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  <link:labelLink xlink:role="http://www.xbrl.org/2003/role/link" xlink:type="extended">
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    <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" xml:lang="en-US">Other Short-Term Investments</link:label>
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    <link:label id="lab_us-gaap_StockAppreciationRightsSARSMember_label_en-US" xlink:label="lab_us-gaap_StockAppreciationRightsSARSMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Stock Appreciation Rights (SARs) [Member]</link:label>
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    <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" 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/2023/elts/us-gaap-2023.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_ecd_PayVsPerformanceDisclosureLineItems_label_en-US" xlink:label="lab_ecd_PayVsPerformanceDisclosureLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Pay vs Performance Disclosure [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PayVsPerformanceDisclosureLineItems" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_PayVsPerformanceDisclosureLineItems"/>
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    <link:label id="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt_cea3a5f8-bc9a-4f58-84fa-132165979929_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.xsd#us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt"/>
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    <link:label id="lab_skwd_SMA1Member_63cfa744-16d7-4eda-82b8-aa1f9d098252_terseLabel_en-US" xlink:label="lab_skwd_SMA1Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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" xml:lang="en-US">SMA1</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_SMA1Member" xlink:href="skwd-20240331.xsd#skwd_SMA1Member"/>
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    <link:label id="lab_srt_RangeMember_b4d9c60b-10de-47ef-ab39-e67bc6aa3744_terseLabel_en-US" xlink:label="lab_srt_RangeMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/srt-2023.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_LineOfCreditFacilityMaximumBorrowingCapacity_cd077eb6-7707-4951-8e27-cfb07f16f438_terseLabel_en-US" xlink:label="lab_us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_ecd_UndrlygSecurityMktPriceChngPct_terseLabel_en-US" xlink:label="lab_ecd_UndrlygSecurityMktPriceChngPct" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Underlying Security Market Price Change</link:label>
    <link:label id="lab_ecd_UndrlygSecurityMktPriceChngPct_label_en-US" xlink:label="lab_ecd_UndrlygSecurityMktPriceChngPct" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Underlying Security Market Price Change, Percent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_UndrlygSecurityMktPriceChngPct" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_UndrlygSecurityMktPriceChngPct"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_UndrlygSecurityMktPriceChngPct" xlink:to="lab_ecd_UndrlygSecurityMktPriceChngPct" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RelatedPartyTransactionLineItems_ceea74db-2e09-4e81-8bca-a8e7abbe1a9f_terseLabel_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetIssues_9c43a959-2f50-4115-8a1d-178f658c2f0b_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetIssues" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Issuances</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetIssues_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetIssues" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Measurement with Unobservable Inputs Reconciliation, Recurring Basis, Asset, Issuances</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetIssues" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetIssues"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetIssues" xlink:to="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetIssues" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain_237b6ae0-0442-4c49-880c-7fbe32fe184d_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_ecd_AwardGrantDateFairValue_terseLabel_en-US" xlink:label="lab_ecd_AwardGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value as of Grant Date</link:label>
    <link:label id="lab_ecd_AwardGrantDateFairValue_label_en-US" xlink:label="lab_ecd_AwardGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Grant Date Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardGrantDateFairValue" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_AwardGrantDateFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardGrantDateFairValue" xlink:to="lab_ecd_AwardGrantDateFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_EquityMethodInvesteeNameDomain_76179cb5-30e1-4c03-9964-0fae3a6338c0_terseLabel_en-US" xlink:label="lab_srt_EquityMethodInvesteeNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/srt-2023.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_DebtDisclosureTextBlock_897ca644-8cdd-4f45-b7df-7116975472fe_verboseLabel_en-US" xlink:label="lab_us-gaap_DebtDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Notes Payable &amp; Subordinated Debt</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" 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/2023/elts/us-gaap-2023.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_skwd_FixedMaturitySecuritiesAvailableForSaleMember_04f7b683-36c4-4084-8e84-59b957b7f8bf_terseLabel_en-US" xlink:label="lab_skwd_FixedMaturitySecuritiesAvailableForSaleMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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" 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-20240331.xsd#skwd_FixedMaturitySecuritiesAvailableForSaleMember"/>
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    <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" 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/2023/elts/us-gaap-2023.xsd#us-gaap_StatementOfStockholdersEquityAbstract"/>
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    <link:label id="lab_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock_0ec81148-56ea-4603-92e6-c9e52250460a_terseLabel_en-US" xlink:label="lab_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" xml:lang="en-US">Debt Securities, Trading, and Equity Securities, FV-NI [Table Text Block]</link:label>
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    <link:label id="lab_us-gaap_CorporateDebtSecuritiesMember_7e654519-e4ad-4c7b-8df7-84316e02506e_terseLabel_en-US" xlink:label="lab_us-gaap_CorporateDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Corporate securities and miscellaneous</link:label>
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    <link:label id="lab_ecd_InsiderTradingPoliciesProcLineItems_label_en-US" xlink:label="lab_ecd_InsiderTradingPoliciesProcLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insider Trading Policies and Procedures [Line Items]</link:label>
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    <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" xml:lang="en-US">Indirect Loans and Loan Collateral</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_IndirectLoansAndLoanCollateralMember" xlink:href="skwd-20240331.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_srt_OwnershipAxis_745835e7-db18-43a4-a5ce-3accdd174b22_terseLabel_en-US" xlink:label="lab_srt_OwnershipAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/srt-2023.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_us-gaap_SubordinatedDebtMember_b962d214-79b6-46b7-8f85-eda25cda5a55_terseLabel_en-US" xlink:label="lab_us-gaap_SubordinatedDebtMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subordinated debt, net of debt issuance costs</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" 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/2023/elts/us-gaap-2023.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_skwd_UnsecuredSubordinatedNotesMember_624e67b7-7983-4f26-9b72-b2da4f0fdb83_terseLabel_en-US" xlink:label="lab_skwd_UnsecuredSubordinatedNotesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Unsecured subordinated notes</link:label>
    <link:label id="lab_skwd_UnsecuredSubordinatedNotesMember_label_en-US" xlink:label="lab_skwd_UnsecuredSubordinatedNotesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Unsecured Subordinated Notes [Member]</link:label>
    <link:label id="lab_skwd_UnsecuredSubordinatedNotesMember_documentation_en-US" xlink:label="lab_skwd_UnsecuredSubordinatedNotesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Unsecured Subordinated Notes</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_UnsecuredSubordinatedNotesMember" xlink:href="skwd-20240331.xsd#skwd_UnsecuredSubordinatedNotesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_UnsecuredSubordinatedNotesMember" xlink:to="lab_skwd_UnsecuredSubordinatedNotesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesBeforeReclassificationAdjustmentsTax_4335bf9f-5729-4546-8053-7d97942c6743_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesBeforeReclassificationAdjustmentsTax" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_skwd_OfficePortfolioSegmentMember_1613e064-b809-44f6-8cfc-d35e091d8685_terseLabel_en-US" xlink:label="lab_skwd_OfficePortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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" xml:lang="en-US">Office Portfolio Segment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_OfficePortfolioSegmentMember" xlink:href="skwd-20240331.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_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable_aac51173-d655-4d7e-ad32-5646fe7cc596_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_EarningsPerShareDiluted_c9ed94a6-023c-463a-bbf0-d7eb097f5f79_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareDiluted" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Diluted earnings (loss) 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" 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/2023/elts/us-gaap-2023.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_LineOfCreditFacilityIncreaseAccruedInterest_ac7c1360-f7cc-4e63-9cd2-49c4ff3b5a71_terseLabel_en-US" xlink:label="lab_us-gaap_LineOfCreditFacilityIncreaseAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Line of credit facility, increase, accrued interest</link:label>
    <link:label id="lab_us-gaap_LineOfCreditFacilityIncreaseAccruedInterest_label_en-US" xlink:label="lab_us-gaap_LineOfCreditFacilityIncreaseAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Line of Credit Facility, Increase, Accrued Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LineOfCreditFacilityIncreaseAccruedInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LineOfCreditFacilityIncreaseAccruedInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LineOfCreditFacilityIncreaseAccruedInterest" xlink:to="lab_us-gaap_LineOfCreditFacilityIncreaseAccruedInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest_3e22d491-0278-44c8-aa5f-e33fa3aae2f8_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Allowance for credit losses</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest_571f03f8-084f-47f6-8ebb-85f1c7c56fe0_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Allowance for Credit Losses</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Allowance for Credit Loss, Excluding Accrued Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest" xlink:to="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PeoTotalCompAmt_terseLabel_en-US" xlink:label="lab_ecd_PeoTotalCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">PEO Total Compensation Amount</link:label>
    <link:label id="lab_ecd_PeoTotalCompAmt_label_en-US" xlink:label="lab_ecd_PeoTotalCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">PEO Total Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeoTotalCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_PeoTotalCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PeoTotalCompAmt" xlink:to="lab_ecd_PeoTotalCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_UnderwritingAcquisitionAndInsuranceExpensesTextBlock_92d146d4-6e93-4b77-b068-ff389ffee936_terseLabel_en-US" xlink:label="lab_skwd_UnderwritingAcquisitionAndInsuranceExpensesTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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" xml:lang="en-US">Underwriting, Acquisition and Insurance Expenses</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_UnderwritingAcquisitionAndInsuranceExpensesTextBlock" xlink:href="skwd-20240331.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_us-gaap_ReinsuranceRecoverablesAllowance_b160dba2-21b5-4e04-96fe-daaf5ec80d25_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesAllowance" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Allowance for credit losses</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" 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/2023/elts/us-gaap-2023.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_us-gaap_ReinsurancePayable_0b887c44-e500-48f8-bdc7-80d6a17f1866_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsurancePayable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_us-gaap_AccountingStandardsUpdateExtensibleList_38a61607-1493-46c2-ba36-5e18af3491e0_terseLabel_en-US" xlink:label="lab_us-gaap_AccountingStandardsUpdateExtensibleList" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accounting Standards Update [Extensible Enumeration]</link:label>
    <link:label id="lab_us-gaap_AccountingStandardsUpdateExtensibleList_label_en-US" xlink:label="lab_us-gaap_AccountingStandardsUpdateExtensibleList" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Accounting Standards Update [Extensible Enumeration]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccountingStandardsUpdateExtensibleList" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_AccountingStandardsUpdateExtensibleList"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccountingStandardsUpdateExtensibleList" xlink:to="lab_us-gaap_AccountingStandardsUpdateExtensibleList" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TradingArrByIndTable_terseLabel_en-US" xlink:label="lab_ecd_TradingArrByIndTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Trading Arrangements, by Individual</link:label>
    <link:label id="lab_ecd_TradingArrByIndTable_label_en-US" xlink:label="lab_ecd_TradingArrByIndTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangements, by Individual [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TradingArrByIndTable" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_TradingArrByIndTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TradingArrByIndTable" xlink:to="lab_ecd_TradingArrByIndTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueInputsLevel3Member_03dbb2fa-42d7-4ace-b3cd-3261f15b037d_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel3Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">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" 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/2023/elts/us-gaap-2023.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_LineOfCreditMember_a8d05df8-1e26-4a5e-8e4e-db7260888c68_terseLabel_en-US" xlink:label="lab_us-gaap_LineOfCreditMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_ec4ca832-cea0-4bde-a2a4-e49576c0957a_verboseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity securities, available-for-sale, at fair value (amortized cost of $1,102,190 and $1,047,713, respectively)</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_f01df7cd-967e-45e3-affc-47756d6692ce_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total fixed maturity securities, available-for-sale</link:label>
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    <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" xml:lang="en-US">Debt Securities, Available-for-Sale, Excluding Accrued Interest</link:label>
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    <link:label id="lab_dei_TradingSymbol_5c8f7fe1-8137-48ea-a36e-3e8387991ffb_terseLabel_en-US" xlink:label="lab_dei_TradingSymbol" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Trading Symbol</link:label>
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    <link:label id="lab_us-gaap_LongTermDebtFairValue_ae6236ad-f848-46b8-9fa8-6bf22ae418b1_terseLabel_en-US" xlink:label="lab_us-gaap_LongTermDebtFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Long-term debt</link:label>
    <link:label id="lab_us-gaap_LongTermDebtFairValue_label_en-US" xlink:label="lab_us-gaap_LongTermDebtFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Long-Term Debt, Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LongTermDebtFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LongTermDebtFairValue" xlink:to="lab_us-gaap_LongTermDebtFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_MeasurementInputIncrementalCostOfCapitalMember_e29d4b6b-98b9-40c1-ae76-6b5d251ccf38_terseLabel_en-US" xlink:label="lab_skwd_MeasurementInputIncrementalCostOfCapitalMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measurement Input, Incremental Cost of Capital</link:label>
    <link:label id="lab_skwd_MeasurementInputIncrementalCostOfCapitalMember_label_en-US" xlink:label="lab_skwd_MeasurementInputIncrementalCostOfCapitalMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measurement Input, Incremental Cost of Capital [Member]</link:label>
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    <link:label id="lab_us-gaap_NetIncomeLoss_58cac3c0-dad0-42c9-b5c8-5d79a5ca6d28_totalLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net income</link:label>
    <link:label id="lab_us-gaap_NetIncomeLoss_2fef40c4-a7e6-4523-b809-2298fc0aa8eb_terseLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net income</link:label>
    <link:label id="lab_us-gaap_NetIncomeLoss_699db072-ee47-4d44-b7d3-07af0bb38832_verboseLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLoss" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" 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" xml:lang="en-US">Net Income (Loss)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_NetIncomeLoss"/>
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    <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" 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/2023/elts/us-gaap-2023.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_ecd_ChangedPeerGroupFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_ChangedPeerGroupFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Changed Peer Group, Footnote</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_ecd_ChangedPeerGroupFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_ChangedPeerGroupFnTextBlock"/>
