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    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentOther_label_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentOther" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Property, Plant and Equipment, Other, Gross</link:label>
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    <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>
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    <link:label id="lab_us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity_60a504b9-9411-4a3d-a3ea-5b99585f3aaf_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"/>
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    <link:label id="lab_us-gaap_IncreaseDecreaseInOperatingCapitalAbstract_754df4cc-000b-438c-99b9-4cfa3c8e4170_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInOperatingCapitalAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Changes in operating assets and liabilities:</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInOperatingCapitalAbstract_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInOperatingCapitalAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Operating Capital [Abstract]</link:label>
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    <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"/>
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    <link:label id="lab_us-gaap_ShortDurationInsuranceContractsAccidentYear2017Member_a7820031-200c-414b-be28-1f00392cf7a9_terseLabel_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractsAccidentYear2017Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accident Year 2017</link:label>
    <link:label id="lab_us-gaap_ShortDurationInsuranceContractsAccidentYear2017Member_label_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractsAccidentYear2017Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contracts, Accident Year 2017 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortDurationInsuranceContractsAccidentYear2017Member" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShortDurationInsuranceContractsAccidentYear2017Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortDurationInsuranceContractsAccidentYear2017Member" xlink:to="lab_us-gaap_ShortDurationInsuranceContractsAccidentYear2017Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConvertiblePreferredStockSharesIssuedUponConversion_fd89b0e0-91a0-40d9-bde8-7b8ef9676893_terseLabel_en-US" xlink:label="lab_us-gaap_ConvertiblePreferredStockSharesIssuedUponConversion" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Convertible preferred stock (in shares)</link:label>
    <link:label id="lab_us-gaap_ConvertiblePreferredStockSharesIssuedUponConversion_label_en-US" xlink:label="lab_us-gaap_ConvertiblePreferredStockSharesIssuedUponConversion" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Convertible Preferred Stock, Shares Issued upon Conversion</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConvertiblePreferredStockSharesIssuedUponConversion" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ConvertiblePreferredStockSharesIssuedUponConversion"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConvertiblePreferredStockSharesIssuedUponConversion" xlink:to="lab_us-gaap_ConvertiblePreferredStockSharesIssuedUponConversion" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsGrantsInPeriodExcludingSharesIssuedInConnectionWithAcquisitionWeightedAverageExercisePrice_225d5716-4632-452c-9e21-2a70ce1cde34_terseLabel_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsGrantsInPeriodExcludingSharesIssuedInConnectionWithAcquisitionWeightedAverageExercisePrice" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Granted, weighted average exercise price (in dollars per share)</link:label>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsGrantsInPeriodExcludingSharesIssuedInConnectionWithAcquisitionWeightedAverageExercisePrice_label_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsGrantsInPeriodExcludingSharesIssuedInConnectionWithAcquisitionWeightedAverageExercisePrice" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-based Compensation Arrangements by Share-based Payment Award, Options, Grants in Period, Excluding Shares Issued in Connection with Acquisition, Weighted Average Exercise Price</link:label>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsGrantsInPeriodExcludingSharesIssuedInConnectionWithAcquisitionWeightedAverageExercisePrice_documentation_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsGrantsInPeriodExcludingSharesIssuedInConnectionWithAcquisitionWeightedAverageExercisePrice" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Share-based Compensation Arrangements by Share-based Payment Award, Options, Grants in Period, Excluding Shares Issued in Connection with Acquisition, Weighted Average Exercise Price</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsGrantsInPeriodExcludingSharesIssuedInConnectionWithAcquisitionWeightedAverageExercisePrice" xlink:href="skwd-20231231.xsd#skwd_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsGrantsInPeriodExcludingSharesIssuedInConnectionWithAcquisitionWeightedAverageExercisePrice"/>
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    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetIssues_3bfa1510-111d-4b81-b62e-62d84f0fd6d2_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>
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    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain_5e4b08c5-751a-40c2-a4e7-ce41e4b1f4c1_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_473bf535-4e22-4375-bba7-525383d1006e_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>
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    <link:label id="lab_us-gaap_CommissionsPolicy_9a42f1af-5528-4152-8b3c-23655c48a97e_terseLabel_en-US" xlink:label="lab_us-gaap_CommissionsPolicy" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Commission and Fee Income</link:label>
    <link:label id="lab_us-gaap_CommissionsPolicy_label_en-US" xlink:label="lab_us-gaap_CommissionsPolicy" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Commissions, Policy [Policy Text Block]</link:label>
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    <link:label id="lab_skwd_ContingentlyIssuableInstrumentsPreferredSharesIfConvertedMember_30e28c91-dac1-4667-b5dc-917f0a3b2b70_terseLabel_en-US" xlink:label="lab_skwd_ContingentlyIssuableInstrumentsPreferredSharesIfConvertedMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Preferred shares, if converted</link:label>
    <link:label id="lab_skwd_ContingentlyIssuableInstrumentsPreferredSharesIfConvertedMember_label_en-US" xlink:label="lab_skwd_ContingentlyIssuableInstrumentsPreferredSharesIfConvertedMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Contingently Issuable Instruments, Preferred Shares, If Converted [Member]</link:label>
    <link:label id="lab_skwd_ContingentlyIssuableInstrumentsPreferredSharesIfConvertedMember_documentation_en-US" xlink:label="lab_skwd_ContingentlyIssuableInstrumentsPreferredSharesIfConvertedMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Contingently Issuable Instruments, Preferred Shares, If Converted</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ContingentlyIssuableInstrumentsPreferredSharesIfConvertedMember" xlink:href="skwd-20231231.xsd#skwd_ContingentlyIssuableInstrumentsPreferredSharesIfConvertedMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ContingentlyIssuableInstrumentsPreferredSharesIfConvertedMember" xlink:to="lab_skwd_ContingentlyIssuableInstrumentsPreferredSharesIfConvertedMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsToAcquireBusinessesGross_e37d9fca-5d39-4a91-8ac3-bb83918055db_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireBusinessesGross" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Purchase of intangible assets</link:label>
    <link:label id="lab_us-gaap_PaymentsToAcquireBusinessesGross_label_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireBusinessesGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments to Acquire Businesses, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireBusinessesGross" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PaymentsToAcquireBusinessesGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsToAcquireBusinessesGross" xlink:to="lab_us-gaap_PaymentsToAcquireBusinessesGross" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock_840d20f6-a752-4bc0-9c36-aeea338dbafa_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>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock" xlink:to="lab_us-gaap_TradingSecuritiesAndCertainTradingAssetsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherLongTermInvestments_2c32a288-2c24-4069-9972-6d582cbf9275_terseLabel_en-US" xlink:label="lab_us-gaap_OtherLongTermInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other long-term investments</link:label>
    <link:label id="lab_us-gaap_OtherLongTermInvestments_label_en-US" xlink:label="lab_us-gaap_OtherLongTermInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Long-Term Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherLongTermInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_OtherLongTermInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherLongTermInvestments" xlink:to="lab_us-gaap_OtherLongTermInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesOnPaidLossesGross_045f3313-70b8-43db-903c-3f0b231cd6d3_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesOnPaidLossesGross" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ceded paid losses and LAE</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesOnPaidLossesGross_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesOnPaidLossesGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverables on Paid Losses, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverablesOnPaidLossesGross" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ReinsuranceRecoverablesOnPaidLossesGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverablesOnPaidLossesGross" xlink:to="lab_us-gaap_ReinsuranceRecoverablesOnPaidLossesGross" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_IPOSharesFromCompanyMember_1e357b59-a4fe-4d79-9a22-81aeec17fabf_terseLabel_en-US" xlink:label="lab_skwd_IPOSharesFromCompanyMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">IPO - Shares From Company</link:label>
    <link:label id="lab_skwd_IPOSharesFromCompanyMember_label_en-US" xlink:label="lab_skwd_IPOSharesFromCompanyMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">IPO - Shares From Company [Member]</link:label>
    <link:label id="lab_skwd_IPOSharesFromCompanyMember_documentation_en-US" xlink:label="lab_skwd_IPOSharesFromCompanyMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">IPO - Shares From Company</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_IPOSharesFromCompanyMember" xlink:href="skwd-20231231.xsd#skwd_IPOSharesFromCompanyMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_IPOSharesFromCompanyMember" xlink:to="lab_skwd_IPOSharesFromCompanyMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue_e48be39c-1b14-4fc5-ad6a-062e6f70d5ee_periodStartLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Beginning balance</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue_38974abf-8dcf-4b1d-9369-6aac98a623f7_periodEndLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Ending balance</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue" 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 Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue" xlink:to="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue" xlink:type="arc" order="1"/>
    <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>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_InsiderTradingPoliciesProcLineItems" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_InsiderTradingPoliciesProcLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_InsiderTradingPoliciesProcLineItems" xlink:to="lab_ecd_InsiderTradingPoliciesProcLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_Rule10b51ArrTrmntdFlag_terseLabel_en-US" xlink:label="lab_ecd_Rule10b51ArrTrmntdFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Rule 10b5-1 Arrangement Terminated</link:label>
    <link:label id="lab_ecd_Rule10b51ArrTrmntdFlag_label_en-US" xlink:label="lab_ecd_Rule10b51ArrTrmntdFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Rule 10b5-1 Arrangement Terminated [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_Rule10b51ArrTrmntdFlag" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_Rule10b51ArrTrmntdFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_Rule10b51ArrTrmntdFlag" xlink:to="lab_ecd_Rule10b51ArrTrmntdFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumsWrittenGrossAbstract_2b499698-770c-4419-b506-26e16ac61856_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsWrittenGrossAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Written</link:label>
    <link:label id="lab_us-gaap_PremiumsWrittenGrossAbstract_label_en-US" xlink:label="lab_us-gaap_PremiumsWrittenGrossAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Premiums Written, Gross [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsWrittenGrossAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PremiumsWrittenGrossAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsWrittenGrossAbstract" xlink:to="lab_us-gaap_PremiumsWrittenGrossAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisaggregationOfRevenueLineItems_7524b83e-9e06-4d1b-a958-93e57cd92f33_terseLabel_en-US" xlink:label="lab_us-gaap_DisaggregationOfRevenueLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Disaggregation of Revenue [Line Items]</link:label>
    <link:label id="lab_us-gaap_DisaggregationOfRevenueLineItems_label_en-US" xlink:label="lab_us-gaap_DisaggregationOfRevenueLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disaggregation of Revenue [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisaggregationOfRevenueLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DisaggregationOfRevenueLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisaggregationOfRevenueLineItems" xlink:to="lab_us-gaap_DisaggregationOfRevenueLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFive_c2eb33aa-e120-44c1-a743-fc12a5e63c02_terseLabel_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFive" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2028</link:label>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFive_label_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFive" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Lessee, Operating Lease, Liability, to be Paid, Year Five</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFive" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFive"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFive" xlink:to="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFive" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_RestatementDoesNotRequireRecoveryTextBlock_terseLabel_en-US" xlink:label="lab_ecd_RestatementDoesNotRequireRecoveryTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Restatement does not require Recovery</link:label>
    <link:label id="lab_ecd_RestatementDoesNotRequireRecoveryTextBlock_label_en-US" xlink:label="lab_ecd_RestatementDoesNotRequireRecoveryTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Restatement Does Not Require Recovery [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_RestatementDoesNotRequireRecoveryTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_RestatementDoesNotRequireRecoveryTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_RestatementDoesNotRequireRecoveryTextBlock" xlink:to="lab_ecd_RestatementDoesNotRequireRecoveryTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockholdersEquityNoteDisclosureTextBlock_a14afa82-c81b-449b-9b37-37467521de19_terseLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquityNoteDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stockholders&#8217; Equity</link:label>
    <link:label id="lab_us-gaap_StockholdersEquityNoteDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_StockholdersEquityNoteDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquityNoteDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_StockholdersEquityNoteDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockholdersEquityNoteDisclosureTextBlock" xlink:to="lab_us-gaap_StockholdersEquityNoteDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsVestedAndExpectedToVestOutstandingAggregateIntrinsicValue_85ab1dfc-9f8d-4b23-aafd-fc8a1bb8358c_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsVestedAndExpectedToVestOutstandingAggregateIntrinsicValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aggregate intrinsic value of options</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsVestedAndExpectedToVestOutstandingAggregateIntrinsicValue_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsVestedAndExpectedToVestOutstandingAggregateIntrinsicValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Options, Vested and Expected to Vest, Outstanding, Aggregate Intrinsic Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsVestedAndExpectedToVestOutstandingAggregateIntrinsicValue" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsVestedAndExpectedToVestOutstandingAggregateIntrinsicValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsVestedAndExpectedToVestOutstandingAggregateIntrinsicValue" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsVestedAndExpectedToVestOutstandingAggregateIntrinsicValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromStockPlans_4eabac1b-2c5c-43aa-b877-cbf949de5701_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromStockPlans" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Employee share purchases</link:label>
    <link:label id="lab_us-gaap_ProceedsFromStockPlans_label_en-US" xlink:label="lab_us-gaap_ProceedsFromStockPlans" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Stock Plans</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromStockPlans" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ProceedsFromStockPlans"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromStockPlans" xlink:to="lab_us-gaap_ProceedsFromStockPlans" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_OwnershipAxis_b7c8ef58-47a4-48e4-bc57-527add19613e_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_8e0d5dd8-91a6-4a2c-8ba7-6125e10dddf1_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</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_970e00dd-d58b-4dc0-b7bc-7eeb3409e24b_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-20231231.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_ReportingUnitDomain_5eca6c49-c635-41e6-8bbb-953f729d4887_terseLabel_en-US" xlink:label="lab_us-gaap_ReportingUnitDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reporting Unit [Domain]</link:label>
    <link:label id="lab_us-gaap_ReportingUnitDomain_label_en-US" xlink:label="lab_us-gaap_ReportingUnitDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reporting Unit [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReportingUnitDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ReportingUnitDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReportingUnitDomain" xlink:to="lab_us-gaap_ReportingUnitDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_DirectorMember_db413ba4-d044-4cb7-835d-684fd1ea6732_terseLabel_en-US" xlink:label="lab_srt_DirectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Director</link:label>
    <link:label id="lab_srt_DirectorMember_label_en-US" xlink:label="lab_srt_DirectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Director [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_DirectorMember" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_DirectorMember"/>
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    <link:label id="lab_us-gaap_PremiumReceivableAllowanceForCreditLossTableTextBlock_0514ace7-4c77-4cd0-96f7-9272dab730b6_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumReceivableAllowanceForCreditLossTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Premium Receivable, Allowance for Credit Loss</link:label>
    <link:label id="lab_us-gaap_PremiumReceivableAllowanceForCreditLossTableTextBlock_label_en-US" xlink:label="lab_us-gaap_PremiumReceivableAllowanceForCreditLossTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Premium Receivable, Allowance for Credit Loss [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumReceivableAllowanceForCreditLossTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PremiumReceivableAllowanceForCreditLossTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumReceivableAllowanceForCreditLossTableTextBlock" xlink:to="lab_us-gaap_PremiumReceivableAllowanceForCreditLossTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_OfficePortfolioSegmentMember_95b117c7-70ad-4f74-a2ed-bd17aa70b464_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-20231231.xsd#skwd_OfficePortfolioSegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_OfficePortfolioSegmentMember" xlink:to="lab_skwd_OfficePortfolioSegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ReinsuranceAgreementMember_6e7ad7ab-d929-4907-b0f1-e87fabc165df_terseLabel_en-US" xlink:label="lab_skwd_ReinsuranceAgreementMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurance agreement</link:label>
    <link:label id="lab_skwd_ReinsuranceAgreementMember_label_en-US" xlink:label="lab_skwd_ReinsuranceAgreementMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Agreement [Member]</link:label>
    <link:label id="lab_skwd_ReinsuranceAgreementMember_documentation_en-US" xlink:label="lab_skwd_ReinsuranceAgreementMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Reinsurance Agreement</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ReinsuranceAgreementMember" xlink:href="skwd-20231231.xsd#skwd_ReinsuranceAgreementMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ReinsuranceAgreementMember" xlink:to="lab_skwd_ReinsuranceAgreementMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_GainLossOnHeldToMaturitySecuritiesAndEquityMethodInvestments_4f0e989b-535e-4a16-aeea-b21f0a2d01e9_negatedTerseLabel_en-US" xlink:label="lab_skwd_GainLossOnHeldToMaturitySecuritiesAndEquityMethodInvestments" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Undistributed loss (earnings) from long-term investments</link:label>
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    <link:label id="lab_skwd_GainLossOnHeldToMaturitySecuritiesAndEquityMethodInvestments_documentation_en-US" xlink:label="lab_skwd_GainLossOnHeldToMaturitySecuritiesAndEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Gain (Loss) On Held-to-Maturity Securities and Equity Method Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_GainLossOnHeldToMaturitySecuritiesAndEquityMethodInvestments" xlink:href="skwd-20231231.xsd#skwd_GainLossOnHeldToMaturitySecuritiesAndEquityMethodInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_GainLossOnHeldToMaturitySecuritiesAndEquityMethodInvestments" xlink:to="lab_skwd_GainLossOnHeldToMaturitySecuritiesAndEquityMethodInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillImpairedAccumulatedImpairmentLoss_36f2027c-7fee-4ba7-91a3-c26e4238122b_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_GoodwillImpairedAccumulatedImpairmentLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Accumulated impairment</link:label>
    <link:label id="lab_us-gaap_GoodwillImpairedAccumulatedImpairmentLoss_label_en-US" xlink:label="lab_us-gaap_GoodwillImpairedAccumulatedImpairmentLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill, Impaired, Accumulated Impairment Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillImpairedAccumulatedImpairmentLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_GoodwillImpairedAccumulatedImpairmentLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillImpairedAccumulatedImpairmentLoss" xlink:to="lab_us-gaap_GoodwillImpairedAccumulatedImpairmentLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PreferredStockValue_d54f8db5-6e35-45bb-8e58-252940ca68f7_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Series A preferred stock, $0.01 par value; 10,000,000 and 2,000,000 shares authorized, 0 and 1,969,660 shares issued and outstanding, respectively</link:label>
    <link:label id="lab_us-gaap_PreferredStockValue_label_en-US" xlink:label="lab_us-gaap_PreferredStockValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Preferred Stock, Value, Issued</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockValue" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PreferredStockValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PreferredStockValue" xlink:to="lab_us-gaap_PreferredStockValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubsequentEventTypeDomain_6f1fa55d-f818-4283-8ed7-27cfac2fec44_terseLabel_en-US" xlink:label="lab_us-gaap_SubsequentEventTypeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subsequent Event Type [Domain]</link:label>
    <link:label id="lab_us-gaap_SubsequentEventTypeDomain_label_en-US" xlink:label="lab_us-gaap_SubsequentEventTypeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsequent Event Type [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsequentEventTypeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_SubsequentEventTypeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsequentEventTypeDomain" xlink:to="lab_us-gaap_SubsequentEventTypeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ApplicableMarginRateMember_3b98f778-21a8-4905-a73e-904f1391e9da_terseLabel_en-US" xlink:label="lab_skwd_ApplicableMarginRateMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Applicable Margin Rate</link:label>
    <link:label id="lab_skwd_ApplicableMarginRateMember_label_en-US" xlink:label="lab_skwd_ApplicableMarginRateMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Applicable Margin Rate [Member]</link:label>
    <link:label id="lab_skwd_ApplicableMarginRateMember_documentation_en-US" xlink:label="lab_skwd_ApplicableMarginRateMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Applicable Margin Rate</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ApplicableMarginRateMember" xlink:href="skwd-20231231.xsd#skwd_ApplicableMarginRateMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ApplicableMarginRateMember" xlink:to="lab_skwd_ApplicableMarginRateMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_BToB2Member_e68d00bc-4df7-49e6-9724-8a81547110cd_terseLabel_en-US" xlink:label="lab_skwd_BToB2Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">B to B -</link:label>
    <link:label id="lab_skwd_BToB2Member_label_en-US" xlink:label="lab_skwd_BToB2Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">B to B- (2) [Member]</link:label>
    <link:label id="lab_skwd_BToB2Member_documentation_en-US" xlink:label="lab_skwd_BToB2Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">B to B- (2)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_BToB2Member" xlink:href="skwd-20231231.xsd#skwd_BToB2Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_BToB2Member" xlink:to="lab_skwd_BToB2Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareDiluted_b9e51b63-8bcd-4ea2-8e72-7aa35bebbc63_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 per share (in dollars 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_f9a58133-7bbc-4e93-9a3b-5d72f352a3ea_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">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_7e580389-7698-4eb3-a6b3-f04ad03288be_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_836162e9-1732-4e0a-ad86-56eef9239449_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_us-gaap_TreasuryStockValue_81cb6d15-f5c1-4fb8-923b-bb2d977060fb_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_TreasuryStockValue" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Treasury stock, $0.01 par value, 0 and 233,289 shares, respectively</link:label>
    <link:label id="lab_us-gaap_TreasuryStockValue_label_en-US" xlink:label="lab_us-gaap_TreasuryStockValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Treasury Stock, Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TreasuryStockValue" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_TreasuryStockValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TreasuryStockValue" xlink:to="lab_us-gaap_TreasuryStockValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesAllowance_645347a6-1e16-494b-98d0-ade17dfbde3c_verboseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesAllowance" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Allowance for uncollectable reinsurance</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesAllowance_e9c640c5-3e68-449a-991f-580a21d41ac1_periodStartLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesAllowance" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Allowance for Estimated Uncollectible Reinsurance, beginning balance</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesAllowance_90e37f03-d978-4aad-9646-22a4961b157b_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesAllowance" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cumulative effect of adoption of ASU 2016-13 at January 1, 2023</link:label>
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    <link:label id="lab_us-gaap_ReinsuranceRecoverablesAllowance_ff4a0482-d06d-49f7-b002-218334a50726_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"/>
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    <link:label id="lab_us-gaap_AccountingStandardsUpdateExtensibleList_f4c78ad1-6ebd-486b-a555-e320bd6b2603_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"/>
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    <link:label id="lab_us-gaap_InvestmentTypeCategorizationMember_74c03f85-a291-4028-b78f-8bc4b8166a53_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"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentTypeCategorizationMember" xlink:to="lab_us-gaap_InvestmentTypeCategorizationMember" xlink:type="arc" order="1"/>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFour" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFour"/>
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    <link:label id="lab_dei_LocalPhoneNumber_d23875db-b789-44b5-a645-b875abdc414c_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:loc xlink:type="locator" xlink:label="loc_dei_LocalPhoneNumber" xlink:href="https://xbrl.sec.gov/dei/2023/dei-2023.xsd#dei_LocalPhoneNumber"/>
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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:label id="lab_us-gaap_LetterOfCreditMember_c886e24b-2175-47d7-b879-67854314cdb3_terseLabel_en-US" xlink:label="lab_us-gaap_LetterOfCreditMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Letter of Credit</link:label>
    <link:label id="lab_us-gaap_LetterOfCreditMember_label_en-US" xlink:label="lab_us-gaap_LetterOfCreditMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Letter of Credit [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LetterOfCreditMember" xlink:href="https://xbrl.fasb.org/us-gaap/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"/>
    <link:label id="lab_skwd_ContingentlyIssuableInstrumentsTreasuryStockMethodMember_dff5a27c-9f14-4886-8c36-9e8c0de72408_terseLabel_en-US" xlink:label="lab_skwd_ContingentlyIssuableInstrumentsTreasuryStockMethodMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stock notes</link:label>
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    <link:label id="lab_skwd_ContingentlyIssuableInstrumentsTreasuryStockMethodMember_documentation_en-US" xlink:label="lab_skwd_ContingentlyIssuableInstrumentsTreasuryStockMethodMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Contingently Issuable Instruments, Treasury Stock Method</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ContingentlyIssuableInstrumentsTreasuryStockMethodMember" xlink:href="skwd-20231231.xsd#skwd_ContingentlyIssuableInstrumentsTreasuryStockMethodMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ContingentlyIssuableInstrumentsTreasuryStockMethodMember" xlink:to="lab_skwd_ContingentlyIssuableInstrumentsTreasuryStockMethodMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfComplianceWithRegulatoryCapitalRequirementsUnderBankingRegulationsTextBlock_019a51a0-6269-4872-90e0-5cad38929079_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfComplianceWithRegulatoryCapitalRequirementsUnderBankingRegulationsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Compliance with Regulatory Capital Requirements under Banking Regulations</link:label>
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    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseOpeningBalanceAdjustments_60f82e9c-3b3a-42b8-87ad-03c8828fd2b2_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseOpeningBalanceAdjustments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Liability for unpaid claims and claims adjustment</link:label>
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    <link:label id="lab_skwd_EnergyMember_afb0b834-8cfe-4345-a90a-e1c66ec0c7e9_terseLabel_en-US" xlink:label="lab_skwd_EnergyMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Industry Solutions</link:label>
    <link:label id="lab_skwd_EnergyMember_label_en-US" xlink:label="lab_skwd_EnergyMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Energy [Member]</link:label>
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    <link:label id="lab_us-gaap_AdjustmentsToReconcileNetIncomeLossToCashProvidedByUsedInOperatingActivities_a1e73594-35b7-4d86-b7b8-8a3679738cee_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 used in operating activities</link:label>
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    <link:label id="lab_us-gaap_RestrictedStockUnitsRSUMember_0ed4a2b3-cb80-4a12-a3f6-f4fb36ed330e_terseLabel_en-US" xlink:label="lab_us-gaap_RestrictedStockUnitsRSUMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Service condition awards</link:label>
    <link:label id="lab_us-gaap_RestrictedStockUnitsRSUMember_a05ab8f7-3a96-4c5a-a91c-f56fe42527a8_verboseLabel_en-US" xlink:label="lab_us-gaap_RestrictedStockUnitsRSUMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Awarded stock units</link:label>
    <link:label id="lab_us-gaap_RestrictedStockUnitsRSUMember_label_en-US" xlink:label="lab_us-gaap_RestrictedStockUnitsRSUMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Restricted Stock Units (RSUs) [Member]</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_us-gaap_Depreciation_a5c608ee-1276-425f-8cd3-fb559f35c220_terseLabel_en-US" xlink:label="lab_us-gaap_Depreciation" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Depreciation</link:label>
    <link:label id="lab_us-gaap_Depreciation_label_en-US" xlink:label="lab_us-gaap_Depreciation" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Depreciation</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Depreciation" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_Depreciation"/>
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    <link:label id="lab_skwd_IndustrialPortfolioSegmentMember_deddf6c2-3121-4566-afd7-6ac6497be6ff_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>
    <link:label id="lab_skwd_IndustrialPortfolioSegmentMember_label_en-US" xlink:label="lab_skwd_IndustrialPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Industrial Portfolio Segment [Member]</link:label>
    <link:label id="lab_skwd_IndustrialPortfolioSegmentMember_documentation_en-US" xlink:label="lab_skwd_IndustrialPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Industrial Portfolio Segment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_IndustrialPortfolioSegmentMember" xlink:href="skwd-20231231.xsd#skwd_IndustrialPortfolioSegmentMember"/>
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    <link:label id="lab_skwd_HospitalityPortfolioSegmentMember_4fe4c0b0-ae60-4c79-a9a7-4d0ff673580e_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_us-gaap_TrademarksMember_36b021fc-0f12-4add-959e-1a5dbe4f1b3c_terseLabel_en-US" xlink:label="lab_us-gaap_TrademarksMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Trademarks</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TrademarksMember" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_TrademarksMember"/>
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    <link:label id="lab_us-gaap_CompensationAndRetirementDisclosureAbstract_label_en-US" xlink:label="lab_us-gaap_CompensationAndRetirementDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Retirement Benefits [Abstract]</link:label>
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    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition_06f0a5cf-ab19-4d3d-b363-e52c86fd5454_totalLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition" xlink:href="skwd-20231231.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition" xlink:to="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfDebtInstrumentsTextBlock_276a15a8-63b9-4b39-830d-cbcccc2befe1_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfDebtInstrumentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Summary of Subordinated Debt</link:label>
    <link:label id="lab_us-gaap_ScheduleOfDebtInstrumentsTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfDebtInstrumentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Long-Term Debt Instruments [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfDebtInstrumentsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ScheduleOfDebtInstrumentsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfDebtInstrumentsTextBlock" xlink:to="lab_us-gaap_ScheduleOfDebtInstrumentsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CededCreditRiskAxis_6b7f85d6-c3a9-4879-b004-857346bcb52b_terseLabel_en-US" xlink:label="lab_us-gaap_CededCreditRiskAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurer, Name [Axis]</link:label>
    <link:label id="lab_us-gaap_CededCreditRiskAxis_label_en-US" xlink:label="lab_us-gaap_CededCreditRiskAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurer, Name [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CededCreditRiskAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_CededCreditRiskAxis"/>
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    <link:label id="lab_skwd_ShortTermInvestmentFairValueDisclosure_cac2ad01-720b-4530-b6c0-bb4e3e02931c_terseLabel_en-US" xlink:label="lab_skwd_ShortTermInvestmentFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Short-term investments</link:label>
    <link:label id="lab_skwd_ShortTermInvestmentFairValueDisclosure_label_en-US" xlink:label="lab_skwd_ShortTermInvestmentFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short Term Investment, Fair Value Disclosure</link:label>
