac-5878-4132-83f2-a18815fb47fb_terseLabel_en-US" xlink:label="lab_us-gaap_LimitedLiabilityCompanyLLCOrLimitedPartnershipLPManagingMemberOrGeneralPartnerOwnershipInterest" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ownership interest</link:label>
    <link:label id="lab_us-gaap_LimitedLiabilityCompanyLLCOrLimitedPartnershipLPManagingMemberOrGeneralPartnerOwnershipInterest_label_en-US" xlink:label="lab_us-gaap_LimitedLiabilityCompanyLLCOrLimitedPartnershipLPManagingMemberOrGeneralPartnerOwnershipInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Limited Liability Company (LLC) or Limited Partnership (LP), Managing Member or General Partner, Ownership Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LimitedLiabilityCompanyLLCOrLimitedPartnershipLPManagingMemberOrGeneralPartnerOwnershipInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LimitedLiabilityCompanyLLCOrLimitedPartnershipLPManagingMemberOrGeneralPartnerOwnershipInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LimitedLiabilityCompanyLLCOrLimitedPartnershipLPManagingMemberOrGeneralPartnerOwnershipInterest" xlink:to="lab_us-gaap_LimitedLiabilityCompanyLLCOrLimitedPartnershipLPManagingMemberOrGeneralPartnerOwnershipInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredTaxAssetsGross_1f99e24e-e0ca-40a4-a21f-8927116d4513_totalLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsGross" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total deferred tax assets</link:label>
    <link:label id="lab_us-gaap_DeferredTaxAssetsGross_label_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Tax Assets, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxAssetsGross" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DeferredTaxAssetsGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredTaxAssetsGross" xlink:to="lab_us-gaap_DeferredTaxAssetsGross" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsMember_74f0ac7a-9e5c-463e-bc02-446a1ba74779_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity method investments</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsMember_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Method Investments [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EquityMethodInvestmentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentsMember" xlink:to="lab_us-gaap_EquityMethodInvestmentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedGain_d24bdacc-01d1-46f8-8524-e3d72e348339_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedGain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fixed maturity securities, available-for sale</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedGain_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedGain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Realized Gain</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleRealizedGain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleRealizedGain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleRealizedGain" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedGain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityUndiscountedExcessAmount_e2da30ee-796d-4664-b995-6fcd299c9c79_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityUndiscountedExcessAmount" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Less imputed interest</link:label>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityUndiscountedExcessAmount_label_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityUndiscountedExcessAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Lessee, Operating Lease, Liability, Undiscounted Excess Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeaseLiabilityUndiscountedExcessAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LesseeOperatingLeaseLiabilityUndiscountedExcessAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LesseeOperatingLeaseLiabilityUndiscountedExcessAmount" xlink:to="lab_us-gaap_LesseeOperatingLeaseLiabilityUndiscountedExcessAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted_c7bffd1d-537b-46c4-b1ee-53b60f8519f7_terseLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net income (numerator for diluted earnings per share under the two-class method)</link:label>
    <link:label id="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted_label_en-US" xlink:label="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net Income (Loss) Available to Common Stockholders, Diluted</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted" xlink:to="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareDiluted_5cb5c987-96cb-4e78-8d07-cfbe137fb7b1_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareDiluted" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Diluted earnings per share (in dollar per share)</link:label>
    <link:label id="lab_us-gaap_EarningsPerShareDiluted_label_en-US" xlink:label="lab_us-gaap_EarningsPerShareDiluted" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Earnings Per Share, Diluted</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerShareDiluted" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EarningsPerShareDiluted"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerShareDiluted" xlink:to="lab_us-gaap_EarningsPerShareDiluted" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SaleOfStockNameOfTransactionDomain_4654c63a-892f-440e-8c4a-678b26cc7ea9_terseLabel_en-US" xlink:label="lab_us-gaap_SaleOfStockNameOfTransactionDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Sale of Stock [Domain]</link:label>
    <link:label id="lab_us-gaap_SaleOfStockNameOfTransactionDomain_label_en-US" xlink:label="lab_us-gaap_SaleOfStockNameOfTransactionDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Sale of Stock [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SaleOfStockNameOfTransactionDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SaleOfStockNameOfTransactionDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SaleOfStockNameOfTransactionDomain" xlink:to="lab_us-gaap_SaleOfStockNameOfTransactionDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentLineItems_e7848c47-a230-43fb-9355-157f7ef028cd_terseLabel_en-US" xlink:label="lab_srt_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-17, Insurance Companies, Reinsurance [Line Items]</link:label>
    <link:label id="lab_srt_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentLineItems_label_en-US" xlink:label="lab_srt_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-17, Insurance Companies, Reinsurance [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentLineItems" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentLineItems" xlink:to="lab_srt_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfStockByClassTextBlock_8913b7a9-a61e-4e58-9506-f63d4d550a31_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfStockByClassTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Stock by Class</link:label>