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    <link:label id="lab_ecd_CoSelectedMeasureName_terseLabel_en-US" xlink:label="lab_ecd_CoSelectedMeasureName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Company Selected Measure Name</link:label>
    <link:label id="lab_ecd_CoSelectedMeasureName_label_en-US" xlink:label="lab_ecd_CoSelectedMeasureName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Company Selected Measure Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_CoSelectedMeasureName" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_CoSelectedMeasureName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_CoSelectedMeasureName" xlink:to="lab_ecd_CoSelectedMeasureName" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract_e83f1a7e-a56e-4f24-b8c1-5ac014799b2c_terseLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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" 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-20240331.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_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost_b9f9a513-8021-49f6-9344-207d2b0493d6_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost"/>
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    <link:label id="lab_us-gaap_DeferredPolicyAcquisitionCosts_75d0b14e-da2b-4ed9-a509-276e4077f7da_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredPolicyAcquisitionCosts" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_us-gaap_LiabilitiesAndStockholdersEquityAbstract_14abb890-66b3-47ca-b8da-7dfe137422a8_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilitiesAndStockholdersEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_dei_EntityExTransitionPeriod_77ed0ce2-f6eb-4a9c-a494-e8d19e720536_terseLabel_en-US" xlink:label="lab_dei_EntityExTransitionPeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/dei-2023.xsd#dei_EntityExTransitionPeriod"/>
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    <link:label id="lab_us-gaap_ScheduleOfEquityMethodInvestmentsTable_881ea149-ec25-4c7c-b285-bf732e93b6ff_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfEquityMethodInvestmentsTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Equity Method Investments [Table]</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfEquityMethodInvestmentsTable" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ScheduleOfEquityMethodInvestmentsTable"/>
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    <link:label id="lab_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock_c840ff35-30d6-46ba-9e95-4ed97556b065_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Earnings Per Share, Basic and Diluted</link:label>
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    <link:label id="lab_ecd_ExecutiveCategoryAxis_terseLabel_en-US" xlink:label="lab_ecd_ExecutiveCategoryAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Executive Category:</link:label>
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    <link:label id="lab_us-gaap_CededPremiumsWritten_72e253c7-d44d-46cb-afa6-a3a9e82c2b58_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_CededPremiumsWritten" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock_e248db03-5ddf-4a97-bc1e-853fd8624aff_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation</link:label>
    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock"/>
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    <link:label id="lab_us-gaap_SignificantAccountingPoliciesTextBlock_253f94df-019e-4931-9c1f-81197bcc3abc_terseLabel_en-US" xlink:label="lab_us-gaap_SignificantAccountingPoliciesTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_FairValueInputsLevel1Member_a0d70295-e88f-45ab-82bb-c64f7adf9ad3_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel1Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">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" 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/2023/elts/us-gaap-2023.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_ecd_MeasureName_terseLabel_en-US" xlink:label="lab_ecd_MeasureName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Name</link:label>
    <link:label id="lab_ecd_MeasureName_label_en-US" xlink:label="lab_ecd_MeasureName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measure Name</link:label>
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    <link:label id="lab_us-gaap_CarryingReportedAmountFairValueDisclosureMember_951c36ee-ba55-40da-8139-cf9af1e83d19_terseLabel_en-US" xlink:label="lab_us-gaap_CarryingReportedAmountFairValueDisclosureMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Carrying 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" 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/2023/elts/us-gaap-2023.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_us-gaap_StatementEquityComponentsAxis_a0af386c-da9a-4f4b-a084-ac83a1a3ddc7_terseLabel_en-US" xlink:label="lab_us-gaap_StatementEquityComponentsAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain_49cebbcb-f116-487e-8ca2-311ed740901d_terseLabel_en-US" xlink:label="lab_us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.xsd#us-gaap_TransfersAndServicingOfFinancialInstrumentsTypesOfFinancialInstrumentsDomain"/>
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    <link:label id="lab_ecd_Additional402vDisclosureTextBlock_terseLabel_en-US" xlink:label="lab_ecd_Additional402vDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Additional 402(v) Disclosure</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_Additional402vDisclosureTextBlock" xlink:to="lab_ecd_Additional402vDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerOtherMember_9490ff49-f1bb-49fc-b1f9-524d14678221_terseLabel_en-US" xlink:label="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerOtherMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other</link:label>
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    <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" xml:lang="en-US">Managing General Insurance Agent And Broker, Other</link:label>
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    <link:label id="lab_us-gaap_InvestmentTypeAxis_fa25ab5c-7209-4a23-8fc7-1f07f0cbdffe_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1_b8ccc261-79eb-4664-ba0d-4ae508781036_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidCurrentYear1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Current period</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueByMeasurementBasisAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueByMeasurementBasisAxis"/>
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    <link:label id="lab_dei_EntitySmallBusiness_7d9af557-b295-4b0d-844f-99d1b50e0752_terseLabel_en-US" xlink:label="lab_dei_EntitySmallBusiness" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Small Business</link:label>
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    <link:label id="lab_us-gaap_InvestmentTypeCategorizationMember_20209d50-7b8e-4060-9f19-e2288dd3cd26_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentTypeCategorizationMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.xsd#us-gaap_InvestmentTypeCategorizationMember"/>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1"/>
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    <link:label id="lab_dei_LocalPhoneNumber_2f1f639c-77ee-4a80-9ca7-237478eccb15_terseLabel_en-US" xlink:label="lab_dei_LocalPhoneNumber" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Local Phone Number</link:label>
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    <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_FairValueDisclosureItemAmountsDomain_23fd7296-4c0a-490b-8720-eca974dad0f0_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueDisclosureItemAmountsDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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"/>
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    <link:label id="lab_ecd_RecoveryOfErrCompDisclosureLineItems_label_en-US" xlink:label="lab_ecd_RecoveryOfErrCompDisclosureLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Recovery of Erroneously Awarded Compensation Disclosure [Line Items]</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LetterOfCreditMember" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.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"/>
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    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:href="skwd-20240331.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_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems_1812170b-d9e2-4ff1-9225-fe7e7a96f33c_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net Investment Income [Line Items]</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryLineItems"/>
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    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract_f977d196-28b0-4d38-8c3a-3809eac80c66_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Incurred, net of reinsurance, related to:</link:label>
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    <link:label id="lab_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock_6d383338-2757-46c2-abdd-8270ec1ab328_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investments Classified by Contractual Maturity Date</link:label>
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    <link:label id="lab_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivities_a6ecda41-2d65-4e0d-91ee-ef6c162c10cc_terseLabel_en-US" xlink:label="lab_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adjustments to reconcile net income to net cash provided by operating activities</link:label>
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    <link:label id="lab_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt_terseLabel_en-US" xlink:label="lab_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Forgone Recovery due to Violation of Home Country Law, Amount</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_ForgoneRecoveryDueToViolationOfHomeCountryLawAmt"/>
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    <link:label id="lab_skwd_IndustrialPortfolioSegmentMember_1d64a485-b94c-4213-8c4a-df6903e6f157_terseLabel_en-US" xlink:label="lab_skwd_IndustrialPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Industrial</link:label>
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    <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" xml:lang="en-US">Industrial Portfolio Segment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_IndustrialPortfolioSegmentMember" xlink:href="skwd-20240331.xsd#skwd_IndustrialPortfolioSegmentMember"/>
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    <link:label id="lab_us-gaap_DebtInstrumentNameDomain_9b6f4edf-88c2-4f83-ba80-a278b58cca47_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Instrument, Name [Domain]</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DebtInstrumentNameDomain"/>
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    <link:label id="lab_skwd_HospitalityPortfolioSegmentMember_5ef2fab5-7e53-431a-bd6f-0e4d329de12e_terseLabel_en-US" xlink:label="lab_skwd_HospitalityPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Hospitality</link:label>
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    <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" xml:lang="en-US">Hospitality Portfolio Segment</link:label>
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    <link:label id="lab_srt_CumulativeEffectPeriodOfAdoptionAdjustmentMember_ed916e4b-60d4-47d0-ac78-485aa61064bf_terseLabel_en-US" xlink:label="lab_srt_CumulativeEffectPeriodOfAdoptionAdjustmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Period of adoption, adjustment</link:label>
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    <link:label id="lab_skwd_StockUnitsMember_a4453a86-864a-4378-8512-c1951a133f3f_terseLabel_en-US" xlink:label="lab_skwd_StockUnitsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stock units</link:label>
    <link:label id="lab_skwd_StockUnitsMember_label_en-US" xlink:label="lab_skwd_StockUnitsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Stock Units [Member]</link:label>
    <link:label id="lab_skwd_StockUnitsMember_documentation_en-US" xlink:label="lab_skwd_StockUnitsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Stock Units</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_StockUnitsMember" xlink:href="skwd-20240331.xsd#skwd_StockUnitsMember"/>
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    <link:label id="lab_us-gaap_DepositContractsAssets_48f84891-c030-43bd-bee1-8eed2c646271_terseLabel_en-US" xlink:label="lab_us-gaap_DepositContractsAssets" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Deposit asset</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition" xlink:href="skwd-20240331.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition"/>
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    <link:label id="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill_3550ad80-7687-4094-a97d-ac000dcad1dc_terseLabel_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Goodwill and intangible assets, net</link:label>
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    <link:label id="lab_skwd_HudsonVenturesFund2LPMember_2526d4ef-87e0-4197-a29d-a6c970464f91_terseLabel_en-US" xlink:label="lab_skwd_HudsonVenturesFund2LPMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Hudson Ventures Fund II LP units</link:label>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost_780e21bb-c38e-4148-b0dd-2661c6974dbf_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Due after ten years</link:label>
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    <link:label id="lab_srt_ProductsAndServicesDomain_aebbf984-6733-4a49-894b-664aaeb89c10_terseLabel_en-US" xlink:label="lab_srt_ProductsAndServicesDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Product and Service [Domain]</link:label>
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    <link:label id="lab_us-gaap_CommercialMortgageBackedSecuritiesMember_0d5f4a5b-1299-492e-8725-fc8654502c78_terseLabel_en-US" xlink:label="lab_us-gaap_CommercialMortgageBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Commercial mortgage-backed securities</link:label>
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    <link:label id="lab_ecd_TrdArrSecuritiesAggAvailAmt_terseLabel_en-US" xlink:label="lab_ecd_TrdArrSecuritiesAggAvailAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aggregate Available</link:label>
    <link:label id="lab_ecd_TrdArrSecuritiesAggAvailAmt_label_en-US" xlink:label="lab_ecd_TrdArrSecuritiesAggAvailAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement, Securities Aggregate Available Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrSecuritiesAggAvailAmt" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_TrdArrSecuritiesAggAvailAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrSecuritiesAggAvailAmt" xlink:to="lab_ecd_TrdArrSecuritiesAggAvailAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherExpenses_3f8676b7-bc95-4dcd-8cb7-933c9165d56b_terseLabel_en-US" xlink:label="lab_us-gaap_OtherExpenses" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other expenses</link:label>
    <link:label id="lab_us-gaap_OtherExpenses_label_en-US" xlink:label="lab_us-gaap_OtherExpenses" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Expenses</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherExpenses" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_OtherExpenses"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherExpenses" xlink:to="lab_us-gaap_OtherExpenses" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract_c3926ae9-5655-456e-9f52-ccd8bc795d78_terseLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_skwd_DeferredCedingCommission_bcf577bd-3c1d-4a79-82e7-66f0a662e637_terseLabel_en-US" xlink:label="lab_skwd_DeferredCedingCommission" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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" xml:lang="en-US">Deferred Ceding Commission</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DeferredCedingCommission" xlink:href="skwd-20240331.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_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock_terseLabel_en-US" xlink:label="lab_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Insider Trading Policies and Procedures Not Adopted</link:label>
    <link:label id="lab_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock_label_en-US" xlink:label="lab_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insider Trading Policies and Procedures Not Adopted [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock" xlink:to="lab_ecd_InsiderTrdPoliciesProcNotAdoptedTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount_263c998f-93eb-4f01-9605-321d967b5b36_terseLabel_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_AwardTypeAxis_4b421d70-e2ed-4b11-8486-220691567b59_terseLabel_en-US" xlink:label="lab_us-gaap_AwardTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_dei_DocumentQuarterlyReport_56e1f2f5-d4d9-472e-b136-bbab501da3a2_terseLabel_en-US" xlink:label="lab_dei_DocumentQuarterlyReport" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Document Quarterly Report</link:label>
    <link:label id="lab_dei_DocumentQuarterlyReport_label_en-US" xlink:label="lab_dei_DocumentQuarterlyReport" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Document Quarterly Report</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentQuarterlyReport" xlink:href="https://xbrl.sec.gov/dei/2023/dei-2023.xsd#dei_DocumentQuarterlyReport"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentQuarterlyReport" xlink:to="lab_dei_DocumentQuarterlyReport" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_WestaimHIIGLPMember_f7d73fa9-46fb-4689-af23-7ff820348d91_terseLabel_en-US" xlink:label="lab_skwd_WestaimHIIGLPMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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" xml:lang="en-US">Westaim HIIG LP</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_WestaimHIIGLPMember" xlink:href="skwd-20240331.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_InterestExpense_1b57a2e3-5e2f-4d22-8b0f-4e1cbc4d36ff_terseLabel_en-US" xlink:label="lab_us-gaap_InterestExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_PaymentsForLossesAndLossAdjustmentExpense_4ab30845-25f5-4be8-b827-faf6df5ab098_totalLabel_en-US" xlink:label="lab_us-gaap_PaymentsForLossesAndLossAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_FairValueMeasurementsFairValueHierarchyDomain_1d5fe3f1-03ea-4d31-9d9b-37ef3f7764c4_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract_fe78321e-c665-4ad7-9714-eb5f3f584f66_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_ecd_TradingArrAxis_terseLabel_en-US" xlink:label="lab_ecd_TradingArrAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Trading Arrangement:</link:label>