    <link:label id="lab_skwd_ShortTermInvestmentFairValueDisclosure_documentation_en-US" xlink:label="lab_skwd_ShortTermInvestmentFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Short Term Investment, Fair Value Disclosure</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ShortTermInvestmentFairValueDisclosure" xlink:href="skwd-20231231.xsd#skwd_ShortTermInvestmentFairValueDisclosure"/>
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    <link:label id="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill_284b0e49-2df6-4441-be32-1ede93c28e82_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>
    <link:label id="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill_label_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Assets, Net (Including Goodwill)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_IntangibleAssetsNetIncludingGoodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:to="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtInstrumentFixedInterestRatePeriodOneMember_d476edb9-ec19-4983-96cd-d7a2eb972e3d_terseLabel_en-US" xlink:label="lab_skwd_DebtInstrumentFixedInterestRatePeriodOneMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Interest Rate, First 8 Years</link:label>
    <link:label id="lab_skwd_DebtInstrumentFixedInterestRatePeriodOneMember_label_en-US" xlink:label="lab_skwd_DebtInstrumentFixedInterestRatePeriodOneMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Fixed Interest Rate, Period One [Member]</link:label>
    <link:label id="lab_skwd_DebtInstrumentFixedInterestRatePeriodOneMember_documentation_en-US" xlink:label="lab_skwd_DebtInstrumentFixedInterestRatePeriodOneMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Fixed Interest Rate, Period One</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtInstrumentFixedInterestRatePeriodOneMember" xlink:href="skwd-20231231.xsd#skwd_DebtInstrumentFixedInterestRatePeriodOneMember"/>
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    <link:label id="lab_skwd_HudsonVenturesFund2LPMember_17b1ea3e-bb92-4044-be0a-4fa540b38af8_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 2 LP units</link:label>
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    <link:label id="lab_skwd_HudsonVenturesFund2LPMember_documentation_en-US" xlink:label="lab_skwd_HudsonVenturesFund2LPMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Hudson Ventures Fund 2, L.P.</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_HudsonVenturesFund2LPMember" xlink:href="skwd-20231231.xsd#skwd_HudsonVenturesFund2LPMember"/>
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    <link:label id="lab_us-gaap_EquityMethodInvestmentsTextBlock_643c37a0-1da1-4db4-be83-ea2456834582_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Carrying Value of Equity Method Investments</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsTextBlock_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investments [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_EquityMethodInvestmentsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentsTextBlock" xlink:to="lab_us-gaap_EquityMethodInvestmentsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_8763d103-fbdb-4bda-8229-637662911237_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Less than 12 Months</link:label>
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    <link:label id="lab_srt_ScheduleOfSupplementalInformationForPropertyCasualtyInsuranceUnderwritersTextBlock_55a559fe-cfba-4cde-9fa2-1b6ab180820e_terseLabel_en-US" xlink:label="lab_srt_ScheduleOfSupplementalInformationForPropertyCasualtyInsuranceUnderwritersTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">SCHEDULE VI&#160;&#8212; SUPPLEMENTAL INFORMATION CONCERNING PROPERTY-CASUALTY INSURANCE OPERATIONS</link:label>
    <link:label id="lab_srt_ScheduleOfSupplementalInformationForPropertyCasualtyInsuranceUnderwritersTextBlock_label_en-US" xlink:label="lab_srt_ScheduleOfSupplementalInformationForPropertyCasualtyInsuranceUnderwritersTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-18, Supplemental Information, Property-Casualty Insurance Underwriters [Text Block]</link:label>
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    <link:label id="lab_us-gaap_MortgagesMember_58deec64-5a08-4433-b71c-2795798f6064_terseLabel_en-US" xlink:label="lab_us-gaap_MortgagesMember" 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_MortgagesMember_label_en-US" xlink:label="lab_us-gaap_MortgagesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Mortgages [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MortgagesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_MortgagesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MortgagesMember" xlink:to="lab_us-gaap_MortgagesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SaleOfStockNumberOfSharesIssuedInTransaction_c0c260d7-f4c5-4d9c-b617-510aaf72495d_terseLabel_en-US" xlink:label="lab_us-gaap_SaleOfStockNumberOfSharesIssuedInTransaction" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Sale of stock, number of shares issued (in shares)</link:label>
    <link:label id="lab_us-gaap_SaleOfStockNumberOfSharesIssuedInTransaction_label_en-US" xlink:label="lab_us-gaap_SaleOfStockNumberOfSharesIssuedInTransaction" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Sale of Stock, Number of Shares Issued in Transaction</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SaleOfStockNumberOfSharesIssuedInTransaction" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_SaleOfStockNumberOfSharesIssuedInTransaction"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SaleOfStockNumberOfSharesIssuedInTransaction" xlink:to="lab_us-gaap_SaleOfStockNumberOfSharesIssuedInTransaction" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost_b1105691-f5e7-4dcf-a58a-043ab1b170e2_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>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Amortized Cost, Maturity, Allocated and Single Maturity Date, after Year 10</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost"/>
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    <link:label id="lab_us-gaap_Revenues_cd825322-b380-4d25-b7a5-09506a6ee0e1_totalLabel_en-US" xlink:label="lab_us-gaap_Revenues" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total revenues</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Revenues" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_Revenues"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Revenues" xlink:to="lab_us-gaap_Revenues" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_LongTermIncentivePlanMember_5000a8ba-3e4e-4a67-9fc6-50e0387712e2_terseLabel_en-US" xlink:label="lab_skwd_LongTermIncentivePlanMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Long Term Incentive Plan</link:label>
    <link:label id="lab_skwd_LongTermIncentivePlanMember_label_en-US" xlink:label="lab_skwd_LongTermIncentivePlanMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Long Term Incentive Plan [Member]</link:label>
    <link:label id="lab_skwd_LongTermIncentivePlanMember_documentation_en-US" xlink:label="lab_skwd_LongTermIncentivePlanMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Long Term Incentive Plan</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_LongTermIncentivePlanMember" xlink:href="skwd-20231231.xsd#skwd_LongTermIncentivePlanMember"/>
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    <link:label id="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock_55d47bd7-c134-478b-9356-2cb8bd337e13_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Antidilutive Securities Excluded from Computation of Earnings Per Share</link:label>
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    <link:label id="lab_us-gaap_CollateralizedSecuritiesMember_88c988d2-0c09-4181-94e7-e4631d84848d_terseLabel_en-US" xlink:label="lab_us-gaap_CollateralizedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mortgage-backed securities</link:label>
    <link:label id="lab_us-gaap_CollateralizedSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_CollateralizedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Collateralized Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CollateralizedSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_CollateralizedSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CollateralizedSecuritiesMember" xlink:to="lab_us-gaap_CollateralizedSecuritiesMember" xlink:type="arc" order="1"/>
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    <link:label id="lab_us-gaap_OtherExpenses_54d38f71-9c53-4519-bdd2-5b7ff0cf54e5_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>
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    <link:label id="lab_us-gaap_PaymentsForLossesAndLossAdjustmentExpense_dfd87750-ab02-42c7-aed4-a5f1422e451d_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>
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    <link:label id="lab_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract_786d26d0-e6f6-4e62-9410-0fcc1e1e9774_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>
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    <link:label id="lab_skwd_ContingentlyIssuableInstrumentsCommonSharesMember_3f16b7f6-0351-478c-afe5-d8c1669a891a_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>
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    <link:label id="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2021Member_label_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2021Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contract, Accident Year 2021 [Member]</link:label>
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    <link:label id="lab_us-gaap_UnearnedPremiums_50a30400-3e6d-462a-a391-76eb8660b7b6_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_PropertyPlantAndEquipmentLineItems_0443b5ed-f5cc-4843-987c-24d59622172b_terseLabel_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Property, Plant and Equipment [Line Items]</link:label>
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    <link:label id="lab_us-gaap_NewAccountingPronouncementsPolicyPolicyTextBlock_0c765b46-61bc-4dc9-b77f-5e8679bfac03_terseLabel_en-US" xlink:label="lab_us-gaap_NewAccountingPronouncementsPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Recent Accounting Standards Adopted and Not Yet Adopted</link:label>
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    <link:label id="lab_us-gaap_ValuationAllowanceOfDeferredTaxAssetsMember_47cff6b5-2605-470a-8203-bb4e5df03a7b_terseLabel_en-US" xlink:label="lab_us-gaap_ValuationAllowanceOfDeferredTaxAssetsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Valuation Allowance For Deferred Tax Assets</link:label>
    <link:label id="lab_us-gaap_ValuationAllowanceOfDeferredTaxAssetsMember_label_en-US" xlink:label="lab_us-gaap_ValuationAllowanceOfDeferredTaxAssetsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-09, Valuation Allowance, Deferred Tax Asset [Member]</link:label>
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    <link:label id="lab_us-gaap_DeferredTaxAssetsCapitalLossCarryforwards_c32f1ff8-c8dc-4435-ac30-19030eae2717_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsCapitalLossCarryforwards" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Capital loss carryover</link:label>
    <link:label id="lab_us-gaap_DeferredTaxAssetsCapitalLossCarryforwards_label_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsCapitalLossCarryforwards" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Tax Assets, Capital Loss Carryforwards</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxAssetsCapitalLossCarryforwards" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DeferredTaxAssetsCapitalLossCarryforwards"/>
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    <link:label id="lab_srt_RepurchaseAgreementCounterpartyNameDomain_bcfecf82-a959-42e3-9cf2-61093443eace_terseLabel_en-US" xlink:label="lab_srt_RepurchaseAgreementCounterpartyNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Counterparty Name [Domain]</link:label>
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    <link:label id="lab_skwd_ContingentlyIssuableInstrumentsMember_32c067ed-b074-4463-8bef-b083e1586649_terseLabel_en-US" xlink:label="lab_skwd_ContingentlyIssuableInstrumentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Contingently issuable instruments</link:label>
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    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearTwo_e744e5e3-73a5-44c9-af58-54119903cf36_terseLabel_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearTwo" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2025</link:label>
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    <link:label id="lab_ecd_StkPrcOrTsrEstimationMethodTextBlock_terseLabel_en-US" xlink:label="lab_ecd_StkPrcOrTsrEstimationMethodTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stock Price or TSR Estimation Method</link:label>
    <link:label id="lab_ecd_StkPrcOrTsrEstimationMethodTextBlock_label_en-US" xlink:label="lab_ecd_StkPrcOrTsrEstimationMethodTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Stock Price or TSR Estimation Method [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_StkPrcOrTsrEstimationMethodTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_StkPrcOrTsrEstimationMethodTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_StkPrcOrTsrEstimationMethodTextBlock" xlink:to="lab_ecd_StkPrcOrTsrEstimationMethodTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_PurchaseOfCommonStockMember_ddc5599b-cadf-4c0a-8fb6-4672a6d68c87_terseLabel_en-US" xlink:label="lab_skwd_PurchaseOfCommonStockMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Purchase Of Common Stock</link:label>
    <link:label id="lab_skwd_PurchaseOfCommonStockMember_label_en-US" xlink:label="lab_skwd_PurchaseOfCommonStockMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Purchase Of Common Stock [Member]</link:label>
    <link:label id="lab_skwd_PurchaseOfCommonStockMember_documentation_en-US" xlink:label="lab_skwd_PurchaseOfCommonStockMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Purchase Of Common Stock</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_PurchaseOfCommonStockMember" xlink:href="skwd-20231231.xsd#skwd_PurchaseOfCommonStockMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_PurchaseOfCommonStockMember" xlink:to="lab_skwd_PurchaseOfCommonStockMember" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_SecurityExchangeName_c54957d3-242b-4688-a2f4-81802b4ef614_terseLabel_en-US" xlink:label="lab_dei_SecurityExchangeName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Security Exchange Name</link:label>
    <link:label id="lab_dei_SecurityExchangeName_label_en-US" xlink:label="lab_dei_SecurityExchangeName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Security Exchange Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_SecurityExchangeName" xlink:href="https://xbrl.sec.gov/dei/2023/dei-2023.xsd#dei_SecurityExchangeName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_SecurityExchangeName" xlink:to="lab_dei_SecurityExchangeName" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ProceedsFromPaymentsForDepositAccounting_9164848f-bf42-41ee-acfc-e7a07c8b46b1_terseLabel_en-US" xlink:label="lab_skwd_ProceedsFromPaymentsForDepositAccounting" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash provided by deposit accounting</link:label>
    <link:label id="lab_skwd_ProceedsFromPaymentsForDepositAccounting_label_en-US" xlink:label="lab_skwd_ProceedsFromPaymentsForDepositAccounting" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds From (Payments For) Deposit Accounting</link:label>
    <link:label id="lab_skwd_ProceedsFromPaymentsForDepositAccounting_documentation_en-US" xlink:label="lab_skwd_ProceedsFromPaymentsForDepositAccounting" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Proceeds From (Payments For) Deposit Accounting</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ProceedsFromPaymentsForDepositAccounting" xlink:href="skwd-20231231.xsd#skwd_ProceedsFromPaymentsForDepositAccounting"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ProceedsFromPaymentsForDepositAccounting" xlink:to="lab_skwd_ProceedsFromPaymentsForDepositAccounting" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CededCreditRiskReinsurerDomain_e3580638-2483-4fb4-8ca0-2242947bdefc_terseLabel_en-US" xlink:label="lab_us-gaap_CededCreditRiskReinsurerDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurer, Name [Domain]</link:label>
    <link:label id="lab_us-gaap_CededCreditRiskReinsurerDomain_label_en-US" xlink:label="lab_us-gaap_CededCreditRiskReinsurerDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurer, Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CededCreditRiskReinsurerDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_CededCreditRiskReinsurerDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CededCreditRiskReinsurerDomain" xlink:to="lab_us-gaap_CededCreditRiskReinsurerDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationOptionAndIncentivePlansPolicy_64c044c6-6d28-4cf4-a30c-099b20707701_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationOptionAndIncentivePlansPolicy" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stock Based Compensation</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationOptionAndIncentivePlansPolicy_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationOptionAndIncentivePlansPolicy" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Payment Arrangement [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationOptionAndIncentivePlansPolicy" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShareBasedCompensationOptionAndIncentivePlansPolicy"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationOptionAndIncentivePlansPolicy" xlink:to="lab_us-gaap_ShareBasedCompensationOptionAndIncentivePlansPolicy" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable_02efc48a-4dbe-4da5-9bac-2e2437be3783_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment Income [Table]</link:label>
    <link:label id="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment Income [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:to="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_LoansHeldForInvestmentTerm_56306159-52e1-4c0f-969c-cf768fef7677_terseLabel_en-US" xlink:label="lab_skwd_LoansHeldForInvestmentTerm" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Loans held-for-investment, term</link:label>
    <link:label id="lab_skwd_LoansHeldForInvestmentTerm_label_en-US" xlink:label="lab_skwd_LoansHeldForInvestmentTerm" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Loans Held-for-Investment, Term</link:label>
    <link:label id="lab_skwd_LoansHeldForInvestmentTerm_documentation_en-US" xlink:label="lab_skwd_LoansHeldForInvestmentTerm" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Loans Held-for-Investment, Term</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_LoansHeldForInvestmentTerm" xlink:href="skwd-20231231.xsd#skwd_LoansHeldForInvestmentTerm"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_LoansHeldForInvestmentTerm" xlink:to="lab_skwd_LoansHeldForInvestmentTerm" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerNumberOfPositions_a0843b9c-8341-4de1-b55c-1bc045bf6547_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerNumberOfPositions" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Unrealized loss position aged over 12 months, number of positions</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerNumberOfPositions_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerNumberOfPositions" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Continuous Unrealized Loss Position, 12 Months or Longer, Number of Positions</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerNumberOfPositions" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerNumberOfPositions"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerNumberOfPositions" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerNumberOfPositions" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax_33120c38-9258-459e-a6f1-726737bd3c05_terseLabel_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax" 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_AccumulatedOtherComprehensiveIncomeLossNetOfTax_label_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Accumulated Other Comprehensive Income (Loss), Net of Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax" xlink:to="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EmployeeStockOptionMember_0fbf287a-0558-4243-8318-a99dcf8b9013_terseLabel_en-US" xlink:label="lab_us-gaap_EmployeeStockOptionMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Awarded options</link:label>
    <link:label id="lab_us-gaap_EmployeeStockOptionMember_label_en-US" xlink:label="lab_us-gaap_EmployeeStockOptionMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Employee Stock Option [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EmployeeStockOptionMember" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_EmployeeStockOptionMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EmployeeStockOptionMember" xlink:to="lab_us-gaap_EmployeeStockOptionMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2019Member_5c1939c0-83a8-4bf0-939f-7946ffa7b5bd_terseLabel_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2019Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accident Year 2019</link:label>
    <link:label id="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2019Member_label_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2019Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contract, Accident Year 2019 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortDurationInsuranceContractAccidentYear2019Member" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShortDurationInsuranceContractAccidentYear2019Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortDurationInsuranceContractAccidentYear2019Member" xlink:to="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2019Member" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_UnsecuredSubordinatedNotesDue2039Member_dd0c4dfd-2215-49f6-b1b0-6368a7e932f9_terseLabel_en-US" xlink:label="lab_skwd_UnsecuredSubordinatedNotesDue2039Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subordinate Debt Due 2039</link:label>
    <link:label id="lab_skwd_UnsecuredSubordinatedNotesDue2039Member_label_en-US" xlink:label="lab_skwd_UnsecuredSubordinatedNotesDue2039Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Unsecured Subordinated Notes Due 2039 [Member]</link:label>
    <link:label id="lab_skwd_UnsecuredSubordinatedNotesDue2039Member_documentation_en-US" xlink:label="lab_skwd_UnsecuredSubordinatedNotesDue2039Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Unsecured Subordinated Notes Due 2039</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_UnsecuredSubordinatedNotesDue2039Member" xlink:href="skwd-20231231.xsd#skwd_UnsecuredSubordinatedNotesDue2039Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_UnsecuredSubordinatedNotesDue2039Member" xlink:to="lab_skwd_UnsecuredSubordinatedNotesDue2039Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentPolicyTextBlock_e02d4e86-df73-47fb-b7e7-0dc002fa5d98_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentPolicyTextBlock" 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_InvestmentPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_InvestmentPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investment, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_InvestmentPolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentPolicyTextBlock" xlink:to="lab_us-gaap_InvestmentPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_MaximumMember_2bf4aacf-b9c8-4667-aefd-d9a9d467fd8b_terseLabel_en-US" xlink:label="lab_srt_MaximumMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Maximum</link:label>
    <link:label id="lab_srt_MaximumMember_label_en-US" xlink:label="lab_srt_MaximumMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Maximum [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_MaximumMember" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_MaximumMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_MaximumMember" xlink:to="lab_srt_MaximumMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities_ffca423a-6dde-46ed-9c14-5c1b605d4599_negatedTerseLabel_en-US" xlink:label="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Payable for securities sold</link:label>
    <link:label id="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities_label_en-US" xlink:label="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" 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-20231231.xsd#skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities" xlink:to="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DepreciationAmortizationAndAccretionNet_88b8b6d8-e00e-477a-a01d-9aff0f05b1a1_terseLabel_en-US" xlink:label="lab_us-gaap_DepreciationAmortizationAndAccretionNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Depreciation and amortization expense</link:label>
    <link:label id="lab_us-gaap_DepreciationAmortizationAndAccretionNet_label_en-US" xlink:label="lab_us-gaap_DepreciationAmortizationAndAccretionNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Depreciation, Amortization and Accretion, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DepreciationAmortizationAndAccretionNet" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DepreciationAmortizationAndAccretionNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DepreciationAmortizationAndAccretionNet" xlink:to="lab_us-gaap_DepreciationAmortizationAndAccretionNet" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentType_6668daaf-2266-4a96-af36-146d44825045_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_2ea193c1-7ae9-4833-aebe-9ede8e060e3d_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"/>
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    <link:label id="lab_us-gaap_BenefitsLossesAndExpenses_d9846bdc-3671-4639-89d7-39261046f8a7_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_14d3d65b-1d59-49c9-a637-f2724252f02c_terseLabel_en-US" xlink:label="lab_us-gaap_BenefitsLossesAndExpenses" xlink:role="http://www.xbrl.org/2003/role/terseLabel" 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>
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    <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"/>
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    <link:label id="lab_us-gaap_DeferredTaxAssetsOperatingLossCarryforwardsSubjectToExpiration_b02c96d0-7a08-4530-b8c0-0ea07914ef25_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsOperatingLossCarryforwardsSubjectToExpiration" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Deferred tax subject to expiration</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxAssetsOperatingLossCarryforwardsSubjectToExpiration" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DeferredTaxAssetsOperatingLossCarryforwardsSubjectToExpiration"/>
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    <link:label id="lab_srt_CumulativeEffectPeriodOfAdoptionDomain_c9060cee-27c1-44ed-a084-59a2f8e3b1ab_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>
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    <link:loc xlink:type="locator" xlink:label="loc_srt_CumulativeEffectPeriodOfAdoptionDomain" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_CumulativeEffectPeriodOfAdoptionDomain"/>
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    <link:label id="lab_us-gaap_AntidilutiveSecuritiesNameDomain_b4698abf-3fc7-4aa9-b992-4e669be9e912_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_6d69db28-a4ba-456f-b6f3-572282adcc5a_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>
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    <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"/>
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    <link:label id="lab_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock_e1619c62-fa1e-4121-a1df-cb6801b309d3_terseLabel_en-US" xlink:label="lab_us-gaap_DisclosureOfCompensationRelatedCostsShareBasedPaymentsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stock Based Compensation</link:label>
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    <link:label id="lab_us-gaap_DebtSecuritiesUnrealizedGainLossAbstract_0b246764-3f53-4936-92f8-813b5ca85725_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"/>
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    <link:label id="lab_skwd_EverestReinsuranceCoMember_89d0abc6-b79c-4625-8ee1-dd4173e57727_terseLabel_en-US" xlink:label="lab_skwd_EverestReinsuranceCoMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Everest Reinsurance Co</link:label>
    <link:label id="lab_skwd_EverestReinsuranceCoMember_label_en-US" xlink:label="lab_skwd_EverestReinsuranceCoMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Everest Reinsurance Co [Member]</link:label>
    <link:label id="lab_skwd_EverestReinsuranceCoMember_documentation_en-US" xlink:label="lab_skwd_EverestReinsuranceCoMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Everest Reinsurance Co</link:label>
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    <link:label id="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock_498ed7d5-9927-494e-9b67-c51da46828bf_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>
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    <link:label id="lab_skwd_AgencyAgreementMember_1e0fedf1-8efd-44ee-9246-b0c06460189d_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>
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    <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-20231231.xsd#skwd_AgencyAgreementMember"/>
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    <link:label id="lab_us-gaap_PaymentsToAcquireAvailableForSaleSecuritiesDebt_a0295a17-8788-4a39-b666-2d1cf6fa6189_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"/>
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    <link:label id="lab_us-gaap_SecSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersCurrentYearClaimAndClaimAdjustmentExpense_3d95d2d6-5f55-4429-84fc-809cec332661_terseLabel_en-US" xlink:label="lab_us-gaap_SecSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersCurrentYearClaimAndClaimAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Losses and loss adjustment expenses (current year)</link:label>
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    <link:label id="lab_skwd_DeferredIncomeTaxExpenseBenefitTemporaryDifferences_46926e70-22ed-44e2-9adb-39fa0aa939f5_terseLabel_en-US" xlink:label="lab_skwd_DeferredIncomeTaxExpenseBenefitTemporaryDifferences" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Deferred tax expense</link:label>
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    <link:label id="lab_skwd_FixedMaturitiesHeldToMaturityMember_3934cd77-2ded-4cbf-83da-9b72a02f9f67_terseLabel_en-US" xlink:label="lab_skwd_FixedMaturitiesHeldToMaturityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" 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_VariableRateAxis_b89e0005-a446-4ca5-ab15-360738c3badc_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>
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    <link:label id="lab_skwd_ArenaSOPLPMember_0fff02ae-6f4f-4076-9f6f-d6b9d0f8bc3a_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-20231231.xsd#skwd_ArenaSOPLPMember"/>
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    <link:label id="lab_us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities_97c40d3d-82a6-44d1-9c57-6f298de681c0_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accounts payable and accrued liabilities</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Accounts Payable and Accrued Liabilities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities"/>
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    <link:label id="lab_us-gaap_CostsAndExpensesAbstract_b8674a9f-659f-4e09-8379-c7ad97aa1be3_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_566b02f5-0b8c-4821-8900-8acb39fd647f_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_903823c9-3667-4cc5-9a37-6c8a99bc3bf5_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_ba4c7499-1fff-4752-bd30-d08b81a05ab2_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_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestAfterAllowanceForCreditLoss_a438350b-90c0-460a-bab7-43afb44876d6_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_5303f9f9-7f74-48a2-ad89-4bd789fe7da4_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_us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract_1a1e38eb-005a-4055-b221-3b5580178a7b_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">Total fixed maturity securities, available-for-sale</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" 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_833b3391-e46a-44a8-8668-55de267abe70_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_AAndAboveMember_2c46ccb2-7947-487a-ba0d-05f21d12364e_terseLabel_en-US" xlink:label="lab_skwd_AAndAboveMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">A- and above</link:label>
    <link:label id="lab_skwd_AAndAboveMember_label_en-US" xlink:label="lab_skwd_AAndAboveMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">A- and Above [Member]</link:label>
    <link:label id="lab_skwd_AAndAboveMember_documentation_en-US" xlink:label="lab_skwd_AAndAboveMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">A- and Above</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_AAndAboveMember" xlink:href="skwd-20231231.xsd#skwd_AAndAboveMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_AAndAboveMember" xlink:to="lab_skwd_AAndAboveMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommercialPortfolioSegmentMember_73145b8c-ef15-4d51-98e0-5f28a4e4ee7c_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_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill_3d71f31f-7113-42ab-85e3-88788a1c7e4f_periodStartLabel_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Beginning balance</link:label>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill_06f287c7-b3c6-4f36-b300-b9576190de60_periodEndLabel_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Ending balance</link:label>
    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill_label_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Indefinite-Lived Intangible Assets (Excluding Goodwill)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill" xlink:to="lab_us-gaap_IndefiniteLivedIntangibleAssetsExcludingGoodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_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_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue_4353dc18-cbac-4968-83d2-de94f681a03c_periodStartLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Non-vested, beginning period (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue_3aa8e603-2ee9-48fc-af3c-5f74bfd78384_periodEndLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Non-vested, ending period (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Nonvested, Weighted Average Grant Date Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedWeightedAverageGrantDateFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_SubordinatedDebtNetMember_8f8ac535-2096-4c06-9669-b876eb9806cc_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-20231231.xsd#skwd_SubordinatedDebtNetMember"/>
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    <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_us-gaap_SecSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersPriorYearClaimAndClaimAdjustmentExpense_33d65771-4b3b-468a-b7b0-67da15c51b40_terseLabel_en-US" xlink:label="lab_us-gaap_SecSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersPriorYearClaimAndClaimAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Losses and loss adjustment expenses (prior years)</link:label>
    <link:label id="lab_us-gaap_SecSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersPriorYearClaimAndClaimAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_SecSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersPriorYearClaimAndClaimAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-18, Supplemental Information, Property-Casualty Insurance Underwriters, Prior Year Claim and Claim Adjustment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SecSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersPriorYearClaimAndClaimAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_SecSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersPriorYearClaimAndClaimAdjustmentExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SecSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersPriorYearClaimAndClaimAdjustmentExpense" xlink:to="lab_us-gaap_SecSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersPriorYearClaimAndClaimAdjustmentExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_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_ScheduleOfAccountsNotesLoansAndFinancingReceivableTextBlock_952e960c-0e77-431c-931c-19ac6af19817_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"/>
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    <link:label id="lab_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract_label_en-US" xlink:label="lab_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Payment Arrangement [Abstract]</link:label>
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    <link:label id="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2022Member_80b63329-26b1-440b-9e8c-6e937ed1dfd6_terseLabel_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2022Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accident Year 2022</link:label>
    <link:label id="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2022Member_label_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2022Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contract, Accident Year 2022 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortDurationInsuranceContractAccidentYear2022Member" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShortDurationInsuranceContractAccidentYear2022Member"/>
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    <link:label id="lab_us-gaap_LeaseCost_0ad1462e-f5ea-45ed-9121-a706cb11d24b_totalLabel_en-US" xlink:label="lab_us-gaap_LeaseCost" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total lease expense</link:label>
    <link:label id="lab_us-gaap_LeaseCost_label_en-US" xlink:label="lab_us-gaap_LeaseCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Lease, Cost</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LeaseCost" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LeaseCost"/>
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    <link:label id="lab_us-gaap_EmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsCapitalizedAmount_label_en-US" xlink:label="lab_us-gaap_EmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsCapitalizedAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Payment Arrangement, Amount Capitalized</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsCapitalizedAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_EmployeeServiceShareBasedCompensationAllocationOfRecognizedPeriodCostsCapitalizedAmount"/>