    <link:label id="lab_us-gaap_ScheduleOfStockByClassTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfStockByClassTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Stock by Class [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfStockByClassTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfStockByClassTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfStockByClassTextBlock" xlink:to="lab_us-gaap_ScheduleOfStockByClassTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_RelatedPartyTransactionOwnershipInterestThresholdForTermination_9c7ef666-308e-4c4d-9db4-c3f3cd3a7252_terseLabel_en-US" xlink:label="lab_skwd_RelatedPartyTransactionOwnershipInterestThresholdForTermination" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ownership interest threshold (less than)</link:label>
    <link:label id="lab_skwd_RelatedPartyTransactionOwnershipInterestThresholdForTermination_label_en-US" xlink:label="lab_skwd_RelatedPartyTransactionOwnershipInterestThresholdForTermination" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Related Party Transaction, Ownership Interest, Threshold for Termination</link:label>
    <link:label id="lab_skwd_RelatedPartyTransactionOwnershipInterestThresholdForTermination_documentation_en-US" xlink:label="lab_skwd_RelatedPartyTransactionOwnershipInterestThresholdForTermination" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Related Party Transaction, Ownership Interest, Threshold for Termination</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RelatedPartyTransactionOwnershipInterestThresholdForTermination" xlink:href="skwd-20221231.xsd#skwd_RelatedPartyTransactionOwnershipInterestThresholdForTermination"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_RelatedPartyTransactionOwnershipInterestThresholdForTermination" xlink:to="lab_skwd_RelatedPartyTransactionOwnershipInterestThresholdForTermination" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearTwo_3ca699ab-c10e-411a-ba7f-97a7153cf957_terseLabel_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearTwo" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">2024</link:label>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearTwo_label_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearTwo" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Lessee, Operating Lease, Liability, to be Paid, Year Two</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearTwo" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearTwo"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearTwo" xlink:to="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearTwo" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_OSICMember_2174f140-fa07-4ae0-8863-72d1e6dd35df_terseLabel_en-US" xlink:label="lab_skwd_OSICMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">OSIC</link:label>
    <link:label id="lab_skwd_OSICMember_label_en-US" xlink:label="lab_skwd_OSICMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">OSIC [Member]</link:label>
    <link:label id="lab_skwd_OSICMember_documentation_en-US" xlink:label="lab_skwd_OSICMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">OSIC</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_OSICMember" xlink:href="skwd-20221231.xsd#skwd_OSICMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_OSICMember" xlink:to="lab_skwd_OSICMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue_2c0777a7-5176-4e15-a7dc-37e5b890b9e1_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Due after ten years</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Fair Value, Maturity, Allocated and Single Maturity Date, after Year 10</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_WestaimMember_1fb71a88-3dd1-4339-abd4-f7f209ab3e81_terseLabel_en-US" xlink:label="lab_skwd_WestaimMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Westaim</link:label>
    <link:label id="lab_skwd_WestaimMember_label_en-US" xlink:label="lab_skwd_WestaimMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Westaim [Member]</link:label>
    <link:label id="lab_skwd_WestaimMember_documentation_en-US" xlink:label="lab_skwd_WestaimMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Westaim</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_WestaimMember" xlink:href="skwd-20221231.xsd#skwd_WestaimMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_WestaimMember" xlink:to="lab_skwd_WestaimMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredTaxAssetsNet_56d980ef-8602-4c10-abc9-f4fcce8b0b12_totalLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total deferred tax assets after valuation allowance</link:label>
    <link:label id="lab_us-gaap_DeferredTaxAssetsNet_label_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Tax Assets, Net of Valuation Allowance</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxAssetsNet" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DeferredTaxAssetsNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredTaxAssetsNet" xlink:to="lab_us-gaap_DeferredTaxAssetsNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesMember_99eb4687-73fd-47e9-b223-357eebfc9e71_terseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity securities:</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesMember_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EquitySecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesMember" xlink:to="lab_us-gaap_EquitySecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_MultiLineSolutionsMember_c4a2b54c-bf3c-4d12-b33d-2a238b9d0cc0_terseLabel_en-US" xlink:label="lab_skwd_MultiLineSolutionsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Multi-line Solutions</link:label>
    <link:label id="lab_skwd_MultiLineSolutionsMember_label_en-US" xlink:label="lab_skwd_MultiLineSolutionsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Multi-line Solutions [Member]</link:label>
    <link:label id="lab_skwd_MultiLineSolutionsMember_documentation_en-US" xlink:label="lab_skwd_MultiLineSolutionsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Multi-line Solutions</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_MultiLineSolutionsMember" xlink:href="skwd-20221231.xsd#skwd_MultiLineSolutionsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_MultiLineSolutionsMember" xlink:to="lab_skwd_MultiLineSolutionsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CorporateDebtSecuritiesMember_a0620652-c7ad-43df-a484-e5c79afe8067_terseLabel_en-US" xlink:label="lab_us-gaap_CorporateDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Corporate securities and miscellaneous</link:label>
    <link:label id="lab_us-gaap_CorporateDebtSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_CorporateDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Corporate Debt Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CorporateDebtSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CorporateDebtSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CorporateDebtSecuritiesMember" xlink:to="lab_us-gaap_CorporateDebtSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentIncomeInvestmentExpense_3c22f13e-e66b-434d-a3f2-ae15e5e89af5_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_InvestmentIncomeInvestmentExpense" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment expenses</link:label>