    <link:label id="lab_ecd_TradingArrAxis_label_en-US" xlink:label="lab_ecd_TradingArrAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TradingArrAxis" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_TradingArrAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TradingArrAxis" xlink:to="lab_ecd_TradingArrAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ContingentlyIssuableInstrumentsCommonSharesMember_006f33aa-0ac6-4378-8593-418c64cae055_terseLabel_en-US" xlink:label="lab_skwd_ContingentlyIssuableInstrumentsCommonSharesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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" xml:lang="en-US">Contingently Issuable Instruments, Common Shares</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ContingentlyIssuableInstrumentsCommonSharesMember" xlink:href="skwd-20240331.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_us-gaap_RelatedPartyTransactionsDisclosureTextBlock_e56fbdf1-2670-4d94-8841-aecd9f2123a2_terseLabel_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_GainOnSaleOfOtherInvestments_c6bc6c50-1923-4b2e-a4f2-bedbf7adea35_terseLabel_en-US" xlink:label="lab_skwd_GainOnSaleOfOtherInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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" 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-20240331.xsd#skwd_GainOnSaleOfOtherInvestments"/>
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    <link:label id="lab_us-gaap_UseOfEstimates_69314d6e-7ab2-4f03-aed9-83ea0e09ceb7_terseLabel_en-US" xlink:label="lab_us-gaap_UseOfEstimates" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_ecd_PeoActuallyPaidCompAmt_terseLabel_en-US" xlink:label="lab_ecd_PeoActuallyPaidCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">PEO Actually Paid Compensation Amount</link:label>
    <link:label id="lab_ecd_PeoActuallyPaidCompAmt_label_en-US" xlink:label="lab_ecd_PeoActuallyPaidCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">PEO Actually Paid Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeoActuallyPaidCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_PeoActuallyPaidCompAmt"/>
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    <link:label id="lab_us-gaap_UnearnedPremiums_81d6fe85-df09-46d8-accb-07886e4c1b60_terseLabel_en-US" xlink:label="lab_us-gaap_UnearnedPremiums" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" xml:lang="en-US">Unearned Premiums</link:label>
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    <link:label id="lab_us-gaap_FinancingReceivablePortfolioSegmentDomain_5459bd77-d0f6-4789-83f7-dd68bb790a57_terseLabel_en-US" xlink:label="lab_us-gaap_FinancingReceivablePortfolioSegmentDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_PaymentsForProceedsFromSaleAndCollectionOfSecurities_1c4a8286-b5ca-4456-a4a5-4e203fc4d005_negatedTerseLabel_en-US" xlink:label="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Change in receivable/payable for securities</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" 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" 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-20240331.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_dei_DocumentType_ef500d8e-1843-4469-91c0-a3933ae3a9fb_terseLabel_en-US" xlink:label="lab_dei_DocumentType" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/dei-2023.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_ScheduleOfRelatedPartyTransactionsTableTextBlock_870ad950-515d-4c7c-9814-aaf4704c7c19_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfRelatedPartyTransactionsTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_us-gaap_BenefitsLossesAndExpenses_19e674af-32fe-4444-858d-81906831f2e1_totalLabel_en-US" xlink:label="lab_us-gaap_BenefitsLossesAndExpenses" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_ecd_TabularListTableTextBlock_terseLabel_en-US" xlink:label="lab_ecd_TabularListTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Tabular List, Table</link:label>
    <link:label id="lab_ecd_TabularListTableTextBlock_label_en-US" xlink:label="lab_ecd_TabularListTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Tabular List [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TabularListTableTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_TabularListTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TabularListTableTextBlock" xlink:to="lab_ecd_TabularListTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressAddressLine1_f044ca1e-351e-491f-a60e-eed19e7af352_terseLabel_en-US" xlink:label="lab_dei_EntityAddressAddressLine1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/dei-2023.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_dei_EntityAddressAddressLine2_fbfbe6c4-8a30-45c8-a65e-cff41e787082_terseLabel_en-US" xlink:label="lab_dei_EntityAddressAddressLine2" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/dei-2023.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_srt_CumulativeEffectPeriodOfAdoptionDomain_04a654b3-df3b-4258-99c0-3e88bcae2d93_terseLabel_en-US" xlink:label="lab_srt_CumulativeEffectPeriodOfAdoptionDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/srt-2023.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_AntidilutiveSecuritiesNameDomain_f3e9b07c-0d84-4f00-b2b8-befd370334b4_terseLabel_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingGain_bda25a6c-8953-4bb7-a198-34cea8074d3a_terseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingGain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_us-gaap_DebtSecuritiesUnrealizedGainLossAbstract_eef9f40f-0036-4849-b9cb-6104b9ad489b_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesUnrealizedGainLossAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_us-gaap_BasisOfAccountingPolicyPolicyTextBlock_bb02ad00-10ef-4221-ab3a-907d2c5bef07_terseLabel_en-US" xlink:label="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_skwd_AgencyAgreementMember_7bc11705-a845-4c77-87cf-a862d582a3be_terseLabel_en-US" xlink:label="lab_skwd_AgencyAgreementMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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" xml:lang="en-US">Agency Agreement</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_AgencyAgreementMember" xlink:href="skwd-20240331.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_PaymentsToAcquireAvailableForSaleSecuritiesDebt_c308705a-6433-47e9-9298-775df4158a96_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_FundsHeldUnderReinsuranceAgreementsAsset_53dff56e-a6b4-40f2-811c-e22c1346fb77_terseLabel_en-US" xlink:label="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_VariableRateAxis_941f3bd8-e18e-4b32-af32-956340fbceb0_terseLabel_en-US" xlink:label="lab_us-gaap_VariableRateAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_skwd_ArenaSOPLPMember_c62dd78b-aa41-4ff4-88ee-fe19e6a14ddc_terseLabel_en-US" xlink:label="lab_skwd_ArenaSOPLPMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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" xml:lang="en-US">Arena SOP LP</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ArenaSOPLPMember" xlink:href="skwd-20240331.xsd#skwd_ArenaSOPLPMember"/>
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    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue_252149fb-027a-493d-9ac8-3465d1c40e3e_terseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_IncomeStatementAbstract_label_en-US" xlink:label="lab_us-gaap_IncomeStatementAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" 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/2023/elts/us-gaap-2023.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_CostsAndExpensesAbstract_f9ced58c-d471-45eb-8666-eb00677adf8b_terseLabel_en-US" xlink:label="lab_us-gaap_CostsAndExpensesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_us-gaap_NetInvestmentIncome_668c38de-b555-443c-b1a4-48787849342b_terseLabel_en-US" xlink:label="lab_us-gaap_NetInvestmentIncome" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net investment income</link:label>
    <link:label id="lab_us-gaap_NetInvestmentIncome_97373d67-2cf9-44e4-bbac-e9514291d18b_totalLabel_en-US" xlink:label="lab_us-gaap_NetInvestmentIncome" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_dei_Security12bTitle_066fac57-ee3c-4d1b-997d-432123c26c64_terseLabel_en-US" xlink:label="lab_dei_Security12bTitle" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/dei-2023.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_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract_3f1699cb-21e1-405c-b587-2732f2f16bdd_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">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" 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/2023/elts/us-gaap-2023.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_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestAfterAllowanceForCreditLoss_770c983c-58f2-4abc-8906-6bc5653b387e_verboseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestAfterAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Amortized cost</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestAfterAllowanceForCreditLoss_d13ab73d-2de1-41ba-b207-3e97d60c47c5_totalLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestAfterAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_ecd_InsiderTrdPoliciesProcAdoptedFlag_terseLabel_en-US" xlink:label="lab_ecd_InsiderTrdPoliciesProcAdoptedFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Insider Trading Policies and Procedures Adopted</link:label>
    <link:label id="lab_ecd_InsiderTrdPoliciesProcAdoptedFlag_label_en-US" xlink:label="lab_ecd_InsiderTrdPoliciesProcAdoptedFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insider Trading Policies and Procedures Adopted [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_InsiderTrdPoliciesProcAdoptedFlag" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_InsiderTrdPoliciesProcAdoptedFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_InsiderTrdPoliciesProcAdoptedFlag" xlink:to="lab_ecd_InsiderTrdPoliciesProcAdoptedFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract_c4290063-a53a-40ff-aa19-26cfd19470d6_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">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" 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/2023/elts/us-gaap-2023.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_RelatedPartyDomain_691424b0-c5a8-4550-945f-47b75e4c1471_terseLabel_en-US" xlink:label="lab_us-gaap_RelatedPartyDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" xml:lang="en-US">Related Party, Type [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RelatedPartyDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.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_skwd_BrewerLaneVenturesFundIILPMember_501a55f5-0078-4f29-852d-64bc3d468f37_terseLabel_en-US" xlink:label="lab_skwd_BrewerLaneVenturesFundIILPMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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" 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-20240331.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_CommercialPortfolioSegmentMember_319521b6-3745-4a36-adc1-a634bfb353ef_terseLabel_en-US" xlink:label="lab_us-gaap_CommercialPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_ecd_AggtErrCompNotYetDeterminedTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AggtErrCompNotYetDeterminedTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aggregate Erroneous Compensation Not Yet Determined</link:label>
    <link:label id="lab_ecd_AggtErrCompNotYetDeterminedTextBlock_label_en-US" xlink:label="lab_ecd_AggtErrCompNotYetDeterminedTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Aggregate Erroneous Compensation Not Yet Determined [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AggtErrCompNotYetDeterminedTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_AggtErrCompNotYetDeterminedTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AggtErrCompNotYetDeterminedTextBlock" xlink:to="lab_ecd_AggtErrCompNotYetDeterminedTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_SubordinatedDebtNetMember_b8ba46e7-c30a-42c2-9ac7-be6f79424940_terseLabel_en-US" xlink:label="lab_skwd_SubordinatedDebtNetMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subordinated debt, net of debt issuance costs</link:label>
    <link:label id="lab_skwd_SubordinatedDebtNetMember_label_en-US" xlink:label="lab_skwd_SubordinatedDebtNetMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subordinated Debt, Net [Member]</link:label>
    <link:label id="lab_skwd_SubordinatedDebtNetMember_documentation_en-US" xlink:label="lab_skwd_SubordinatedDebtNetMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Subordinated Debt, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_SubordinatedDebtNetMember" xlink:href="skwd-20240331.xsd#skwd_SubordinatedDebtNetMember"/>
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    <link:label id="lab_us-gaap_StockIssuedDuringPeriodValueShareBasedCompensation_28f90be0-e7ef-4b33-9e62-9c104547af91_terseLabel_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodValueShareBasedCompensation" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Issuance of common stock</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" 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/2023/elts/us-gaap-2023.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_IncomeTaxDisclosureAbstract_label_en-US" xlink:label="lab_us-gaap_IncomeTaxDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" 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/2023/elts/us-gaap-2023.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_skwd_GrossInvestmentIncomeExpenseOperating_2925ded6-2cba-4ccd-a583-c81d5b9300d1_terseLabel_en-US" xlink:label="lab_skwd_GrossInvestmentIncomeExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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" xml:lang="en-US">Gross Investment Income (Expense), Operating</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_GrossInvestmentIncomeExpenseOperating" xlink:href="skwd-20240331.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_ecd_ForgoneRecoveryDueToExpenseOfEnforcementAmt_terseLabel_en-US" xlink:label="lab_ecd_ForgoneRecoveryDueToExpenseOfEnforcementAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Forgone Recovery due to Expense of Enforcement, Amount</link:label>
    <link:label id="lab_ecd_ForgoneRecoveryDueToExpenseOfEnforcementAmt_label_en-US" xlink:label="lab_ecd_ForgoneRecoveryDueToExpenseOfEnforcementAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Forgone Recovery due to Expense of Enforcement, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ForgoneRecoveryDueToExpenseOfEnforcementAmt" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_ForgoneRecoveryDueToExpenseOfEnforcementAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ForgoneRecoveryDueToExpenseOfEnforcementAmt" xlink:to="lab_ecd_ForgoneRecoveryDueToExpenseOfEnforcementAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncrementalCommonSharesAttributableToConversionOfPreferredStock_c9f7fe33-e0c4-46ae-aa49-a20eb65ab2ba_terseLabel_en-US" xlink:label="lab_us-gaap_IncrementalCommonSharesAttributableToConversionOfPreferredStock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Diluted effect of preferred shares (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" 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/2023/elts/us-gaap-2023.xsd#us-gaap_IncrementalCommonSharesAttributableToConversionOfPreferredStock"/>
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    <link:label id="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense_5e53f33e-5535-46c8-acf3-88ebfd06fdd3_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.xsd#us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense"/>
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    <link:label id="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTextBlock_2d30d64f-24d4-49d0-b317-4677d2c00ac5_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_us-gaap_ReinsuranceTextBlock_137e08ad-79ef-4237-9353-5d0eba425365_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_dei_EntityTaxIdentificationNumber_f41661d9-991d-4954-ba41-3b6eb06570c8_terseLabel_en-US" xlink:label="lab_dei_EntityTaxIdentificationNumber" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" xml:lang="en-US">Entity Tax Identification Number</link:label>
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    <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_EquityMethodInvestments_f47b8a62-7d62-41bd-a21d-77a0bdb15ec8_verboseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Equity method investments</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestments_99fb84da-7550-4b16-a095-d0e8a67a6f25_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Recorded investment balance</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" 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/2023/elts/us-gaap-2023.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_skwd_DebtInstrumentVariableRate_be9358cf-80bd-447f-9c13-23ada2a71654_terseLabel_en-US" xlink:label="lab_skwd_DebtInstrumentVariableRate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Six-month SOFR</link:label>
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    <link:label id="lab_skwd_DebtInstrumentVariableRate_documentation_en-US" xlink:label="lab_skwd_DebtInstrumentVariableRate" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Variable Rate</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtInstrumentVariableRate" xlink:href="skwd-20240331.xsd#skwd_DebtInstrumentVariableRate"/>