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    <link:label id="lab_srt_RangeAxis_e214c7d9-ff4a-4f6e-ad41-e9fc56f43c94_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_srt_CumulativeEffectPeriodOfAdoptionAxis_5db9f9c5-792a-40ab-b4c0-1f811675d1b0_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>
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    <link:loc xlink:type="locator" xlink:label="loc_srt_CumulativeEffectPeriodOfAdoptionAxis" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_CumulativeEffectPeriodOfAdoptionAxis"/>
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    <link:label id="lab_dei_EntityInteractiveDataCurrent_bfc1679c-d161-433a-aa2c-607a1a11f465_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:label id="lab_us-gaap_DisaggregationOfRevenueTable_e26a090e-382f-45d8-be96-e2e0402e3a8e_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>
    <link:label id="lab_us-gaap_DisaggregationOfRevenueTable_label_en-US" xlink:label="lab_us-gaap_DisaggregationOfRevenueTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disaggregation of Revenue [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisaggregationOfRevenueTable" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DisaggregationOfRevenueTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisaggregationOfRevenueTable" xlink:to="lab_us-gaap_DisaggregationOfRevenueTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleTable_d70cf0bd-c19a-4b46-a7f4-86211d552166_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"/>
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    <link:label id="lab_us-gaap_GoodwillAndIntangibleAssetsPolicyTextBlock_049520a6-b30a-4cae-8699-35e6c0415660_terseLabel_en-US" xlink:label="lab_us-gaap_GoodwillAndIntangibleAssetsPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Goodwill and Intangible Assets</link:label>
    <link:label id="lab_us-gaap_GoodwillAndIntangibleAssetsPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_GoodwillAndIntangibleAssetsPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill and Intangible Assets, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillAndIntangibleAssetsPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_GoodwillAndIntangibleAssetsPolicyTextBlock"/>
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    <link:label id="lab_skwd_ReinsuranceRecoveriesUnderTheLPT_9abbd4f6-c75a-43df-bf1e-ee346d16494e_verboseLabel_en-US" xlink:label="lab_skwd_ReinsuranceRecoveriesUnderTheLPT" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Reinsurance recoveries under the LPT</link:label>
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    <link:label id="lab_dei_EntityWellKnownSeasonedIssuer_837dcf14-b810-49fb-a605-826d339b82ca_terseLabel_en-US" xlink:label="lab_dei_EntityWellKnownSeasonedIssuer" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Well-known Seasoned Issuer</link:label>
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    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearFive_208a72eb-1748-4a82-83e1-2a2cd3de0eea_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearFive" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Year 5</link:label>
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    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems_c1bc1127-ce6e-4318-b053-ec5a2affc0d8_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award [Line Items]</link:label>
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    <link:label id="lab_us-gaap_RevenueRecognitionPremiumsEarnedPolicy_0ecaab16-1d1c-4c9d-baf1-cf5cab33e03b_terseLabel_en-US" xlink:label="lab_us-gaap_RevenueRecognitionPremiumsEarnedPolicy" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Premiums</link:label>
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    <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>
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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>
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    <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>
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    <link:label id="lab_dei_EntityIncorporationStateCountryCode_cb8cceab-6af8-4023-a1ce-c5c7723a7e8f_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>
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    <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_ShortdurationInsuranceContractsHistoricalClaimsDurationLineItems_430f2eeb-0856-4918-979b-e04bc77dd03d_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationLineItems"/>
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    <link:label id="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent_cd5899a8-3a90-49ed-a89f-71a251e3fabe_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"/>
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    <link:label id="lab_us-gaap_ScheduleOfDeferredTaxAssetsAndLiabilitiesTableTextBlock_e3a61576-83ff-419a-9c85-d80693d13937_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfDeferredTaxAssetsAndLiabilitiesTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Deferred Tax Assets and Liabilities</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfDeferredTaxAssetsAndLiabilitiesTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ScheduleOfDeferredTaxAssetsAndLiabilitiesTableTextBlock"/>
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    <link:loc xlink:type="locator" xlink:label="loc_skwd_CreditLossTable" xlink:href="skwd-20231231.xsd#skwd_CreditLossTable"/>
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    <link:label id="lab_us-gaap_IncreaseDecreaseInPrepaidReinsurancePremiums_f5564226-4d93-4e63-ba05-56a7447356a2_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInPrepaidReinsurancePremiums" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Ceded unearned premium</link:label>
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    <link:label id="lab_srt_CreditRatingAMBestDomain_label_en-US" xlink:label="lab_srt_CreditRatingAMBestDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Credit Rating, AM Best [Domain]</link:label>
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    <link:label id="lab_us-gaap_ReinsuranceRecoverables_b658b408-1531-401d-ad02-7b1dd3d1035b_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverables" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurance collateral from reinsurers</link:label>
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    <link:label id="lab_ecd_PeoMember_terseLabel_en-US" xlink:label="lab_ecd_PeoMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">PEO</link:label>
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    <link:label id="lab_us-gaap_EquityMethodInvestmentsMember_58f80063-c080-41b3-b7df-881573d80889_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_us-gaap_ShortdurationInsuranceContractsAccidentYearDomain_0cd0c713-3c17-4da9-a1a2-d6ab701ccba8_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsAccidentYearDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contracts, Accident Year [Domain]</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsAccidentYearDomain_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsAccidentYearDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contracts, Accident Year [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsAccidentYearDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShortdurationInsuranceContractsAccidentYearDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsAccidentYearDomain" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsAccidentYearDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_TermLoanDueDecember2024Member_8b49e9f6-8773-45df-bd51-31d22f5d1eac_terseLabel_en-US" xlink:label="lab_skwd_TermLoanDueDecember2024Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Term loan</link:label>
    <link:label id="lab_skwd_TermLoanDueDecember2024Member_label_en-US" xlink:label="lab_skwd_TermLoanDueDecember2024Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Term Loan Due December 2024 [Member]</link:label>
    <link:label id="lab_skwd_TermLoanDueDecember2024Member_documentation_en-US" xlink:label="lab_skwd_TermLoanDueDecember2024Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Term Loan Due December 2024</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_TermLoanDueDecember2024Member" xlink:href="skwd-20231231.xsd#skwd_TermLoanDueDecember2024Member"/>
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    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsGrantsInPeriodFairValue_b0ac4545-7589-47df-98fa-0c24029bf52e_terseLabel_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsGrantsInPeriodFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stock options granted to employees</link:label>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsGrantsInPeriodFairValue_label_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsGrantsInPeriodFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Options, Grants in Period, Fair Value</link:label>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsGrantsInPeriodFairValue_documentation_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsGrantsInPeriodFairValue" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Options, Grants in Period, Fair Value</link:label>
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    <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>
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    <link:label id="lab_us-gaap_AllowanceForDoubtfulAccountsPremiumsAndOtherReceivables_ed19da8a-0450-4cec-9f60-5ca87479a18b_terseLabel_en-US" xlink:label="lab_us-gaap_AllowanceForDoubtfulAccountsPremiumsAndOtherReceivables" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Allowance for premiums receivable</link:label>
    <link:label id="lab_us-gaap_AllowanceForDoubtfulAccountsPremiumsAndOtherReceivables_label_en-US" xlink:label="lab_us-gaap_AllowanceForDoubtfulAccountsPremiumsAndOtherReceivables" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Allowance for Doubtful Accounts, Premiums and Other Receivables</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AllowanceForDoubtfulAccountsPremiumsAndOtherReceivables" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_AllowanceForDoubtfulAccountsPremiumsAndOtherReceivables"/>
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    <link:label id="lab_us-gaap_InvestmentsInAffiliatesSubsidiariesAssociatesAndJointVentures_c02f7177-9aca-4746-a205-4a24cbd1574d_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentsInAffiliatesSubsidiariesAssociatesAndJointVentures" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment in subsidiaries</link:label>
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    <link:label id="lab_us-gaap_PreferredStockMember_4d87b4b6-763e-46f8-97e2-37c93d1d588a_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_fb69e453-7fc4-47e7-8896-e29bc23b87a0_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">Total preferred stocks</link:label>
    <link:label id="lab_us-gaap_PreferredStockMember_fd9d9397-7aa7-4c7f-8937-6b0b7d4af0f1_verboseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" 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>
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    <link:label id="lab_us-gaap_EquitySecuritiesMember_8419df9a-c877-4858-a5c0-64c2bc1a8170_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"/>
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    <link:label id="lab_us-gaap_SupplementalCashFlowInformationAbstract_a9d5cc2b-1cf7-4069-82e6-59efc8cfbb25_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>
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    <link:label id="lab_us-gaap_CededCreditRiskLineItems_4a3c97a6-4f9f-4bb3-bedd-63ca8bf38971_terseLabel_en-US" xlink:label="lab_us-gaap_CededCreditRiskLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ceded Credit Risk [Line Items]</link:label>
    <link:label id="lab_us-gaap_CededCreditRiskLineItems_label_en-US" xlink:label="lab_us-gaap_CededCreditRiskLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Ceded Credit Risk [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CededCreditRiskLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_CededCreditRiskLineItems"/>
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    <link:label id="lab_skwd_JuniorSubordinatedInterestDebenturesMember_5f9baa5d-6fdb-4381-9489-99478b2da1e5_terseLabel_en-US" xlink:label="lab_skwd_JuniorSubordinatedInterestDebenturesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Junior subordinated interest debentures</link:label>
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    <link:label id="lab_skwd_JuniorSubordinatedInterestDebenturesMember_documentation_en-US" xlink:label="lab_skwd_JuniorSubordinatedInterestDebenturesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Junior Subordinated Interest Debentures</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_JuniorSubordinatedInterestDebenturesMember" xlink:href="skwd-20231231.xsd#skwd_JuniorSubordinatedInterestDebenturesMember"/>
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    <link:label id="lab_us-gaap_EarningsPerSharePolicyTextBlock_59fcce8e-8611-4161-a57c-a4ccee9f55e5_terseLabel_en-US" xlink:label="lab_us-gaap_EarningsPerSharePolicyTextBlock" 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_EarningsPerSharePolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_EarningsPerSharePolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Earnings Per Share, Policy [Policy Text Block]</link:label>
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    <link:label id="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock_652dd2e8-ac8c-4d19-a2a9-fb8a88e3ce8b_terseLabel_en-US" xlink:label="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Goodwill and Intangible Assets</link:label>
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    <link:label id="lab_skwd_CaptexBancsharesMember_afd1cdf4-9957-45e6-9d29-2e377cbd9112_terseLabel_en-US" xlink:label="lab_skwd_CaptexBancsharesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Captex Bancshares</link:label>
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    <link:label id="lab_skwd_CaptexBancsharesMember_documentation_en-US" xlink:label="lab_skwd_CaptexBancsharesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Captex Bancshares</link:label>
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    <link:label id="lab_us-gaap_ConcentrationRiskPercentage1_0dd96cb1-1d59-4d72-9bf1-f9cd79be6eab_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskPercentage1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Concentration risk, percentage</link:label>
    <link:label id="lab_us-gaap_ConcentrationRiskPercentage1_label_en-US" xlink:label="lab_us-gaap_ConcentrationRiskPercentage1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Concentration Risk, Percentage</link:label>
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    <link:label id="lab_us-gaap_PreferredStockConvertibleConversionPrice_bf1e1b2d-adae-4239-b736-4aa58e343f4e_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockConvertibleConversionPrice" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Preferred stock, convertible, conversion price (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_PreferredStockConvertibleConversionPrice_label_en-US" xlink:label="lab_us-gaap_PreferredStockConvertibleConversionPrice" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Preferred Stock, Convertible, Conversion Price</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockConvertibleConversionPrice" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PreferredStockConvertibleConversionPrice"/>
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    <link:label id="lab_us-gaap_DeferredTaxAssetsGross_label_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Tax Assets, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxAssetsGross" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DeferredTaxAssetsGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredTaxAssetsGross" xlink:to="lab_us-gaap_DeferredTaxAssetsGross" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ParentCompanyMember_3a40841f-48d3-4b21-8798-2083348899c7_terseLabel_en-US" xlink:label="lab_srt_ParentCompanyMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Parent Company</link:label>
    <link:label id="lab_srt_ParentCompanyMember_label_en-US" xlink:label="lab_srt_ParentCompanyMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Parent Company [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ParentCompanyMember" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_ParentCompanyMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ParentCompanyMember" xlink:to="lab_srt_ParentCompanyMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_MarketConditionAwardsMember_b07905b9-2faf-45c4-ac9a-c49eb9704c8c_terseLabel_en-US" xlink:label="lab_skwd_MarketConditionAwardsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Market condition awards</link:label>
    <link:label id="lab_skwd_MarketConditionAwardsMember_label_en-US" xlink:label="lab_skwd_MarketConditionAwardsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Market Condition Awards [Member]</link:label>
    <link:label id="lab_skwd_MarketConditionAwardsMember_documentation_en-US" xlink:label="lab_skwd_MarketConditionAwardsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Market Condition Awards</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_MarketConditionAwardsMember" xlink:href="skwd-20231231.xsd#skwd_MarketConditionAwardsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_MarketConditionAwardsMember" xlink:to="lab_skwd_MarketConditionAwardsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueNextTwelveMonths_0debf2a0-b42d-4130-ad3d-d734499f3fb5_terseLabel_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueNextTwelveMonths" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2024</link:label>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueNextTwelveMonths_label_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueNextTwelveMonths" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Lessee, Operating Lease, Liability, to be Paid, Year One</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueNextTwelveMonths" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueNextTwelveMonths"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueNextTwelveMonths" xlink:to="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueNextTwelveMonths" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts_ef2c1e6e-d50b-4505-bb34-bb749dcf6c57_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Deferred policy acquisition costs</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Deferred Policy Acquisition Costs</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts" xlink:to="lab_us-gaap_IncreaseDecreaseInDeferredPolicyAcquisitionCosts" xlink:type="arc" order="1"/>
    <link:label id="lab_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_5b02a0a5-9e39-4c5e-b8a7-ba14d1d571a3_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_us-gaap_CommonStockMember_104e03c9-2d2d-49f7-9dc1-3d2910d751ee_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_b44af4d6-6e0d-45c1-9a8c-a863f960df3c_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">Total common stocks</link:label>
    <link:label id="lab_us-gaap_CommonStockMember_b8f61533-a54d-4fc0-a85f-8d64a4f6f703_verboseLabel_en-US" xlink:label="lab_us-gaap_CommonStockMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" 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_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPaidClaimsAndClaimsAdjustmentExpense_d0741bc8-a114-42ad-99f3-7dd3159a90ff_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPaidClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Paid claims and claim adjustment expenses</link:label>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPaidClaimsAndClaimsAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPaidClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-18, Supplemental Information, Property-Casualty Insurance Underwriters, Paid Claim and Claim Adjustment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPaidClaimsAndClaimsAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPaidClaimsAndClaimsAdjustmentExpense"/>
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    <link:label id="lab_us-gaap_ValuationAllowancesAndReservesTypeAxis_8fd32c59-3782-4364-a9ea-c1e2633e95cb_terseLabel_en-US" xlink:label="lab_us-gaap_ValuationAllowancesAndReservesTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-09, Valuation Allowances and Reserves Type [Axis]</link:label>
    <link:label id="lab_us-gaap_ValuationAllowancesAndReservesTypeAxis_label_en-US" xlink:label="lab_us-gaap_ValuationAllowancesAndReservesTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-09, Valuation Allowances and Reserves Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ValuationAllowancesAndReservesTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ValuationAllowancesAndReservesTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ValuationAllowancesAndReservesTypeAxis" xlink:to="lab_us-gaap_ValuationAllowancesAndReservesTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressPostalZipCode_4cf2221f-c7a7-4ed3-9b9a-b5da0a8bc399_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_skwd_FollowOnOfferingSharesFromCompanyMember_37c2d62c-6056-42d5-92a5-70293b4f3c04_terseLabel_en-US" xlink:label="lab_skwd_FollowOnOfferingSharesFromCompanyMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Follow-On Offering - Shares From Company</link:label>
    <link:label id="lab_skwd_FollowOnOfferingSharesFromCompanyMember_label_en-US" xlink:label="lab_skwd_FollowOnOfferingSharesFromCompanyMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Follow-On Offering - Shares From Company [Member]</link:label>
    <link:label id="lab_skwd_FollowOnOfferingSharesFromCompanyMember_documentation_en-US" xlink:label="lab_skwd_FollowOnOfferingSharesFromCompanyMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Follow-On Offering - Shares From Company</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_FollowOnOfferingSharesFromCompanyMember" xlink:href="skwd-20231231.xsd#skwd_FollowOnOfferingSharesFromCompanyMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_FollowOnOfferingSharesFromCompanyMember" xlink:to="lab_skwd_FollowOnOfferingSharesFromCompanyMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ValuationAllowancesAndReservesDomain_70220c81-8412-4fcc-af61-03aef5d52bd4_terseLabel_en-US" xlink:label="lab_us-gaap_ValuationAllowancesAndReservesDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-09, Valuation Allowances and Reserves [Domain]</link:label>
    <link:label id="lab_us-gaap_ValuationAllowancesAndReservesDomain_label_en-US" xlink:label="lab_us-gaap_ValuationAllowancesAndReservesDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-09, Valuation Allowances and Reserves [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ValuationAllowancesAndReservesDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ValuationAllowancesAndReservesDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ValuationAllowancesAndReservesDomain" xlink:to="lab_us-gaap_ValuationAllowancesAndReservesDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForFuturePolicyBenefitsAndUnpaidClaimsDisclosureTextBlock_f12cd49c-ac95-49f5-a5cf-f3ad7f392d99_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">Reserves for Losses and Loss Adjustment Expenses</link:label>
    <link:label id="lab_us-gaap_LiabilityForFuturePolicyBenefitsAndUnpaidClaimsDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_LiabilityForFuturePolicyBenefitsAndUnpaidClaimsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" 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_37c7ee9c-9349-40c6-8333-a155a96f6dc7_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>
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    <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_us-gaap_InvestmentsAbstract_e3e25476-718f-4c09-b32c-5da58955a8c8_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_44ff973f-a1e1-457e-a310-08ba2b825052_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_3dbedafb-257a-4ed1-a406-aa8bb3572b88_terseLabel_en-US" xlink:label="lab_srt_MinimumMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Minimum</link:label>
    <link:label id="lab_srt_MinimumMember_label_en-US" xlink:label="lab_srt_MinimumMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" 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_PropertyPlantAndEquipmentNet_3c0fa39a-6684-4aa9-992c-ae0303c389fc_totalLabel_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentNet_label_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Property, Plant and Equipment, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentNet" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PropertyPlantAndEquipmentNet"/>
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    <link:label id="lab_srt_CondensedBalanceSheetStatementTable_4737c102-957c-4eae-bb09-473795d1c316_terseLabel_en-US" xlink:label="lab_srt_CondensedBalanceSheetStatementTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Condensed Balance Sheet Statement [Table]</link:label>
    <link:label id="lab_srt_CondensedBalanceSheetStatementTable_label_en-US" xlink:label="lab_srt_CondensedBalanceSheetStatementTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Condensed Balance Sheet Statement [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_CondensedBalanceSheetStatementTable" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_CondensedBalanceSheetStatementTable"/>
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    <link:label id="lab_skwd_IncreaseDecreaseInDeferredCedingCommission_47ca6cfd-4dd8-48dc-935c-0a27940058c5_terseLabel_en-US" xlink:label="lab_skwd_IncreaseDecreaseInDeferredCedingCommission" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Deferred ceding commission</link:label>
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    <link:label id="lab_skwd_IncreaseDecreaseInDeferredCedingCommission_documentation_en-US" xlink:label="lab_skwd_IncreaseDecreaseInDeferredCedingCommission" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Deferred Ceding Commission</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_IncreaseDecreaseInDeferredCedingCommission" xlink:href="skwd-20231231.xsd#skwd_IncreaseDecreaseInDeferredCedingCommission"/>
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    <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_3e6f9700-dfcf-42ca-b083-f0ff9914f1f8_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_56ab52ef-db98-4e20-ac46-04e96f181143_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_42777027-bebf-41a9-b296-2768ec1d8a6e_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_d66111c6-41c4-46d4-870f-4114c4cf768e_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_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_ac9d995d-81e7-4561-b51d-97181fd6f1dc_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"/>
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    <link:label id="lab_srt_ScheduleOfValuationAndQualifyingAccountsDisclosureTextBlock_f4c2f5ff-456a-4bb2-9ae8-f79eff724db4_terseLabel_en-US" xlink:label="lab_srt_ScheduleOfValuationAndQualifyingAccountsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">SCHEDULE V&#160;&#8212; VALUATION AND QUALIFYING ACCOUNTS</link:label>
    <link:label id="lab_srt_ScheduleOfValuationAndQualifyingAccountsDisclosureTextBlock_label_en-US" xlink:label="lab_srt_ScheduleOfValuationAndQualifyingAccountsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-09, Schedule of Valuation and Qualifying Accounts Disclosure [Text Block]</link:label>
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    <link:label id="lab_us-gaap_DeferredTaxAssetsOther_1b88a088-8a3a-4ad7-9b28-0cb80d16f59d_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsOther" 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_DeferredTaxAssetsOther_label_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsOther" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Tax Assets, Other</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxAssetsOther" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DeferredTaxAssetsOther"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredTaxAssetsOther" xlink:to="lab_us-gaap_DeferredTaxAssetsOther" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilitiesAbstract_c48f8acc-1003-4aa9-805e-17378e5cd418_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>
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    <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_5ca1b712-7567-418f-8595-4c206f025d82_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 provided by financing activities</link:label>
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    <link:label id="lab_us-gaap_DeferredIncomeTaxAssetsNet_08f8c9c7-15ca-439c-b31a-614a2a6fd210_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, net</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>
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    <link:label id="lab_us-gaap_CommercialAndIndustrialSectorMember_4e0bae6b-1336-450f-b770-ddd39af958e9_terseLabel_en-US" xlink:label="lab_us-gaap_CommercialAndIndustrialSectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Industrial</link:label>
    <link:label id="lab_us-gaap_CommercialAndIndustrialSectorMember_label_en-US" xlink:label="lab_us-gaap_CommercialAndIndustrialSectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Commercial and Industrial Sector [Member]</link:label>
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    <link:label id="lab_us-gaap_LesseeLeaseDescriptionLineItems_c322bc26-cde3-422d-9123-c8be9420dd70_terseLabel_en-US" xlink:label="lab_us-gaap_LesseeLeaseDescriptionLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Lessee, Lease, Description [Line Items]</link:label>
    <link:label id="lab_us-gaap_LesseeLeaseDescriptionLineItems_label_en-US" xlink:label="lab_us-gaap_LesseeLeaseDescriptionLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Lessee, Lease, Description [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeLeaseDescriptionLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LesseeLeaseDescriptionLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LesseeLeaseDescriptionLineItems" xlink:to="lab_us-gaap_LesseeLeaseDescriptionLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock_22550864-c6be-4a63-ba9f-f213bdf817ba_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>
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    <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>
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    <link:label id="lab_skwd_LineOfCreditFacilityAccordionFeatureIncreaseLimit_768a5798-33b7-4d30-9d87-e6b87f5f9660_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>
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    <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</link:label>
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    <link:label id="lab_skwd_PaymentsToAcquireHeldToMaturitySecuritiesAndEquityMethodInvestments_add8d982-ef7b-40a2-84cf-aed932fe5f4f_negatedTerseLabel_en-US" xlink:label="lab_skwd_PaymentsToAcquireHeldToMaturitySecuritiesAndEquityMethodInvestments" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Purchase of illiquid investments</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_skwd_PaymentsToAcquireHeldToMaturitySecuritiesAndEquityMethodInvestments" xlink:href="skwd-20231231.xsd#skwd_PaymentsToAcquireHeldToMaturitySecuritiesAndEquityMethodInvestments"/>
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    <link:label id="lab_skwd_MortgageLoansMember_90c1a2c9-4254-4b34-9f58-9f3afd74bf75_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-20231231.xsd#skwd_MortgageLoansMember"/>
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    <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>
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    <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_DebtSecuritiesHeldToMaturityExcludingAccruedInterestBeforeAllowanceForCreditLoss_44a2cc34-14e4-499d-bef1-4b7167fe418b_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_6d962c7d-1c11-4fd6-9e02-eef7288ea3f2_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 per share (in dollars 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_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_us-gaap_SaleOfStockNameOfTransactionDomain_ed1f9caa-0e70-4ed7-9c51-9c477e58c1b6_terseLabel_en-US" xlink:label="lab_us-gaap_SaleOfStockNameOfTransactionDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Sale of Stock [Domain]</link:label>
    <link:label id="lab_us-gaap_SaleOfStockNameOfTransactionDomain_label_en-US" xlink:label="lab_us-gaap_SaleOfStockNameOfTransactionDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Sale of Stock [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SaleOfStockNameOfTransactionDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_SaleOfStockNameOfTransactionDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SaleOfStockNameOfTransactionDomain" xlink:to="lab_us-gaap_SaleOfStockNameOfTransactionDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_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_skwd_DeferredTaxAssetsOperatingLossCarryforwardsSubjectToExpirationTaxEffected_3f75d876-4698-4c1b-9367-6d0dcb8e277f_terseLabel_en-US" xlink:label="lab_skwd_DeferredTaxAssetsOperatingLossCarryforwardsSubjectToExpirationTaxEffected" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Deferred tax effected by expiration</link:label>
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    <link:label id="lab_skwd_DeferredTaxAssetsOperatingLossCarryforwardsSubjectToExpirationTaxEffected_documentation_en-US" xlink:label="lab_skwd_DeferredTaxAssetsOperatingLossCarryforwardsSubjectToExpirationTaxEffected" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Deferred Tax Assets, Operating Loss Carryforwards, Subject to Expiration, Tax Effected</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DeferredTaxAssetsOperatingLossCarryforwardsSubjectToExpirationTaxEffected" xlink:href="skwd-20231231.xsd#skwd_DeferredTaxAssetsOperatingLossCarryforwardsSubjectToExpirationTaxEffected"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DeferredTaxAssetsOperatingLossCarryforwardsSubjectToExpirationTaxEffected" xlink:to="lab_skwd_DeferredTaxAssetsOperatingLossCarryforwardsSubjectToExpirationTaxEffected" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearSeven_9cbd7544-41a0-4ca2-8c77-8d69aedb7994_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearSeven" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Year 7</link:label>
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    <link:label id="lab_us-gaap_DeferredTaxAssetsLiabilitiesNet_63d41ec7-89b0-4d4e-b2c3-7aab21cadf70_totalLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsLiabilitiesNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Deferred income taxes</link:label>
    <link:label id="lab_us-gaap_DeferredTaxAssetsLiabilitiesNet_label_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsLiabilitiesNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Tax Assets, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxAssetsLiabilitiesNet" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DeferredTaxAssetsLiabilitiesNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredTaxAssetsLiabilitiesNet" xlink:to="lab_us-gaap_DeferredTaxAssetsLiabilitiesNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReceivablesFromStockholderMember_8b49e257-b666-4b7b-adb6-b8f893c94bd6_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"/>
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    <link:label id="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccounts_4c3a5f21-2bce-4e45-a7d2-373a6d5b40d0_periodStartLabel_en-US" xlink:label="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccounts" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Allowance for Estimated Uncollectible Premiums, beginning balance</link:label>
    <link:label id="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccounts_b4bbb7a6-6e01-44a8-89c4-34acb6af6392_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccounts" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cumulative effect of adoption of ASU 2016-13 at January 1, 2023</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccounts" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PremiumsReceivableAllowanceForDoubtfulAccounts"/>
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    <link:label id="lab_skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod_3b4fbb25-3205-422a-8134-2dad2d5d55ce_terseLabel_en-US" xlink:label="lab_skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Useful life</link:label>
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    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract_77f1ce86-3f76-44a2-9e84-917cfe57053c_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Paid, net of reinsurance, related to:</link:label>
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    <link:label id="lab_us-gaap_TechnologySectorMember_92fa2946-cca2-4ecf-9987-0c147f0800a1_terseLabel_en-US" xlink:label="lab_us-gaap_TechnologySectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Information technology</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAccumulatedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAccumulatedLoss"/>
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    <link:label id="lab_us-gaap_DebtInstrumentPeriodicPaymentInterest_bdf7615e-9290-46de-8a2b-46ed24effa76_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentPeriodicPaymentInterest" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Interest payments on terminated term loan</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentPeriodicPaymentInterest_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentPeriodicPaymentInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Periodic Payment, Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentPeriodicPaymentInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DebtInstrumentPeriodicPaymentInterest"/>
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    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentAbstract_label_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Property, Plant and Equipment [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PropertyPlantAndEquipmentAbstract"/>