    <link:label id="lab_us-gaap_InvestmentIncomeInvestmentExpense_label_en-US" xlink:label="lab_us-gaap_InvestmentIncomeInvestmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Investment Income, Investment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentIncomeInvestmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_InvestmentIncomeInvestmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentIncomeInvestmentExpense" xlink:to="lab_us-gaap_InvestmentIncomeInvestmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CumulativeEffectPeriodOfAdoptionAdjustmentMember_f051b8bc-9be1-4c61-a0b0-2d16983b5bdf_terseLabel_en-US" xlink:label="lab_srt_CumulativeEffectPeriodOfAdoptionAdjustmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Period of adoption, adjustment</link:label>
    <link:label id="lab_srt_CumulativeEffectPeriodOfAdoptionAdjustmentMember_label_en-US" xlink:label="lab_srt_CumulativeEffectPeriodOfAdoptionAdjustmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cumulative Effect, Period of Adoption, Adjustment [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_CumulativeEffectPeriodOfAdoptionAdjustmentMember" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_CumulativeEffectPeriodOfAdoptionAdjustmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_CumulativeEffectPeriodOfAdoptionAdjustmentMember" xlink:to="lab_srt_CumulativeEffectPeriodOfAdoptionAdjustmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromIssuanceOfPreferredStockAndPreferenceStock_d7f5db0f-f5ac-4d67-8a40-ec9afd8d9533_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromIssuanceOfPreferredStockAndPreferenceStock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash proceeds from sale of preferred stock</link:label>
    <link:label id="lab_us-gaap_ProceedsFromIssuanceOfPreferredStockAndPreferenceStock_label_en-US" xlink:label="lab_us-gaap_ProceedsFromIssuanceOfPreferredStockAndPreferenceStock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Proceeds from Issuance of Preferred Stock and Preference Stock</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromIssuanceOfPreferredStockAndPreferenceStock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ProceedsFromIssuanceOfPreferredStockAndPreferenceStock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromIssuanceOfPreferredStockAndPreferenceStock" xlink:to="lab_us-gaap_ProceedsFromIssuanceOfPreferredStockAndPreferenceStock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityMaturityTableTextBlock_c45679ed-4742-49fc-9fdc-bd5ee4936be5_terseLabel_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityMaturityTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Lessee, Operating Lease, Liability, Maturity</link:label>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityMaturityTableTextBlock_label_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityMaturityTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Lessee, Operating Lease, Liability, Maturity [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeaseLiabilityMaturityTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LesseeOperatingLeaseLiabilityMaturityTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LesseeOperatingLeaseLiabilityMaturityTableTextBlock" xlink:to="lab_us-gaap_LesseeOperatingLeaseLiabilityMaturityTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressAddressLine2_dfd5b1bc-e614-4141-9b1f-482ecd696b25_terseLabel_en-US" xlink:label="lab_dei_EntityAddressAddressLine2" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Address, Address Line Two</link:label>
    <link:label id="lab_dei_EntityAddressAddressLine2_label_en-US" xlink:label="lab_dei_EntityAddressAddressLine2" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Address, Address Line Two</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressAddressLine2" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityAddressAddressLine2"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityAddressAddressLine2" xlink:to="lab_dei_EntityAddressAddressLine2" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressAddressLine1_f05342bf-d894-4f8d-aff6-5860a1bc4662_terseLabel_en-US" xlink:label="lab_dei_EntityAddressAddressLine1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Address, Address Line One</link:label>
    <link:label id="lab_dei_EntityAddressAddressLine1_label_en-US" xlink:label="lab_dei_EntityAddressAddressLine1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Entity Address, Address Line One</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressAddressLine1" xlink:href="https://xbrl.sec.gov/dei/2022/dei-2022.xsd#dei_EntityAddressAddressLine1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityAddressAddressLine1" xlink:to="lab_dei_EntityAddressAddressLine1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_BenefitsLossesAndExpenses_726e8ad5-a403-40e2-a138-01a049ccd308_totalLabel_en-US" xlink:label="lab_us-gaap_BenefitsLossesAndExpenses" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total expenses</link:label>
    <link:label id="lab_us-gaap_BenefitsLossesAndExpenses_cdf63b79-18fd-42f3-8157-b40e77d685a7_terseLabel_en-US" xlink:label="lab_us-gaap_BenefitsLossesAndExpenses" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total expenses</link:label>
    <link:label id="lab_us-gaap_BenefitsLossesAndExpenses_label_en-US" xlink:label="lab_us-gaap_BenefitsLossesAndExpenses" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Benefits, Losses and Expenses</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BenefitsLossesAndExpenses" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_BenefitsLossesAndExpenses"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BenefitsLossesAndExpenses" xlink:to="lab_us-gaap_BenefitsLossesAndExpenses" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesTable_ead2036d-f20d-41f7-b271-7581ad70551f_terseLabel_en-US" xlink:label="lab_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-15, Insurance Companies, Summary of Investments, Other than Investments in Related Parties [Table]</link:label>
    <link:label id="lab_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesTable_label_en-US" xlink:label="lab_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-15, Insurance Companies, Summary of Investments, Other than Investments in Related Parties [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesTable" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesTable" xlink:to="lab_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesTable" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ProductOrServiceAxis_6ff204f7-729f-41cb-a8e3-782570ea345a_terseLabel_en-US" xlink:label="lab_srt_ProductOrServiceAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Product and Service [Axis]</link:label>
