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    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersNetInvestmentIncome_label_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersNetInvestmentIncome" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-18, Supplemental Information, Property-Casualty Insurance Underwriters, Net Investment Income</link:label>
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    <link:label id="lab_us-gaap_RelatedPartyTransactionsDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Related Party Transactions Disclosure [Text Block]</link:label>
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    <link:label id="lab_us-gaap_RepaymentsOfLongTermDebt_153b5370-99d2-435e-a760-e560e35a8282_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">Payments on long term borrowings and trust preferred</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>
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    <link:label id="lab_dei_CoverAbstract_label_en-US" xlink:label="lab_dei_CoverAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cover [Abstract]</link:label>
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    <link:label id="lab_skwd_ShareBasedCompensationArrangementsByShareBasedPaymentAwardOptionsGrantsInPeriodExcludingSharesIssuedInConnectionWithAcquisitionWeightedAverageExercisePrice_80cdf6c4-34e1-411c-af23-67716c9ffac8_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 dollar per share)</link:label>
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    <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>
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    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueAfterYearFive_2ecf10aa-3982-40f0-bf4d-1e4208f4f4a8_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>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueAfterYearFive_label_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueAfterYearFive" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Lessee, Operating Lease, Liability, to be Paid, after Year Five</link:label>
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    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsAccidentYear2016Member_0f0db40a-2403-49f3-b0cf-28e8b0a229d6_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsAccidentYear2016Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accident Year 2016</link:label>
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    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityMaturityTableTextBlock_697794d2-6bd2-4692-9508-4cd1eca76ffa_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>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostAllowanceForCreditLossExcludingAccruedInterest_878daeed-b109-4443-90dd-e76be867aef1_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/2024/elts/us-gaap-2024.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_ContingentlyIssuableInstrumentsPreferredSharesIfConvertedMember_72e1b88b-da6f-41c8-9ea5-a1651103f203_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-20241231.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_skwd_FixedMaturitySecuritiesMeasurementInput_a6ce766d-d1f7-4c1e-9237-b964e3882ed3_terseLabel_en-US" xlink:label="lab_skwd_FixedMaturitySecuritiesMeasurementInput" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity securities, measurement input</link:label>
    <link:label id="lab_skwd_FixedMaturitySecuritiesMeasurementInput_label_en-US" xlink:label="lab_skwd_FixedMaturitySecuritiesMeasurementInput" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fixed Maturity Securities, Measurement Input</link:label>
    <link:label id="lab_skwd_FixedMaturitySecuritiesMeasurementInput_documentation_en-US" xlink:label="lab_skwd_FixedMaturitySecuritiesMeasurementInput" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Fixed Maturity Securities, Measurement Input</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_FixedMaturitySecuritiesMeasurementInput" xlink:href="skwd-20241231.xsd#skwd_FixedMaturitySecuritiesMeasurementInput"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_FixedMaturitySecuritiesMeasurementInput" xlink:to="lab_skwd_FixedMaturitySecuritiesMeasurementInput" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CondensedIncomeStatementsCaptionsLineItems_39856a66-cc15-45be-9e47-8612ccf31f6f_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/2024/elts/srt-2024.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_dei_TradingSymbol_1affe51c-ac99-4ac8-bbeb-d05e4d507a25_terseLabel_en-US" xlink:label="lab_dei_TradingSymbol" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Trading Symbol</link:label>
    <link:label id="lab_dei_TradingSymbol_label_en-US" xlink:label="lab_dei_TradingSymbol" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Symbol</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_TradingSymbol" xlink:href="https://xbrl.sec.gov/dei/2024/dei-2024.xsd#dei_TradingSymbol"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_TradingSymbol" xlink:to="lab_dei_TradingSymbol" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage_1edb18eb-6bf4-443d-ad2c-ee42ce1cc0d0_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity method investments ownership percentage</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Ownership Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_EquityMethodInvestmentOwnershipPercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:to="lab_us-gaap_EquityMethodInvestmentOwnershipPercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_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/2024/ecd-2024.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_LongTermDebtTerm_827c773e-f00a-4ee1-902d-800070957180_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/2024/elts/us-gaap-2024.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_skwd_IPOSharesFromCompanyMember_279d26ea-af49-442b-8d88-6663a029db68_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-20241231.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_CollateralizedSecuritiesMember_63071862-9ce4-4da1-97f5-98ffdd67b9a4_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/2024/elts/us-gaap-2024.xsd#us-gaap_CollateralizedSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CollateralizedSecuritiesMember" xlink:to="lab_us-gaap_CollateralizedSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PreferredStockConvertibleConversionPrice_da110289-93b6-49ef-b76e-48124136cb22_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 dollar 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/2024/elts/us-gaap-2024.xsd#us-gaap_PreferredStockConvertibleConversionPrice"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PreferredStockConvertibleConversionPrice" xlink:to="lab_us-gaap_PreferredStockConvertibleConversionPrice" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortTermInvestmentsMember_56ce4835-55da-461f-a3fc-11e01441d62b_terseLabel_en-US" xlink:label="lab_us-gaap_ShortTermInvestmentsMember" 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_us-gaap_ShortTermInvestmentsMember_label_en-US" xlink:label="lab_us-gaap_ShortTermInvestmentsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Term Investments [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortTermInvestmentsMember" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ShortTermInvestmentsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortTermInvestmentsMember" xlink:to="lab_us-gaap_ShortTermInvestmentsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTable_a5894762-0b25-4808-95cf-46e643805ef5_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTable" 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 [Table]</link:label>