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    <link:label id="lab_skwd_LossOnSaleOfOtherInvestments_78007037-a5b7-467e-b13a-750e4890a738_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>
    <link:label id="lab_skwd_LossOnSaleOfOtherInvestments_label_en-US" xlink:label="lab_skwd_LossOnSaleOfOtherInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Loss on Sale of Other Investments</link:label>
    <link:label id="lab_skwd_LossOnSaleOfOtherInvestments_documentation_en-US" xlink:label="lab_skwd_LossOnSaleOfOtherInvestments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Loss on Sale of Other Investments</link:label>
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    <link:label id="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_8d66915e-b386-4551-a80a-4c8487053b03_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_12300428-417c-4545-8091-607f381254df_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>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_a91cdc73-06ba-4c7f-9580-5ee0f396f0dc_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total reinsurance recoverable on unpaid claims</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_e966f535-505d-43ae-9c12-01058ec8da6e_verboseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Ceded unpaid losses and LAE</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverable for Unpaid Claims and Claims Adjustments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments"/>
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    <link:label id="lab_us-gaap_ReinsuranceRecoverableAllowanceForCreditLossRollForward_23ed43fc-a7bf-4267-b35a-5094ea55c8d6_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableAllowanceForCreditLossRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverable, Allowance for Credit Loss [Roll Forward]</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableAllowanceForCreditLossRollForward_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableAllowanceForCreditLossRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverable, Allowance for Credit Loss [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverableAllowanceForCreditLossRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ReinsuranceRecoverableAllowanceForCreditLossRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverableAllowanceForCreditLossRollForward" xlink:to="lab_us-gaap_ReinsuranceRecoverableAllowanceForCreditLossRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentCarryingAmount_cd1ff010-500b-4504-8c6f-a5e8df0584dc_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentCarryingAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Principal</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentCarryingAmount_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentCarryingAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Long-Term Debt, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentCarryingAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DebtInstrumentCarryingAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentCarryingAmount" xlink:to="lab_us-gaap_DebtInstrumentCarryingAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_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_LimitedLiabilityCompanyLLCOrLimitedPartnershipLPManagingMemberOrGeneralPartnerOwnershipInterest_70097176-0773-4d51-ac9b-f6cba1145485_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_4d04f9a5-c9ae-4a8b-b02c-c878c36f8083_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_us-gaap_CashAndCashEquivalentsRestrictedCashAndCashEquivalentsPolicy_8758a19a-2920-45ac-9a5e-a5f11fdf868a_terseLabel_en-US" xlink:label="lab_us-gaap_CashAndCashEquivalentsRestrictedCashAndCashEquivalentsPolicy" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Restricted Cash</link:label>
    <link:label id="lab_us-gaap_CashAndCashEquivalentsRestrictedCashAndCashEquivalentsPolicy_label_en-US" xlink:label="lab_us-gaap_CashAndCashEquivalentsRestrictedCashAndCashEquivalentsPolicy" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash and Cash Equivalents, Restricted Cash and Cash Equivalents, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashAndCashEquivalentsRestrictedCashAndCashEquivalentsPolicy" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_CashAndCashEquivalentsRestrictedCashAndCashEquivalentsPolicy"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CashAndCashEquivalentsRestrictedCashAndCashEquivalentsPolicy" xlink:to="lab_us-gaap_CashAndCashEquivalentsRestrictedCashAndCashEquivalentsPolicy" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardPurchasePeriod_41e3b35b-792e-486c-b29f-b6791be751ab_terseLabel_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardPurchasePeriod" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Purchase period</link:label>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardPurchasePeriod_label_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardPurchasePeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement By Share-based Payment Award, Purchase Period</link:label>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardPurchasePeriod_documentation_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardPurchasePeriod" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement By Share-based Payment Award, Purchase Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardPurchasePeriod" xlink:href="skwd-20231231.xsd#skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardPurchasePeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardPurchasePeriod" xlink:to="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardPurchasePeriod" 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_ShortdurationInsuranceContractsNumberOfReportedClaims_60ff21c4-1e11-417a-9c81-02acc33b456d_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsNumberOfReportedClaims" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contract, Cumulative Number of Reported Claims</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsNumberOfReportedClaims_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsNumberOfReportedClaims" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contract, Cumulative Number of Reported Claims</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsNumberOfReportedClaims" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShortdurationInsuranceContractsNumberOfReportedClaims"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsNumberOfReportedClaims" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsNumberOfReportedClaims" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis_e868b525-3bac-4cdc-8928-4b754b2a07fd_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_ReinsuranceRecoverableMember_4529ac73-39d6-4747-be03-051468f79a94_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurance recoverable including reinsurance premium paid</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableMember_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverable Including Reinsurance Premium Paid [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverableMember" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ReinsuranceRecoverableMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverableMember" xlink:to="lab_us-gaap_ReinsuranceRecoverableMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccountsWriteOffsAgainstAllowance_67a65012-4dc6-4f6f-b4fd-1081a7ccd6f4_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccountsWriteOffsAgainstAllowance" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Write-offs of uncollectible premiums receivable</link:label>
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    <link:label id="lab_us-gaap_DeferredIncomeTaxExpenseBenefit_1fc551f9-fc86-44c1-ba24-9daad6e2e0ca_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredIncomeTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Deferred income tax, net</link:label>
    <link:label id="lab_us-gaap_DeferredIncomeTaxExpenseBenefit_label_en-US" xlink:label="lab_us-gaap_DeferredIncomeTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Income Tax Expense (Benefit)</link:label>
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    <link:label id="lab_us-gaap_SubsequentEventTypeAxis_6054e554-f1ca-4fe7-bdda-1b6a3401c6c4_terseLabel_en-US" xlink:label="lab_us-gaap_SubsequentEventTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subsequent Event Type [Axis]</link:label>
    <link:label id="lab_us-gaap_SubsequentEventTypeAxis_label_en-US" xlink:label="lab_us-gaap_SubsequentEventTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsequent Event Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsequentEventTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_SubsequentEventTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsequentEventTypeAxis" xlink:to="lab_us-gaap_SubsequentEventTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentFinStmtErrorCorrectionFlag_1e19446c-0862-421b-a618-58848834b351_terseLabel_en-US" xlink:label="lab_dei_DocumentFinStmtErrorCorrectionFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Document Financial Statement Error Correction [Flag]</link:label>
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    <link:label id="lab_skwd_FollowOnOfferingMember_020f24c7-8ac4-46bb-bef8-b1a1708f9217_terseLabel_en-US" xlink:label="lab_skwd_FollowOnOfferingMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Follow-On Offering</link:label>
    <link:label id="lab_skwd_FollowOnOfferingMember_label_en-US" xlink:label="lab_skwd_FollowOnOfferingMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Follow-On Offering [Member]</link:label>
    <link:label id="lab_skwd_FollowOnOfferingMember_documentation_en-US" xlink:label="lab_skwd_FollowOnOfferingMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Follow-On Offering</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_FollowOnOfferingMember" xlink:href="skwd-20231231.xsd#skwd_FollowOnOfferingMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_FollowOnOfferingMember" xlink:to="lab_skwd_FollowOnOfferingMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod_2da29f06-bb1e-4b0d-95c9-97aaa920b57a_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Forfeited (in shares)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Forfeited in Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeitedInPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtInstrumentFixedRatePeriodAxis_2d2af463-e76d-4143-95cb-15e9795811ea_terseLabel_en-US" xlink:label="lab_skwd_DebtInstrumentFixedRatePeriodAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Interest Rage Range [Axis]</link:label>
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    <link:label id="lab_skwd_DebtInstrumentFixedRatePeriodAxis_documentation_en-US" xlink:label="lab_skwd_DebtInstrumentFixedRatePeriodAxis" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Fixed Rate, Period</link:label>
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    <link:label id="lab_us-gaap_ProceedsFromEquityMethodInvestmentDividendsOrDistributionsReturnOfCapital_label_en-US" xlink:label="lab_us-gaap_ProceedsFromEquityMethodInvestmentDividendsOrDistributionsReturnOfCapital" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Equity Method Investment, Distribution, Return of Capital</link:label>
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    <link:label id="lab_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock_d1e6bc1b-2a9d-4d5e-99c2-4092385f85df_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Intangible Assets and Goodwill</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OperatingLeaseLiabilityStatementOfFinancialPositionExtensibleList_8e0f22a8-9d9f-48ae-8101-140950424e8f_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingLeaseLiabilityStatementOfFinancialPositionExtensibleList" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Operating Lease, Liability, Statement of Financial Position [Extensible Enumeration]</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseLiabilityStatementOfFinancialPositionExtensibleList" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_OperatingLeaseLiabilityStatementOfFinancialPositionExtensibleList"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OperatingLeaseLiabilityStatementOfFinancialPositionExtensibleList" xlink:to="lab_us-gaap_OperatingLeaseLiabilityStatementOfFinancialPositionExtensibleList" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_SuretyMember_9680b6c4-398a-459b-840b-2a8952bbfc73_terseLabel_en-US" xlink:label="lab_skwd_SuretyMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Surety</link:label>
    <link:label id="lab_skwd_SuretyMember_label_en-US" xlink:label="lab_skwd_SuretyMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Surety [Member]</link:label>
    <link:label id="lab_skwd_SuretyMember_documentation_en-US" xlink:label="lab_skwd_SuretyMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Surety</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_SuretyMember" xlink:href="skwd-20231231.xsd#skwd_SuretyMember"/>
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    <link:label id="lab_us-gaap_OtherAssets_b0d552ba-ab08-4650-9aa4-ce3cef3cdc1e_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>
    <link:label id="lab_us-gaap_OtherAssets_label_en-US" xlink:label="lab_us-gaap_OtherAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_OtherAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherAssets" xlink:to="lab_us-gaap_OtherAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_AgentRelationshipMember_855d0833-b4fa-4ca7-a150-caca63830f02_terseLabel_en-US" xlink:label="lab_skwd_AgentRelationshipMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Agent Relationships</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_skwd_AgentRelationshipMember" xlink:href="skwd-20231231.xsd#skwd_AgentRelationshipMember"/>
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    <link:label id="lab_us-gaap_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements_f04b5b6c-5e2c-434c-a33c-f953c97af83c_terseLabel_en-US" xlink:label="lab_us-gaap_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Awards (in shares)</link:label>
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    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersUnearnedPremiums_2909619a-b5ed-47c2-9ad8-44ce77c01ed0_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersUnearnedPremiums" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Unearned premiums</link:label>
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    <link:label id="lab_srt_CondensedCashFlowStatementsCaptionsLineItems_eaba4aed-cd46-4c1e-aa8e-7d37873102ed_terseLabel_en-US" xlink:label="lab_srt_CondensedCashFlowStatementsCaptionsLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Condensed Cash Flow Statements, Captions [Line Items]</link:label>
    <link:label id="lab_srt_CondensedCashFlowStatementsCaptionsLineItems_label_en-US" xlink:label="lab_srt_CondensedCashFlowStatementsCaptionsLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Condensed Cash Flow Statements, Captions [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_CondensedCashFlowStatementsCaptionsLineItems" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_CondensedCashFlowStatementsCaptionsLineItems"/>
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    <link:label id="lab_dei_DocumentsIncorporatedByReferenceTextBlock_a93ce614-3beb-434b-9c97-34fb57002dfc_terseLabel_en-US" xlink:label="lab_dei_DocumentsIncorporatedByReferenceTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Documents Incorporated by Reference</link:label>
    <link:label id="lab_dei_DocumentsIncorporatedByReferenceTextBlock_label_en-US" xlink:label="lab_dei_DocumentsIncorporatedByReferenceTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Documents Incorporated by Reference [Text Block]</link:label>
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    <link:label id="lab_dei_DocumentPeriodEndDate_e33b2b7d-610d-424e-8c0f-09a1fb27f159_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>
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    <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>
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    <link:label id="lab_us-gaap_ReinsuranceRecoverableAllowanceForCreditLossTableTextBlock_02cfb557-6fde-4013-aabc-8648b84e5241_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableAllowanceForCreditLossTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverable, Allowance for Credit Loss</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableAllowanceForCreditLossTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableAllowanceForCreditLossTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverable, Allowance for Credit Loss [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverableAllowanceForCreditLossTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ReinsuranceRecoverableAllowanceForCreditLossTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverableAllowanceForCreditLossTableTextBlock" xlink:to="lab_us-gaap_ReinsuranceRecoverableAllowanceForCreditLossTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CreditLossAbstract_label_en-US" xlink:label="lab_us-gaap_CreditLossAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Credit Loss [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CreditLossAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_CreditLossAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CreditLossAbstract" xlink:to="lab_us-gaap_CreditLossAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DirectPremiumsWritten_13088129-4a6a-41e9-81af-2a960ad996df_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_085d4598-a0d4-42e3-b44a-87611d078ee1_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_us-gaap_MortgageReceivablesMember_0ccfb5ba-0920-479a-a05e-f61c9c239fed_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_LossContingencyAccrualAtCarryingValue_7ab5e80b-953f-4938-8f5c-0eff36b0859e_terseLabel_en-US" xlink:label="lab_us-gaap_LossContingencyAccrualAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Loss contingency accrual</link:label>
    <link:label id="lab_us-gaap_LossContingencyAccrualAtCarryingValue_label_en-US" xlink:label="lab_us-gaap_LossContingencyAccrualAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Loss Contingency Accrual</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LossContingencyAccrualAtCarryingValue" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LossContingencyAccrualAtCarryingValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LossContingencyAccrualAtCarryingValue" xlink:to="lab_us-gaap_LossContingencyAccrualAtCarryingValue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxExpenseBenefit_4b06d4b2-34d8-43c9-b9b5-76d09ee4b829_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_30059139-b592-4d38-994a-9a0c9d0648c8_totalLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Income tax expense</link:label>
    <link:label id="lab_us-gaap_IncomeTaxExpenseBenefit_8b2bd723-faeb-493a-bb42-c85588b5a6fc_verboseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Income tax expense (benefit)</link:label>
    <link:label id="lab_us-gaap_IncomeTaxExpenseBenefit_label_en-US" xlink:label="lab_us-gaap_IncomeTaxExpenseBenefit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Tax Expense (Benefit)</link:label>
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    <link:label id="lab_skwd_RelatedPartyOwnershipInterest_393a2a3a-809c-47c4-a125-821b5a851c0f_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>
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    <link:label id="lab_us-gaap_FairValueDisclosuresTextBlock_0982bbf4-cad4-47de-8bc9-ffd6599a29a4_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueDisclosuresTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value Measurements</link:label>
    <link:label id="lab_us-gaap_FairValueDisclosuresTextBlock_label_en-US" xlink:label="lab_us-gaap_FairValueDisclosuresTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Disclosures [Text Block]</link:label>
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    <link:label id="lab_us-gaap_NumberOfOperatingSegments_4e57fdd7-386d-44bd-a388-d45541a23df8_terseLabel_en-US" xlink:label="lab_us-gaap_NumberOfOperatingSegments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Number of operating segments</link:label>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss_7c90a2c0-8f26-46e0-ad55-12bee86ab8a7_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">12 Months or More</link:label>
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    <link:label id="lab_skwd_DebtInstrumentFixedInterestRatePeriodTwoMember_eabff7d8-a18f-40d7-be7c-c94cf91bf0d0_terseLabel_en-US" xlink:label="lab_skwd_DebtInstrumentFixedInterestRatePeriodTwoMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Interest Rate, After Year 8</link:label>
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    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearSix_b9232f91-e815-4d02-bd10-7c8158c7c823_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearSix" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Year 6</link:label>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_94adc627-b6d3-44c4-bafc-45a4735ac34f_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Less than 12 Months</link:label>
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    <link:label id="lab_us-gaap_CashAndCashEquivalentsAtCarryingValue_e57a99f4-d1db-4eaf-bf8d-c3ea2c5c32de_terseLabel_en-US" xlink:label="lab_us-gaap_CashAndCashEquivalentsAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash and cash equivalents</link:label>
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    <link:label id="lab_skwd_FixedMaturitiesAvailableForSaleMember_1ff93f94-5b0b-4f27-bca5-22b08d995557_terseLabel_en-US" xlink:label="lab_skwd_FixedMaturitiesAvailableForSaleMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity securities, available for sale:</link:label>
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    <link:label id="lab_us-gaap_CreditFacilityDomain_37f7ebc8-b5da-4b3c-810a-e7b0944e23d7_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>
    <link:label id="lab_us-gaap_CreditFacilityDomain_label_en-US" xlink:label="lab_us-gaap_CreditFacilityDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Credit Facility [Domain]</link:label>
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    <link:label id="lab_us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquityAbstract_49d06d4a-7313-4f74-91b3-fef447f7ccf6_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Difference Between Carrying Amount and Underlying Equity [Abstract]</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquityAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_EquityMethodInvestmentDifferenceBetweenCarryingAmountAndUnderlyingEquityAbstract"/>
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    <link:label id="lab_us-gaap_AllowanceForReinsuranceRecoverableMember_41c31570-b5b2-48e3-8871-035de79d6b44_terseLabel_en-US" xlink:label="lab_us-gaap_AllowanceForReinsuranceRecoverableMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Allowance for Uncollectible Reinsurance Recoverable</link:label>
    <link:label id="lab_us-gaap_AllowanceForReinsuranceRecoverableMember_label_en-US" xlink:label="lab_us-gaap_AllowanceForReinsuranceRecoverableMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-09, Allowance, Reinsurance Recoverable [Member]</link:label>
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    <link:label id="lab_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1_723801c8-c863-4eca-af51-af4406dc6539_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">Basis spread on variable rate</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentBasisSpreadOnVariableRate1" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DebtInstrumentBasisSpreadOnVariableRate1"/>
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    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentUsefulLife_bf36bf6d-5e01-4e4f-855c-e8833da49a3f_terseLabel_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentUsefulLife" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Property, plant and equipment, useful life</link:label>
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    <link:label id="lab_us-gaap_LongTermDebtTerm_13fdaa65-b189-4346-942d-cf1e48292567_terseLabel_en-US" xlink:label="lab_us-gaap_LongTermDebtTerm" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt term</link:label>
    <link:label id="lab_us-gaap_LongTermDebtTerm_label_en-US" xlink:label="lab_us-gaap_LongTermDebtTerm" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Long-Term Debt, Term</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtTerm" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LongTermDebtTerm"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LongTermDebtTerm" xlink:to="lab_us-gaap_LongTermDebtTerm" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SoftwareDevelopmentMember_79bc7f3a-042a-44a4-b538-a12dd1c6a20c_terseLabel_en-US" xlink:label="lab_us-gaap_SoftwareDevelopmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Software</link:label>
    <link:label id="lab_us-gaap_SoftwareDevelopmentMember_label_en-US" xlink:label="lab_us-gaap_SoftwareDevelopmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Software Development [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SoftwareDevelopmentMember" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_SoftwareDevelopmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SoftwareDevelopmentMember" xlink:to="lab_us-gaap_SoftwareDevelopmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ReinsuranceRecoverableForLossPortfolioTransfer_e62fa961-ab04-407d-a78d-d9b8981b938d_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>
    <link:label id="lab_skwd_ReinsuranceRecoverableForLossPortfolioTransfer_label_en-US" xlink:label="lab_skwd_ReinsuranceRecoverableForLossPortfolioTransfer" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverable For Loss Portfolio Transfer</link:label>
    <link:label id="lab_skwd_ReinsuranceRecoverableForLossPortfolioTransfer_documentation_en-US" xlink:label="lab_skwd_ReinsuranceRecoverableForLossPortfolioTransfer" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverable For Loss Portfolio Transfer</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ReinsuranceRecoverableForLossPortfolioTransfer" xlink:href="skwd-20231231.xsd#skwd_ReinsuranceRecoverableForLossPortfolioTransfer"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ReinsuranceRecoverableForLossPortfolioTransfer" xlink:to="lab_skwd_ReinsuranceRecoverableForLossPortfolioTransfer" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ShortTailMonolineSpecialtyMember_b73debf3-31e3-4e79-8d0a-8155edce2c11_terseLabel_en-US" xlink:label="lab_skwd_ShortTailMonolineSpecialtyMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Short Tail/Monoline Specialty</link:label>
    <link:label id="lab_skwd_ShortTailMonolineSpecialtyMember_label_en-US" xlink:label="lab_skwd_ShortTailMonolineSpecialtyMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short Tail/Monoline Specialty [Member]</link:label>
    <link:label id="lab_skwd_ShortTailMonolineSpecialtyMember_documentation_en-US" xlink:label="lab_skwd_ShortTailMonolineSpecialtyMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Short Tail/Monoline Specialty</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ShortTailMonolineSpecialtyMember" xlink:href="skwd-20231231.xsd#skwd_ShortTailMonolineSpecialtyMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ShortTailMonolineSpecialtyMember" xlink:to="lab_skwd_ShortTailMonolineSpecialtyMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ContractWithCustomerAssetAndLiabilityTableTextBlock_380d6aef-8f3d-4e6e-844e-4d77505cf933_terseLabel_en-US" xlink:label="lab_us-gaap_ContractWithCustomerAssetAndLiabilityTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Contract Asset</link:label>
    <link:label id="lab_us-gaap_ContractWithCustomerAssetAndLiabilityTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ContractWithCustomerAssetAndLiabilityTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Contract with Customer, Contract Asset, Contract Liability, and Receivable [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ContractWithCustomerAssetAndLiabilityTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ContractWithCustomerAssetAndLiabilityTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ContractWithCustomerAssetAndLiabilityTableTextBlock" xlink:to="lab_us-gaap_ContractWithCustomerAssetAndLiabilityTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearNine_ce1609ea-48fc-4a86-b29e-d4d9a46b19ea_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearNine" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Year 9</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearNine_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearNine" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contracts, Historical Claims Duration, Year Nine</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearNine" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearNine"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearNine" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearNine" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RevenueFromContractWithCustomerTextBlock_3f624051-cb92-47f2-81b3-086211fabf39_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>
    <link:label id="lab_us-gaap_RevenueFromContractWithCustomerTextBlock_label_en-US" xlink:label="lab_us-gaap_RevenueFromContractWithCustomerTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Revenue from Contract with Customer [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RevenueFromContractWithCustomerTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_RevenueFromContractWithCustomerTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RevenueFromContractWithCustomerTextBlock" xlink:to="lab_us-gaap_RevenueFromContractWithCustomerTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AdditionalPaidInCapitalMember_b959ab4e-1bd0-4b84-925d-f1841f93a49f_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>
    <link:label id="lab_us-gaap_AdditionalPaidInCapitalMember_label_en-US" xlink:label="lab_us-gaap_AdditionalPaidInCapitalMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Additional Paid-in Capital [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdditionalPaidInCapitalMember" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_AdditionalPaidInCapitalMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AdditionalPaidInCapitalMember" xlink:to="lab_us-gaap_AdditionalPaidInCapitalMember" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_DocumentAnnualReport_1172c975-7907-4e19-822a-7d979d167350_terseLabel_en-US" xlink:label="lab_dei_DocumentAnnualReport" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Document Annual Report</link:label>
    <link:label id="lab_dei_DocumentAnnualReport_label_en-US" xlink:label="lab_dei_DocumentAnnualReport" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Document Annual Report</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentAnnualReport" xlink:href="https://xbrl.sec.gov/dei/2023/dei-2023.xsd#dei_DocumentAnnualReport"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentAnnualReport" xlink:to="lab_dei_DocumentAnnualReport" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi_5e9e4f26-0a39-4c17-9a53-6b0c6516b1bc_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi" 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_ProceedsFromSaleOfEquitySecuritiesFvNi_label_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Sale of Equity Securities, FV-NI</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi" xlink:to="lab_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_RelatedPartyTransactionConsiderationReceived_ab90b692-578b-466b-898c-3a539a90731f_terseLabel_en-US" xlink:label="lab_skwd_RelatedPartyTransactionConsiderationReceived" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Related party transaction, consideration received</link:label>
    <link:label id="lab_skwd_RelatedPartyTransactionConsiderationReceived_label_en-US" xlink:label="lab_skwd_RelatedPartyTransactionConsiderationReceived" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Related Party Transaction, Consideration Received</link:label>
    <link:label id="lab_skwd_RelatedPartyTransactionConsiderationReceived_documentation_en-US" xlink:label="lab_skwd_RelatedPartyTransactionConsiderationReceived" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Related Party Transaction, Consideration Received</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RelatedPartyTransactionConsiderationReceived" xlink:href="skwd-20231231.xsd#skwd_RelatedPartyTransactionConsiderationReceived"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_RelatedPartyTransactionConsiderationReceived" xlink:to="lab_skwd_RelatedPartyTransactionConsiderationReceived" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustmentAbstract_6a4510df-b0a6-4f34-90cd-cadf4d1b1444_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"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustmentAbstract" xlink:to="lab_us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustmentAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_CommoditySectorMember_060dacc9-90ee-4fc1-8f81-c884c4344e0e_terseLabel_en-US" xlink:label="lab_skwd_CommoditySectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Commodity</link:label>
    <link:label id="lab_skwd_CommoditySectorMember_label_en-US" xlink:label="lab_skwd_CommoditySectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Commodity Sector [Member]</link:label>
    <link:label id="lab_skwd_CommoditySectorMember_documentation_en-US" xlink:label="lab_skwd_CommoditySectorMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Commodity Sector</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_CommoditySectorMember" xlink:href="skwd-20231231.xsd#skwd_CommoditySectorMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_CommoditySectorMember" xlink:to="lab_skwd_CommoditySectorMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredTaxLiabilitiesInvestments_d532f997-5427-4b0a-a662-466cc19ee694_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxLiabilitiesInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other long-term investments</link:label>
    <link:label id="lab_us-gaap_DeferredTaxLiabilitiesInvestments_label_en-US" xlink:label="lab_us-gaap_DeferredTaxLiabilitiesInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Tax Liabilities, Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxLiabilitiesInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DeferredTaxLiabilitiesInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredTaxLiabilitiesInvestments" xlink:to="lab_us-gaap_DeferredTaxLiabilitiesInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_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>
    <link:loc xlink:type="locator" xlink:label="loc_dei_CoverAbstract" xlink:href="https://xbrl.sec.gov/dei/2023/dei-2023.xsd#dei_CoverAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_CoverAbstract" xlink:to="lab_dei_CoverAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InsuranceCommissions_a85525ee-2250-4ab1-8780-08615c6c718d_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">Gross written commissions</link:label>
    <link:label id="lab_us-gaap_InsuranceCommissions_label_en-US" xlink:label="lab_us-gaap_InsuranceCommissions" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" 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_c6bc27f6-4c25-4a70-bb97-99ae5a711a64_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_ExitedLinesMember_210642ab-c40c-4338-8ee8-c968478193ce_terseLabel_en-US" xlink:label="lab_skwd_ExitedLinesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Exited Lines</link:label>
    <link:label id="lab_skwd_ExitedLinesMember_label_en-US" xlink:label="lab_skwd_ExitedLinesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Exited Lines [Member]</link:label>
    <link:label id="lab_skwd_ExitedLinesMember_documentation_en-US" xlink:label="lab_skwd_ExitedLinesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Exited Lines</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ExitedLinesMember" xlink:href="skwd-20231231.xsd#skwd_ExitedLinesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ExitedLinesMember" xlink:to="lab_skwd_ExitedLinesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DowlingCapitalPartnersLPMember_bc838b6f-f779-4445-a08b-d1e8ce561051_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-20231231.xsd#skwd_DowlingCapitalPartnersLPMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DowlingCapitalPartnersLPMember" xlink:to="lab_skwd_DowlingCapitalPartnersLPMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumsReceivableAtCarryingValue_f036b141-16e6-480d-9c7f-234cc421eefc_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_9d7cc6ed-3cef-4115-9e9e-8ad545f3bf47_periodStartLabel_en-US" xlink:label="lab_us-gaap_PremiumsReceivableAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Premiums Receivable, Net, beginning balance</link:label>
    <link:label id="lab_us-gaap_PremiumsReceivableAtCarryingValue_fe3798f0-c67d-411f-baba-79c497fe98be_periodEndLabel_en-US" xlink:label="lab_us-gaap_PremiumsReceivableAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Premiums Receivable, Net, ending balance</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>
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    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue_b918fb94-3ecb-4aad-acbc-0e0aa88c2105_totalLabel_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total future minimum operating lease payments</link:label>
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    <link:label id="lab_skwd_SECSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersDeferredCedingCommission_1545c58f-6c2f-478f-9df1-287ee10b13ab_terseLabel_en-US" xlink:label="lab_skwd_SECSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersDeferredCedingCommission" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Deferred ceding commission</link:label>
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    <link:label id="lab_us-gaap_EquityComponentDomain_c1465d17-fcfd-4b4d-87cc-8fcc5f8a6c8d_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>
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    <link:label id="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsLiability_ee40a40e-0cd0-44fd-bf45-db1e5eab9d56_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_a9a3ec81-166d-4288-9eb1-2d4495ba7bf6_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 equity offerings</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_srt_ConsolidatedEntitiesDomain_50dca80f-1b4f-418b-9579-bb8a9e87e0b6_terseLabel_en-US" xlink:label="lab_srt_ConsolidatedEntitiesDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Consolidated Entities [Domain]</link:label>