    <link:label id="lab_srt_ProductOrServiceAxis_label_en-US" xlink:label="lab_srt_ProductOrServiceAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Product and Service [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ProductOrServiceAxis" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_ProductOrServiceAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ProductOrServiceAxis" xlink:to="lab_srt_ProductOrServiceAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CededPremiumsWritten_5562dee8-8d8e-4483-a8e8-6e484b354a46_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_CededPremiumsWritten" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ceded premiums</link:label>
    <link:label id="lab_us-gaap_CededPremiumsWritten_label_en-US" xlink:label="lab_us-gaap_CededPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Ceded Premiums Written</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CededPremiumsWritten" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CededPremiumsWritten"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CededPremiumsWritten" xlink:to="lab_us-gaap_CededPremiumsWritten" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InterestExpense_e260a936-dd04-4c63-9245-9792e4a15c9a_terseLabel_en-US" xlink:label="lab_us-gaap_InterestExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Interest expense</link:label>
    <link:label id="lab_us-gaap_InterestExpense_label_en-US" xlink:label="lab_us-gaap_InterestExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Interest Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_InterestExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InterestExpense" xlink:to="lab_us-gaap_InterestExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GrossInvestmentIncomeOperating_02acd7ff-9292-4448-b3a7-490a4fc12c93_terseLabel_en-US" xlink:label="lab_us-gaap_GrossInvestmentIncomeOperating" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total investment income</link:label>
    <link:label id="lab_us-gaap_GrossInvestmentIncomeOperating_label_en-US" xlink:label="lab_us-gaap_GrossInvestmentIncomeOperating" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gross Investment Income, Operating</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GrossInvestmentIncomeOperating" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_GrossInvestmentIncomeOperating"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GrossInvestmentIncomeOperating" xlink:to="lab_us-gaap_GrossInvestmentIncomeOperating" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersEarnedPremiums_a387827a-f620-4f68-87c5-9a28fa95b583_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersEarnedPremiums" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net earned premium</link:label>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersEarnedPremiums_label_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersEarnedPremiums" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-18, Supplemental Information, Property-Casualty Insurance Underwriters, Earned Premium</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersEarnedPremiums" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersEarnedPremiums"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersEarnedPremiums" xlink:to="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersEarnedPremiums" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfDebtInstrumentsTextBlock_f5ef4f73-486b-4960-b132-72ce3e540da0_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfDebtInstrumentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Summary of Subordinated Debt</link:label>
    <link:label id="lab_us-gaap_ScheduleOfDebtInstrumentsTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfDebtInstrumentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Schedule of Long-Term Debt Instruments [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfDebtInstrumentsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ScheduleOfDebtInstrumentsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfDebtInstrumentsTextBlock" xlink:to="lab_us-gaap_ScheduleOfDebtInstrumentsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_IncrementalCommonSharesAttributableToDilutiveEffectOfConversionOfMarketConditionAwards_014761b5-f7f1-46cc-92d8-bad75e705765_terseLabel_en-US" xlink:label="lab_skwd_IncrementalCommonSharesAttributableToDilutiveEffectOfConversionOfMarketConditionAwards" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Market condition awards (contingently issuable) (in shares)</link:label>
    <link:label id="lab_skwd_IncrementalCommonSharesAttributableToDilutiveEffectOfConversionOfMarketConditionAwards_label_en-US" xlink:label="lab_skwd_IncrementalCommonSharesAttributableToDilutiveEffectOfConversionOfMarketConditionAwards" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Incremental Common Shares Attributable to Dilutive Effect of Conversion of Market Condition Awards</link:label>
    <link:label id="lab_skwd_IncrementalCommonSharesAttributableToDilutiveEffectOfConversionOfMarketConditionAwards_documentation_en-US" xlink:label="lab_skwd_IncrementalCommonSharesAttributableToDilutiveEffectOfConversionOfMarketConditionAwards" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Incremental Common Shares Attributable to Dilutive Effect of Conversion of Market Condition Awards</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_IncrementalCommonSharesAttributableToDilutiveEffectOfConversionOfMarketConditionAwards" xlink:href="skwd-20221231.xsd#skwd_IncrementalCommonSharesAttributableToDilutiveEffectOfConversionOfMarketConditionAwards"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_IncrementalCommonSharesAttributableToDilutiveEffectOfConversionOfMarketConditionAwards" xlink:to="lab_skwd_IncrementalCommonSharesAttributableToDilutiveEffectOfConversionOfMarketConditionAwards" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_JuniorSubordinatedNotesDue2036CommonStockMember_dd38fd59-68cd-41ee-a10b-0d15784680b5_terseLabel_en-US" xlink:label="lab_skwd_JuniorSubordinatedNotesDue2036CommonStockMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Junior Subordinated Notes Due 2036, Common Stock</link:label>
    <link:label id="lab_skwd_JuniorSubordinatedNotesDue2036CommonStockMember_label_en-US" xlink:label="lab_skwd_JuniorSubordinatedNotesDue2036CommonStockMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Junior Subordinated Notes Due 2036, Common Stock [Member]</link:label>