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    <link:label id="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating_5951734f-a7a7-4962-b93a-08e33503b212_terseLabel_en-US" xlink:label="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Underwriting, acquisition and insurance expenses</link:label>
    <link:label id="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating_04ca954b-905f-4a12-a35e-746da028f561_totalLabel_en-US" xlink:label="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" 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" 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" 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-20240331.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_srt_RangeAxis_0ffb9ce1-7d6a-4196-8bbb-6859b5f224d5_terseLabel_en-US" xlink:label="lab_srt_RangeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/srt-2023.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_FinancialInstrumentAxis_28ae1c6e-7fb9-4bca-9514-5867e8235718_terseLabel_en-US" xlink:label="lab_us-gaap_FinancialInstrumentAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_srt_CumulativeEffectPeriodOfAdoptionAxis_42675d67-325e-4b61-a8fe-251f1295ca89_terseLabel_en-US" xlink:label="lab_srt_CumulativeEffectPeriodOfAdoptionAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/srt-2023.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_dei_EntityInteractiveDataCurrent_4d7a650f-c101-45a8-9b0f-4f59b8806257_terseLabel_en-US" xlink:label="lab_dei_EntityInteractiveDataCurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Interactive Data Current</link:label>
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    <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_us-gaap_DisaggregationOfRevenueTable_1ef88ed3-c260-411c-8e19-5e3389ac443e_terseLabel_en-US" xlink:label="lab_us-gaap_DisaggregationOfRevenueTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Disaggregation of Revenue [Table]</link:label>
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    <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_skwd_RealizedInvestmentGains_0dbe9824-1bcb-4ad7-b0e0-c3db7948f552_totalLabel_en-US" xlink:label="lab_skwd_RealizedInvestmentGains" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
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    <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" xml:lang="en-US">Realized Investment Gains</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RealizedInvestmentGains" xlink:href="skwd-20240331.xsd#skwd_RealizedInvestmentGains"/>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleTable_4feab055-3dee-41fd-b1ce-7745978ee601_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments_3474b5aa-c267-4b9b-b4e0-e6f1134646b8_terseLabel_en-US" xlink:label="lab_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment in direct and indirect loans</link:label>
    <link:label id="lab_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments_label_en-US" xlink:label="lab_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds From (Payments To Acquire) Equity Method Investments</link:label>
    <link:label id="lab_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments_documentation_en-US" xlink:label="lab_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Proceeds From (Payments To Acquire) Equity Method Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments" xlink:href="skwd-20240331.xsd#skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments" xlink:to="lab_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TotalShareholderRtnAmt_terseLabel_en-US" xlink:label="lab_ecd_TotalShareholderRtnAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total Shareholder Return Amount</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_ecd_TotalShareholderRtnAmt" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_TotalShareholderRtnAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TotalShareholderRtnAmt" xlink:to="lab_ecd_TotalShareholderRtnAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityCommonStockSharesOutstanding_a6059040-1445-42dc-83a2-358d845f23ba_terseLabel_en-US" xlink:label="lab_dei_EntityCommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/dei-2023.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_ecd_AdjToPeoCompFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AdjToPeoCompFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adjustment To PEO Compensation, Footnote</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_ecd_AdjToPeoCompFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_AdjToPeoCompFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AdjToPeoCompFnTextBlock" xlink:to="lab_ecd_AdjToPeoCompFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger_a2a664cc-213a-454e-9b53-13bf33a2c3d2_terseLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">12 Months or More</link:label>
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    <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" 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-20240331.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger"/>
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    <link:label id="lab_us-gaap_FairValueByFairValueHierarchyLevelAxis_98088850-5021-41c0-9a2a-168df04c067b_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueByFairValueHierarchyLevelAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_RetainedEarningsAccumulatedDeficit_f868b124-bf27-4286-ba26-298f8c9dac48_terseLabel_en-US" xlink:label="lab_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Retained earnings (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" 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/2023/elts/us-gaap-2023.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_ecd_MeasureAxis_terseLabel_en-US" xlink:label="lab_ecd_MeasureAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measure:</link:label>
    <link:label id="lab_ecd_MeasureAxis_label_en-US" xlink:label="lab_ecd_MeasureAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measure [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_MeasureAxis" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_MeasureAxis"/>
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    <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" 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/2023/elts/us-gaap-2023.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_ecd_OutstandingRecoveryIndName_terseLabel_en-US" xlink:label="lab_ecd_OutstandingRecoveryIndName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Name</link:label>
    <link:label id="lab_ecd_OutstandingRecoveryIndName_label_en-US" xlink:label="lab_ecd_OutstandingRecoveryIndName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Outstanding Recovery, Individual Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_OutstandingRecoveryIndName" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_OutstandingRecoveryIndName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_OutstandingRecoveryIndName" xlink:to="lab_ecd_OutstandingRecoveryIndName" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAbstract_0e902724-6bcb-495b-9bc7-117f03cce136_terseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_SMA2Member_90ba04f6-2805-4b2b-94a8-5c52b5215618_terseLabel_en-US" xlink:label="lab_skwd_SMA2Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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" xml:lang="en-US">SMA2</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_SMA2Member" xlink:href="skwd-20240331.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_skwd_RISCOMMember_2e42d84e-82cd-4a84-b28e-002ef37ce395_terseLabel_en-US" xlink:label="lab_skwd_RISCOMMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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" xml:lang="en-US">RISCOM</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RISCOMMember" xlink:href="skwd-20240331.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_us-gaap_DebtInstrumentFaceAmount_98c56d6d-adfa-4131-b750-765582506ad8_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentFaceAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_dei_EntityIncorporationStateCountryCode_0d87f780-6f82-43ee-8e95-6934c21b6acd_terseLabel_en-US" xlink:label="lab_dei_EntityIncorporationStateCountryCode" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/dei-2023.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_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense_abba6beb-6c9a-465c-9e48-68042db609a4_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Prior years</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" 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/2023/elts/us-gaap-2023.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_skwd_CreditSpreadAdjustmentMember_121612ec-d1bd-4fbf-83f4-b886a2a5e79e_terseLabel_en-US" xlink:label="lab_skwd_CreditSpreadAdjustmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Credit Spread Adjustment</link:label>
    <link:label id="lab_skwd_CreditSpreadAdjustmentMember_label_en-US" xlink:label="lab_skwd_CreditSpreadAdjustmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Credit Spread Adjustment [Member]</link:label>
    <link:label id="lab_skwd_CreditSpreadAdjustmentMember_documentation_en-US" xlink:label="lab_skwd_CreditSpreadAdjustmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Credit Spread Adjustment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_CreditSpreadAdjustmentMember" xlink:href="skwd-20240331.xsd#skwd_CreditSpreadAdjustmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_CreditSpreadAdjustmentMember" xlink:to="lab_skwd_CreditSpreadAdjustmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain_6d72a650-fc70-4aab-9f0a-9969d4fa4bf0_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent_e0486f0f-91d4-4376-921b-ae598058b080_terseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_dei_EntityAddressStateOrProvince_7f5ee095-d047-4555-8093-fb989b3357b2_terseLabel_en-US" xlink:label="lab_dei_EntityAddressStateOrProvince" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/dei-2023.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_ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Total Shareholder Return</link:label>
    <link:label id="lab_ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock_label_en-US" xlink:label="lab_ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Total Shareholder Return [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock" xlink:to="lab_ecd_CompActuallyPaidVsTotalShareholderRtnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CounterpartyNameAxis_dc48095f-12a6-43cc-b7ee-481f5e37280a_terseLabel_en-US" xlink:label="lab_srt_CounterpartyNameAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/srt-2023.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_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months_b35a0c84-24fb-4d26-85a0-ea00266f7c17_terseLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Continuous Unrealized Loss Position, Less than 12 Months</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months" xlink:href="skwd-20240331.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months"/>
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    <link:label id="lab_us-gaap_OtherCostAndExpenseOperating_b8cc9eca-6883-42a2-83d4-cc612fe11885_terseLabel_en-US" xlink:label="lab_us-gaap_OtherCostAndExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other operating and general expenses</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProfessionalFees" xlink:to="lab_us-gaap_ProfessionalFees" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperations_2225f149-9f10-4b93-95d4-27fc040a2fe4_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperations" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_us-gaap_DebtInstrumentAxis_1df44f90-6260-43d2-a6d7-fa84aa938264_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_InvestmentHoldingsScheduleOfInvestmentsTextBlock_409e8359-a893-4b68-95d6-61a3654b9753_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentHoldingsScheduleOfInvestmentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" xml:lang="en-US">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/2023/elts/us-gaap-2023.xsd#us-gaap_InvestmentHoldingsScheduleOfInvestmentsTextBlock"/>
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    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLoss_c0b5158f-ed07-4f23-9ef8-d709896e0b71_negatedTotalLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTotalLabel" xlink:type="resource" 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" 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" 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-20240331.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_ecd_OutstandingAggtErrCompAmt_terseLabel_en-US" xlink:label="lab_ecd_OutstandingAggtErrCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Outstanding Aggregate Erroneous Compensation Amount</link:label>
    <link:label id="lab_ecd_OutstandingAggtErrCompAmt_label_en-US" xlink:label="lab_ecd_OutstandingAggtErrCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Outstanding Aggregate Erroneous Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_OutstandingAggtErrCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_OutstandingAggtErrCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_OutstandingAggtErrCompAmt" xlink:to="lab_ecd_OutstandingAggtErrCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperations_9d111061-cbee-40bd-80ab-c3333247b56d_terseLabel_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperations" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Effective tax rate</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" 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/2023/elts/us-gaap-2023.xsd#us-gaap_EffectiveIncomeTaxRateContinuingOperations"/>
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    <link:label id="lab_skwd_CapitalizationOfTrustPercentage_b29744b1-cad1-4d70-a322-a2d72c94e48d_terseLabel_en-US" xlink:label="lab_skwd_CapitalizationOfTrustPercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Capitalization of trust, percent</link:label>
    <link:label id="lab_skwd_CapitalizationOfTrustPercentage_label_en-US" xlink:label="lab_skwd_CapitalizationOfTrustPercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Capitalization of Trust, Percentage</link:label>
    <link:label id="lab_skwd_CapitalizationOfTrustPercentage_documentation_en-US" xlink:label="lab_skwd_CapitalizationOfTrustPercentage" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Capitalization of Trust, Percentage</link:label>
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    <link:label id="lab_us-gaap_MeasurementInputTypeDomain_4c87b11c-82f7-4a9a-ab35-0bf77a3424f7_terseLabel_en-US" xlink:label="lab_us-gaap_MeasurementInputTypeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measurement Input Type [Domain]</link:label>
    <link:label id="lab_us-gaap_MeasurementInputTypeDomain_label_en-US" xlink:label="lab_us-gaap_MeasurementInputTypeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measurement Input Type [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MeasurementInputTypeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_MeasurementInputTypeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MeasurementInputTypeDomain" xlink:to="lab_us-gaap_MeasurementInputTypeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CreditFacilityAxis_a0a19626-ad4f-4b33-a8b1-92c3376870e5_terseLabel_en-US" xlink:label="lab_us-gaap_CreditFacilityAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_us-gaap_Liabilities_f971a56a-f909-4f9a-add4-6bdb17358946_totalLabel_en-US" xlink:label="lab_us-gaap_Liabilities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_CurrentIncomeTaxExpenseBenefit_6a0f35b6-221e-4526-a720-1798d9310c53_terseLabel_en-US" xlink:label="lab_us-gaap_CurrentIncomeTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">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" 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/2023/elts/us-gaap-2023.xsd#us-gaap_CurrentIncomeTaxExpenseBenefit"/>
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    <link:label id="lab_ecd_TotalShareholderRtnVsPeerGroupTextBlock_terseLabel_en-US" xlink:label="lab_ecd_TotalShareholderRtnVsPeerGroupTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total Shareholder Return Vs Peer Group</link:label>
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    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember_145501ae-6f93-42b4-85ea-fbb40c92f9d0_terseLabel_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accumulated other comprehensive loss:</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" xml:lang="en-US">AOCI Attributable to Parent [Member]</link:label>
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    <link:label id="lab_ecd_AggtErrCompAmt_terseLabel_en-US" xlink:label="lab_ecd_AggtErrCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aggregate Erroneous Compensation Amount</link:label>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition_6de161f0-aaf1-4a6d-b13d-98d4c2a3cc38_totalLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