    <link:label id="lab_srt_ConsolidatedEntitiesDomain_label_en-US" xlink:label="lab_srt_ConsolidatedEntitiesDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Consolidated Entities [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ConsolidatedEntitiesDomain" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_ConsolidatedEntitiesDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ConsolidatedEntitiesDomain" xlink:to="lab_srt_ConsolidatedEntitiesDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredIncomeTaxLiabilities_45b36c33-4f56-4fb0-b676-9d86d4a3656e_totalLabel_en-US" xlink:label="lab_us-gaap_DeferredIncomeTaxLiabilities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total deferred tax liabilities</link:label>
    <link:label id="lab_us-gaap_DeferredIncomeTaxLiabilities_label_en-US" xlink:label="lab_us-gaap_DeferredIncomeTaxLiabilities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Tax Liabilities, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredIncomeTaxLiabilities" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DeferredIncomeTaxLiabilities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredIncomeTaxLiabilities" xlink:to="lab_us-gaap_DeferredIncomeTaxLiabilities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubordinatedDebt_0f1254ef-7816-4835-ad3f-cbeac0f97b22_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_us-gaap_EstimateOfFairValueFairValueDisclosureMember_1288f5cb-3673-4b62-976a-0a88bb46065d_terseLabel_en-US" xlink:label="lab_us-gaap_EstimateOfFairValueFairValueDisclosureMember" 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_EstimateOfFairValueFairValueDisclosureMember_label_en-US" xlink:label="lab_us-gaap_EstimateOfFairValueFairValueDisclosureMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Estimate of Fair Value Measurement [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EstimateOfFairValueFairValueDisclosureMember" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_EstimateOfFairValueFairValueDisclosureMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EstimateOfFairValueFairValueDisclosureMember" xlink:to="lab_us-gaap_EstimateOfFairValueFairValueDisclosureMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentPolicyTextBlock_388b2827-24ac-412f-b683-33aae9a40b3b_terseLabel_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Property and Equipment</link:label>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Property, Plant and Equipment, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PropertyPlantAndEquipmentPolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentPolicyTextBlock" xlink:to="lab_us-gaap_PropertyPlantAndEquipmentPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract_c624c7a3-1de7-4422-bc97-b774f06fc517_terseLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Comprehensive income:</link:label>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract_label_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Comprehensive Income (Loss), Net of Tax [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract" xlink:to="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPeriodIncreaseDecreaseAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInReinsurancePayables_8c22f878-6142-4518-8a30-cc6292ecee11_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInReinsurancePayables" 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_IncreaseDecreaseInReinsurancePayables_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInReinsurancePayables" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Reinsurance Payables</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInReinsurancePayables" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_IncreaseDecreaseInReinsurancePayables"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInReinsurancePayables" xlink:to="lab_us-gaap_IncreaseDecreaseInReinsurancePayables" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ScenarioUnspecifiedDomain_58c56e3e-ddc0-4a32-a610-c936413fb678_terseLabel_en-US" xlink:label="lab_srt_ScenarioUnspecifiedDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Scenario [Domain]</link:label>
    <link:label id="lab_srt_ScenarioUnspecifiedDomain_label_en-US" xlink:label="lab_srt_ScenarioUnspecifiedDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Scenario [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ScenarioUnspecifiedDomain" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_ScenarioUnspecifiedDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ScenarioUnspecifiedDomain" xlink:to="lab_srt_ScenarioUnspecifiedDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt_terseLabel_en-US" xlink:label="lab_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Forgone Recovery due to Disqualification of Tax Benefits, Amount</link:label>
    <link:label id="lab_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt_label_en-US" xlink:label="lab_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Forgone Recovery due to Disqualification of Tax Benefits, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt" xlink:to="lab_ecd_ForgoneRecoveryDueToDisqualificationOfTaxBenefitsAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardsCloseToMnpiDiscTable_terseLabel_en-US" xlink:label="lab_ecd_AwardsCloseToMnpiDiscTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Awards Close in Time to MNPI Disclosures</link:label>
    <link:label id="lab_ecd_AwardsCloseToMnpiDiscTable_label_en-US" xlink:label="lab_ecd_AwardsCloseToMnpiDiscTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Awards Close in Time to MNPI Disclosures [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardsCloseToMnpiDiscTable" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_AwardsCloseToMnpiDiscTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardsCloseToMnpiDiscTable" xlink:to="lab_ecd_AwardsCloseToMnpiDiscTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LineOfCredit_da69747e-d32b-42e7-a6b1-05da34831b6f_terseLabel_en-US" xlink:label="lab_us-gaap_LineOfCredit" 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_LineOfCredit_label_en-US" xlink:label="lab_us-gaap_LineOfCredit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Long-Term Line of Credit</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LineOfCredit" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LineOfCredit"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LineOfCredit" xlink:to="lab_us-gaap_LineOfCredit" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_SkywardSpecialtyInsuranceGroupMember_7f7e4c94-ef64-4b9b-a2b3-6c32ae2d0857_terseLabel_en-US" xlink:label="lab_skwd_SkywardSpecialtyInsuranceGroupMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Skyward Specialty Insurance Group</link:label>
    <link:label id="lab_skwd_SkywardSpecialtyInsuranceGroupMember_label_en-US" xlink:label="lab_skwd_SkywardSpecialtyInsuranceGroupMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Skyward Specialty Insurance Group [Member]</link:label>
    <link:label id="lab_skwd_SkywardSpecialtyInsuranceGroupMember_documentation_en-US" xlink:label="lab_skwd_SkywardSpecialtyInsuranceGroupMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Skyward Specialty Insurance Group</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_SkywardSpecialtyInsuranceGroupMember" xlink:href="skwd-20231231.xsd#skwd_SkywardSpecialtyInsuranceGroupMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_SkywardSpecialtyInsuranceGroupMember" xlink:to="lab_skwd_SkywardSpecialtyInsuranceGroupMember" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ConsolidatedEntitiesAxis_9227bce4-1b75-43bc-bd5e-e72e275b59c5_terseLabel_en-US" xlink:label="lab_srt_ConsolidatedEntitiesAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Consolidated Entities [Axis]</link:label>
    <link:label id="lab_srt_ConsolidatedEntitiesAxis_label_en-US" xlink:label="lab_srt_ConsolidatedEntitiesAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Consolidated Entities [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ConsolidatedEntitiesAxis" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_ConsolidatedEntitiesAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ConsolidatedEntitiesAxis" xlink:to="lab_srt_ConsolidatedEntitiesAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_VariableRateDomain_77bcfdfa-f7b2-4898-91bb-75c47215e43f_terseLabel_en-US" xlink:label="lab_us-gaap_VariableRateDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Variable Rate [Domain]</link:label>
    <link:label id="lab_us-gaap_VariableRateDomain_label_en-US" xlink:label="lab_us-gaap_VariableRateDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" 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"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PayVsPerformanceDisclosureLineItems" xlink:to="lab_ecd_PayVsPerformanceDisclosureLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityVoluntaryFilers_3ac755b4-b13b-4395-9c4b-4ad3a5b81095_terseLabel_en-US" xlink:label="lab_dei_EntityVoluntaryFilers" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Voluntary Filers</link:label>
    <link:label id="lab_dei_EntityVoluntaryFilers_label_en-US" xlink:label="lab_dei_EntityVoluntaryFilers" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Voluntary Filers</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityVoluntaryFilers" xlink:href="https://xbrl.sec.gov/dei/2023/dei-2023.xsd#dei_EntityVoluntaryFilers"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityVoluntaryFilers" xlink:to="lab_dei_EntityVoluntaryFilers" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_RangeMember_2a006b2e-2fa0-43bb-9c38-84d554e546ea_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_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"/>
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    <link:label id="lab_us-gaap_CapitalRequiredForCapitalAdequacy_label_en-US" xlink:label="lab_us-gaap_CapitalRequiredForCapitalAdequacy" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Banking Regulation, Total Risk-Based Capital, Capital Adequacy, Minimum</link:label>
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    <link:label id="lab_us-gaap_LesseeLeasesPolicyTextBlock_98abebcf-e1f9-4baa-94e0-092df20ef285_terseLabel_en-US" xlink:label="lab_us-gaap_LesseeLeasesPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Leases</link:label>
    <link:label id="lab_us-gaap_LesseeLeasesPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_LesseeLeasesPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Lessee, Leases [Policy Text Block]</link:label>
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    <link:label id="lab_us-gaap_IncreaseDecreaseInUnearnedPremiums_937425ce-28e6-4a76-aa62-5518cc8bc8db_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInUnearnedPremiums" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Unearned premiums</link:label>
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    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsAccidentYearAxis_e7aabe72-a24d-4607-ba2b-0b3a259c9706_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsAccidentYearAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contracts, Accident Year [Axis]</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsAccidentYearAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShortdurationInsuranceContractsAccidentYearAxis"/>
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    <link:label id="lab_us-gaap_PreferredStockParOrStatedValuePerShare_cbc59009-66b6-414d-ab95-7420c0dd785b_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockParOrStatedValuePerShare" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Preferred stock, par value (in dollars per share)</link:label>
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    <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"/>
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    <link:label id="lab_us-gaap_ScheduleOfPropertyPlantAndEquipmentTable_c2085752-7ee0-4a37-b351-a0f25acb0cf1_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfPropertyPlantAndEquipmentTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Property, Plant and Equipment [Table]</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfPropertyPlantAndEquipmentTable" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ScheduleOfPropertyPlantAndEquipmentTable"/>
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    <link:label id="lab_us-gaap_GoodwillRollForward_e425b408-3ebc-49e0-940c-2e4576388366_terseLabel_en-US" xlink:label="lab_us-gaap_GoodwillRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Goodwill [Roll Forward]</link:label>
    <link:label id="lab_us-gaap_GoodwillRollForward_label_en-US" xlink:label="lab_us-gaap_GoodwillRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_GoodwillRollForward"/>
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    <link:label id="lab_us-gaap_ReinsurancePayable_b70ea495-1c9b-46df-aea5-7841609df833_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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest"/>
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    <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"/>
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    <link:label id="lab_us-gaap_NetIncomeLoss_119188d9-4a47-4296-a0bd-b6dfef6f6dc2_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_9b9e326a-a1f0-440c-b4d4-9bd2a903adaf_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_3ce7f628-7e28-4053-a23c-a63afca0396a_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_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>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost_b1fbc672-4605-40ec-9516-1b35c2bcc8e4_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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeasesTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LesseeOperatingLeasesTextBlock"/>
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    <link:label id="lab_us-gaap_DeferredPolicyAcquisitionCosts_e4124b32-9184-4075-861b-877735683be6_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"/>
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    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearThree_bf71dfe5-1594-4291-8dde-547e993017c4_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearThree" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Year 3</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearThree_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearThree" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contracts, Historical Claims Duration, Year Three</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearThree" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearThree"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearThree" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearThree" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilitiesAndStockholdersEquityAbstract_19912677-8112-4945-bc17-21f661fa709b_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_edb27d86-4e9b-4b9b-908b-53e43e4f8a62_verboseLabel_en-US" xlink:label="lab_us-gaap_LiabilitiesAndStockholdersEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" 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"/>
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    <link:label id="lab_dei_EntityExTransitionPeriod_a786d647-ba9a-43f2-a4a6-7d5e832221cf_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>
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    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsLineItems_c3a08761-9bbd-4999-be85-ff837e0fdf00_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Finite-Lived Intangible Assets [Line Items]</link:label>
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    <link:label id="lab_us-gaap_ConcentrationRiskBenchmarkDomain_fedd884c-f145-4bc0-b957-b1cde4c3c0ac_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskBenchmarkDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Concentration Risk Benchmark [Domain]</link:label>
    <link:label id="lab_us-gaap_ConcentrationRiskBenchmarkDomain_label_en-US" xlink:label="lab_us-gaap_ConcentrationRiskBenchmarkDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Concentration Risk Benchmark [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConcentrationRiskBenchmarkDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ConcentrationRiskBenchmarkDomain"/>
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    <link:label id="lab_skwd_ConsumerDiscretionarySectorMember_65e9a629-cdfa-4055-bf66-2ad5e9a6939f_terseLabel_en-US" xlink:label="lab_skwd_ConsumerDiscretionarySectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Consumer discretionary</link:label>
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    <link:label id="lab_us-gaap_PrincipalOwnerMember_0f3336ed-6da8-42fb-a58a-e5f91d15f937_terseLabel_en-US" xlink:label="lab_us-gaap_PrincipalOwnerMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Principal Owner</link:label>
    <link:label id="lab_us-gaap_PrincipalOwnerMember_label_en-US" xlink:label="lab_us-gaap_PrincipalOwnerMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Principal Owner [Member]</link:label>
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    <link:label id="lab_us-gaap_Goodwill_a0305f20-baec-41e5-8cc6-bd0df546eeda_netLabel_en-US" xlink:label="lab_us-gaap_Goodwill" xlink:role="http://www.xbrl.org/2009/role/netLabel" xlink:type="resource" xml:lang="en-US">Goodwill, net balance</link:label>
    <link:label id="lab_us-gaap_Goodwill_label_en-US" xlink:label="lab_us-gaap_Goodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Goodwill" xlink:to="lab_us-gaap_Goodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LesseeLeaseDescriptionTable_264787ac-eb8a-4d3d-92f0-df64e1fb33af_terseLabel_en-US" xlink:label="lab_us-gaap_LesseeLeaseDescriptionTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Lessee, Lease, Description [Table]</link:label>
    <link:label id="lab_us-gaap_LesseeLeaseDescriptionTable_label_en-US" xlink:label="lab_us-gaap_LesseeLeaseDescriptionTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Lessee, Lease, Description [Table]</link:label>
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    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1_306e4527-fc39-43df-b1eb-bacbac55e77a_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidPriorYears1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Prior years</link:label>
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    <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"/>
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    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss_5184cda9-0acc-431c-a2a1-059671c6ada5_negatedTerseLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">12 Months or More</link:label>
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    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract_38a52de5-d0a5-4fea-85ef-a50e9720eca6_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>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Incurred Claims [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract"/>
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    <link:label id="lab_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock_bf018873-f493-451e-b2b2-119307298325_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>
    <link:label id="lab_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock_label_en-US" xlink:label="lab_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investments Classified by Contractual Maturity Date [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock"/>
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    <link:label id="lab_us-gaap_DebtInstrumentNameDomain_b25d0e00-75ba-40a8-963b-f3b2e50f1369_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>
    <link:label id="lab_us-gaap_DebtInstrumentNameDomain_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DebtInstrumentNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentNameDomain" xlink:to="lab_us-gaap_DebtInstrumentNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable_ba12b68f-f72b-47cf-98c6-82e21e6c7bde_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value Measurement Inputs and Valuation Techniques [Table]</link:label>
    <link:label id="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Measurement Inputs and Valuation Techniques [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable" xlink:to="lab_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisValuationTechniquesTable" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CumulativeEffectPeriodOfAdoptionAdjustmentMember_c6d8063d-b1e8-4158-95fb-7a4360f79c06_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>
    <link:label id="lab_srt_CumulativeEffectPeriodOfAdoptionAdjustmentMember_label_en-US" xlink:label="lab_srt_CumulativeEffectPeriodOfAdoptionAdjustmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cumulative Effect, Period of Adoption, Adjustment [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_CumulativeEffectPeriodOfAdoptionAdjustmentMember" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_CumulativeEffectPeriodOfAdoptionAdjustmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_CumulativeEffectPeriodOfAdoptionAdjustmentMember" xlink:to="lab_srt_CumulativeEffectPeriodOfAdoptionAdjustmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DepositContractsAssets_5e409b42-a3ae-43f5-83ac-882ded0fb696_verboseLabel_en-US" xlink:label="lab_us-gaap_DepositContractsAssets" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Deposit contracts, assets</link:label>
    <link:label id="lab_us-gaap_DepositContractsAssets_label_en-US" xlink:label="lab_us-gaap_DepositContractsAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deposit Contracts, Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DepositContractsAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DepositContractsAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DepositContractsAssets" xlink:to="lab_us-gaap_DepositContractsAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract_bcecd864-1c2d-4679-8451-4280dac2c1c8_terseLabel_en-US" xlink:label="lab_us-gaap_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract" 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_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract_label_en-US" xlink:label="lab_us-gaap_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financial Instruments, Financial Assets, Balance Sheet Groupings [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract" xlink:to="lab_us-gaap_FinancialInstrumentsFinancialAssetsBalanceSheetGroupingsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityMaturityTableTextBlock_9e4afaec-1520-4901-9863-7148070df437_terseLabel_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityMaturityTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Lessee, Operating Lease, Liability, Maturity</link:label>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityMaturityTableTextBlock_label_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityMaturityTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Lessee, Operating Lease, Liability, to be Paid, Maturity [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeaseLiabilityMaturityTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LesseeOperatingLeaseLiabilityMaturityTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LesseeOperatingLeaseLiabilityMaturityTableTextBlock" xlink:to="lab_us-gaap_LesseeOperatingLeaseLiabilityMaturityTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersAbstract_label_en-US" xlink:label="lab_srt_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-18, Supplemental Information, Property-Casualty Insurance Underwriters [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersAbstract" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersAbstract" xlink:to="lab_srt_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CashAndCashEquivalentsPolicyTextBlock_eeba8e8a-23f7-47f8-aa2d-3851eb528261_terseLabel_en-US" xlink:label="lab_us-gaap_CashAndCashEquivalentsPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash and Cash Equivalents</link:label>
    <link:label id="lab_us-gaap_CashAndCashEquivalentsPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_CashAndCashEquivalentsPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash and Cash Equivalents, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashAndCashEquivalentsPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_CashAndCashEquivalentsPolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CashAndCashEquivalentsPolicyTextBlock" xlink:to="lab_us-gaap_CashAndCashEquivalentsPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsGrantsInPeriodExcludingSharesIssuedInConnectionWithAcquisition_8eb367eb-3fc5-4935-9af4-53fb3ee357ff_terseLabel_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsGrantsInPeriodExcludingSharesIssuedInConnectionWithAcquisition" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Granted (in shares)</link:label>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsGrantsInPeriodExcludingSharesIssuedInConnectionWithAcquisition_label_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsGrantsInPeriodExcludingSharesIssuedInConnectionWithAcquisition" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Options, Grants in Period, Excluding Shares Issued in Connection with Acquisition</link:label>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsGrantsInPeriodExcludingSharesIssuedInConnectionWithAcquisition_documentation_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsGrantsInPeriodExcludingSharesIssuedInConnectionWithAcquisition" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Share-based Compensation Arrangement by Share-based Payment Award, Options, Grants in Period, Excluding Shares Issued in Connection with Acquisition</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsGrantsInPeriodExcludingSharesIssuedInConnectionWithAcquisition" xlink:href="skwd-20231231.xsd#skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsGrantsInPeriodExcludingSharesIssuedInConnectionWithAcquisition"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsGrantsInPeriodExcludingSharesIssuedInConnectionWithAcquisition" xlink:to="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsGrantsInPeriodExcludingSharesIssuedInConnectionWithAcquisition" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ProductsAndServicesDomain_00fd9bf8-51b7-4a1c-855b-009ac4e926f2_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>
    <link:label id="lab_srt_ProductsAndServicesDomain_label_en-US" xlink:label="lab_srt_ProductsAndServicesDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Product and Service [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ProductsAndServicesDomain" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_ProductsAndServicesDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ProductsAndServicesDomain" xlink:to="lab_srt_ProductsAndServicesDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommercialMortgageBackedSecuritiesMember_4b4df66b-e49b-44b6-8b52-3c7424e4da07_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>
    <link:label id="lab_us-gaap_CommercialMortgageBackedSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_CommercialMortgageBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Commercial Mortgage-Backed Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommercialMortgageBackedSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_CommercialMortgageBackedSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommercialMortgageBackedSecuritiesMember" xlink:to="lab_us-gaap_CommercialMortgageBackedSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_OtherPerfMeasureAmt_terseLabel_en-US" xlink:label="lab_ecd_OtherPerfMeasureAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other Performance Measure, Amount</link:label>
    <link:label id="lab_ecd_OtherPerfMeasureAmt_label_en-US" xlink:label="lab_ecd_OtherPerfMeasureAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Performance Measure, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_OtherPerfMeasureAmt" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_OtherPerfMeasureAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_OtherPerfMeasureAmt" xlink:to="lab_ecd_OtherPerfMeasureAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_2609aeda-297f-4ddd-bbb1-dc3940fbe65a_periodStartLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Reserves for losses and LAE, beginning of period, net of reinsurance</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_7e4248b1-1cb1-4820-982a-03cd7220f8e9_periodEndLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Net reserves for losses and LAE, end of period</link:label>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNet" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_OtherSectorsMember_6f5620c3-80f1-480a-8ec2-1f97d80fdda8_terseLabel_en-US" xlink:label="lab_skwd_OtherSectorsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other</link:label>
    <link:label id="lab_skwd_OtherSectorsMember_label_en-US" xlink:label="lab_skwd_OtherSectorsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Sectors [Member]</link:label>
    <link:label id="lab_skwd_OtherSectorsMember_documentation_en-US" xlink:label="lab_skwd_OtherSectorsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Other Sectors</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_OtherSectorsMember" xlink:href="skwd-20231231.xsd#skwd_OtherSectorsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_OtherSectorsMember" xlink:to="lab_skwd_OtherSectorsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LeaseCostTableTextBlock_78c2111f-7146-438d-91ef-31d257a73c33_terseLabel_en-US" xlink:label="lab_us-gaap_LeaseCostTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Lease, Cost</link:label>
    <link:label id="lab_us-gaap_LeaseCostTableTextBlock_label_en-US" xlink:label="lab_us-gaap_LeaseCostTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Lease, Cost [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LeaseCostTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LeaseCostTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LeaseCostTableTextBlock" xlink:to="lab_us-gaap_LeaseCostTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract_0a91f26e-9f32-4a5f-ba4a-001beaadf884_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>
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    <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"/>
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    <link:label id="lab_skwd_DeferredCedingCommission_31254da0-32e9-492a-8e99-a35b150684d5_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-20231231.xsd#skwd_DeferredCedingCommission"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DeferredCedingCommission" xlink:to="lab_skwd_DeferredCedingCommission" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_SECSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersCededUnearnedPremium_eee8379f-395f-4ae2-9d59-ac020c909520_terseLabel_en-US" xlink:label="lab_skwd_SECSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersCededUnearnedPremium" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ceded unearned premium</link:label>
    <link:label id="lab_skwd_SECSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersCededUnearnedPremium_label_en-US" xlink:label="lab_skwd_SECSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersCededUnearnedPremium" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-18, Supplemental Information, Property-Casualty Insurance Underwriters, Ceded Unearned Premium</link:label>
    <link:label id="lab_skwd_SECSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersCededUnearnedPremium_documentation_en-US" xlink:label="lab_skwd_SECSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersCededUnearnedPremium" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-18, Supplemental Information, Property-Casualty Insurance Underwriters, Ceded Unearned Premium</link:label>
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    <link:label id="lab_us-gaap_RegulatoryCapitalRequirementsUnderBankingRegulationsTextBlock_2c4d7c8e-8a35-453e-863f-87add0886a7a_terseLabel_en-US" xlink:label="lab_us-gaap_RegulatoryCapitalRequirementsUnderBankingRegulationsTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Statutory Accounting Principles and Regulatory Matters</link:label>
    <link:label id="lab_us-gaap_RegulatoryCapitalRequirementsUnderBankingRegulationsTextBlock_label_en-US" xlink:label="lab_us-gaap_RegulatoryCapitalRequirementsUnderBankingRegulationsTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Regulatory Capital Requirements under Banking Regulations [Text Block]</link:label>
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    <link:label id="lab_us-gaap_PlanNameDomain_b67e3675-00fd-469a-ac8a-993e17f81a7e_terseLabel_en-US" xlink:label="lab_us-gaap_PlanNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Plan Name [Domain]</link:label>
    <link:label id="lab_us-gaap_PlanNameDomain_label_en-US" xlink:label="lab_us-gaap_PlanNameDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Plan Name [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PlanNameDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PlanNameDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PlanNameDomain" xlink:to="lab_us-gaap_PlanNameDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InterestExpense_4aa862b5-cdf4-4eea-a47b-cd4d6aec0cc0_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_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions_fef2be7b-0c2c-41b2-a779-06d1d9b667d1_terseLabel_en-US" xlink:label="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Unrecognized compensation cost</link:label>
    <link:label id="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions_label_en-US" xlink:label="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Payment Arrangement, Nonvested Award, Excluding Option, Cost Not yet Recognized, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions"/>
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    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAuthorized_61cb6d47-337a-40a3-b92a-1943bb5dbd08_verboseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAuthorized" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Authorized target common share (in shares)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAuthorized_519d7611-92cf-469f-b82e-70d57ed9310e_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAuthorized" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Authorized target common shares (in shares)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAuthorized_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAuthorized" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Number of Shares Authorized</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAuthorized" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAuthorized"/>
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    <link:label id="lab_us-gaap_FinitelivedIntangibleAssetsAcquired1_74dc579c-6a33-4da2-a16d-04ba0044d132_terseLabel_en-US" xlink:label="lab_us-gaap_FinitelivedIntangibleAssetsAcquired1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Additions</link:label>
    <link:label id="lab_us-gaap_FinitelivedIntangibleAssetsAcquired1_label_en-US" xlink:label="lab_us-gaap_FinitelivedIntangibleAssetsAcquired1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Finite-Lived Intangible Assets Acquired</link:label>
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    <link:label id="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardOptionsOutstandingWeightedAverageRemainingContractualTerm2_5a3dd53d-15b6-41fc-b69a-077bf6e4667c_terseLabel_en-US" xlink:label="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardOptionsOutstandingWeightedAverageRemainingContractualTerm2" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Weighted average remaining contractual life of options</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardOptionsOutstandingWeightedAverageRemainingContractualTerm2" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardOptionsOutstandingWeightedAverageRemainingContractualTerm2"/>
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    <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>
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    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardPayoutPercentage_33c9fa60-0375-4682-b129-7c9894073c1e_terseLabel_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardPayoutPercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Payout Range</link:label>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardPayoutPercentage_label_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardPayoutPercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Award Payout, Percentage</link:label>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardPayoutPercentage_documentation_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardPayoutPercentage" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Award Payout, Percentage</link:label>
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    <link:label id="lab_us-gaap_UseOfEstimates_ee73aa95-090a-4b35-9d8b-dd6cf1603cb7_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"/>
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    <link:label id="lab_us-gaap_PreferredStockDividendsAndOtherAdjustmentsAbstract_9a59349c-700f-485c-aaa2-975cba510563_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockDividendsAndOtherAdjustmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Numerator</link:label>
    <link:label id="lab_us-gaap_PreferredStockDividendsAndOtherAdjustmentsAbstract_label_en-US" xlink:label="lab_us-gaap_PreferredStockDividendsAndOtherAdjustmentsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Preferred Stock Dividends and Other Adjustments [Abstract]</link:label>
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    <link:label id="lab_us-gaap_LongtermDebtTypeDomain_d1e02e64-ba38-4014-8c15-f99ee1631a00_terseLabel_en-US" xlink:label="lab_us-gaap_LongtermDebtTypeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Long-Term Debt, Type [Domain]</link:label>
    <link:label id="lab_us-gaap_LongtermDebtTypeDomain_label_en-US" xlink:label="lab_us-gaap_LongtermDebtTypeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Long-Term Debt, Type [Domain]</link:label>
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    <link:label id="lab_dei_EntityFileNumber_a565feae-cbef-409e-98d3-20757832c445_terseLabel_en-US" xlink:label="lab_dei_EntityFileNumber" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity File Number</link:label>