    <link:label id="lab_skwd_JuniorSubordinatedNotesDue2036CommonStockMember_documentation_en-US" xlink:label="lab_skwd_JuniorSubordinatedNotesDue2036CommonStockMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Junior Subordinated Notes Due 2036, Common Stock</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_JuniorSubordinatedNotesDue2036CommonStockMember" xlink:href="skwd-20221231.xsd#skwd_JuniorSubordinatedNotesDue2036CommonStockMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_JuniorSubordinatedNotesDue2036CommonStockMember" xlink:to="lab_skwd_JuniorSubordinatedNotesDue2036CommonStockMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAmortizedCostAbstract_3f6dfb1c-a5e5-4301-84c8-85a3f700e842_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAmortizedCostAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Amortized Cost</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAmortizedCostAbstract_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAmortizedCostAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Amortized Cost, Fiscal Year Maturity [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAmortizedCostAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAmortizedCostAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAmortizedCostAbstract" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAmortizedCostAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInPremiumsReceivable_b67b9ae0-0bca-439a-ad21-5cfb143e1906_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInPremiumsReceivable" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Premiums receivable, net</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInPremiumsReceivable_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInPremiumsReceivable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Increase (Decrease) in Premiums Receivable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInPremiumsReceivable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInPremiumsReceivable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInPremiumsReceivable" xlink:to="lab_us-gaap_IncreaseDecreaseInPremiumsReceivable" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ConsumerStaplesSectorMember_780b08a0-aa48-4f4d-a0fd-6414a03dd765_terseLabel_en-US" xlink:label="lab_skwd_ConsumerStaplesSectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Consumer staples</link:label>
    <link:label id="lab_skwd_ConsumerStaplesSectorMember_label_en-US" xlink:label="lab_skwd_ConsumerStaplesSectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Consumer Staples Sector [Member]</link:label>
    <link:label id="lab_skwd_ConsumerStaplesSectorMember_documentation_en-US" xlink:label="lab_skwd_ConsumerStaplesSectorMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Consumer Staples Sector</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ConsumerStaplesSectorMember" xlink:href="skwd-20221231.xsd#skwd_ConsumerStaplesSectorMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ConsumerStaplesSectorMember" xlink:to="lab_skwd_ConsumerStaplesSectorMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisaggregationOfRevenueTableTextBlock_bd1e8f5f-19e2-457e-95f5-98d8e50253f9_terseLabel_en-US" xlink:label="lab_us-gaap_DisaggregationOfRevenueTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Disaggregation of Revenue</link:label>
    <link:label id="lab_us-gaap_DisaggregationOfRevenueTableTextBlock_label_en-US" xlink:label="lab_us-gaap_DisaggregationOfRevenueTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Disaggregation of Revenue [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisaggregationOfRevenueTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DisaggregationOfRevenueTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisaggregationOfRevenueTableTextBlock" xlink:to="lab_us-gaap_DisaggregationOfRevenueTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredIncomeTaxLiabilities_cdce9622-7ae5-4915-8c15-c57223a979b9_totalLabel_en-US" xlink:label="lab_us-gaap_DeferredIncomeTaxLiabilities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Total deferred tax liabilities</link:label>
    <link:label id="lab_us-gaap_DeferredIncomeTaxLiabilities_label_en-US" xlink:label="lab_us-gaap_DeferredIncomeTaxLiabilities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Deferred Tax Liabilities, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredIncomeTaxLiabilities" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DeferredIncomeTaxLiabilities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredIncomeTaxLiabilities" xlink:to="lab_us-gaap_DeferredIncomeTaxLiabilities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RevenueFromContractWithCustomerAbstract_label_en-US" xlink:label="lab_us-gaap_RevenueFromContractWithCustomerAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Revenue from Contract with Customer [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RevenueFromContractWithCustomerAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RevenueFromContractWithCustomerAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RevenueFromContractWithCustomerAbstract" xlink:to="lab_us-gaap_RevenueFromContractWithCustomerAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsToAcquireEquitySecuritiesFvNi_8e243a2e-06fc-4b99-9a0b-1cde4801b055_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireEquitySecuritiesFvNi" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Purchase of equity securities</link:label>
    <link:label id="lab_us-gaap_PaymentsToAcquireEquitySecuritiesFvNi_label_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireEquitySecuritiesFvNi" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Payments to Acquire Equity Securities, FV-NI</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireEquitySecuritiesFvNi" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PaymentsToAcquireEquitySecuritiesFvNi"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsToAcquireEquitySecuritiesFvNi" xlink:to="lab_us-gaap_PaymentsToAcquireEquitySecuritiesFvNi" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_FixedIncomeSectorMember_3f6d7a95-8562-4a2f-9916-7258ddbade0f_terseLabel_en-US" xlink:label="lab_skwd_FixedIncomeSectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fixed income</link:label>
    <link:label id="lab_skwd_FixedIncomeSectorMember_label_en-US" xlink:label="lab_skwd_FixedIncomeSectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fixed Income Sector [Member]</link:label>
    <link:label id="lab_skwd_FixedIncomeSectorMember_documentation_en-US" xlink:label="lab_skwd_FixedIncomeSectorMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fixed Income Sector</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_FixedIncomeSectorMember" xlink:href="skwd-20221231.xsd#skwd_FixedIncomeSectorMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_FixedIncomeSectorMember" xlink:to="lab_skwd_FixedIncomeSectorMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearEight_d580e14f-e923-476b-bff5-9198bad98b04_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearEight" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Year 8</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearEight_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearEight" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Historical Claims Duration, Year Eight</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearEight" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearEight"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearEight" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearEight" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ScheduleOfValuationAndQualifyingAccountsDisclosureTextBlock_236274fd-9c12-4cc1-b442-e3eec25ab0c9_terseLabel_en-US" xlink:label="lab_srt_ScheduleOfValuationAndQualifyingAccountsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SCHEDULE V&#160;&#8212; VALUATION AND QUALIFYING ACCOUNTS</link:label>