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    <link:label id="lab_us-gaap_AssumedPremiumsEarned_5e887998-19cb-4461-8532-0db9734c791f_terseLabel_en-US" xlink:label="lab_us-gaap_AssumedPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Assumed premiums</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsForRepurchaseOfTrustPreferredSecurities" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PaymentsForRepurchaseOfTrustPreferredSecurities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsForRepurchaseOfTrustPreferredSecurities" xlink:to="lab_us-gaap_PaymentsForRepurchaseOfTrustPreferredSecurities" 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" 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/2023/elts/us-gaap-2023.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_MortgageLoansOnRealEstatePrincipalAmountPercentageOfPropertyAppraisalValue_7911fef4-0e09-4951-a80c-79dab0bc3e55_terseLabel_en-US" xlink:label="lab_skwd_MortgageLoansOnRealEstatePrincipalAmountPercentageOfPropertyAppraisalValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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" 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-20240331.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_RelatedPartyTransactionDomain_c9863257-843c-4dfe-ab1e-f459956d5cf0_terseLabel_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_EarningsPerShareAbstract_85cfbf30-af82-4f14-ae7f-bbc3c338f477_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_srt_AffiliatedEntityMember_00394b47-2052-4e2f-8ad6-17e5a3b9199b_terseLabel_en-US" xlink:label="lab_srt_AffiliatedEntityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/srt-2023.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_us-gaap_CommonStockValue_3164e069-0a9f-4dc3-9ddb-17be91db6c24_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Common stock, $0.01 par value, 500,000,000 shares authorized, 39,995,027 and 39,863,756 shares issued and outstanding, 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" 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/2023/elts/us-gaap-2023.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_us-gaap_USGovernmentDebtSecuritiesMember_54b411ff-8c8e-453a-9c72-1529da6d1c7a_terseLabel_en-US" xlink:label="lab_us-gaap_USGovernmentDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months_d9d7290f-0ae7-4dab-9a49-11dfe0bb78e0_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue_cfcd9dc9-dffa-4438-8594-786370f29e6b_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest_aa9e74a4-7618-447a-8399-babe2cb378b9_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Allowance for Credit Losses</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Allowance for Credit Loss, Excluding Accrued Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsMember_3f191c40-5ca6-427e-b7fb-9b272a8cc5ed_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_ecd_AwardsCloseToMnpiDiscTableTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AwardsCloseToMnpiDiscTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Awards Close in Time to MNPI Disclosures, Table</link:label>
    <link:label id="lab_ecd_AwardsCloseToMnpiDiscTableTextBlock_label_en-US" xlink:label="lab_ecd_AwardsCloseToMnpiDiscTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Awards Close in Time to MNPI Disclosures [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardsCloseToMnpiDiscTableTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_AwardsCloseToMnpiDiscTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardsCloseToMnpiDiscTableTextBlock" xlink:to="lab_ecd_AwardsCloseToMnpiDiscTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_JVMFundsLLCMember_8bda6b67-e406-4810-91ff-01e61a1e3e7a_terseLabel_en-US" xlink:label="lab_skwd_JVMFundsLLCMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">JVM Funds LLC</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" 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" xml:lang="en-US">JVM Funds LLC</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_JVMFundsLLCMember" xlink:href="skwd-20240331.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_PreferredStockMember_751eee0f-464a-4b41-9cf3-ab07929f5651_netLabel_en-US" xlink:label="lab_us-gaap_PreferredStockMember" xlink:role="http://www.xbrl.org/2009/role/netLabel" xlink:type="resource" xml:lang="en-US">Preferred stock:</link:label>
    <link:label id="lab_us-gaap_PreferredStockMember_bd5cf96e-4a20-43df-a87f-3ed8b075c76a_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_EquitySecuritiesMember_32b4dd51-faa0-41d3-bb02-89915621bcd7_terseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_us-gaap_RevenueFromContractWithCustomerAbstract_label_en-US" xlink:label="lab_us-gaap_RevenueFromContractWithCustomerAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" 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/2023/elts/us-gaap-2023.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_ecd_AllIndividualsMember_terseLabel_en-US" xlink:label="lab_ecd_AllIndividualsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">All Individuals</link:label>
    <link:label id="lab_ecd_AllIndividualsMember_label_en-US" xlink:label="lab_ecd_AllIndividualsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">All Individuals [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AllIndividualsMember" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_AllIndividualsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AllIndividualsMember" xlink:to="lab_ecd_AllIndividualsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SupplementalCashFlowInformationAbstract_8f1befe7-fee2-4b66-a1bb-2bddc4442c07_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalCashFlowInformationAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_dei_EntityFilerCategory_bb265cc2-bf85-4e69-8859-852c9a627af0_terseLabel_en-US" xlink:label="lab_dei_EntityFilerCategory" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/dei-2023.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_ScheduleOfEquityMethodInvestmentsLineItems_142ccfcb-bb9d-4d7e-99c1-076e0d5d82aa_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Equity Method Investments [Line Items]</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfEquityMethodInvestmentsLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ScheduleOfEquityMethodInvestmentsLineItems"/>
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    <link:label id="lab_dei_CurrentFiscalYearEndDate_a5ba792c-f8c8-48ce-97b5-b43474801a50_terseLabel_en-US" xlink:label="lab_dei_CurrentFiscalYearEndDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Current Fiscal Year End Date</link:label>
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    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesFairValue_2e2ebf5c-cafa-4ef0-ac6e-c6c83d599fe0_terseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total fixed maturity securities, held-to-maturity</link:label>
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    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTable_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTable" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTable"/>
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    <link:label id="lab_us-gaap_FairValueMeasurementPolicyPolicyTextBlock_7678788a-e4b3-4cbc-9d0c-c81e4e13b94a_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementPolicyPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Measurement, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementPolicyPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueMeasurementPolicyPolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementPolicyPolicyTextBlock" xlink:to="lab_us-gaap_FairValueMeasurementPolicyPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_RetailPortfolioSegmentMember_e9708c39-2dc3-463f-9054-79f65c7789aa_terseLabel_en-US" xlink:label="lab_skwd_RetailPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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" xml:lang="en-US">Retail Portfolio Segment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RetailPortfolioSegmentMember" xlink:href="skwd-20240331.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_PaymentsForProceedsFromShortTermInvestments_460224ad-c133-496b-a738-974518a4b37c_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsForProceedsFromShortTermInvestments" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Change in short-term investments</link:label>
    <link:label id="lab_us-gaap_PaymentsForProceedsFromShortTermInvestments_label_en-US" xlink:label="lab_us-gaap_PaymentsForProceedsFromShortTermInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments for (Proceeds from) Short-Term Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsForProceedsFromShortTermInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PaymentsForProceedsFromShortTermInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsForProceedsFromShortTermInvestments" xlink:to="lab_us-gaap_PaymentsForProceedsFromShortTermInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareReconciliationAbstract_9c5ccbb6-20db-478c-9f22-c0ae78d1e173_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareReconciliationAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_us-gaap_StockIssuedDuringPeriodSharesConversionOfConvertibleSecurities_38071a33-fb6e-4343-bde4-b96aa93178a2_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodSharesConversionOfConvertibleSecurities" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Preferred stock conversion to common shares (in shares)</link:label>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodSharesConversionOfConvertibleSecurities_label_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodSharesConversionOfConvertibleSecurities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Stock Issued During Period, Shares, Conversion of Convertible Securities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockIssuedDuringPeriodSharesConversionOfConvertibleSecurities" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_StockIssuedDuringPeriodSharesConversionOfConvertibleSecurities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockIssuedDuringPeriodSharesConversionOfConvertibleSecurities" xlink:to="lab_us-gaap_StockIssuedDuringPeriodSharesConversionOfConvertibleSecurities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueInputsLevel2Member_6f419d23-ea5d-4c79-8d87-fa52580779b9_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel2Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">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" 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/2023/elts/us-gaap-2023.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_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense_7f5e6b29-ca6d-49b1-964c-34da67e5b7eb_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersCurrentYearClaimsAndClaimsAdjustmentExpense"/>
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    <link:label id="lab_us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquity_2ee97ad6-4244-4e63-9482-a98ce2677c94_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquity" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.xsd#us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquity"/>
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    <link:label id="lab_us-gaap_OtherAggregatedInvestmentsMember_c8c52518-0824-4369-a920-6351de247a0b_terseLabel_en-US" xlink:label="lab_us-gaap_OtherAggregatedInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" xml:lang="en-US">Other Security Investments [Member]</link:label>
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    <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_dei_EntityEmergingGrowthCompany_72a17045-d1bb-4cf2-8e45-f930deb96942_terseLabel_en-US" xlink:label="lab_dei_EntityEmergingGrowthCompany" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Emerging Growth Company</link:label>
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    <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_skwd_ArenaSpecialOpportunitiesFundLPMember_525e972a-01dc-4bab-b851-45bc3e55041f_terseLabel_en-US" xlink:label="lab_skwd_ArenaSpecialOpportunitiesFundLPMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Arena Special Opportunities Fund, LP units</link:label>
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    <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_AvailableForSaleSecuritiesDebtMaturitiesFairValueAbstract_406677e1-f7bf-45d1-a1d9-2ee318eaa8e5_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesFairValueAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_PaymentsToAcquireEquitySecuritiesFvNi_fea055db-8096-439e-be25-8faa52d39925_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireEquitySecuritiesFvNi" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_ShortTermInvestmentsAndCashMember_ac304e8e-d5ff-43e5-bc43-0db8abe5380e_terseLabel_en-US" xlink:label="lab_skwd_ShortTermInvestmentsAndCashMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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" xml:lang="en-US">Short-term Investments And Cash</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ShortTermInvestmentsAndCashMember" xlink:href="skwd-20240331.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_IncreaseDecreaseInStockholdersEquityRollForward_36fc5356-6570-46fd-a500-7f7cc5998d2d_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" xml:lang="en-US">Increase (Decrease) in Stockholders' Equity [Roll Forward]</link:label>
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    <link:label id="lab_ecd_NamedExecutiveOfficersFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_NamedExecutiveOfficersFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Named Executive Officers, Footnote</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NamedExecutiveOfficersFnTextBlock" xlink:to="lab_ecd_NamedExecutiveOfficersFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentFiscalPeriodFocus_37c75ffc-8165-4725-ac50-af761cbe595d_terseLabel_en-US" xlink:label="lab_dei_DocumentFiscalPeriodFocus" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/dei-2023.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_MortgageLoansInProcessOfForeclosureAmount_d0126a85-f621-4403-8321-a96a8f3a90bb_terseLabel_en-US" xlink:label="lab_us-gaap_MortgageLoansInProcessOfForeclosureAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded_33584180-936a-43c9-9b2c-388a225ac630_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_ecd_PvpTableTextBlock_terseLabel_en-US" xlink:label="lab_ecd_PvpTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pay vs Performance Disclosure, Table</link:label>
    <link:label id="lab_ecd_PvpTableTextBlock_label_en-US" xlink:label="lab_ecd_PvpTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Pay vs Performance [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PvpTableTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_PvpTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PvpTableTextBlock" xlink:to="lab_ecd_PvpTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis_aa4b4e95-f36a-4754-bc3b-241485b9b103_terseLabel_en-US" xlink:label="lab_us-gaap_AntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareByAntidilutiveSecuritiesAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_ecd_TrdArrIndTitle_terseLabel_en-US" xlink:label="lab_ecd_TrdArrIndTitle" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Title</link:label>
    <link:label id="lab_ecd_TrdArrIndTitle_label_en-US" xlink:label="lab_ecd_TrdArrIndTitle" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement, Individual Title</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrIndTitle" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_TrdArrIndTitle"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrIndTitle" xlink:to="lab_ecd_TrdArrIndTitle" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_WeightedAverageMember_6d4a0c88-7f3e-4b6b-9eb4-b638c713a5ed_terseLabel_en-US" xlink:label="lab_srt_WeightedAverageMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Weighted average</link:label>
    <link:label id="lab_srt_WeightedAverageMember_label_en-US" xlink:label="lab_srt_WeightedAverageMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Weighted Average [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_WeightedAverageMember" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_WeightedAverageMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_WeightedAverageMember" xlink:to="lab_srt_WeightedAverageMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_BrewerLaneVentureFundIILPMember_e9d5fe53-1a0f-4ebf-9775-e32d86b5e87b_terseLabel_en-US" xlink:label="lab_skwd_BrewerLaneVentureFundIILPMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Brewer Lane Ventures Fund II LP</link:label>
    <link:label id="lab_skwd_BrewerLaneVentureFundIILPMember_label_en-US" xlink:label="lab_skwd_BrewerLaneVentureFundIILPMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Brewer Lane Venture Fund II LP [Member]</link:label>
    <link:label id="lab_skwd_BrewerLaneVentureFundIILPMember_documentation_en-US" xlink:label="lab_skwd_BrewerLaneVentureFundIILPMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Brewer Lane Venture Fund II LP</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_BrewerLaneVentureFundIILPMember" xlink:href="skwd-20240331.xsd#skwd_BrewerLaneVentureFundIILPMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_BrewerLaneVentureFundIILPMember" xlink:to="lab_skwd_BrewerLaneVentureFundIILPMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockMember_db3d367f-3cff-4de9-aedc-d60b6f27fb55_netLabel_en-US" xlink:label="lab_us-gaap_CommonStockMember" xlink:role="http://www.xbrl.org/2009/role/netLabel" xlink:type="resource" xml:lang="en-US">Common stock:</link:label>
    <link:label id="lab_us-gaap_CommonStockMember_599d2204-f9fd-4664-8df0-1e88208c985d_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_ecd_IndividualAxis_terseLabel_en-US" xlink:label="lab_ecd_IndividualAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Individual:</link:label>
    <link:label id="lab_ecd_IndividualAxis_label_en-US" xlink:label="lab_ecd_IndividualAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Individual [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_IndividualAxis" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_IndividualAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_IndividualAxis" xlink:to="lab_ecd_IndividualAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_CityAreaCode_8baa7ff4-e3b0-4528-b808-fb231641fffe_terseLabel_en-US" xlink:label="lab_dei_CityAreaCode" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/dei-2023.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_dei_EntityAddressPostalZipCode_ab7e3de3-4b01-4aab-b6e2-416c20c00474_terseLabel_en-US" xlink:label="lab_dei_EntityAddressPostalZipCode" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/dei-2023.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_srt_ProductOrServiceAxis_798add8b-3d2b-4791-8bc4-2eac93739dc6_terseLabel_en-US" xlink:label="lab_srt_ProductOrServiceAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/srt-2023.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_skwd_MultiFamilyPortfolioSegmentMember_2f0bb806-eb1a-4632-a97e-43654c0848d1_terseLabel_en-US" xlink:label="lab_skwd_MultiFamilyPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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" xml:lang="en-US">Multi-Family Portfolio Segment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_MultiFamilyPortfolioSegmentMember" xlink:href="skwd-20240331.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_EarningsPerShareTextBlock_7d573f69-ded7-42d4-98ee-a6b1eb4be703_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_LiabilityForFuturePolicyBenefitsAndUnpaidClaimsDisclosureTextBlock_6b451456-695f-47cc-9b25-8a8d6089b68a_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForFuturePolicyBenefitsAndUnpaidClaimsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">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" 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/2023/elts/us-gaap-2023.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_us-gaap_FairValueLiabilitiesMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock_d85df0df-58e6-4d3b-9c2f-aa0993d232cd_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueLiabilitiesMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value, Liabilities Measured on Recurring Basis, Unobservable Input Reconciliation</link:label>