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    <link:label id="lab_us-gaap_LineOfCreditFacilityPeriodicPaymentInterest_040572ca-7417-480d-8d17-bba76b4223aa_terseLabel_en-US" xlink:label="lab_us-gaap_LineOfCreditFacilityPeriodicPaymentInterest" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Interest payments on revolving credit facility</link:label>
    <link:label id="lab_us-gaap_LineOfCreditFacilityPeriodicPaymentInterest_label_en-US" xlink:label="lab_us-gaap_LineOfCreditFacilityPeriodicPaymentInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Line of Credit Facility, Periodic Payment, Interest</link:label>
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    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueAfterYearFive_070e3e4f-b2c1-4cf9-a4c8-49747d41af3b_terseLabel_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueAfterYearFive" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Thereafter</link:label>
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    <link:label id="lab_skwd_DeferredTaxLiabilitiesSection148aAdjustment_75e173c6-dca6-4bd9-91e2-c845cc308ad4_terseLabel_en-US" xlink:label="lab_skwd_DeferredTaxLiabilitiesSection148aAdjustment" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Section 481(a) adjustment</link:label>
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    <link:label id="lab_skwd_DeferredTaxLiabilitiesSection148aAdjustment_documentation_en-US" xlink:label="lab_skwd_DeferredTaxLiabilitiesSection148aAdjustment" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Deferred Tax Liabilities, Section 148(a) Adjustment</link:label>
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    <link:label id="lab_dei_AuditorFirmId_1a058376-d99e-49ea-8b41-2c178e7b6f55_terseLabel_en-US" xlink:label="lab_dei_AuditorFirmId" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Auditor Firm ID</link:label>
    <link:label id="lab_dei_AuditorFirmId_label_en-US" xlink:label="lab_dei_AuditorFirmId" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Auditor Firm ID</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_AuditorFirmId" xlink:href="https://xbrl.sec.gov/dei/2023/dei-2023.xsd#dei_AuditorFirmId"/>
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    <link:label id="lab_us-gaap_AmortizationOfIntangibleAssets_ab79685f-c791-4810-aca8-7e9b3afa9cc2_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_AmortizationOfIntangibleAssets" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Amortization</link:label>
    <link:label id="lab_us-gaap_AmortizationOfIntangibleAssets_16eea6a1-e677-4246-ab9d-5f5574afa4fb_verboseLabel_en-US" xlink:label="lab_us-gaap_AmortizationOfIntangibleAssets" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Amortization of intangible assets</link:label>
    <link:label id="lab_us-gaap_AmortizationOfIntangibleAssets_label_en-US" xlink:label="lab_us-gaap_AmortizationOfIntangibleAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Amortization of Intangible Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AmortizationOfIntangibleAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_AmortizationOfIntangibleAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AmortizationOfIntangibleAssets" xlink:to="lab_us-gaap_AmortizationOfIntangibleAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityShellCompany_2ec1c295-3083-414e-b141-76005cec61c8_terseLabel_en-US" xlink:label="lab_dei_EntityShellCompany" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Shell Company</link:label>
    <link:label id="lab_dei_EntityShellCompany_label_en-US" xlink:label="lab_dei_EntityShellCompany" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Shell Company</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityShellCompany" xlink:href="https://xbrl.sec.gov/dei/2023/dei-2023.xsd#dei_EntityShellCompany"/>
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    <link:label id="lab_skwd_MortgageLoansNotProducingIncomeAmount_e589b5ad-3a0d-47e0-ba84-e8e754f15383_terseLabel_en-US" xlink:label="lab_skwd_MortgageLoansNotProducingIncomeAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mortgage loans not producing income</link:label>
    <link:label id="lab_skwd_MortgageLoansNotProducingIncomeAmount_label_en-US" xlink:label="lab_skwd_MortgageLoansNotProducingIncomeAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Mortgage Loans not Producing Income, Amount</link:label>
    <link:label id="lab_skwd_MortgageLoansNotProducingIncomeAmount_documentation_en-US" xlink:label="lab_skwd_MortgageLoansNotProducingIncomeAmount" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Mortgage Loans not Producing Income, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_MortgageLoansNotProducingIncomeAmount" xlink:href="skwd-20231231.xsd#skwd_MortgageLoansNotProducingIncomeAmount"/>
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    <link:label id="lab_ecd_RestatementDeterminationDate_terseLabel_en-US" xlink:label="lab_ecd_RestatementDeterminationDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Restatement Determination Date</link:label>
    <link:label id="lab_ecd_RestatementDeterminationDate_label_en-US" xlink:label="lab_ecd_RestatementDeterminationDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Restatement Determination Date</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_RestatementDeterminationDate" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_RestatementDeterminationDate"/>
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    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTableTextBlock_ee4c7090-645b-4654-b464-7ec87a68918f_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reconciliation of Claims Development to Liability</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contracts, Reconciliation of Claims Development to Liability [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTableTextBlock"/>
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    <link:label id="lab_ecd_Rule10b51ArrAdoptedFlag_terseLabel_en-US" xlink:label="lab_ecd_Rule10b51ArrAdoptedFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Rule 10b5-1 Arrangement Adopted</link:label>
    <link:label id="lab_ecd_Rule10b51ArrAdoptedFlag_label_en-US" xlink:label="lab_ecd_Rule10b51ArrAdoptedFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Rule 10b5-1 Arrangement Adopted [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_Rule10b51ArrAdoptedFlag" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_Rule10b51ArrAdoptedFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_Rule10b51ArrAdoptedFlag" xlink:to="lab_ecd_Rule10b51ArrAdoptedFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_410c1974-9085-4b2b-b835-9c8b02f0706e_periodStartLabel_en-US" xlink:label="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Cash and cash equivalents and restricted cash at beginning of year</link:label>
    <link:label id="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_8dbaf645-9dda-464a-a785-506108cb527f_periodEndLabel_en-US" xlink:label="lab_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Cash and cash equivalents and restricted cash at end of year</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents"/>
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    <link:label id="lab_us-gaap_FairValueByAssetClassAxis_be3c0dc6-24a1-4dbf-a744-1120cbdd2860_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueByAssetClassAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Asset Class [Axis]</link:label>
    <link:label id="lab_us-gaap_FairValueByAssetClassAxis_label_en-US" xlink:label="lab_us-gaap_FairValueByAssetClassAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Asset Class [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueByAssetClassAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FairValueByAssetClassAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueByAssetClassAxis" xlink:to="lab_us-gaap_FairValueByAssetClassAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_GrossRealizedInvestmentGainsAbstract_21994d15-4096-4fc3-b5ef-7da00af7c856_terseLabel_en-US" xlink:label="lab_skwd_GrossRealizedInvestmentGainsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gross realized gains</link:label>
    <link:label id="lab_skwd_GrossRealizedInvestmentGainsAbstract_label_en-US" xlink:label="lab_skwd_GrossRealizedInvestmentGainsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gross Realized Investment Gains [Abstract]</link:label>
    <link:label id="lab_skwd_GrossRealizedInvestmentGainsAbstract_documentation_en-US" xlink:label="lab_skwd_GrossRealizedInvestmentGainsAbstract" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Gross Realized Investment Gains</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_GrossRealizedInvestmentGainsAbstract" xlink:href="skwd-20231231.xsd#skwd_GrossRealizedInvestmentGainsAbstract"/>
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    <link:label id="lab_us-gaap_EquitySecuritiesFvNiRealizedLoss_81339b3d-0f8a-4840-a230-5b77c31a11a8_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiRealizedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Equity securities</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiRealizedLoss_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiRealizedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Securities, FV-NI, Realized Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesFvNiRealizedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_EquitySecuritiesFvNiRealizedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesFvNiRealizedLoss" xlink:to="lab_us-gaap_EquitySecuritiesFvNiRealizedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent_57bf62d3-d228-49cd-a72b-b7ae235ae92e_terseLabel_en-US" xlink:label="lab_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accounts payable and accrued liabilities</link:label>
    <link:label id="lab_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent_label_en-US" xlink:label="lab_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Accounts Payable and Accrued Liabilities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent" xlink:to="lab_us-gaap_AccountsPayableAndAccruedLiabilitiesCurrentAndNoncurrent" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesCost_0e46033d-ac9c-4bfe-8329-c8808d67e5be_terseLabel_en-US" xlink:label="lab_us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cost</link:label>
    <link:label id="lab_us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesCost_label_en-US" xlink:label="lab_us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-15, Insurance Companies, Summary of Investments, Other than Investments in Related Parties, Cost</link:label>
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    <link:label id="lab_us-gaap_OperatingLeaseCost_401216dd-50e3-4d95-afc8-e727198eb66f_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingLeaseCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Operating lease expense</link:label>
    <link:label id="lab_us-gaap_OperatingLeaseCost_label_en-US" xlink:label="lab_us-gaap_OperatingLeaseCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Operating Lease, Cost</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseCost" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_OperatingLeaseCost"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OperatingLeaseCost" xlink:to="lab_us-gaap_OperatingLeaseCost" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInPremiumsReceivable_0cad5a43-becb-4064-92fc-375fceb0be86_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInPremiumsReceivable" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Premiums receivable, net</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInPremiumsReceivable_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInPremiumsReceivable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Premiums Receivable</link:label>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger_335375ca-cf67-47d9-8e80-a549a4a1e536_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger" 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_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger" 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, 12 Months or Longer</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger"/>
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    <link:label id="lab_us-gaap_CommonStockSharesIssued_cfcb07b0-53c5-4546-ac62-7df62b7fd0ce_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockSharesIssued" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Common stock, shares issued (in shares)</link:label>
    <link:label id="lab_us-gaap_CommonStockSharesIssued_label_en-US" xlink:label="lab_us-gaap_CommonStockSharesIssued" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock, Shares, Issued</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockSharesIssued" xlink:to="lab_us-gaap_CommonStockSharesIssued" xlink:type="arc" order="1"/>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriod"/>
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    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingLoss_27a6b617-7802-4d3d-b912-785f25fd039c_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Gross Unrealized Losses</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingLoss"/>
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    <link:label id="lab_us-gaap_LongTermDebt_428e6dba-07ac-4220-9e32-dd6105bc5789_totalLabel_en-US" xlink:label="lab_us-gaap_LongTermDebt" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Subordinated debt, net of debt issuance costs</link:label>
    <link:label id="lab_us-gaap_LongTermDebt_label_en-US" xlink:label="lab_us-gaap_LongTermDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Long-Term Debt</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LongTermDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LongTermDebt" xlink:to="lab_us-gaap_LongTermDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AssetsFairValueDisclosure_fb80220a-62ee-41c4-95b5-696b0843eb1e_totalLabel_en-US" xlink:label="lab_us-gaap_AssetsFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total investments</link:label>
    <link:label id="lab_us-gaap_AssetsFairValueDisclosure_label_en-US" xlink:label="lab_us-gaap_AssetsFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Assets, Fair Value Disclosure</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetsFairValueDisclosure" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_AssetsFairValueDisclosure"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssetsFairValueDisclosure" xlink:to="lab_us-gaap_AssetsFairValueDisclosure" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_LoansReceivableMeasurementInput_534d0f0b-3681-45e2-acea-7bb6367c532c_terseLabel_en-US" xlink:label="lab_skwd_LoansReceivableMeasurementInput" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Loans receivable</link:label>
    <link:label id="lab_skwd_LoansReceivableMeasurementInput_label_en-US" xlink:label="lab_skwd_LoansReceivableMeasurementInput" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Loans Receivable, Measurement Input</link:label>
    <link:label id="lab_skwd_LoansReceivableMeasurementInput_documentation_en-US" xlink:label="lab_skwd_LoansReceivableMeasurementInput" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Loans Receivable, Measurement Input</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_LoansReceivableMeasurementInput" xlink:href="skwd-20231231.xsd#skwd_LoansReceivableMeasurementInput"/>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss_7519941b-6abd-4aba-94e6-d89a012688d2_negatedTotalLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTotalLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Unrealized Loss Position, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableCreditQualityIndicatorTableTextBlock_3d7f5047-f9db-414b-8e69-5982da98926e_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableCreditQualityIndicatorTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverable, Credit Quality Indicator</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableCreditQualityIndicatorTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableCreditQualityIndicatorTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverable, Credit Quality Indicator [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverableCreditQualityIndicatorTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ReinsuranceRecoverableCreditQualityIndicatorTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverableCreditQualityIndicatorTableTextBlock" xlink:to="lab_us-gaap_ReinsuranceRecoverableCreditQualityIndicatorTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SaleOfStockConsiderationReceivedOnTransaction_bffe75b8-b42c-47ec-8da3-9d3ef1ea1132_terseLabel_en-US" xlink:label="lab_us-gaap_SaleOfStockConsiderationReceivedOnTransaction" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Sale of stock, consideration</link:label>
    <link:label id="lab_us-gaap_SaleOfStockConsiderationReceivedOnTransaction_label_en-US" xlink:label="lab_us-gaap_SaleOfStockConsiderationReceivedOnTransaction" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Sale of Stock, Consideration Received on Transaction</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SaleOfStockConsiderationReceivedOnTransaction" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_SaleOfStockConsiderationReceivedOnTransaction"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SaleOfStockConsiderationReceivedOnTransaction" xlink:to="lab_us-gaap_SaleOfStockConsiderationReceivedOnTransaction" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet_32b921b8-9f85-4d8c-b5da-2d5dc5b341ab_totalLabel_en-US" xlink:label="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total incurred, net of reinsurance</link:label>
    <link:label id="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet_label_en-US" xlink:label="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability For Unpaid Claims And Claims Adjustment Expense, Incurred Claims, Net</link:label>
    <link:label id="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet_documentation_en-US" xlink:label="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Liability For Unpaid Claims And Claims Adjustment Expense, Incurred Claims, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet" xlink:href="skwd-20231231.xsd#skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet" xlink:to="lab_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ValuationAllowancesAndReservesBalance_1823c72c-2099-4594-b90b-810f727def4a_periodStartLabel_en-US" xlink:label="lab_us-gaap_ValuationAllowancesAndReservesBalance" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Beginning balance</link:label>
    <link:label id="lab_us-gaap_ValuationAllowancesAndReservesBalance_9d9fd952-5e38-4e72-bff0-a30870dd26eb_periodEndLabel_en-US" xlink:label="lab_us-gaap_ValuationAllowancesAndReservesBalance" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Ending balance</link:label>
    <link:label id="lab_us-gaap_ValuationAllowancesAndReservesBalance_label_en-US" xlink:label="lab_us-gaap_ValuationAllowancesAndReservesBalance" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-09, Valuation Allowances and Reserves, Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ValuationAllowancesAndReservesBalance" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ValuationAllowancesAndReservesBalance"/>
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    <link:label id="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedPeriodForRecognition1_71f7d117-c609-4d02-9e4a-e18375529a54_terseLabel_en-US" xlink:label="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedPeriodForRecognition1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Unrecognized compensation cost, recognition period</link:label>
    <link:label id="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedPeriodForRecognition1_label_en-US" xlink:label="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedPeriodForRecognition1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Payment Arrangement, Nonvested Award, Cost Not yet Recognized, Period for Recognition</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedPeriodForRecognition1" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedPeriodForRecognition1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedPeriodForRecognition1" xlink:to="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedPeriodForRecognition1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsurerConcentrationRiskMember_a111d928-d2ea-4a84-902b-cf9da5591a57_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsurerConcentrationRiskMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurer concentration risk</link:label>
    <link:label id="lab_us-gaap_ReinsurerConcentrationRiskMember_label_en-US" xlink:label="lab_us-gaap_ReinsurerConcentrationRiskMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurer Concentration Risk [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsurerConcentrationRiskMember" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ReinsurerConcentrationRiskMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsurerConcentrationRiskMember" xlink:to="lab_us-gaap_ReinsurerConcentrationRiskMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ComprehensiveIncomeNetOfTax_c3fd3792-ed4b-48fb-90f6-94db24dad545_totalLabel_en-US" xlink:label="lab_us-gaap_ComprehensiveIncomeNetOfTax" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Comprehensive income (loss)</link:label>
    <link:label id="lab_us-gaap_ComprehensiveIncomeNetOfTax_label_en-US" xlink:label="lab_us-gaap_ComprehensiveIncomeNetOfTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Comprehensive Income (Loss), Net of Tax, Attributable to Parent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ComprehensiveIncomeNetOfTax" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ComprehensiveIncomeNetOfTax"/>
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    <link:label id="lab_us-gaap_FinancingReceivablePortfolioSegmentDomain_0e6ebf66-9c94-40fc-8eaa-12be53f57f77_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_us-gaap_ReinsuranceRecoverableCreditLossExpenseReversal_e50e0eb5-7411-4a43-a8df-3b21a25112da_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableCreditLossExpenseReversal" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Current period change for estimated uncollectible reinsurance</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableCreditLossExpenseReversal_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverableCreditLossExpenseReversal" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverable, Credit Loss Expense (Reversal)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverableCreditLossExpenseReversal" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ReinsuranceRecoverableCreditLossExpenseReversal"/>
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    <link:label id="lab_us-gaap_ShortTermLeaseCost_ea3944f2-e551-4b1c-9bdb-7b3f8e7d2963_terseLabel_en-US" xlink:label="lab_us-gaap_ShortTermLeaseCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Short-term lease expense</link:label>
    <link:label id="lab_us-gaap_ShortTermLeaseCost_label_en-US" xlink:label="lab_us-gaap_ShortTermLeaseCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Term Lease, Cost</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortTermLeaseCost" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShortTermLeaseCost"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortTermLeaseCost" xlink:to="lab_us-gaap_ShortTermLeaseCost" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressAddressLine1_a9a5046d-7908-4bc8-a0cb-c447161c8ea0_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"/>
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    <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_us-gaap_SubsequentEventTable_bc8abf2e-8255-4390-a343-93a8374c0b23_terseLabel_en-US" xlink:label="lab_us-gaap_SubsequentEventTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subsequent Event [Table]</link:label>
    <link:label id="lab_us-gaap_SubsequentEventTable_label_en-US" xlink:label="lab_us-gaap_SubsequentEventTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsequent Event [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsequentEventTable" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_SubsequentEventTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsequentEventTable" xlink:to="lab_us-gaap_SubsequentEventTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingWeightedAverageExercisePriceRollforward_a81f0ad6-3785-4b0e-a58f-963ee8fdb1db_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingWeightedAverageExercisePriceRollforward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Weighted-Average Exercise Price</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingWeightedAverageExercisePriceRollforward_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingWeightedAverageExercisePriceRollforward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Options, Outstanding, Weighted Average Exercise Price [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingWeightedAverageExercisePriceRollforward" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingWeightedAverageExercisePriceRollforward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingWeightedAverageExercisePriceRollforward" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingWeightedAverageExercisePriceRollforward" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsAsset_066d3ee0-972d-4563-a5df-d30b1f7b88bf_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_SubsequentEventMember_388c40f6-d708-450d-ab3f-7933ef0a0868_terseLabel_en-US" xlink:label="lab_us-gaap_SubsequentEventMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subsequent event</link:label>
    <link:label id="lab_us-gaap_SubsequentEventMember_label_en-US" xlink:label="lab_us-gaap_SubsequentEventMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsequent Event [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsequentEventMember" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_SubsequentEventMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsequentEventMember" xlink:to="lab_us-gaap_SubsequentEventMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_CreditLossLineItems_8ad55fa6-6eaa-4734-b874-3ef926ec8b3e_terseLabel_en-US" xlink:label="lab_skwd_CreditLossLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Credit Loss [Line Items]</link:label>
    <link:label id="lab_skwd_CreditLossLineItems_label_en-US" xlink:label="lab_skwd_CreditLossLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Credit Loss [Line Items]</link:label>
    <link:label id="lab_skwd_CreditLossLineItems_documentation_en-US" xlink:label="lab_skwd_CreditLossLineItems" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Credit Loss [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_CreditLossLineItems" xlink:href="skwd-20231231.xsd#skwd_CreditLossLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_CreditLossLineItems" xlink:to="lab_skwd_CreditLossLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OperatingLossCarryforwards_1695f9ed-188f-4a88-ab92-d3416e587d34_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingLossCarryforwards" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Operating loss carryforwards</link:label>
    <link:label id="lab_us-gaap_OperatingLossCarryforwards_label_en-US" xlink:label="lab_us-gaap_OperatingLossCarryforwards" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Operating Loss Carryforwards</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLossCarryforwards" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_OperatingLossCarryforwards"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OperatingLossCarryforwards" xlink:to="lab_us-gaap_OperatingLossCarryforwards" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue_8b95de14-740d-4fc2-a048-098021865e3c_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_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract_5c322161-a138-4f8f-aaf1-99e0f0c8f61b_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">Total fixed maturity securities, held-to-maturity</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" 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_GoodwillGross_9e3e159b-aab1-42c2-90c9-bf398dbeab0f_verboseLabel_en-US" xlink:label="lab_us-gaap_GoodwillGross" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Goodwill, gross balance</link:label>
    <link:label id="lab_us-gaap_GoodwillGross_label_en-US" xlink:label="lab_us-gaap_GoodwillGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillGross" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_GoodwillGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillGross" xlink:to="lab_us-gaap_GoodwillGross" xlink:type="arc" order="1"/>
    <link:label id="lab_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_skwd_BrewerLaneVenturesFundIILPMember_df13091d-ecd9-4fe2-9b15-958c995d9514_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>
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    <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_StockIssuedDuringPeriodValueShareBasedCompensation_ca1e8c34-961c-488f-b08f-895a4af918c7_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_skwd_LondonInterbankOfferedRateLIBOR1Member_16a43b9e-e233-4756-b103-711e9afd1377_terseLabel_en-US" xlink:label="lab_skwd_LondonInterbankOfferedRateLIBOR1Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">London Interbank Offered Rate (LIBOR)</link:label>
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    <link:label id="lab_skwd_LondonInterbankOfferedRateLIBOR1Member_documentation_en-US" xlink:label="lab_skwd_LondonInterbankOfferedRateLIBOR1Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">London Interbank Offered Rate (LIBOR) 1</link:label>
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    <link:label id="lab_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesAbstract_label_en-US" xlink:label="lab_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-15, Insurance Companies, Summary of Investments, Other than Investments in Related Parties [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesAbstract" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesAbstract"/>
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    <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-20231231.xsd#skwd_GrossInvestmentIncomeExpenseOperating"/>
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    <link:label id="lab_us-gaap_IncomeTaxReconciliationIncomeTaxExpenseBenefitAtFederalStatutoryIncomeTaxRate_f38a670c-7122-46f2-9358-8c3bae140fc3_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxReconciliationIncomeTaxExpenseBenefitAtFederalStatutoryIncomeTaxRate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income tax expense at federal statutory rate</link:label>
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    <link:label id="lab_us-gaap_SubsidiaryOrEquityMethodInvesteeSaleOfStockBySubsidiaryOrEquityInvesteeTable_768476ea-b6bd-41d7-a612-05aa68d5320b_terseLabel_en-US" xlink:label="lab_us-gaap_SubsidiaryOrEquityMethodInvesteeSaleOfStockBySubsidiaryOrEquityInvesteeTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subsidiary or Equity Method Investee, Sale of Stock by Subsidiary or Equity Investee [Table]</link:label>
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    <link:label id="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense_6922b500-4e45-4096-a41a-fca24fa2213c_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>
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    <link:label id="lab_us-gaap_ReinsuranceTextBlock_325f89d1-c4c3-4a5a-8b09-839af90005eb_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"/>
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    <link:label id="lab_us-gaap_EquityMethodInvestments_f23409d6-7737-4b7e-8a21-7a1f3bc494b9_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>
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    <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_PaymentsForContributionsToSubsidiaries_83e10567-333d-4b44-8173-e0690d7a3e67_negatedTerseLabel_en-US" xlink:label="lab_skwd_PaymentsForContributionsToSubsidiaries" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Capital contributions to subsidiaries</link:label>
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    <link:label id="lab_skwd_PaymentsForContributionsToSubsidiaries_documentation_en-US" xlink:label="lab_skwd_PaymentsForContributionsToSubsidiaries" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Payments For Contributions To Subsidiaries</link:label>
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    <link:label id="lab_skwd_DebtInstrumentVariableRate_92e7d880-9902-419e-b9c8-a88d9d592d55_terseLabel_en-US" xlink:label="lab_skwd_DebtInstrumentVariableRate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt instrument, variable rate</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-20231231.xsd#skwd_DebtInstrumentVariableRate"/>
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    <link:label id="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating_9ae1d4a6-1a0e-4202-aadb-e1712468fd24_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>
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    <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>
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    <link:loc xlink:type="locator" xlink:label="loc_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating" xlink:href="skwd-20231231.xsd#skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating"/>
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    <link:label id="lab_us-gaap_EquitySecuritiesByIndustryAxis_bd8196e8-aa31-478b-99fd-5f80336043b2_terseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesByIndustryAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Industry Sector [Axis]</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesByIndustryAxis_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesByIndustryAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Industry Sector [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesByIndustryAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_EquitySecuritiesByIndustryAxis"/>
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    <link:label id="lab_us-gaap_FinancialInstrumentAxis_45b48201-6e2d-426f-93b4-b005b06da0c5_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"/>
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    <link:label id="lab_skwd_RealizedInvestmentGains_7ef7cfaf-86b0-4b8e-aa07-140c9761cf06_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-20231231.xsd#skwd_RealizedInvestmentGains"/>
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    <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:label id="lab_dei_EntityCommonStockSharesOutstanding_ba5d8ae8-2712-4726-9790-c1d849a12145_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>
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    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNet_6cc8621a-0215-40c1-a656-132d16514d3d_totalLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total net reserves for loss and LAE</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNet_0376faf9-4dbc-4cb2-9fcc-f1054150fbbb_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reserves for losses and LAE, net of reinsurance</link:label>
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    <link:label id="lab_srt_ProFormaMember_b76630bc-3068-4b33-b0ee-44f2fb749e24_terseLabel_en-US" xlink:label="lab_srt_ProFormaMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pro forma</link:label>
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    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsRollForward_28566c02-8fe9-418b-a3bb-78f0d3ce03b4_terseLabel_en-US" xlink:label="lab_us-gaap_IndefiniteLivedIntangibleAssetsRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Indefinite-Lived</link:label>
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    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger_8961610e-86f3-4b68-8ea6-c50bd602e430_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:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:href="skwd-20231231.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:to="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueByFairValueHierarchyLevelAxis_14f039d4-6dbc-496b-b51f-1edccffef324_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_2c838869-d2ae-4623-84a6-e454ac7b6e5e_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">Accumulated deficit</link:label>
    <link:label id="lab_us-gaap_RetainedEarningsAccumulatedDeficit_a47d783c-ffb6-43aa-85c6-1ad94f2720d4_verboseLabel_en-US" xlink:label="lab_us-gaap_RetainedEarningsAccumulatedDeficit" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" 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_us-gaap_ProceedsFromSaleOfShortTermInvestments_dfa1f558-f61d-44bb-a6bb-9c6103aa8f6e_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfShortTermInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Change in short-term investments</link:label>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfShortTermInvestments_label_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfShortTermInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Sale of Short-Term Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromSaleOfShortTermInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ProceedsFromSaleOfShortTermInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromSaleOfShortTermInvestments" xlink:to="lab_us-gaap_ProceedsFromSaleOfShortTermInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_RISCOMMember_b3a64115-e704-4a93-b7ac-a86aef0b0c07_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-20231231.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_172b14ac-4045-430e-b184-0d1ed2d87a8d_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_skwd_BToBMember_9a727a9b-c3e0-4bbe-a452-dd24e870a1ba_terseLabel_en-US" xlink:label="lab_skwd_BToBMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">B++ to B+</link:label>
    <link:label id="lab_skwd_BToBMember_label_en-US" xlink:label="lab_skwd_BToBMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">B++ to B+ [Member]</link:label>