    <link:label id="lab_srt_ScheduleOfValuationAndQualifyingAccountsDisclosureTextBlock_label_en-US" xlink:label="lab_srt_ScheduleOfValuationAndQualifyingAccountsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-09, Schedule of Valuation and Qualifying Accounts Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ScheduleOfValuationAndQualifyingAccountsDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/srt/2022/elts/srt-2022.xsd#srt_ScheduleOfValuationAndQualifyingAccountsDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ScheduleOfValuationAndQualifyingAccountsDisclosureTextBlock" xlink:to="lab_srt_ScheduleOfValuationAndQualifyingAccountsDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFive_c716c083-1464-4e4a-9a5c-929fa22aba0c_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFive" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">2027</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFive_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFive" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Finite-Lived Intangible Asset, Expected Amortization, Year Five</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFive" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFive"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFive" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFive" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValueRollForward_372625c0-1ba7-4e40-8d15-1431a6a1ba9a_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValueRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Weighted-Average Grant-Date Fair&#160;Value</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValueRollForward_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValueRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Nonvested, Weighted Average Grant Date Fair Value [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValueRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValueRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValueRollForward" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValueRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersAmortizationOfDeferredPolicyAcquisitionCosts_0060fe20-86f4-450c-a78d-2059fbc5578c_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersAmortizationOfDeferredPolicyAcquisitionCosts" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Amortization of policy acquisition costs</link:label>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersAmortizationOfDeferredPolicyAcquisitionCosts_label_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersAmortizationOfDeferredPolicyAcquisitionCosts" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-18, Supplemental Information, Property-Casualty Insurance Underwriters, Amortization of Deferred Policy Acquisition Cost</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersAmortizationOfDeferredPolicyAcquisitionCosts" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersAmortizationOfDeferredPolicyAcquisitionCosts"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersAmortizationOfDeferredPolicyAcquisitionCosts" xlink:to="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersAmortizationOfDeferredPolicyAcquisitionCosts" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesAllowance_958e6ea5-94e7-4eb2-abc8-1837c04d1499_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesAllowance" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Allowance for uncollectible reinsurance recoverable</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesAllowance_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesAllowance" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Reinsurance Recoverable, Allowance for Credit Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverablesAllowance" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ReinsuranceRecoverablesAllowance"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverablesAllowance" xlink:to="lab_us-gaap_ReinsuranceRecoverablesAllowance" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_OperatingLossCarryforwardsLimitationsOnUseAmount_9495a533-e61e-4f3b-b769-c394a29ff364_terseLabel_en-US" xlink:label="lab_skwd_OperatingLossCarryforwardsLimitationsOnUseAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Operating loss carryforwards, limitations on use, amount</link:label>
    <link:label id="lab_skwd_OperatingLossCarryforwardsLimitationsOnUseAmount_label_en-US" xlink:label="lab_skwd_OperatingLossCarryforwardsLimitationsOnUseAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Operating Loss Carryforwards, Limitations on Use, Amount</link:label>
    <link:label id="lab_skwd_OperatingLossCarryforwardsLimitationsOnUseAmount_documentation_en-US" xlink:label="lab_skwd_OperatingLossCarryforwardsLimitationsOnUseAmount" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Operating Loss Carryforwards, Limitations on Use, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_OperatingLossCarryforwardsLimitationsOnUseAmount" xlink:href="skwd-20221231.xsd#skwd_OperatingLossCarryforwardsLimitationsOnUseAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_OperatingLossCarryforwardsLimitationsOnUseAmount" xlink:to="lab_skwd_OperatingLossCarryforwardsLimitationsOnUseAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ImpairmentOfIntangibleAssetsExcludingGoodwill_a6c6cdd3-60bc-4fc4-879d-cbbed66b6f21_terseLabel_en-US" xlink:label="lab_us-gaap_ImpairmentOfIntangibleAssetsExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Impairment</link:label>
    <link:label id="lab_us-gaap_ImpairmentOfIntangibleAssetsExcludingGoodwill_7acac6cf-d443-44c2-b72b-34ce4108208b_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_ImpairmentOfIntangibleAssetsExcludingGoodwill" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Impairment</link:label>
    <link:label id="lab_us-gaap_ImpairmentOfIntangibleAssetsExcludingGoodwill_label_en-US" xlink:label="lab_us-gaap_ImpairmentOfIntangibleAssetsExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Impairment of Intangible Assets (Excluding Goodwill)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ImpairmentOfIntangibleAssetsExcludingGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ImpairmentOfIntangibleAssetsExcludingGoodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ImpairmentOfIntangibleAssetsExcludingGoodwill" xlink:to="lab_us-gaap_ImpairmentOfIntangibleAssetsExcludingGoodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LongtermDebtTypeDomain_46a77335-4ca2-44c4-a28b-3a8555702ba7_terseLabel_en-US" xlink:label="lab_us-gaap_LongtermDebtTypeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long-Term Debt, Type [Domain]</link:label>