    <link:label id="lab_us-gaap_FairValueLiabilitiesMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock_label_en-US" xlink:label="lab_us-gaap_FairValueLiabilitiesMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Liabilities Measured on Recurring Basis, Unobservable Input Reconciliation [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueLiabilitiesMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueLiabilitiesMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueLiabilitiesMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:to="lab_us-gaap_FairValueLiabilitiesMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_RevolvingLineOfCreditDueDecember2024Member_2b1130ef-2020-4952-b1a5-2764ed68439c_terseLabel_en-US" xlink:label="lab_skwd_RevolvingLineOfCreditDueDecember2024Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Revolving credit facility</link:label>
    <link:label id="lab_skwd_RevolvingLineOfCreditDueDecember2024Member_49b931f4-ea94-4236-9a0f-4439e230c08f_verboseLabel_en-US" xlink:label="lab_skwd_RevolvingLineOfCreditDueDecember2024Member" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" 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" 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" 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-20240331.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_dei_DocumentFiscalYearFocus_b06f0e1d-0193-4e1f-9c62-c07c16541e8a_terseLabel_en-US" xlink:label="lab_dei_DocumentFiscalYearFocus" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/dei-2023.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_InvestmentsAbstract_357bf450-58c7-4bcb-97c1-9e72d036578c_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_GrossRealizedInvestmentLossesAbstract_a05be855-a987-437d-941f-c8596bcc6b12_terseLabel_en-US" xlink:label="lab_skwd_GrossRealizedInvestmentLossesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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" xml:lang="en-US">Gross Realized Investment Losses</link:label>
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    <link:label id="lab_srt_MinimumMember_92218971-a961-4a47-a043-6a2ad75b56d9_terseLabel_en-US" xlink:label="lab_srt_MinimumMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Low</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" 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/2023/elts/srt-2023.xsd#srt_MinimumMember"/>
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    <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" 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/2023/elts/us-gaap-2023.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_ecd_AwardExrcPrice_terseLabel_en-US" xlink:label="lab_ecd_AwardExrcPrice" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Exercise Price</link:label>
    <link:label id="lab_ecd_AwardExrcPrice_label_en-US" xlink:label="lab_ecd_AwardExrcPrice" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Exercise Price</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardExrcPrice" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_AwardExrcPrice"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardExrcPrice" xlink:to="lab_ecd_AwardExrcPrice" 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" 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/2023/elts/us-gaap-2023.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_ScheduleOfCededCreditRiskByReinsurerTextBlock_0b42d5b3-1042-4d37-833f-3411228e8749_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_AssetsAbstract_4cb6a99f-45a2-4689-a40c-230e0fca60c0_terseLabel_en-US" xlink:label="lab_us-gaap_AssetsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_ecd_AwardTmgMnpiDiscTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AwardTmgMnpiDiscTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Timing MNPI Disclosure</link:label>
    <link:label id="lab_ecd_AwardTmgMnpiDiscTextBlock_label_en-US" xlink:label="lab_ecd_AwardTmgMnpiDiscTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Timing MNPI Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardTmgMnpiDiscTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_AwardTmgMnpiDiscTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardTmgMnpiDiscTextBlock" xlink:to="lab_ecd_AwardTmgMnpiDiscTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_eaca7f5b-5481-4f52-b166-eff737fc264d_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_us-gaap_ProceedsFromIssuanceOfLongTermDebt_d459fc29-5313-4e69-8352-261c239d4cf6_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromIssuanceOfLongTermDebt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Proceeds from long-term debt</link:label>
    <link:label id="lab_us-gaap_ProceedsFromIssuanceOfLongTermDebt_809316fc-8e09-4e81-845a-2d3552fdc8f3_verboseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromIssuanceOfLongTermDebt" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Amount</link:label>
    <link:label id="lab_us-gaap_ProceedsFromIssuanceOfLongTermDebt_label_en-US" xlink:label="lab_us-gaap_ProceedsFromIssuanceOfLongTermDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Issuance of Long-Term Debt</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromIssuanceOfLongTermDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ProceedsFromIssuanceOfLongTermDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromIssuanceOfLongTermDebt" xlink:to="lab_us-gaap_ProceedsFromIssuanceOfLongTermDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue_bc1d45ae-b3b8-4dfc-ab64-e8c9084285e4_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_us-gaap_LiabilitiesAbstract_fca84acf-07ae-40be-abb3-2ced97f2c002_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_us-gaap_NetCashProvidedByUsedInFinancingActivities_7342989e-b635-405c-8e25-61f8264f370c_totalLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net cash (used in) 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" 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/2023/elts/us-gaap-2023.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_DeferredIncomeTaxAssetsNet_541d81b3-7727-4907-9017-8abd70c76973_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredIncomeTaxAssetsNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_CommitmentsAndContingenciesDisclosureTextBlock_cf88851a-12d8-4e80-afee-ec243e74db15_terseLabel_en-US" xlink:label="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax_cddae489-ff0c-48a7-892b-3c539fcc6d80_terseLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net change in unrealized (losses) gains 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" 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/2023/elts/us-gaap-2023.xsd#us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax"/>
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    <link:label id="lab_us-gaap_UndistributedEarningsLossAllocatedToParticipatingSecuritiesBasic_19e70e6e-cf86-48d0-acbc-c706f0c34f5f_terseLabel_en-US" xlink:label="lab_us-gaap_UndistributedEarningsLossAllocatedToParticipatingSecuritiesBasic" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net income attributable to participating securities</link:label>
    <link:label id="lab_us-gaap_UndistributedEarningsLossAllocatedToParticipatingSecuritiesBasic_d77d60ba-a4fe-4a32-89de-ce7bd277ceb4_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_UndistributedEarningsLossAllocatedToParticipatingSecuritiesBasic" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Less: Undistributed income allocated to participating securities</link:label>
    <link:label id="lab_us-gaap_UndistributedEarningsLossAllocatedToParticipatingSecuritiesBasic_5abecf6a-915c-4416-9749-b6cab1c74fd4_verboseLabel_en-US" xlink:label="lab_us-gaap_UndistributedEarningsLossAllocatedToParticipatingSecuritiesBasic" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" 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" xml:lang="en-US">Undistributed Earnings (Loss) Allocated to Participating Securities, Basic</link:label>
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    <link:label id="lab_us-gaap_RetainedEarningsMember_e5ce7861-483d-40ae-946a-f79f43317bb3_terseLabel_en-US" xlink:label="lab_us-gaap_RetainedEarningsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Retained earnings (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" 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/2023/elts/us-gaap-2023.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_LineOfCreditFacilityAccordionFeatureIncreaseLimit_00b0fe4d-376a-490b-8764-ccc867886cef_terseLabel_en-US" xlink:label="lab_skwd_LineOfCreditFacilityAccordionFeatureIncreaseLimit" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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" xml:lang="en-US">Line of credit facility, accordion feature, increase limit, subject to certain conditions by obtaining additional commitments from existing and/or new lenders.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_LineOfCreditFacilityAccordionFeatureIncreaseLimit" xlink:href="skwd-20240331.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_MortgageLoansMember_8c2d1d03-c086-478c-bfbe-9159326f2cac_terseLabel_en-US" xlink:label="lab_skwd_MortgageLoansMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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" xml:lang="en-US">Mortgage Loans</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_MortgageLoansMember" xlink:href="skwd-20240331.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_ecd_AdjToNonPeoNeoCompFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AdjToNonPeoNeoCompFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adjustment to Non-PEO NEO Compensation Footnote</link:label>
    <link:label id="lab_ecd_AdjToNonPeoNeoCompFnTextBlock_label_en-US" xlink:label="lab_ecd_AdjToNonPeoNeoCompFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Adjustment to Non-PEO NEO Compensation Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AdjToNonPeoNeoCompFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_AdjToNonPeoNeoCompFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AdjToNonPeoNeoCompFnTextBlock" xlink:to="lab_ecd_AdjToNonPeoNeoCompFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilitiesAndStockholdersEquity_864daebe-d492-4b9b-9b0d-ce185b2cf7d5_totalLabel_en-US" xlink:label="lab_us-gaap_LiabilitiesAndStockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total liabilities and stockholders&#8217; 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" 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/2023/elts/us-gaap-2023.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_skwd_NotesPayableMember_5210c2d4-3a55-4d11-a7a8-58e9ff789e88_terseLabel_en-US" xlink:label="lab_skwd_NotesPayableMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Notes payable</link:label>
    <link:label id="lab_skwd_NotesPayableMember_label_en-US" xlink:label="lab_skwd_NotesPayableMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Notes Payable [Member]</link:label>
    <link:label id="lab_skwd_NotesPayableMember_documentation_en-US" xlink:label="lab_skwd_NotesPayableMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Notes Payable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_NotesPayableMember" xlink:href="skwd-20240331.xsd#skwd_NotesPayableMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_NotesPayableMember" xlink:to="lab_skwd_NotesPayableMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PeerGroupTotalShareholderRtnAmt_terseLabel_en-US" xlink:label="lab_ecd_PeerGroupTotalShareholderRtnAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Peer Group Total Shareholder Return Amount</link:label>
    <link:label id="lab_ecd_PeerGroupTotalShareholderRtnAmt_label_en-US" xlink:label="lab_ecd_PeerGroupTotalShareholderRtnAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Peer Group Total Shareholder Return Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeerGroupTotalShareholderRtnAmt" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_PeerGroupTotalShareholderRtnAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PeerGroupTotalShareholderRtnAmt" xlink:to="lab_ecd_PeerGroupTotalShareholderRtnAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_OwnershipDomain_ac609c95-a242-41da-b78f-1a7e8f1db9d9_terseLabel_en-US" xlink:label="lab_srt_OwnershipDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/srt-2023.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_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestBeforeAllowanceForCreditLoss_2551a94b-0806-4e39-a9fb-ed81afc9618a_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestBeforeAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gross Amortized Cost</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestBeforeAllowanceForCreditLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestBeforeAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Excluding Accrued Interest, before Allowance for Credit Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestBeforeAllowanceForCreditLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestBeforeAllowanceForCreditLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestBeforeAllowanceForCreditLoss" xlink:to="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestBeforeAllowanceForCreditLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareBasic_348d7a32-648e-497d-9d38-6f8235d6d13a_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerShareBasic" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Basic earnings (loss) 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" 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/2023/elts/us-gaap-2023.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_DebtInstrumentTable_90fa5212-5143-4a2e-8fd6-ba8856e6d2d4_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_AccountingPoliciesAbstract_label_en-US" xlink:label="lab_us-gaap_AccountingPoliciesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" 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/2023/elts/us-gaap-2023.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_ecd_EquityValuationAssumptionDifferenceFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_EquityValuationAssumptionDifferenceFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Valuation Assumption Difference, Footnote</link:label>
    <link:label id="lab_ecd_EquityValuationAssumptionDifferenceFnTextBlock_label_en-US" xlink:label="lab_ecd_EquityValuationAssumptionDifferenceFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Valuation Assumption Difference, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_EquityValuationAssumptionDifferenceFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_EquityValuationAssumptionDifferenceFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_EquityValuationAssumptionDifferenceFnTextBlock" xlink:to="lab_ecd_EquityValuationAssumptionDifferenceFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ErrCompAnalysisTextBlock_terseLabel_en-US" xlink:label="lab_ecd_ErrCompAnalysisTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Erroneous Compensation Analysis</link:label>
    <link:label id="lab_ecd_ErrCompAnalysisTextBlock_label_en-US" xlink:label="lab_ecd_ErrCompAnalysisTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Erroneous Compensation Analysis [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ErrCompAnalysisTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_ErrCompAnalysisTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ErrCompAnalysisTextBlock" xlink:to="lab_ecd_ErrCompAnalysisTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReceivablesFromStockholderMember_5bfa512a-0c08-4fd6-93f4-e8609ae86c5f_terseLabel_en-US" xlink:label="lab_us-gaap_ReceivablesFromStockholderMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted_22c807ae-ed31-4382-a6aa-207ec19acfe8_terseLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_ecd_TrdArrDuration_terseLabel_en-US" xlink:label="lab_ecd_TrdArrDuration" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Arrangement Duration</link:label>
    <link:label id="lab_ecd_TrdArrDuration_label_en-US" xlink:label="lab_ecd_TrdArrDuration" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement Duration</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrDuration" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_TrdArrDuration"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrDuration" xlink:to="lab_ecd_TrdArrDuration" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock_8090f76e-f69d-43f6-89ae-ba7606625a9e_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_InvestmentIncomeInvestmentExpense_389b1061-cfe7-4ecc-9f2d-19e26dc15312_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_InvestmentIncomeInvestmentExpense" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_dei_EntityAddressCityOrTown_14e39a52-12fa-4d9a-81f8-c75bacb01b37_terseLabel_en-US" xlink:label="lab_dei_EntityAddressCityOrTown" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/dei-2023.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_ecd_AwardTmgMnpiCnsdrdFlag_terseLabel_en-US" xlink:label="lab_ecd_AwardTmgMnpiCnsdrdFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Timing MNPI Considered</link:label>
    <link:label id="lab_ecd_AwardTmgMnpiCnsdrdFlag_label_en-US" xlink:label="lab_ecd_AwardTmgMnpiCnsdrdFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Timing MNPI Considered [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardTmgMnpiCnsdrdFlag" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_AwardTmgMnpiCnsdrdFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardTmgMnpiCnsdrdFlag" xlink:to="lab_ecd_AwardTmgMnpiCnsdrdFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_NetUnrealizedLossesAndGainsOnInvestmentsAbstract_5a1297f2-cb36-4de6-b926-185029d6eae3_terseLabel_en-US" xlink:label="lab_skwd_NetUnrealizedLossesAndGainsOnInvestmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net unrealized gains on investments</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" 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" xml:lang="en-US">Net Unrealized Losses and Gains on Investments</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_AvailableForSaleSecuritiesContinuousUnrealizedLossPositionAccumulatedLossAbstract"/>