    <link:label id="lab_skwd_BToBMember_documentation_en-US" xlink:label="lab_skwd_BToBMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">B++ to B+</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_BToBMember" xlink:href="skwd-20231231.xsd#skwd_BToBMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_BToBMember" xlink:to="lab_skwd_BToBMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTable_1d910123-e689-43bf-96c5-4b31dba84bfa_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contracts, Claims Development [Table]</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTable_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contracts, Claims Development [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTable" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTable" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LeasesAbstract_label_en-US" xlink:label="lab_us-gaap_LeasesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Leases [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LeasesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LeasesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LeasesAbstract" xlink:to="lab_us-gaap_LeasesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense_759fe626-5c56-4510-b9f5-33c3253967c1_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_5535f4b0-505d-4367-9354-5d1d79698114_verboseLabel_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Prior year claims incurred, unfavorable (favorable) development</link:label>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPriorYearClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" 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_us-gaap_CapitalizationOfDeferredPolicyAcquisitionCostsPolicy_d06e7f33-8b38-419a-9744-f67f79668a23_terseLabel_en-US" xlink:label="lab_us-gaap_CapitalizationOfDeferredPolicyAcquisitionCostsPolicy" 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_CapitalizationOfDeferredPolicyAcquisitionCostsPolicy_label_en-US" xlink:label="lab_us-gaap_CapitalizationOfDeferredPolicyAcquisitionCostsPolicy" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Policy Acquisition Costs, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CapitalizationOfDeferredPolicyAcquisitionCostsPolicy" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_CapitalizationOfDeferredPolicyAcquisitionCostsPolicy"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CapitalizationOfDeferredPolicyAcquisitionCostsPolicy" xlink:to="lab_us-gaap_CapitalizationOfDeferredPolicyAcquisitionCostsPolicy" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_CreditSpreadAdjustmentMember_08904aeb-0834-4abc-bfdd-91e61f33b28b_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-20231231.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_0da790d1-05bf-4891-93da-1aa3e9eb7a2e_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_ShortDurationInsuranceContractAccidentYear2020Member_d9b10807-a17e-4e8b-8ec0-4ef867f9bd6d_terseLabel_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2020Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accident Year 2020</link:label>
    <link:label id="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2020Member_label_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2020Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contract, Accident Year 2020 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortDurationInsuranceContractAccidentYear2020Member" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShortDurationInsuranceContractAccidentYear2020Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortDurationInsuranceContractAccidentYear2020Member" xlink:to="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2020Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ComponentsOfDeferredTaxAssetsAbstract_f29603cb-b902-4e2d-8d7f-fe4c6368d045_terseLabel_en-US" xlink:label="lab_us-gaap_ComponentsOfDeferredTaxAssetsAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Deferred tax assets:</link:label>
    <link:label id="lab_us-gaap_ComponentsOfDeferredTaxAssetsAbstract_label_en-US" xlink:label="lab_us-gaap_ComponentsOfDeferredTaxAssetsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Components of Deferred Tax Assets [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ComponentsOfDeferredTaxAssetsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ComponentsOfDeferredTaxAssetsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ComponentsOfDeferredTaxAssetsAbstract" xlink:to="lab_us-gaap_ComponentsOfDeferredTaxAssetsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressStateOrProvince_74fc0bfc-88e7-4be7-b7bc-f864c446b21e_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_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months_069b45a4-61e0-4790-bb4a-0ee1404de7a0_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:label id="lab_us-gaap_ResidentialMortgageBackedSecuritiesMember_42ae3f04-d64d-4b2e-b8bd-a6cee444f96b_terseLabel_en-US" xlink:label="lab_us-gaap_ResidentialMortgageBackedSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Residential mortgage-backed securities</link:label>
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    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPremiumsWritten_537bd295-5aa7-4278-a532-132391257940_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net premiums written</link:label>
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    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems_9eb3a860-e424-4e9f-b936-dc82194133a5_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Liability for Claims and Claims Adjustment Expense [Line Items]</link:label>
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    <link:label id="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember_04eb0e83-be91-4696-8df9-b624cbabf863_terseLabel_en-US" xlink:label="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">SUA commission revenue</link:label>
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    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationByAssetClassDomain_d5b48a4d-a5a8-44a1-a9dc-af73262623e8_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationByAssetClassDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Asset Class [Domain]</link:label>
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    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationOtherAdjustments_c1a470e5-bdba-46bc-ad94-660d74790eea_terseLabel_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationOtherAdjustments" 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_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic_7b0b5ebe-5d84-49e4-a310-a2c192e4bc47_totalLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net income attributable to common shareholders</link:label>
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    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsAccidentYear2015Member_fbb3ee1f-170a-4695-a411-57c3986c235f_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsAccidentYear2015Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accident Year 2015</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:to="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:type="arc" order="1"/>
    <link:label id="lab_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>
    <link:label id="lab_ecd_AggtErrCompAmt_label_en-US" xlink:label="lab_ecd_AggtErrCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Aggregate Erroneous Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AggtErrCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_AggtErrCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AggtErrCompAmt" xlink:to="lab_ecd_AggtErrCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ValuationAllowancesAndReservesChargedToCostAndExpense_9d0f0335-2f89-434b-82eb-8473a8f079ca_terseLabel_en-US" xlink:label="lab_us-gaap_ValuationAllowancesAndReservesChargedToCostAndExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Charged to costs and expenses</link:label>
    <link:label id="lab_us-gaap_ValuationAllowancesAndReservesChargedToCostAndExpense_label_en-US" xlink:label="lab_us-gaap_ValuationAllowancesAndReservesChargedToCostAndExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-09, Valuation Allowances and Reserves, Additions, Charge to Cost and Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ValuationAllowancesAndReservesChargedToCostAndExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ValuationAllowancesAndReservesChargedToCostAndExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ValuationAllowancesAndReservesChargedToCostAndExpense" xlink:to="lab_us-gaap_ValuationAllowancesAndReservesChargedToCostAndExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DefinedContributionPlanCostRecognized_4a52fa4a-5a9c-428b-990f-6de1f008f67b_terseLabel_en-US" xlink:label="lab_us-gaap_DefinedContributionPlanCostRecognized" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Defined contribution plan</link:label>
    <link:label id="lab_us-gaap_DefinedContributionPlanCostRecognized_label_en-US" xlink:label="lab_us-gaap_DefinedContributionPlanCostRecognized" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Defined Contribution Plan, Cost</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DefinedContributionPlanCostRecognized" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DefinedContributionPlanCostRecognized"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DefinedContributionPlanCostRecognized" xlink:to="lab_us-gaap_DefinedContributionPlanCostRecognized" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AllExecutiveCategoriesMember_terseLabel_en-US" xlink:label="lab_ecd_AllExecutiveCategoriesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">All Executive Categories</link:label>
    <link:label id="lab_ecd_AllExecutiveCategoriesMember_label_en-US" xlink:label="lab_ecd_AllExecutiveCategoriesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">All Executive Categories [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AllExecutiveCategoriesMember" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_AllExecutiveCategoriesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AllExecutiveCategoriesMember" xlink:to="lab_ecd_AllExecutiveCategoriesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PlanNameAxis_b5963558-759b-4ba3-bba8-e9875c14d2e7_terseLabel_en-US" xlink:label="lab_us-gaap_PlanNameAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Plan Name [Axis]</link:label>
    <link:label id="lab_us-gaap_PlanNameAxis_label_en-US" xlink:label="lab_us-gaap_PlanNameAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Plan Name [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PlanNameAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PlanNameAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PlanNameAxis" xlink:to="lab_us-gaap_PlanNameAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_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_60c9d6fa-41b1-4641-b9a2-352cb6779ad7_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-20231231.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_LiabilityForClaimsAndClaimsAdjustmentExpenseTable_e20ffd12-b9f4-4a4f-9b2d-6faea8cf3729_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Liability for Claims and Claims Adjustment Expense [Table]</link:label>
    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseTable_label_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Claims and Claims Adjustment Expense [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseTable" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseTable" xlink:to="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumReceivableCreditLossExpenseReversal_e90a310c-0a83-4997-b075-4c479982b0fb_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumReceivableCreditLossExpenseReversal" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Current period change for estimated uncollectible premiums</link:label>
    <link:label id="lab_us-gaap_PremiumReceivableCreditLossExpenseReversal_label_en-US" xlink:label="lab_us-gaap_PremiumReceivableCreditLossExpenseReversal" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Premium Receivable, Credit Loss Expense (Reversal)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumReceivableCreditLossExpenseReversal" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PremiumReceivableCreditLossExpenseReversal"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumReceivableCreditLossExpenseReversal" xlink:to="lab_us-gaap_PremiumReceivableCreditLossExpenseReversal" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerShareAbstract_8cbd46b1-ba29-493b-8beb-28e233873364_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_us-gaap_PremiumsPercentageAssumedToNet_d5a9d096-30bc-4638-a6cd-e940c628a7a6_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsPercentageAssumedToNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Percentage of amount assumed to net</link:label>
    <link:label id="lab_us-gaap_PremiumsPercentageAssumedToNet_label_en-US" xlink:label="lab_us-gaap_PremiumsPercentageAssumedToNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-17, Insurance Companies, Reinsurance, Premium, Percentage Assumed to Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsPercentageAssumedToNet" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PremiumsPercentageAssumedToNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsPercentageAssumedToNet" xlink:to="lab_us-gaap_PremiumsPercentageAssumedToNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearOne_b6f8dbb0-235e-4ace-8ef7-e40ec6511880_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearOne" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Year 1</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearOne_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearOne" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contracts, Historical Claims Duration, Year One</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearOne" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearOne"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearOne" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearOne" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockValue_1bd954f1-c816-46e6-8367-2a31df979173_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 and 168,000,000 shares authorized, 39,863,756 and 16,832,955 shares issued, respectively</link:label>
    <link:label id="lab_us-gaap_CommonStockValue_label_en-US" xlink:label="lab_us-gaap_CommonStockValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" 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_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue_95656c63-1de1-4ded-b47d-051b26e111eb_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_be805684-6975-460f-a59f-34d4b4802ebb_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_skwd_JVMFundsLLCMember_d69b9f92-5776-4d5e-ac06-ac5168f44206_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 units</link:label>
    <link:label id="lab_skwd_JVMFundsLLCMember_label_en-US" xlink:label="lab_skwd_JVMFundsLLCMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" 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-20231231.xsd#skwd_JVMFundsLLCMember"/>
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    <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_ShortdurationInsuranceContractsClaimsDevelopmentTableTextBlock_809cae43-a16d-4ae8-b9ef-f220578ced10_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Short-Duration Insurance Contracts</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsClaimsDevelopmentTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contracts, Claims Development [Table Text Block]</link:label>
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    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersDeferredPolicyAcquisitionCosts_label_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersDeferredPolicyAcquisitionCosts" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-18, Supplemental Information, Property-Casualty Insurance Underwriters, Deferred Policy Acquisition Cost</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersDeferredPolicyAcquisitionCosts" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersDeferredPolicyAcquisitionCosts"/>
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    <link:label id="lab_skwd_ArenaSpecialOpportunitiesFundLPMember_8a041ad4-e502-418c-9a76-782c2476cad6_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>
    <link:label id="lab_skwd_ArenaSpecialOpportunitiesFundLPMember_label_en-US" xlink:label="lab_skwd_ArenaSpecialOpportunitiesFundLPMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Arena Special Opportunities Fund, LP [Member]</link:label>
    <link:label id="lab_skwd_ArenaSpecialOpportunitiesFundLPMember_documentation_en-US" xlink:label="lab_skwd_ArenaSpecialOpportunitiesFundLPMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Arena Special Opportunities Fund, LP</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ArenaSpecialOpportunitiesFundLPMember" xlink:href="skwd-20231231.xsd#skwd_ArenaSpecialOpportunitiesFundLPMember"/>
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    <link:label id="lab_us-gaap_PaymentsToAcquireEquitySecuritiesFvNi_36e4bbe3-6396-47a5-8162-3989e8917a84_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"/>
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    <link:label id="lab_srt_CondensedIncomeStatementTable_c86f0ad6-89e1-46c1-9842-43efd85b16d9_terseLabel_en-US" xlink:label="lab_srt_CondensedIncomeStatementTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Condensed Income Statement [Table]</link:label>
    <link:label id="lab_srt_CondensedIncomeStatementTable_label_en-US" xlink:label="lab_srt_CondensedIncomeStatementTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Condensed Income Statement [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_CondensedIncomeStatementTable" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_CondensedIncomeStatementTable"/>
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    <link:label id="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward_a13b10f6-f00b-498e-a3c3-b0d9202fabb4_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>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_IncreaseDecreaseInStockholdersEquityRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:to="lab_us-gaap_IncreaseDecreaseInStockholdersEquityRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_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:label id="lab_dei_DocumentFiscalPeriodFocus_6bdba900-74c7-41fd-a013-e80161f9a7ff_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_skwd_ProceedsFromDistributionsFromConsolidatedEntities_5450f949-4957-4b58-ac95-174b5daf2b49_terseLabel_en-US" xlink:label="lab_skwd_ProceedsFromDistributionsFromConsolidatedEntities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Distributions from investment in subsidiaries</link:label>
    <link:label id="lab_skwd_ProceedsFromDistributionsFromConsolidatedEntities_label_en-US" xlink:label="lab_skwd_ProceedsFromDistributionsFromConsolidatedEntities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds From Distributions From Consolidated Entities</link:label>
    <link:label id="lab_skwd_ProceedsFromDistributionsFromConsolidatedEntities_documentation_en-US" xlink:label="lab_skwd_ProceedsFromDistributionsFromConsolidatedEntities" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Proceeds From Distributions From Consolidated Entities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ProceedsFromDistributionsFromConsolidatedEntities" xlink:href="skwd-20231231.xsd#skwd_ProceedsFromDistributionsFromConsolidatedEntities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ProceedsFromDistributionsFromConsolidatedEntities" xlink:to="lab_skwd_ProceedsFromDistributionsFromConsolidatedEntities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MortgageLoansInProcessOfForeclosureAmount_0be4bdb3-330e-489f-a99c-d89a392ec71d_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_FiniteLivedIntangibleAssetUsefulLife_476b3dff-c1bf-42c6-a36f-2a5e0e068146_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetUsefulLife" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Useful life</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetUsefulLife_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetUsefulLife" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Finite-Lived Intangible Asset, Useful Life</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetUsefulLife" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FiniteLivedIntangibleAssetUsefulLife"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetUsefulLife" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetUsefulLife" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LineOfCreditFacilityRemainingBorrowingCapacity_7dbde139-47cb-4b60-b304-58b0a81caf08_terseLabel_en-US" xlink:label="lab_us-gaap_LineOfCreditFacilityRemainingBorrowingCapacity" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Remaining borrowing capacity</link:label>
    <link:label id="lab_us-gaap_LineOfCreditFacilityRemainingBorrowingCapacity_label_en-US" xlink:label="lab_us-gaap_LineOfCreditFacilityRemainingBorrowingCapacity" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Line of Credit Facility, Remaining Borrowing Capacity</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LineOfCreditFacilityRemainingBorrowingCapacity" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LineOfCreditFacilityRemainingBorrowingCapacity"/>
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    <link:label id="lab_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded_9ad0de17-a3b6-448a-b241-b6f567c81f3d_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"/>
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    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFour_78dccda4-f335-49e1-833c-9b4b1980d771_terseLabel_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFour" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2027</link:label>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFour_label_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFour" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Lessee, Operating Lease, Liability, to be Paid, Year Four</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFour" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFour"/>
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    <link:label id="lab_us-gaap_OperatingLeaseExpense_label_en-US" xlink:label="lab_us-gaap_OperatingLeaseExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Operating Lease, Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_OperatingLeaseExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OperatingLeaseExpense" xlink:to="lab_us-gaap_OperatingLeaseExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensation_a44333a1-5402-46e2-a3f8-151d290eafa1_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensation" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stock-based compensation expense</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensation_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensation" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Payment Arrangement, Noncash Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensation" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShareBasedCompensation"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensation" xlink:to="lab_us-gaap_ShareBasedCompensation" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_WeightedAverageMember_12e76386-0868-4b05-befc-bcb4d290437a_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>
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    <link:loc xlink:type="locator" xlink:label="loc_srt_WeightedAverageMember" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_WeightedAverageMember"/>
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    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsIncurredClaimsAndAllocatedClaimAdjustmentExpenseNet_14d3cf9e-cb41-4e16-9ecc-5c50fb778234_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsIncurredClaimsAndAllocatedClaimAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Incurred losses and ALAE, net of reinsurance</link:label>
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    <link:label id="lab_skwd_TreasuryStockParValue_40ac7b3b-2229-4cb3-a98b-c9c6710c95dd_terseLabel_en-US" xlink:label="lab_skwd_TreasuryStockParValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Treasury stock, par value (in dollars per share)</link:label>
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    <link:label id="lab_skwd_TreasuryStockParValue_documentation_en-US" xlink:label="lab_skwd_TreasuryStockParValue" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Treasury Stock, Par Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_TreasuryStockParValue" xlink:href="skwd-20231231.xsd#skwd_TreasuryStockParValue"/>
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    <link:label id="lab_dei_CityAreaCode_79f91ab7-1616-4e65-9e78-932ab09e9dd6_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"/>
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    <link:label id="lab_srt_ProductOrServiceAxis_d535fd55-8718-4a37-87bd-d2c509376aa6_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_2cd8c311-e484-434b-835b-6fe75ca56b01_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-20231231.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_e4528cf0-205d-46cd-8907-a29020c41767_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_ScheduleOfNonvestedShareActivityTableTextBlock_2e7c45de-7c8c-4f5e-b42a-092b29114c48_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfNonvestedShareActivityTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Nonvested Share Activity</link:label>
    <link:label id="lab_us-gaap_ScheduleOfNonvestedShareActivityTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfNonvestedShareActivityTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Nonvested Share Activity [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfNonvestedShareActivityTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ScheduleOfNonvestedShareActivityTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfNonvestedShareActivityTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfNonvestedShareActivityTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CondensedIncomeStatementsCaptionsLineItems_f6771c35-0d9b-4fe9-9726-adeeb714b369_terseLabel_en-US" xlink:label="lab_srt_CondensedIncomeStatementsCaptionsLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Condensed Income Statements, Captions [Line Items]</link:label>
    <link:label id="lab_srt_CondensedIncomeStatementsCaptionsLineItems_label_en-US" xlink:label="lab_srt_CondensedIncomeStatementsCaptionsLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Condensed Income Statements, Captions [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_CondensedIncomeStatementsCaptionsLineItems" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_CondensedIncomeStatementsCaptionsLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_CondensedIncomeStatementsCaptionsLineItems" xlink:to="lab_srt_CondensedIncomeStatementsCaptionsLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_RevolvingLineOfCreditDueDecember2024Member_9a9ce702-f14e-49f6-91b2-1c147dec573f_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_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-20231231.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_9b6c589b-9f23-4c45-8d03-b089e7fce60e_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_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_FiniteLivedIntangibleAssetsByMajorClassAxis_588c6ee6-4c81-4138-9e5a-bf154e37739d_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Finite-Lived Intangible Assets by Major Class [Axis]</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Finite-Lived Intangible Assets by Major Class [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract_label_en-US" xlink:label="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Goodwill and Intangible Assets Disclosure [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract" xlink:to="lab_us-gaap_GoodwillAndIntangibleAssetsDisclosureAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OperatingLeaseRightOfUseAssetStatementOfFinancialPositionExtensibleList_989c3350-eaeb-47eb-ba34-e041abd0620b_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingLeaseRightOfUseAssetStatementOfFinancialPositionExtensibleList" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Operating Lease, Right-of-Use Asset, Statement of Financial Position [Extensible Enumeration]</link:label>
    <link:label id="lab_us-gaap_OperatingLeaseRightOfUseAssetStatementOfFinancialPositionExtensibleList_label_en-US" xlink:label="lab_us-gaap_OperatingLeaseRightOfUseAssetStatementOfFinancialPositionExtensibleList" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Operating Lease, Right-of-Use Asset, Statement of Financial Position [Extensible Enumeration]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseRightOfUseAssetStatementOfFinancialPositionExtensibleList" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_OperatingLeaseRightOfUseAssetStatementOfFinancialPositionExtensibleList"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OperatingLeaseRightOfUseAssetStatementOfFinancialPositionExtensibleList" xlink:to="lab_us-gaap_OperatingLeaseRightOfUseAssetStatementOfFinancialPositionExtensibleList" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeTaxesPaidNet_0ab60acd-5cce-4f12-b48c-ffec7f81eb81_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxesPaidNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash paid for federal income taxes</link:label>
    <link:label id="lab_us-gaap_IncomeTaxesPaidNet_label_en-US" xlink:label="lab_us-gaap_IncomeTaxesPaidNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Taxes Paid, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxesPaidNet" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_IncomeTaxesPaidNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxesPaidNet" xlink:to="lab_us-gaap_IncomeTaxesPaidNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax_4c57bac1-7fd4-4970-8794-a71f08c30679_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 gains (losses) on investments, net of tax</link:label>
    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax_label_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" 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_ValuationAllowancesAndReservesRecoveries_4b40fc28-ab71-4389-a95b-816d9b599ba9_terseLabel_en-US" xlink:label="lab_us-gaap_ValuationAllowancesAndReservesRecoveries" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Recoveries of amounts previously written off</link:label>
    <link:label id="lab_us-gaap_ValuationAllowancesAndReservesRecoveries_label_en-US" xlink:label="lab_us-gaap_ValuationAllowancesAndReservesRecoveries" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-09, Valuation Allowances and Reserves, Addition, Recovery</link:label>
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    <link:label id="lab_us-gaap_LiabilitiesAndStockholdersEquity_10048940-1ca5-4132-963b-9f0d0c62539d_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>
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    <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_516fa352-6043-477f-ab49-f783359d98d6_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>
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    <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-20231231.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>
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    <link:label id="lab_srt_OwnershipDomain_e477f6a6-df0e-48eb-a348-e4006b2943b0_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"/>
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    <link:label id="lab_us-gaap_OperatingLeaseRightOfUseAsset_23d728ae-bf0d-435d-9270-43ab1ad096bc_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingLeaseRightOfUseAsset" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Operating lease right-of-use assets</link:label>
    <link:label id="lab_us-gaap_OperatingLeaseRightOfUseAsset_label_en-US" xlink:label="lab_us-gaap_OperatingLeaseRightOfUseAsset" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Operating Lease, Right-of-Use Asset</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTable" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTable"/>
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    <link:label id="lab_us-gaap_AllowanceForCreditLossesTextBlock_4d5a3925-9090-4023-be71-49f3e84ea44f_terseLabel_en-US" xlink:label="lab_us-gaap_AllowanceForCreditLossesTextBlock" 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_AllowanceForCreditLossesTextBlock_label_en-US" xlink:label="lab_us-gaap_AllowanceForCreditLossesTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Allowance for Credit Losses [Text Block]</link:label>
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    <link:label id="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted_5f4e7692-1dc9-45d8-8ed9-3b58a9bd4b52_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>
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    <link:label id="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccountsRecoveries_6685dc16-d819-44de-8791-323ce8740c79_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccountsRecoveries" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Recoveries of amounts previously written off</link:label>
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    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearFour_6d7e894f-a0e3-422d-8f9e-3e01a3bc4fe7_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearFour" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Year 4</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_skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract_label_en-US" xlink:label="lab_skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract" 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, Accumulated Loss [Abstract]</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:href="skwd-20231231.xsd#skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract"/>
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    <link:label id="lab_us-gaap_IncomeTaxPolicyTextBlock_b3d5984f-3d8c-474a-87f1-694fdc1c2ec8_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income Taxes</link:label>
    <link:label id="lab_us-gaap_IncomeTaxPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_IncomeTaxPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Tax, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_IncomeTaxPolicyTextBlock"/>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearThree" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearThree"/>
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    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersReservesForUnpaidClaimsAndClaimsAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersReservesForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-18, Supplemental Information, Property-Casualty Insurance Underwriters, Reserve for Unpaid Claim and Claim Adjustment Expense</link:label>
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    <link:label id="lab_skwd_DebtInstrumentFixedRatePeriodDomain_481be66c-6bb4-4b65-8b03-e59166bad9c6_terseLabel_en-US" xlink:label="lab_skwd_DebtInstrumentFixedRatePeriodDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Interest Rage Range [Domain]</link:label>
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    <link:label id="lab_skwd_DebtInstrumentFixedRatePeriodDomain_documentation_en-US" xlink:label="lab_skwd_DebtInstrumentFixedRatePeriodDomain" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Fixed Rate, Period [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtInstrumentFixedRatePeriodDomain" xlink:href="skwd-20231231.xsd#skwd_DebtInstrumentFixedRatePeriodDomain"/>
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    <link:label id="lab_us-gaap_MunicipalBondsMember_8053caa0-9a3a-4112-a372-64f2d86e91b0_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>
    <link:label id="lab_us-gaap_MunicipalBondsMember_label_en-US" xlink:label="lab_us-gaap_MunicipalBondsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Municipal Bonds [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MunicipalBondsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_MunicipalBondsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MunicipalBondsMember" xlink:to="lab_us-gaap_MunicipalBondsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_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>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_InsiderTradingArrLineItems" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_InsiderTradingArrLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_InsiderTradingArrLineItems" xlink:to="lab_ecd_InsiderTradingArrLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReceivableFromShareholdersOrAffiliatesForIssuanceOfCapitalStock_ce1b4cf7-67b6-464f-a399-1c92e52581ea_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_ReceivableFromShareholdersOrAffiliatesForIssuanceOfCapitalStock" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Stock notes receivable</link:label>
    <link:label id="lab_us-gaap_ReceivableFromShareholdersOrAffiliatesForIssuanceOfCapitalStock_label_en-US" xlink:label="lab_us-gaap_ReceivableFromShareholdersOrAffiliatesForIssuanceOfCapitalStock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Receivable from Shareholders or Affiliates for Issuance of Capital Stock</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReceivableFromShareholdersOrAffiliatesForIssuanceOfCapitalStock" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ReceivableFromShareholdersOrAffiliatesForIssuanceOfCapitalStock"/>
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    <link:label id="lab_us-gaap_RelatedPartyTransactionsByRelatedPartyAxis_c0e8302d-0a16-4be9-910c-a11a4b698c5b_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>
    <link:label id="lab_us-gaap_RelatedPartyTransactionsByRelatedPartyAxis_label_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionsByRelatedPartyAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Related Party, Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RelatedPartyTransactionsByRelatedPartyAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_RelatedPartyTransactionsByRelatedPartyAxis"/>
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    <link:label id="lab_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock_c93778ff-148a-4eb7-9d2c-e1fc2e271fb7_terseLabel_en-US" xlink:label="lab_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Underwriting, Acquisition and Insurance Expenses</link:label>
    <link:label id="lab_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock_label_en-US" xlink:label="lab_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule Of Underwriting, Acquisition and Insurance Expenses [Table Text Block]</link:label>
    <link:label id="lab_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock_documentation_en-US" xlink:label="lab_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Schedule Of Underwriting, Acquisition and Insurance Expenses</link:label>
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    <link:label id="lab_dei_EntityRegistrantName_label_en-US" xlink:label="lab_dei_EntityRegistrantName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Registrant Name</link:label>