    <link:label id="lab_us-gaap_LongtermDebtTypeDomain_label_en-US" xlink:label="lab_us-gaap_LongtermDebtTypeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Long-Term Debt, Type [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongtermDebtTypeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LongtermDebtTypeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LongtermDebtTypeDomain" xlink:to="lab_us-gaap_LongtermDebtTypeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CompensationAndRetirementDisclosureAbstract_label_en-US" xlink:label="lab_us-gaap_CompensationAndRetirementDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Retirement Benefits [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CompensationAndRetirementDisclosureAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CompensationAndRetirementDisclosureAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CompensationAndRetirementDisclosureAbstract" xlink:to="lab_us-gaap_CompensationAndRetirementDisclosureAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LineOfCreditFacilityPeriodicPaymentInterest_3c7160dd-5390-40cf-94aa-37d3630afb14_terseLabel_en-US" xlink:label="lab_us-gaap_LineOfCreditFacilityPeriodicPaymentInterest" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Interest payments on revolving line of credit</link:label>
    <link:label id="lab_us-gaap_LineOfCreditFacilityPeriodicPaymentInterest_label_en-US" xlink:label="lab_us-gaap_LineOfCreditFacilityPeriodicPaymentInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Line of Credit Facility, Periodic Payment, Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LineOfCreditFacilityPeriodicPaymentInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LineOfCreditFacilityPeriodicPaymentInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LineOfCreditFacilityPeriodicPaymentInterest" xlink:to="lab_us-gaap_LineOfCreditFacilityPeriodicPaymentInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementOfStockholdersEquityAbstract_label_en-US" xlink:label="lab_us-gaap_StatementOfStockholdersEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Statement of Stockholders' Equity [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementOfStockholdersEquityAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StatementOfStockholdersEquityAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementOfStockholdersEquityAbstract" xlink:to="lab_us-gaap_StatementOfStockholdersEquityAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTable_b39c63ca-a94f-4d24-b45c-5a9d1734fa4b_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Reconciliation of Claims Development to Liability [Table]</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTable_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Short-Duration Insurance Contracts, Reconciliation of Claims Development to Liability [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTable" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTable" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DirectPremiumsWritten_1ac92c84-d2ba-444b-b326-1c2612c03910_terseLabel_en-US" xlink:label="lab_us-gaap_DirectPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Direct premiums</link:label>
    <link:label id="lab_us-gaap_DirectPremiumsWritten_label_en-US" xlink:label="lab_us-gaap_DirectPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Direct Premiums Written</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DirectPremiumsWritten" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DirectPremiumsWritten"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DirectPremiumsWritten" xlink:to="lab_us-gaap_DirectPremiumsWritten" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxReconciliationIncomeTaxExpenseBenefitAtFederalStatutoryIncomeTaxRate_d4616593-23c1-49aa-9e7e-4603d00e14aa_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxReconciliationIncomeTaxExpenseBenefitAtFederalStatutoryIncomeTaxRate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Income tax expense at federal statutory rate</link:label>
    <link:label id="lab_us-gaap_IncomeTaxReconciliationIncomeTaxExpenseBenefitAtFederalStatutoryIncomeTaxRate_label_en-US" xlink:label="lab_us-gaap_IncomeTaxReconciliationIncomeTaxExpenseBenefitAtFederalStatutoryIncomeTaxRate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Effective Income Tax Rate Reconciliation at Federal Statutory Income Tax Rate, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxReconciliationIncomeTaxExpenseBenefitAtFederalStatutoryIncomeTaxRate" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncomeTaxReconciliationIncomeTaxExpenseBenefitAtFederalStatutoryIncomeTaxRate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxReconciliationIncomeTaxExpenseBenefitAtFederalStatutoryIncomeTaxRate" xlink:to="lab_us-gaap_IncomeTaxReconciliationIncomeTaxExpenseBenefitAtFederalStatutoryIncomeTaxRate" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesFairValue_2afbb1c9-0664-4715-9f46-fad2e3d76d48_terseLabel_en-US" xlink:label="lab_us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value</link:label>
    <link:label id="lab_us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesFairValue_label_en-US" xlink:label="lab_us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">SEC Schedule, 12-15, Insurance Companies, Summary of Investments, Other than Investments in Related Parties, Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesFairValue" xlink:to="lab_us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract_6994d355-8865-4c89-96b1-443d6a8ae7a5_terseLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Cash flows from financing activities:</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net Cash Provided by (Used in) Financing Activities [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract" xlink:to="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GainLossOnInvestmentsTextBlock_68c7dc71-5a98-4583-a3e1-2fcfdbc4d39a_terseLabel_en-US" xlink:label="lab_us-gaap_GainLossOnInvestmentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gain (Loss) on Securities</link:label>
    <link:label id="lab_us-gaap_GainLossOnInvestmentsTextBlock_label_en-US" xlink:label="lab_us-gaap_GainLossOnInvestmentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Gain (Loss) on Securities [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GainLossOnInvestmentsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_GainLossOnInvestmentsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GainLossOnInvestmentsTextBlock" xlink:to="lab_us-gaap_GainLossOnInvestmentsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommissionsPolicy_50b2f01d-9cba-41a6-8f92-717e93824bc8_terseLabel_en-US" xlink:label="lab_us-gaap_CommissionsPolicy" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Commission and Fee Income</link:label>