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    <link:label id="lab_skwd_LossOnSaleOfOtherInvestments_8c3b2442-92f6-424e-8f02-a8381b7aa046_negatedTerseLabel_en-US" xlink:label="lab_skwd_LossOnSaleOfOtherInvestments" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Other</link:label>
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    <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" xml:lang="en-US">Loss on Sale of Other Investments</link:label>
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    <link:label id="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_2c48e5d7-6394-4df8-9e43-76d5c83ce4ea_negatedPeriodStartLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:role="http://www.xbrl.org/2009/role/negatedPeriodStartLabel" xlink:type="resource" xml:lang="en-US">Less: reinsurance recoverable on unpaid claims, beginning of period</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_cbdc9d8f-0163-49af-86f8-ffdc0408be3c_periodEndLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Plus: reinsurance recoverable on unpaid claims, end of period</link:label>
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    <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" 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/2023/elts/us-gaap-2023.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_ecd_AllTradingArrangementsMember_terseLabel_en-US" xlink:label="lab_ecd_AllTradingArrangementsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">All Trading Arrangements</link:label>
    <link:label id="lab_ecd_AllTradingArrangementsMember_label_en-US" xlink:label="lab_ecd_AllTradingArrangementsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">All Trading Arrangements [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AllTradingArrangementsMember" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_AllTradingArrangementsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AllTradingArrangementsMember" xlink:to="lab_ecd_AllTradingArrangementsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MeasurementInputTypeAxis_5778044c-441c-4669-adab-3192bae17496_terseLabel_en-US" xlink:label="lab_us-gaap_MeasurementInputTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measurement Input Type [Axis]</link:label>
    <link:label id="lab_us-gaap_MeasurementInputTypeAxis_label_en-US" xlink:label="lab_us-gaap_MeasurementInputTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measurement Input Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MeasurementInputTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_MeasurementInputTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MeasurementInputTypeAxis" xlink:to="lab_us-gaap_MeasurementInputTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LimitedLiabilityCompanyLLCOrLimitedPartnershipLPManagingMemberOrGeneralPartnerOwnershipInterest_d7d6d2b0-2b7b-4939-86b6-64b71f113b4d_terseLabel_en-US" xlink:label="lab_us-gaap_LimitedLiabilityCompanyLLCOrLimitedPartnershipLPManagingMemberOrGeneralPartnerOwnershipInterest" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost_5b1084ef-6a4a-457c-97f5-a793f3d7b65d_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_ecd_AllAdjToCompMember_terseLabel_en-US" xlink:label="lab_ecd_AllAdjToCompMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">All Adjustments to Compensation</link:label>
    <link:label id="lab_ecd_AllAdjToCompMember_label_en-US" xlink:label="lab_ecd_AllAdjToCompMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">All Adjustments to Compensation [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AllAdjToCompMember" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_AllAdjToCompMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AllAdjToCompMember" xlink:to="lab_ecd_AllAdjToCompMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardTmgDiscLineItems_label_en-US" xlink:label="lab_ecd_AwardTmgDiscLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Timing Disclosures [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardTmgDiscLineItems" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_AwardTmgDiscLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardTmgDiscLineItems" xlink:to="lab_ecd_AwardTmgDiscLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet_4d9e0b2b-b18a-4e2a-8a02-b5c650a2868b_terseLabel_en-US" xlink:label="lab_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mortgage loans, at fair value</link:label>
    <link:label id="lab_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet_d66b3601-6428-43e8-a479-edb360c40aa0_verboseLabel_en-US" xlink:label="lab_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Total 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" 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/2023/elts/us-gaap-2023.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_skwd_ProfessionalFeesAndReimbursementsMember_a30308de-2da9-40d0-9e77-87c991ebff68_terseLabel_en-US" xlink:label="lab_skwd_ProfessionalFeesAndReimbursementsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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" xml:lang="en-US">Professional Fees And Reimbursements</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ProfessionalFeesAndReimbursementsMember" xlink:href="skwd-20240331.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_ecd_OutstandingRecoveryCompAmt_terseLabel_en-US" xlink:label="lab_ecd_OutstandingRecoveryCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Compensation Amount</link:label>
    <link:label id="lab_ecd_OutstandingRecoveryCompAmt_label_en-US" xlink:label="lab_ecd_OutstandingRecoveryCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Outstanding Recovery Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_OutstandingRecoveryCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_OutstandingRecoveryCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_OutstandingRecoveryCompAmt" xlink:to="lab_ecd_OutstandingRecoveryCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis_44bb6778-3a06-4bbe-9bee-969026808530_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_ScheduleOfAccountsNotesLoansAndFinancingReceivableTable_e1383c17-df20-49dd-987c-9cab7a7255e9_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_skwd_ProceedsFromRepaymentsOfReceivableFromShareholdersOrAffiliatesForIssuanceOfCapitalStock_2500f984-9e3e-483f-af23-76a0967350af_terseLabel_en-US" xlink:label="lab_skwd_ProceedsFromRepaymentsOfReceivableFromShareholdersOrAffiliatesForIssuanceOfCapitalStock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Repayment of stock notes receivable</link:label>
    <link:label id="lab_skwd_ProceedsFromRepaymentsOfReceivableFromShareholdersOrAffiliatesForIssuanceOfCapitalStock_label_en-US" xlink:label="lab_skwd_ProceedsFromRepaymentsOfReceivableFromShareholdersOrAffiliatesForIssuanceOfCapitalStock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds From Repayments Of Receivable From Shareholders Or Affiliates For Issuance Of Capital Stock</link:label>
    <link:label id="lab_skwd_ProceedsFromRepaymentsOfReceivableFromShareholdersOrAffiliatesForIssuanceOfCapitalStock_documentation_en-US" xlink:label="lab_skwd_ProceedsFromRepaymentsOfReceivableFromShareholdersOrAffiliatesForIssuanceOfCapitalStock" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Proceeds From Repayments Of Receivable From Shareholders Or Affiliates For Issuance Of Capital Stock</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ProceedsFromRepaymentsOfReceivableFromShareholdersOrAffiliatesForIssuanceOfCapitalStock" xlink:href="skwd-20240331.xsd#skwd_ProceedsFromRepaymentsOfReceivableFromShareholdersOrAffiliatesForIssuanceOfCapitalStock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ProceedsFromRepaymentsOfReceivableFromShareholdersOrAffiliatesForIssuanceOfCapitalStock" xlink:to="lab_skwd_ProceedsFromRepaymentsOfReceivableFromShareholdersOrAffiliatesForIssuanceOfCapitalStock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GainLossOnInvestments_b63a08d2-a663-4faa-9433-0843647d11e0_terseLabel_en-US" xlink:label="lab_us-gaap_GainLossOnInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net investment gains</link:label>
    <link:label id="lab_us-gaap_GainLossOnInvestments_c7b579ec-eda8-45b6-9cb2-5e661a6b5c07_totalLabel_en-US" xlink:label="lab_us-gaap_GainLossOnInvestments" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net investment gains</link:label>
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    <link:label id="lab_us-gaap_LoansReceivableFairValueDisclosure_cd68302e-c8c8-4943-bdef-827638014664_terseLabel_en-US" xlink:label="lab_us-gaap_LoansReceivableFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mortgage loans</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LoansReceivableFairValueDisclosure" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LoansReceivableFairValueDisclosure"/>
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    <link:label id="lab_us-gaap_MunicipalBondsMember_6263cc45-bc09-4ceb-a183-7ad959bb72e2_terseLabel_en-US" xlink:label="lab_us-gaap_MunicipalBondsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Municipal securities</link:label>
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    <link:label id="lab_ecd_InsiderTradingArrLineItems_label_en-US" xlink:label="lab_ecd_InsiderTradingArrLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insider Trading Arrangements [Line Items]</link:label>
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    <link:label id="lab_us-gaap_RelatedPartyTransactionsByRelatedPartyAxis_39f5dbf8-8ce8-4126-83d9-ee4540a9e349_terseLabel_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionsByRelatedPartyAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Related Party [Axis]</link:label>
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    <link:label id="lab_us-gaap_OtherAssets_5e1cc015-7f5f-43e0-9d2d-cb062c762ebe_terseLabel_en-US" xlink:label="lab_us-gaap_OtherAssets" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other assets</link:label>
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    <link:label id="lab_skwd_RevolvingLineOfCreditDueDecember2023Member_dcafe2a9-e2c8-4f18-9cda-edc35c22bb3b_terseLabel_en-US" xlink:label="lab_skwd_RevolvingLineOfCreditDueDecember2023Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Revolving Line Of Credit Due December 2023</link:label>
    <link:label id="lab_skwd_RevolvingLineOfCreditDueDecember2023Member_label_en-US" xlink:label="lab_skwd_RevolvingLineOfCreditDueDecember2023Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Revolving Line Of Credit Due December 2023 [Member]</link:label>
    <link:label id="lab_skwd_RevolvingLineOfCreditDueDecember2023Member_documentation_en-US" xlink:label="lab_skwd_RevolvingLineOfCreditDueDecember2023Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Revolving Line Of Credit Due December 2023</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RevolvingLineOfCreditDueDecember2023Member" xlink:href="skwd-20240331.xsd#skwd_RevolvingLineOfCreditDueDecember2023Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_RevolvingLineOfCreditDueDecember2023Member" xlink:to="lab_skwd_RevolvingLineOfCreditDueDecember2023Member" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_EquityMethodInvestmentsUnfundedCommitment_4bcb8fc1-84ac-48a1-bbf2-3f29b751eb4a_terseLabel_en-US" xlink:label="lab_skwd_EquityMethodInvestmentsUnfundedCommitment" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity method investments, 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" 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" xml:lang="en-US">Equity Method Investments, Unfunded Commitment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_EquityMethodInvestmentsUnfundedCommitment" xlink:href="skwd-20240331.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_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract_2ab4d8da-3219-41ef-bcd7-ce18b2ac5c88_terseLabel_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other comprehensive (loss) income:</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" 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/2023/elts/us-gaap-2023.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_dei_DocumentPeriodEndDate_ce0498f8-146e-447b-9c57-9cfa023e7a02_terseLabel_en-US" xlink:label="lab_dei_DocumentPeriodEndDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/dei-2023.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_us-gaap_ProceedsFromLinesOfCredit_972c8233-54ee-4a4c-9883-a1ac45e1543d_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromLinesOfCredit" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Draw on revolving line of credit</link:label>
    <link:label id="lab_us-gaap_ProceedsFromLinesOfCredit_label_en-US" xlink:label="lab_us-gaap_ProceedsFromLinesOfCredit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Lines of Credit</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromLinesOfCredit" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ProceedsFromLinesOfCredit"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromLinesOfCredit" xlink:to="lab_us-gaap_ProceedsFromLinesOfCredit" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_CompActuallyPaidVsNetIncomeTextBlock_terseLabel_en-US" xlink:label="lab_ecd_CompActuallyPaidVsNetIncomeTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Net Income</link:label>
    <link:label id="lab_ecd_CompActuallyPaidVsNetIncomeTextBlock_label_en-US" xlink:label="lab_ecd_CompActuallyPaidVsNetIncomeTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Net Income [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_CompActuallyPaidVsNetIncomeTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_CompActuallyPaidVsNetIncomeTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_CompActuallyPaidVsNetIncomeTextBlock" xlink:to="lab_ecd_CompActuallyPaidVsNetIncomeTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TrdArrAdoptionDate_terseLabel_en-US" xlink:label="lab_ecd_TrdArrAdoptionDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adoption Date</link:label>
    <link:label id="lab_ecd_TrdArrAdoptionDate_label_en-US" xlink:label="lab_ecd_TrdArrAdoptionDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement Adoption Date</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrAdoptionDate" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_TrdArrAdoptionDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrAdoptionDate" xlink:to="lab_ecd_TrdArrAdoptionDate" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PeerGroupIssuersFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_PeerGroupIssuersFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Peer Group Issuers, Footnote</link:label>
    <link:label id="lab_ecd_PeerGroupIssuersFnTextBlock_label_en-US" xlink:label="lab_ecd_PeerGroupIssuersFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Peer Group Issuers, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeerGroupIssuersFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_PeerGroupIssuersFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PeerGroupIssuersFnTextBlock" xlink:to="lab_ecd_PeerGroupIssuersFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock_0b351224-cf19-49cd-90d7-1713f9bbbe1a_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_us-gaap_RepaymentsOfLongTermDebt_4205dc18-9166-470e-bbd6-0fb0382f11e3_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_RepaymentsOfLongTermDebt" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Repayment of term loan</link:label>
    <link:label id="lab_us-gaap_RepaymentsOfLongTermDebt_label_en-US" xlink:label="lab_us-gaap_RepaymentsOfLongTermDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Repayments of Long-Term Debt</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RepaymentsOfLongTermDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_RepaymentsOfLongTermDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RepaymentsOfLongTermDebt" xlink:to="lab_us-gaap_RepaymentsOfLongTermDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DirectPremiumsWritten_24da62f6-9afb-417b-aade-83b8c45a496e_terseLabel_en-US" xlink:label="lab_us-gaap_DirectPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_TreasuryStockCommonMember_5927ff8b-5463-4ffc-b720-02f4f6f41c7c_terseLabel_en-US" xlink:label="lab_us-gaap_TreasuryStockCommonMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Treasury stock:</link:label>
    <link:label id="lab_us-gaap_TreasuryStockCommonMember_label_en-US" xlink:label="lab_us-gaap_TreasuryStockCommonMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Treasury Stock, Common [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TreasuryStockCommonMember" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_TreasuryStockCommonMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TreasuryStockCommonMember" xlink:to="lab_us-gaap_TreasuryStockCommonMember" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityCentralIndexKey_35d3056c-d5d3-4881-b9b2-09e82c20cd87_terseLabel_en-US" xlink:label="lab_dei_EntityCentralIndexKey" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/dei-2023.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_MortgageReceivablesMember_fa4690dd-73ea-4c3d-b283-4506ef4e9b04_terseLabel_en-US" xlink:label="lab_us-gaap_MortgageReceivablesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mortgage Loans</link:label>