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    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract_dd152b52-8513-4f5c-81ca-885a4a3d8972_terseLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Available-for-sale and held-to-maturity, gross unrealized losses</link:label>
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    <link:label id="lab_us-gaap_ComponentsOfDeferredTaxLiabilitiesAbstract_575e69b1-c215-448a-b617-b95f55a599cd_terseLabel_en-US" xlink:label="lab_us-gaap_ComponentsOfDeferredTaxLiabilitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Deferred tax liabilities:</link:label>
    <link:label id="lab_us-gaap_ComponentsOfDeferredTaxLiabilitiesAbstract_label_en-US" xlink:label="lab_us-gaap_ComponentsOfDeferredTaxLiabilitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Components of Deferred Tax Liabilities [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ComponentsOfDeferredTaxLiabilitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ComponentsOfDeferredTaxLiabilitiesAbstract"/>
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    <link:label id="lab_skwd_EquityMethodInvestmentsUnfundedCommitment_57eda7fe-94cd-46b0-afc6-1c9fe38b48e3_terseLabel_en-US" xlink:label="lab_skwd_EquityMethodInvestmentsUnfundedCommitment" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Unfunded commitment</link:label>
    <link:label id="lab_skwd_EquityMethodInvestmentsUnfundedCommitment_label_en-US" xlink:label="lab_skwd_EquityMethodInvestmentsUnfundedCommitment" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" 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-20231231.xsd#skwd_EquityMethodInvestmentsUnfundedCommitment"/>
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    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract_acd1cb47-848c-444f-b912-e6887e6a11a7_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 income (loss):</link:label>
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    <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"/>
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    <link:label id="lab_dei_AuditorName_350f9383-d0e7-44e2-b011-a29e4d8758c6_terseLabel_en-US" xlink:label="lab_dei_AuditorName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Auditor Name</link:label>
    <link:label id="lab_dei_AuditorName_label_en-US" xlink:label="lab_dei_AuditorName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Auditor Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_AuditorName" xlink:href="https://xbrl.sec.gov/dei/2023/dei-2023.xsd#dei_AuditorName"/>
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    <link:label id="lab_us-gaap_ProceedsFromLinesOfCredit_d5c24049-d021-44e4-8a15-0f9ae4ad328a_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_110bae84-b34a-4b16-8d91-8044fa4493a0_verboseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromLinesOfCredit" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Proceeds from line of creit</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"/>
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    <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>
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    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeerGroupIssuersFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_PeerGroupIssuersFnTextBlock"/>
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    <link:label id="lab_us-gaap_AccumulatedDepreciationDepletionAndAmortizationPropertyPlantAndEquipment_0d9862ea-9a46-41f9-841f-d912dfe76ec7_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_AccumulatedDepreciationDepletionAndAmortizationPropertyPlantAndEquipment" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Accumulated depreciation</link:label>
    <link:label id="lab_us-gaap_AccumulatedDepreciationDepletionAndAmortizationPropertyPlantAndEquipment_label_en-US" xlink:label="lab_us-gaap_AccumulatedDepreciationDepletionAndAmortizationPropertyPlantAndEquipment" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Accumulated Depreciation, Depletion and Amortization, Property, Plant, and Equipment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedDepreciationDepletionAndAmortizationPropertyPlantAndEquipment" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_AccumulatedDepreciationDepletionAndAmortizationPropertyPlantAndEquipment"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccumulatedDepreciationDepletionAndAmortizationPropertyPlantAndEquipment" xlink:to="lab_us-gaap_AccumulatedDepreciationDepletionAndAmortizationPropertyPlantAndEquipment" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock_e5357dde-1b99-4a65-bc9a-d3e53cb5bdbc_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_72772aed-f67b-4a4c-83eb-c445dbe2aee7_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_dei_EntityCentralIndexKey_8e748241-b251-403e-ae17-6b86eb9f6580_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_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetGainLossIncludedInEarnings1_839c6c40-2cc1-4308-bf5b-333f4f3dd2f6_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 losses 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"/>
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    <link:label id="lab_us-gaap_AllocatedShareBasedCompensationExpense_5edf8ccc-ea01-4565-aa13-e125d2f47fca_terseLabel_en-US" xlink:label="lab_us-gaap_AllocatedShareBasedCompensationExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stock based compensation expense</link:label>
    <link:label id="lab_us-gaap_AllocatedShareBasedCompensationExpense_label_en-US" xlink:label="lab_us-gaap_AllocatedShareBasedCompensationExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Payment Arrangement, Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AllocatedShareBasedCompensationExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_AllocatedShareBasedCompensationExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AllocatedShareBasedCompensationExpense" xlink:to="lab_us-gaap_AllocatedShareBasedCompensationExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_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:label id="lab_us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesFairValue_1ea250e8-df4d-4b48-9424-3dd233e5827c_terseLabel_en-US" xlink:label="lab_us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value (if applicable)</link:label>
    <link:label id="lab_us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesFairValue_label_en-US" xlink:label="lab_us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-15, Insurance Companies, Summary of Investments, Other than Investments in Related Parties, Fair Value</link:label>
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    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsGross_0bcc3970-f55b-4ef1-a565-7bef5e792a76_periodStartLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsGross" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Gross, beginning balance</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsGross_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Finite-Lived Intangible Assets, Gross</link:label>
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    <link:label id="lab_us-gaap_IncrementalCommonSharesAttributableToContingentlyIssuableShares_3d3b99bd-9f96-429a-a251-122f293f95fc_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">Contingently issuable instruments (treasury stock method) (in shares)</link:label>
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    <link:label id="lab_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve_c342f8f9-6787-4525-b7d7-0ea245d823b1_terseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Losses and loss adjustment expenses</link:label>
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    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent_778c6dcf-0972-4da6-9bec-09a9d7f472a1_totalLabel_en-US" xlink:label="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total other comprehensive income (loss)</link:label>
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    <link:label id="lab_us-gaap_StockIssuedDuringPeriodValueNewIssues_0e6b53b7-9754-45af-98be-62ae2a8de919_terseLabel_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodValueNewIssues" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Proceeds from equity offerings, net</link:label>
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    <link:label id="lab_us-gaap_DeferredTaxAssetsUnrealizedLossesOnAvailableforSaleSecuritiesGross_870d472c-ac76-417e-8daa-ca1453a6615f_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsUnrealizedLossesOnAvailableforSaleSecuritiesGross" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Unrealized losses on fixed maturity securities, available-for-sale</link:label>
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    <link:label id="lab_skwd_WestaimMember_a79cca3e-a204-42d4-b51c-85b9941ffeed_terseLabel_en-US" xlink:label="lab_skwd_WestaimMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Westaim</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_skwd_WestaimMember" xlink:href="skwd-20231231.xsd#skwd_WestaimMember"/>
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    <link:label id="lab_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax_07240ea2-57c3-4db0-a578-3f3fb53e043e_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>
    <link:label id="lab_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax_label_en-US" xlink:label="lab_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Revenue from Contract with Customer, Excluding Assessed Tax</link:label>
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    <link:label id="lab_dei_EntityDomain_c77863d3-aec4-49e1-9f97-c02446f0bce1_terseLabel_en-US" xlink:label="lab_dei_EntityDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity [Domain]</link:label>
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    <link:label id="lab_us-gaap_LongtermDebtTypeAxis_37c639c7-6d41-4fbb-88ec-4c402f16969b_terseLabel_en-US" xlink:label="lab_us-gaap_LongtermDebtTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Long-Term Debt, Type [Axis]</link:label>
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    <link:label id="lab_dei_LegalEntityAxis_23f2c0f0-0bac-402f-9167-7824ac7fdadd_terseLabel_en-US" xlink:label="lab_dei_LegalEntityAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Legal Entity [Axis]</link:label>
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    <link:label id="lab_skwd_MultiLineSolutionsMember_2aa84d77-dd58-42db-b8da-bc9d1564187a_terseLabel_en-US" xlink:label="lab_skwd_MultiLineSolutionsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Multi-line Solutions</link:label>
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    <link:label id="lab_us-gaap_OperatingLeaseWeightedAverageDiscountRatePercent_463a7fdd-e671-4b58-bffc-fa29cbb2263a_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingLeaseWeightedAverageDiscountRatePercent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Operating lease weighted-average discount rate</link:label>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue_4bd16540-a05c-438f-918a-406a0979f095_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Due in less than one year</link:label>
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    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract_af3838de-2411-446a-9c82-256d86b78fa6_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>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract"/>
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    <link:label id="lab_us-gaap_LeaseholdImprovementsMember_ca139f9e-b39c-4a25-9c32-f03d147943fa_terseLabel_en-US" xlink:label="lab_us-gaap_LeaseholdImprovementsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Leasehold improvements</link:label>
    <link:label id="lab_us-gaap_LeaseholdImprovementsMember_label_en-US" xlink:label="lab_us-gaap_LeaseholdImprovementsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Leasehold Improvements [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LeaseholdImprovementsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_LeaseholdImprovementsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LeaseholdImprovementsMember" xlink:to="lab_us-gaap_LeaseholdImprovementsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GainLossOnInvestmentsTextBlock_e35e8c8c-0ab0-417e-9e47-bb0ecfbf6bad_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>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GainLossOnInvestmentsTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_GainLossOnInvestmentsTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GainLossOnInvestmentsTextBlock" xlink:to="lab_us-gaap_GainLossOnInvestmentsTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_73cc3623-4fa1-4a8d-87c3-82309aa9e18b_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 weighted-average common shares (in shares)</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_c55c7deb-c8d0-4f66-b5bd-dd083eb6d2b5_totalLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Diluted weighted-average common share equivalents (in shares)</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_label_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Weighted Average Number of Shares Outstanding, Diluted</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:to="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock_terseLabel_en-US" xlink:label="lab_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Forgone Recovery, Explanation of Impracticability</link:label>
    <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>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2023/ecd-2023.xsd#ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock" xlink:to="lab_ecd_ForgoneRecoveryExplanationOfImpracticabilityTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense_45f5229e-cae4-414e-8625-003c016e759f_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>
    <link:label id="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense_label_en-US" xlink:label="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Policy Acquisition Costs, Amortization Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense" xlink:to="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceAccountingPolicy_8f90438f-1301-415c-a9bc-6c1948ab9461_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceAccountingPolicy" 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_ReinsuranceAccountingPolicy_label_en-US" xlink:label="lab_us-gaap_ReinsuranceAccountingPolicy" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Accounting Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceAccountingPolicy" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ReinsuranceAccountingPolicy"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceAccountingPolicy" xlink:to="lab_us-gaap_ReinsuranceAccountingPolicy" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_SupplementalScheduleOfReinsurancePremiumsForInsuranceCompaniesTextBlock_55253048-6962-438d-8b78-85ddde1d4806_terseLabel_en-US" xlink:label="lab_srt_SupplementalScheduleOfReinsurancePremiumsForInsuranceCompaniesTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">SCHEDULE IV&#160;&#8212; REINSURANCE</link:label>
    <link:label id="lab_srt_SupplementalScheduleOfReinsurancePremiumsForInsuranceCompaniesTextBlock_label_en-US" xlink:label="lab_srt_SupplementalScheduleOfReinsurancePremiumsForInsuranceCompaniesTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-17, Insurance Companies, Reinsurance [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_SupplementalScheduleOfReinsurancePremiumsForInsuranceCompaniesTextBlock" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_SupplementalScheduleOfReinsurancePremiumsForInsuranceCompaniesTextBlock"/>
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    <link:label id="lab_us-gaap_IndefinitelivedIntangibleAssetsAcquired_eceae436-5db8-4bfe-b9e5-0d49767c7141_terseLabel_en-US" xlink:label="lab_us-gaap_IndefinitelivedIntangibleAssetsAcquired" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Additions</link:label>
    <link:label id="lab_us-gaap_IndefinitelivedIntangibleAssetsAcquired_label_en-US" xlink:label="lab_us-gaap_IndefinitelivedIntangibleAssetsAcquired" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Indefinite-Lived Intangible Assets Acquired</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IndefinitelivedIntangibleAssetsAcquired" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_IndefinitelivedIntangibleAssetsAcquired"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IndefinitelivedIntangibleAssetsAcquired" xlink:to="lab_us-gaap_IndefinitelivedIntangibleAssetsAcquired" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss_1bc6edf0-8737-451f-9d81-90020f41f0db_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity securities, available-for-sale</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Realized Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment_c515d586-9da0-478e-8a62-c85938d0f0ba_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Purchase of property and equipment</link:label>
    <link:label id="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment_label_en-US" xlink:label="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments to Acquire Property, Plant, and Equipment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PaymentsToAcquirePropertyPlantAndEquipment"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment" xlink:to="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_CoSelectedMeasureAmt_terseLabel_en-US" xlink:label="lab_ecd_CoSelectedMeasureAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Company Selected Measure Amount</link:label>
    <link:label id="lab_ecd_CoSelectedMeasureAmt_label_en-US" xlink:label="lab_ecd_CoSelectedMeasureAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Company Selected Measure Amount</link:label>
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    <link:label id="lab_us-gaap_IncreaseDecreaseInFundsHeldUnderReinsuranceAgreements_52af8d2f-e3d5-4f49-b1a5-b37b785f7f36_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInFundsHeldUnderReinsuranceAgreements" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Funds held for others</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInFundsHeldUnderReinsuranceAgreements_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInFundsHeldUnderReinsuranceAgreements" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Funds Held under Reinsurance Agreements</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInFundsHeldUnderReinsuranceAgreements" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_IncreaseDecreaseInFundsHeldUnderReinsuranceAgreements"/>
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    <link:label id="lab_skwd_JuniorSubordinatedNotesDue2036CommonStockMember_530b6764-bc49-4c77-8500-6afaf784b644_terseLabel_en-US" xlink:label="lab_skwd_JuniorSubordinatedNotesDue2036CommonStockMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Junior Subordinated Notes Due 2036, Common Stock</link:label>
    <link:label id="lab_skwd_JuniorSubordinatedNotesDue2036CommonStockMember_label_en-US" xlink:label="lab_skwd_JuniorSubordinatedNotesDue2036CommonStockMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Junior Subordinated Notes Due 2036, Common Stock [Member]</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_skwd_JuniorSubordinatedNotesDue2036CommonStockMember" xlink:href="skwd-20231231.xsd#skwd_JuniorSubordinatedNotesDue2036CommonStockMember"/>
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    <link:label id="lab_us-gaap_Assets_f7c58370-b633-463d-9276-2ad460d400b4_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>
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    <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_skwd_ConsumerStaplesSectorMember_6ee97f43-6108-4808-9728-a34384840e89_terseLabel_en-US" xlink:label="lab_skwd_ConsumerStaplesSectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Consumer staples</link:label>
    <link:label id="lab_skwd_ConsumerStaplesSectorMember_label_en-US" xlink:label="lab_skwd_ConsumerStaplesSectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Consumer Staples Sector [Member]</link:label>
    <link:label id="lab_skwd_ConsumerStaplesSectorMember_documentation_en-US" xlink:label="lab_skwd_ConsumerStaplesSectorMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Consumer Staples Sector</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ConsumerStaplesSectorMember" xlink:href="skwd-20231231.xsd#skwd_ConsumerStaplesSectorMember"/>
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    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsScheduleOfHistoricalClaimsDurationTableTextBlock_3110717b-6c1e-4329-8d51-7de305c34553_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsScheduleOfHistoricalClaimsDurationTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Historical Claims Duration</link:label>
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    <link:label id="lab_us-gaap_EquipmentMember_18d0b4e5-c0e7-4320-954e-3c6efe9bdfda_terseLabel_en-US" xlink:label="lab_us-gaap_EquipmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equipment</link:label>
    <link:label id="lab_us-gaap_EquipmentMember_label_en-US" xlink:label="lab_us-gaap_EquipmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equipment [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquipmentMember" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_EquipmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquipmentMember" xlink:to="lab_us-gaap_EquipmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AllowanceForUncollectiblePremiumsReceivableMember_cb1441ae-6374-4fea-8b95-61c9ca2961cb_terseLabel_en-US" xlink:label="lab_us-gaap_AllowanceForUncollectiblePremiumsReceivableMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Allowance for Uncollectible Premiums Receivable</link:label>
    <link:label id="lab_us-gaap_AllowanceForUncollectiblePremiumsReceivableMember_label_en-US" xlink:label="lab_us-gaap_AllowanceForUncollectiblePremiumsReceivableMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-09, Allowance, Uncollectible Premium Receivable [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AllowanceForUncollectiblePremiumsReceivableMember" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_AllowanceForUncollectiblePremiumsReceivableMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AllowanceForUncollectiblePremiumsReceivableMember" xlink:to="lab_us-gaap_AllowanceForUncollectiblePremiumsReceivableMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_FixedIncomeSectorMember_338e6492-e9d9-4429-856b-30eb749d1c3b_terseLabel_en-US" xlink:label="lab_skwd_FixedIncomeSectorMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed income</link:label>
    <link:label id="lab_skwd_FixedIncomeSectorMember_label_en-US" xlink:label="lab_skwd_FixedIncomeSectorMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fixed Income Sector [Member]</link:label>
    <link:label id="lab_skwd_FixedIncomeSectorMember_documentation_en-US" xlink:label="lab_skwd_FixedIncomeSectorMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Fixed Income Sector</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_FixedIncomeSectorMember" xlink:href="skwd-20231231.xsd#skwd_FixedIncomeSectorMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_FixedIncomeSectorMember" xlink:to="lab_skwd_FixedIncomeSectorMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CededPremiumsEarned_0f507b69-1838-4b17-a14a-045ebad54a34_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_a7cb8a9f-934e-4a74-ba85-83902db547f7_terseLabel_en-US" xlink:label="lab_us-gaap_CededPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Ceded Premiums Earned</link:label>
    <link:label id="lab_us-gaap_CededPremiumsEarned_37f3cedf-0b4e-464a-a137-fe4bdb5357a6_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_CededPremiumsEarned" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Ceded to other companies</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"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CededPremiumsEarned" xlink:to="lab_us-gaap_CededPremiumsEarned" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectsOfReinsuranceTableTextBlock_c27810da-b04d-4219-9ab6-2c171b96855d_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"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectsOfReinsuranceTableTextBlock" xlink:to="lab_us-gaap_EffectsOfReinsuranceTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue_5f7bcd2a-5c4e-4eac-8f46-97ca5601c283_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Vested (in dollars per share)</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Vested in Period, Weighted Average Grant Date Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsVestedInPeriodWeightedAverageGrantDateFairValue"/>
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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"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonNeosMember" xlink:to="lab_ecd_NonNeosMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses_183aba96-1700-4e19-ab93-76bd610a8377_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_e12b8eba-06d3-496c-b214-e21fc620a783_periodStartLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverables, Net, beginning balance</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses_a9faf9a9-dbfa-496e-8310-43a62b5c0542_periodEndLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverables, Net, ending balance</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses_f6b2454a-5ff2-4bec-b1ca-e317a06a2d3e_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, net</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>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ReinsuranceRecoverablesOnPaidAndUnpaidLosses"/>
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    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward_5fb6b664-dd9d-438e-ad26-2363f8943dac_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward" 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, Calculation [Roll Forward]</link:label>
    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationCalculationRollForward" 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, Calculation [Roll Forward]</link:label>
    <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_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments_31451ebb-cfef-48e2-ac45-05b39bca7393_verboseLabel_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Loss before income tax expense</link:label>
    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments_label_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income (Loss) from Continuing Operations before Equity Method Investments, Income Taxes, Noncontrolling Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments"/>
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    <link:label id="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract_e372140e-c48c-4fce-9781-9788710b1adc_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_bf1d557d-f23e-436e-8c59-01dccf3ae6c2_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 gross 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_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_us-gaap_OtherLongTermInvestmentsMember_95800929-a0c4-4423-9568-9ffbecd6ddcd_terseLabel_en-US" xlink:label="lab_us-gaap_OtherLongTermInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other long-term investments</link:label>
    <link:label id="lab_us-gaap_OtherLongTermInvestmentsMember_label_en-US" xlink:label="lab_us-gaap_OtherLongTermInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Long-Term Investments [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherLongTermInvestmentsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_OtherLongTermInvestmentsMember"/>
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    <link:label id="lab_skwd_OperatingLossCarryforwardsLimitationsOnUseAmount_b20c77ae-e3cc-4651-97ad-7f7f90843152_terseLabel_en-US" xlink:label="lab_skwd_OperatingLossCarryforwardsLimitationsOnUseAmount" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Operating loss carryforwards, limitations on use, amount</link:label>
    <link:label id="lab_skwd_OperatingLossCarryforwardsLimitationsOnUseAmount_label_en-US" xlink:label="lab_skwd_OperatingLossCarryforwardsLimitationsOnUseAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Operating Loss Carryforwards, Limitations on Use, Amount</link:label>
    <link:label id="lab_skwd_OperatingLossCarryforwardsLimitationsOnUseAmount_documentation_en-US" xlink:label="lab_skwd_OperatingLossCarryforwardsLimitationsOnUseAmount" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Operating Loss Carryforwards, Limitations on Use, Amount</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_OperatingLossCarryforwardsLimitationsOnUseAmount" xlink:to="lab_skwd_OperatingLossCarryforwardsLimitationsOnUseAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ContractWithCustomerAssetNet_e1a8172d-d17c-43ee-ac59-780eedbb445d_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 Assets</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_DeferredTaxAssetsOperatingLossCarryforwards_f721fa0b-8bb9-44bb-bead-0c25932e8823_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsOperatingLossCarryforwards" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net operating losses</link:label>
    <link:label id="lab_us-gaap_DeferredTaxAssetsOperatingLossCarryforwards_label_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsOperatingLossCarryforwards" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Tax Assets, Operating Loss Carryforwards</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxAssetsOperatingLossCarryforwards" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DeferredTaxAssetsOperatingLossCarryforwards"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredTaxAssetsOperatingLossCarryforwards" xlink:to="lab_us-gaap_DeferredTaxAssetsOperatingLossCarryforwards" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentLineItems_fc3b3d88-fbde-48e5-bfb1-013497ac6619_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_srt_StatementScenarioAxis_b3f15ec4-423e-47c3-9bb1-3b29436d86d5_terseLabel_en-US" xlink:label="lab_srt_StatementScenarioAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Scenario [Axis]</link:label>
    <link:label id="lab_srt_StatementScenarioAxis_label_en-US" xlink:label="lab_srt_StatementScenarioAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Scenario [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_StatementScenarioAxis" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_StatementScenarioAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_StatementScenarioAxis" xlink:to="lab_srt_StatementScenarioAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfSharesOutstandingBasic_7cfd6cf6-563c-41ac-b702-473b34a96b88_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_us-gaap_DeferredTaxLiabilitiesPropertyPlantAndEquipment_1bef261d-c638-4853-9633-5679fa93dceb_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxLiabilitiesPropertyPlantAndEquipment" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Depreciation</link:label>
    <link:label id="lab_us-gaap_DeferredTaxLiabilitiesPropertyPlantAndEquipment_label_en-US" xlink:label="lab_us-gaap_DeferredTaxLiabilitiesPropertyPlantAndEquipment" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Tax Liabilities, Property, Plant and Equipment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxLiabilitiesPropertyPlantAndEquipment" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_DeferredTaxLiabilitiesPropertyPlantAndEquipment"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredTaxLiabilitiesPropertyPlantAndEquipment" xlink:to="lab_us-gaap_DeferredTaxLiabilitiesPropertyPlantAndEquipment" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConcentrationRiskByBenchmarkAxis_91e0a1c4-2030-4975-8e95-b22829e29525_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskByBenchmarkAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Concentration Risk Benchmark [Axis]</link:label>
    <link:label id="lab_us-gaap_ConcentrationRiskByBenchmarkAxis_label_en-US" xlink:label="lab_us-gaap_ConcentrationRiskByBenchmarkAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Concentration Risk Benchmark [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConcentrationRiskByBenchmarkAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_ConcentrationRiskByBenchmarkAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConcentrationRiskByBenchmarkAxis" xlink:to="lab_us-gaap_ConcentrationRiskByBenchmarkAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentOtherTypesMember_c6a9593a-a916-4c00-bf2f-02bedfc543d5_terseLabel_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentOtherTypesMember" 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_PropertyPlantAndEquipmentOtherTypesMember_label_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentOtherTypesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Property, Plant and Equipment, Other Types [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentOtherTypesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_PropertyPlantAndEquipmentOtherTypesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentOtherTypesMember" xlink:to="lab_us-gaap_PropertyPlantAndEquipmentOtherTypesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentLineItems_3d345b1f-f660-46d3-8a2e-e04da40178af_terseLabel_en-US" xlink:label="lab_srt_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-17, Insurance Companies, Reinsurance [Line Items]</link:label>
    <link:label id="lab_srt_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentLineItems_label_en-US" xlink:label="lab_srt_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-17, Insurance Companies, Reinsurance [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentLineItems" xlink:href="https://xbrl.fasb.org/srt/2023/elts/srt-2023.xsd#srt_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentLineItems" xlink:to="lab_srt_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RevenuesAbstract_5c7be84b-01ad-4eec-88e5-979f53c954ca_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_FiniteLivedIntangibleAssetsFutureAmortizationExpenseAbstract_206b5f8b-fe6e-4be3-b117-cba9bdac43c4_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsFutureAmortizationExpenseAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Finite-Lived Intangible Assets, Net, Amortization Expense, Fiscal Year Maturity [Abstract]</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsFutureAmortizationExpenseAbstract_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsFutureAmortizationExpenseAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Finite-Lived Intangible Assets, Net, Amortization Expense, Fiscal Year Maturity [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsFutureAmortizationExpenseAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2023/elts/us-gaap-2023.xsd#us-gaap_FiniteLivedIntangibleAssetsFutureAmortizationExpenseAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsFutureAmortizationExpenseAbstract" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsFutureAmortizationExpenseAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseLossPortfolioTransfer_9d538047-e4eb-4148-9008-6cb183b3c4b1_terseLabel_en-US" xlink:label="lab_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseLossPortfolioTransfer" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Liability for claims and claims adjustment expense, loss portfolio transfer</link:label>
    <link:label id="lab_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseLossPortfolioTransfer_label_en-US" xlink:label="lab_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseLossPortfolioTransfer" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability For Claims And Claims Adjustment Expense, Loss Portfolio Transfer</link:label>
    <link:label id="lab_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseLossPortfolioTransfer_documentation_en-US" xlink:label="lab_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseLossPortfolioTransfer" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Liability For Claims And Claims Adjustment Expense, Loss Portfolio Transfer</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseLossPortfolioTransfer" xlink:href="skwd-20231231.xsd#skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseLossPortfolioTransfer"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseLossPortfolioTransfer" xlink:to="lab_skwd_LiabilityForClaimsAndClaimsAdjustmentExpenseLossPortfolioTransfer" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_FixedMaturitySecuritiesHeldToMaturityMember_07f6ee58-606d-42c1-9514-0bb1f9a4c7ce_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:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_FixedMaturitySecuritiesHeldToMaturityMember" xlink:to="lab_skwd_FixedMaturitySecuritiesHeldToMaturityMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RelatedPartyTransactionAxis_6abab236-919d-4b1a-bcde-0fae9aaff996_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>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RelatedPartyTransactionAxis" xlink:to="lab_us-gaap_RelatedPartyTransactionAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_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_LineOfCreditFacilityUnusedCapacityCommitmentFeePercentage_c4058c6b-59b6-482c-b395-cd7f2bd7d9f6_terseLabel_en-US" xlink:label="lab_us-gaap_LineOfCreditFacilityUnusedCapacityCommitmentFeePercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Unused capacity, commitment fee percentage</link:label>
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    <link:label id="lab_us-gaap_StatementLineItems_943b4ebb-20d7-4c86-94fa-3736ea99c1a7_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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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementLineItems" xlink:to="lab_us-gaap_StatementLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodValueConversionOfConvertibleSecurities_4c248539-0f9b-48dd-95ab-9fa4420758d0_terseLabel_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodValueConversionOfConvertibleSecurities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Preferred stock conversion to common shares</link:label>
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    <link:label id="lab_us-gaap_ConcentrationRiskTable_6d1eb76c-c3c0-4b81-b900-de86df9071cc_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Concentration Risk [Table]</link:label>
    <link:label id="lab_us-gaap_ConcentrationRiskTable_label_en-US" xlink:label="lab_us-gaap_ConcentrationRiskTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Concentration Risk [Table]</link:label>
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