    <link:label id="lab_us-gaap_CommissionsPolicy_label_en-US" xlink:label="lab_us-gaap_CommissionsPolicy" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Commissions, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommissionsPolicy" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CommissionsPolicy"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommissionsPolicy" xlink:to="lab_us-gaap_CommissionsPolicy" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseLossPortfolioTransfer_fb7bd0be-5da6-4ea0-98f8-eaf8cc4303e4_terseLabel_en-US" xlink:label="lab_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseLossPortfolioTransfer" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability for claims and claims adjustment expense, loss portfolio transfer</link:label>
    <link:label id="lab_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseLossPortfolioTransfer_label_en-US" xlink:label="lab_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseLossPortfolioTransfer" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability For Claims And Claims Adjustment Expense, Loss Portfolio Transfer</link:label>
    <link:label id="lab_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseLossPortfolioTransfer_documentation_en-US" xlink:label="lab_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseLossPortfolioTransfer" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Liability For Claims And Claims Adjustment Expense, Loss Portfolio Transfer</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseLossPortfolioTransfer" xlink:href="skwd-20221231.xsd#skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseLossPortfolioTransfer"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseLossPortfolioTransfer" xlink:to="lab_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseLossPortfolioTransfer" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_FixedMaturitySecuritiesHeldToMaturityMember_3a85b9a7-724b-451a-bfa0-bfd5682a40f9_terseLabel_en-US" xlink:label="lab_skwd_FixedMaturitySecuritiesHeldToMaturityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fixed maturity securities, held-to-maturity</link:label>
    <link:label id="lab_skwd_FixedMaturitySecuritiesHeldToMaturityMember_label_en-US" xlink:label="lab_skwd_FixedMaturitySecuritiesHeldToMaturityMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fixed Maturity Securities, Held-to-Maturity [Member]</link:label>
    <link:label id="lab_skwd_FixedMaturitySecuritiesHeldToMaturityMember_documentation_en-US" xlink:label="lab_skwd_FixedMaturitySecuritiesHeldToMaturityMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fixed Maturity Securities, Held-to-Maturity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_FixedMaturitySecuritiesHeldToMaturityMember" xlink:href="skwd-20221231.xsd#skwd_FixedMaturitySecuritiesHeldToMaturityMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_FixedMaturitySecuritiesHeldToMaturityMember" xlink:to="lab_skwd_FixedMaturitySecuritiesHeldToMaturityMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsDisclosureTextBlock_74cb816e-9f24-4704-951b-9832a95bc170_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Other Long-Term Investments</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Equity Method Investments and Joint Ventures Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentsDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EquityMethodInvestmentsDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentsDisclosureTextBlock" xlink:to="lab_us-gaap_EquityMethodInvestmentsDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_AgentRelationshipsMember_83ee1bd7-2734-42da-aa49-3a050ed9c00c_terseLabel_en-US" xlink:label="lab_skwd_AgentRelationshipsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Agent Relationships</link:label>
    <link:label id="lab_skwd_AgentRelationshipsMember_label_en-US" xlink:label="lab_skwd_AgentRelationshipsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Agent Relationships [Member]</link:label>
    <link:label id="lab_skwd_AgentRelationshipsMember_documentation_en-US" xlink:label="lab_skwd_AgentRelationshipsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Agent Relationships</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_AgentRelationshipsMember" xlink:href="skwd-20221231.xsd#skwd_AgentRelationshipsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_AgentRelationshipsMember" xlink:to="lab_skwd_AgentRelationshipsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesFairValueAbstract_171ca5e5-b258-4ffc-9416-10bb2ed292fc_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesFairValueAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Fair Value</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesFairValueAbstract_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesFairValueAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Debt Securities, Available-for-Sale, Fair Value, Fiscal Year Maturity [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesFairValueAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesFairValueAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesFairValueAbstract" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesFairValueAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisaggregationOfRevenueLineItems_9a59c566-194d-4564-b9e4-e9702be76909_terseLabel_en-US" xlink:label="lab_us-gaap_DisaggregationOfRevenueLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Disaggregation of Revenue [Line Items]</link:label>
    <link:label id="lab_us-gaap_DisaggregationOfRevenueLineItems_label_en-US" xlink:label="lab_us-gaap_DisaggregationOfRevenueLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Disaggregation of Revenue [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisaggregationOfRevenueLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DisaggregationOfRevenueLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisaggregationOfRevenueLineItems" xlink:to="lab_us-gaap_DisaggregationOfRevenueLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromDivestitureOfBusinessesNetOfCashDivested_1da3f38c-a633-48a4-8eb4-a4f890c313a0_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromDivestitureOfBusinessesNetOfCashDivested" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Net proceeds related to sale</link:label>
    <link:label id="lab_us-gaap_ProceedsFromDivestitureOfBusinessesNetOfCashDivested_label_en-US" xlink:label="lab_us-gaap_ProceedsFromDivestitureOfBusinessesNetOfCashDivested" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xmlns:xml="http://www.w3.org/XML/1998/namespace" xml:lang="en-US">Proceeds from Divestiture of Businesses, Net of Cash Divested</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromDivestitureOfBusinessesNetOfCashDivested" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ProceedsFromDivestitureOfBusinessesNetOfCashDivested"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromDivestitureOfBusinessesNetOfCashDivested" xlink:to="lab_us-gaap_ProceedsFromDivestitureOfBusinessesNetOfCashDivested" xlink:type="arc" order="1"/>
  </link:labelLink>
</link:linkbase>