    <link:label id="lab_us-gaap_MortgageReceivablesMember_label_en-US" xlink:label="lab_us-gaap_MortgageReceivablesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Mortgage Receivable [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MortgageReceivablesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_MortgageReceivablesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MortgageReceivablesMember" xlink:to="lab_us-gaap_MortgageReceivablesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1_e470c949-7750-4c65-b75c-850fcccc29cb_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total gains for the period recognized in net investment gains (losses)</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Measurement with Unobservable Inputs Reconciliation, Recurring Basis, Asset, Gain (Loss) Included in Earnings</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1" xlink:to="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_NonRule10b51ArrTrmntdFlag_terseLabel_en-US" xlink:label="lab_ecd_NonRule10b51ArrTrmntdFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-Rule 10b5-1 Arrangement Terminated</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonRule10b51ArrTrmntdFlag" xlink:to="lab_ecd_NonRule10b51ArrTrmntdFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxExpenseBenefit_056a4c6a-3fc5-41eb-8867-7713a3280b4e_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income tax expense</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" 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/2023/elts/us-gaap-2023.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_skwd_RelatedPartyOwnershipInterest_ddc6a385-6dbd-4646-bec7-0f6855ad06a5_terseLabel_en-US" xlink:label="lab_skwd_RelatedPartyOwnershipInterest" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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" xml:lang="en-US">Related Party, Ownership Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RelatedPartyOwnershipInterest" xlink:href="skwd-20240331.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_IncrementalCommonSharesAttributableToContingentlyIssuableShares_0100e208-90a6-46be-9172-c69b6430f13e_verboseLabel_en-US" xlink:label="lab_us-gaap_IncrementalCommonSharesAttributableToContingentlyIssuableShares" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Diluted effect of stock notes (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" xml:lang="en-US">Incremental Common Shares Attributable to Dilutive Effect of Contingently Issuable Shares</link:label>
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    <link:label id="lab_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax_901af301-d3ec-4601-8f28-f5bcda9ef509_terseLabel_en-US" xlink:label="lab_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total commission and fee income</link:label>
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    <link:label id="lab_us-gaap_CreditFacilityDomain_5f7dbb9a-a85e-4598-aedb-2e1a01b55553_terseLabel_en-US" xlink:label="lab_us-gaap_CreditFacilityDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Credit Facility [Domain]</link:label>
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    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract_3b6008ad-e45e-4a7c-93b8-a14b1644f9ca_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract"/>
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    <link:label id="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1_0000b03b-bb2e-4ab9-ad69-5b5ddf602f75_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Margin</link:label>
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    <link:label id="lab_ecd_CompActuallyPaidVsOtherMeasureTextBlock_terseLabel_en-US" xlink:label="lab_ecd_CompActuallyPaidVsOtherMeasureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Other Measure</link:label>
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    <link:label id="lab_us-gaap_GainLossOnInvestmentsTextBlock_615080b7-91e0-4bae-832b-26587c7b8524_terseLabel_en-US" xlink:label="lab_us-gaap_GainLossOnInvestmentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" xml:lang="en-US">Gain (Loss) on Securities [Table Text Block]</link:label>
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    <link:label id="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_6b68c1df-23f7-48cf-a78e-e812f782f3f8_terseLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Diluted (in shares)</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding"/>
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    <link:label id="lab_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock_label_en-US" xlink:label="lab_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Forgone Recovery, Explanation of Impracticability [Text Block]</link:label>
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    <link:label id="lab_skwd_ReinsuranceRecoverableForLossPortfolioTransfer_edd0fbc3-5b89-475a-906e-3f11312e0aa4_terseLabel_en-US" xlink:label="lab_skwd_ReinsuranceRecoverableForLossPortfolioTransfer" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Loss portfolio transfer</link:label>
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    <link:label id="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense_6675dfe0-8100-4af0-9e6d-fe451f19862f_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Amortization of policy acquisition costs</link:label>
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    <link:label id="lab_us-gaap_RevenueFromContractWithCustomerTextBlock_c2d3be5b-49a9-429d-a293-76a5a150f073_terseLabel_en-US" xlink:label="lab_us-gaap_RevenueFromContractWithCustomerTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Commission and Fee Income</link:label>
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    <link:label id="lab_us-gaap_AdditionalPaidInCapitalMember_ad4437f3-9af6-4cc7-83c1-23dce6d2cbd3_terseLabel_en-US" xlink:label="lab_us-gaap_AdditionalPaidInCapitalMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Additional paid-in capital:</link:label>
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    <link:label id="lab_us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustmentAbstract_4236442f-aaad-4e5c-9a6d-77a990edb76c_terseLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustmentAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.xsd#us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustmentAbstract"/>
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    <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" xml:lang="en-US">Junior Subordinated Notes Due 2036, Common Stock</link:label>
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    <link:label id="lab_us-gaap_Assets_c0e7be9c-8ff2-4497-9b5b-056521aba20c_totalLabel_en-US" xlink:label="lab_us-gaap_Assets" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.xsd#us-gaap_Assets"/>
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    <link:label id="lab_ecd_AwardsCloseToMnpiDiscIndName_terseLabel_en-US" xlink:label="lab_ecd_AwardsCloseToMnpiDiscIndName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Name</link:label>
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    <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" xml:lang="en-US">Cover [Abstract]</link:label>
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    <link:label id="lab_us-gaap_InsuranceCommissions_e8eed2c1-8965-47ac-a49a-63dd7bfc7a07_terseLabel_en-US" xlink:label="lab_us-gaap_InsuranceCommissions" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">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" 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/2023/elts/us-gaap-2023.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_DirectPremiumsEarned_fb883aaa-6d62-4b9b-a951-1e7a47e4af3e_terseLabel_en-US" xlink:label="lab_us-gaap_DirectPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_skwd_DowlingCapitalPartnersLPMember_5643e6e2-d12b-412a-8bbb-392591ba29b9_terseLabel_en-US" xlink:label="lab_skwd_DowlingCapitalPartnersLPMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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" xml:lang="en-US">Dowling Capital Partners LP</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DowlingCapitalPartnersLPMember" xlink:href="skwd-20240331.xsd#skwd_DowlingCapitalPartnersLPMember"/>
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    <link:label id="lab_us-gaap_PremiumsReceivableAtCarryingValue_2107858d-b793-49b6-9c40-7c76c78576a0_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsReceivableAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Premiums receivable, net</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" 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/2023/elts/us-gaap-2023.xsd#us-gaap_PremiumsReceivableAtCarryingValue"/>
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    <link:label id="lab_us-gaap_LoansNotesTradeAndOtherReceivablesDisclosureTextBlock_8652ba73-9931-44a9-9ea3-9bcfb02b694d_terseLabel_en-US" xlink:label="lab_us-gaap_LoansNotesTradeAndOtherReceivablesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_us-gaap_CededPremiumsEarned_4e2bcc6a-077d-4ee7-8a62-3d1c8afc8fda_negatedLabel_en-US" xlink:label="lab_us-gaap_CededPremiumsEarned" xlink:role="http://www.xbrl.org/2009/role/negatedLabel" xlink:type="resource" xml:lang="en-US">Ceded premiums</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" 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/2023/elts/us-gaap-2023.xsd#us-gaap_CededPremiumsEarned"/>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss_89624675-a0eb-4525-b6e8-9a81631aab58_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gross Amortized Cost</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Amortized Cost, Excluding Accrued Interest, before Allowance for Credit Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss"/>
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    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesLineItems_69b145e6-cb56-4a08-9662-f3680ca2abcd_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value Measurement Inputs and Valuation Techniques [Line Items]</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesLineItems"/>
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    <link:label id="lab_us-gaap_DebtInstrumentInterestRateDuringPeriod_4754ffda-783b-4428-a7c6-4425d62ff8c4_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentInterestRateDuringPeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net interest rate</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentInterestRateDuringPeriod_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentInterestRateDuringPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Interest Rate During Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentInterestRateDuringPeriod" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DebtInstrumentInterestRateDuringPeriod"/>
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    <link:label id="lab_us-gaap_EffectsOfReinsuranceTableTextBlock_dd573253-0e37-4151-a278-78e8df31b1f9_verboseLabel_en-US" xlink:label="lab_us-gaap_EffectsOfReinsuranceTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.xsd#us-gaap_EffectsOfReinsuranceTableTextBlock"/>
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    <link:label id="lab_ecd_NonNeosMember_terseLabel_en-US" xlink:label="lab_ecd_NonNeosMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-NEOs</link:label>
    <link:label id="lab_ecd_NonNeosMember_label_en-US" xlink:label="lab_ecd_NonNeosMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-NEOs [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonNeosMember" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_NonNeosMember"/>
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    <link:label id="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses_cec15fcd-1153-4ef4-a8e7-b7d646419e89_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurance recoverables, net</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses_4211ea0b-0017-4030-ac15-4a9bcff67e45_totalLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" 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" xml:lang="en-US">Reinsurance Recoverable for Paid and Unpaid Claims and Claims Adjustments</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward"/>
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    <link:label id="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_0993ef3c-e593-4288-bf9c-180645076b6a_totalLabel_en-US" xlink:label="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.xsd#us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect"/>
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    <link:label id="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract_7cefb7f6-7549-47cd-9252-f08ed2efdf73_terseLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_GrossInvestmentIncomeOperating_10382e21-25ba-4d5e-a6c7-904ce1000fb8_terseLabel_en-US" xlink:label="lab_us-gaap_GrossInvestmentIncomeOperating" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_ecd_NonPeoNeoMember_terseLabel_en-US" xlink:label="lab_ecd_NonPeoNeoMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-PEO NEO</link:label>
    <link:label id="lab_ecd_NonPeoNeoMember_label_en-US" xlink:label="lab_ecd_NonPeoNeoMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-PEO NEO [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonPeoNeoMember" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_NonPeoNeoMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonPeoNeoMember" xlink:to="lab_ecd_NonPeoNeoMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityComponentDomain_0d1d3257-90d7-4384-9f1f-aec9c99340f4_terseLabel_en-US" xlink:label="lab_us-gaap_EquityComponentDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_ecd_AdjToCompAxis_terseLabel_en-US" xlink:label="lab_ecd_AdjToCompAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adjustment to Compensation:</link:label>
    <link:label id="lab_ecd_AdjToCompAxis_label_en-US" xlink:label="lab_ecd_AdjToCompAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Adjustment to Compensation [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AdjToCompAxis" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_AdjToCompAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AdjToCompAxis" xlink:to="lab_ecd_AdjToCompAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_NonGaapMeasureDescriptionTextBlock_terseLabel_en-US" xlink:label="lab_ecd_NonGaapMeasureDescriptionTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-GAAP Measure Description</link:label>
    <link:label id="lab_ecd_NonGaapMeasureDescriptionTextBlock_label_en-US" xlink:label="lab_ecd_NonGaapMeasureDescriptionTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-GAAP Measure Description [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonGaapMeasureDescriptionTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_NonGaapMeasureDescriptionTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonGaapMeasureDescriptionTextBlock" xlink:to="lab_ecd_NonGaapMeasureDescriptionTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ContractWithCustomerAssetNet_5d89bfdf-65ae-4783-b413-3e41b1ecc580_terseLabel_en-US" xlink:label="lab_us-gaap_ContractWithCustomerAssetNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Contract asset after allowance for credit loss</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" 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/2023/elts/us-gaap-2023.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_DebtInstrumentLineItems_9c09443c-337e-4aa6-a8cf-bacf606c35f6_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_WeightedAverageNumberOfSharesOutstandingBasic_1f1c55c0-ae8e-48ad-bcc2-273b32134f22_verboseLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Basic (in shares)</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic_f2f983ca-ab0d-4b27-9a4c-eb8b8c8c49ea_terseLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_dei_EntityCurrentReportingStatus_4797a656-b0ce-4ae4-a581-5888fe6b53fc_terseLabel_en-US" xlink:label="lab_dei_EntityCurrentReportingStatus" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" xml:lang="en-US">Entity Current Reporting Status</link:label>
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    <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_us-gaap_FundsHeldUnderReinsuranceAgreementsLiability_08e758a5-a0a4-4e1c-8c5d-c48b36d628c4_terseLabel_en-US" xlink:label="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsLiability" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_ProceedsFromIssuanceInitialPublicOffering_7c43198c-0973-4326-a95c-c49ec4bc763c_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromIssuanceInitialPublicOffering" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Proceeds from initial public offering</link:label>
    <link:label id="lab_us-gaap_ProceedsFromIssuanceInitialPublicOffering_label_en-US" xlink:label="lab_us-gaap_ProceedsFromIssuanceInitialPublicOffering" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Issuance Initial Public Offering</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromIssuanceInitialPublicOffering" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ProceedsFromIssuanceInitialPublicOffering"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromIssuanceInitialPublicOffering" xlink:to="lab_us-gaap_ProceedsFromIssuanceInitialPublicOffering" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RevenuesAbstract_0705fc4f-8499-42cd-adb0-16ac6165edd4_terseLabel_en-US" xlink:label="lab_us-gaap_RevenuesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_SubordinatedDebt_e1796773-8fc2-4e0d-97d9-3c94ff1542f8_terseLabel_en-US" xlink:label="lab_us-gaap_SubordinatedDebt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.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_skwd_FixedMaturitySecuritiesHeldToMaturityMember_9ae58482-3ea7-4ea4-ab39-529f26f5e625_terseLabel_en-US" xlink:label="lab_skwd_FixedMaturitySecuritiesHeldToMaturityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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" xml:lang="en-US">Fixed Maturity Securities, Held-to-Maturity</link:label>
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    <link:label id="lab_us-gaap_RelatedPartyTransactionAxis_c119a310-7166-4605-b24e-6eb044e96401_terseLabel_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" 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/2023/elts/us-gaap-2023.xsd#us-gaap_RelatedPartyTransactionAxis"/>
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    <link:label id="lab_ecd_PvpTable_terseLabel_en-US" xlink:label="lab_ecd_PvpTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pay vs Performance Disclosure</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_ecd_PvpTable" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_PvpTable"/>
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    <link:label id="lab_us-gaap_StatementLineItems_ee9ff465-5a47-4ee5-abdd-a288d16d36a7_terseLabel_en-US" xlink:label="lab_us-gaap_StatementLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" 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" xml:lang="en-US">Statement [Line Items]</link:label>
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