    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTable_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTable" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTable" xlink:to="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsToAcquireEquitySecuritiesFvNi_f3e39ea7-6388-440f-9e8f-ceb158d57a23_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/2024/elts/us-gaap-2024.xsd#us-gaap_PaymentsToAcquireEquitySecuritiesFvNi"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsToAcquireEquitySecuritiesFvNi" xlink:to="lab_us-gaap_PaymentsToAcquireEquitySecuritiesFvNi" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceAccountingPolicy_62e63dac-49d2-4767-a6bb-595a01f80481_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/2024/elts/us-gaap-2024.xsd#us-gaap_ReinsuranceAccountingPolicy"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceAccountingPolicy" xlink:to="lab_us-gaap_ReinsuranceAccountingPolicy" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EarningsPerSharePolicyTextBlock_d4f604bd-3fce-4275-a33f-e76e57f5723c_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>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EarningsPerSharePolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_EarningsPerSharePolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EarningsPerSharePolicyTextBlock" xlink:to="lab_us-gaap_EarningsPerSharePolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_NonRule10b51ArrAdoptedFlag_terseLabel_en-US" xlink:label="lab_ecd_NonRule10b51ArrAdoptedFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-Rule 10b5-1 Arrangement Adopted</link:label>
    <link:label id="lab_ecd_NonRule10b51ArrAdoptedFlag_label_en-US" xlink:label="lab_ecd_NonRule10b51ArrAdoptedFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-Rule 10b5-1 Arrangement Adopted [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonRule10b51ArrAdoptedFlag" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_NonRule10b51ArrAdoptedFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonRule10b51ArrAdoptedFlag" xlink:to="lab_ecd_NonRule10b51ArrAdoptedFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueDisclosuresTextBlock_91b88c45-f7f7-4719-8a1e-32765a2529c7_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>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueDisclosuresTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_FairValueDisclosuresTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueDisclosuresTextBlock" xlink:to="lab_us-gaap_FairValueDisclosuresTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardTmgDiscLineItems_label_en-US" xlink:label="lab_ecd_AwardTmgDiscLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Timing Disclosures [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardTmgDiscLineItems" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_AwardTmgDiscLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardTmgDiscLineItems" xlink:to="lab_ecd_AwardTmgDiscLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_UnsecuredSubordinatedNotesMember_d871e6e8-81b8-422c-9416-165177c87ef5_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>
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    <link:label id="lab_us-gaap_LineOfCreditFacilityIncreaseAccruedInterest_e6a8a27a-81be-4161-8bf5-9a087868bee4_terseLabel_en-US" xlink:label="lab_us-gaap_LineOfCreditFacilityIncreaseAccruedInterest" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Line of credit facility, increase, accrued interest</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsAccidentYearDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ShortdurationInsuranceContractsAccidentYearDomain"/>
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    <link:label id="lab_us-gaap_PortionAtFairValueFairValueDisclosureMember_868ba975-ed65-454e-8bda-172a7e3c4405_terseLabel_en-US" xlink:label="lab_us-gaap_PortionAtFairValueFairValueDisclosureMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Portion at Fair Value Measurement</link:label>
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    <link:label id="lab_us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities_f4b6061b-3c8e-4473-9bb7-4e6418f62674_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Proceeds from the sales of fixed maturity securities, available-for-sale</link:label>
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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>
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    <link:label id="lab_us-gaap_ValuationAllowancesAndReservesTypeAxis_bd3d0d34-a0bc-4a78-9d56-fc29bd8745cd_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>
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    <link:label id="lab_us-gaap_PlanNameDomain_78ed0498-83af-42b7-a391-72d61895ad1f_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>
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    <link:label id="lab_us-gaap_SaleOfStockPricePerShare_fd96a8c1-03cf-47fd-8611-39c5a769359c_terseLabel_en-US" xlink:label="lab_us-gaap_SaleOfStockPricePerShare" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Sale of stock, price per share (in dollar per share)</link:label>
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    <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>
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    <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>
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    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAfterAllowanceForCreditLoss_914b2e42-c660-41fc-9e80-6f5a29aeca5a_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAfterAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity securities, held-to-maturity, at amortized cost (net of allowance for credit losses of $243 and $329, respectively)</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAfterAllowanceForCreditLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAfterAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Excluding Accrued Interest, after Allowance for Credit Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAfterAllowanceForCreditLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAfterAllowanceForCreditLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAfterAllowanceForCreditLoss" xlink:to="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestAfterAllowanceForCreditLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities_e9e58869-de41-4840-9ef8-efc58991b222_totalLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net cash provided by operating activities</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Net Cash Provided by (Used in) Operating Activities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_NetCashProvidedByUsedInOperatingActivities"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities" xlink:to="lab_us-gaap_NetCashProvidedByUsedInOperatingActivities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract_0d2bba58-a1f1-4b3b-8a3c-e68bd04ebf55_terseLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash flows from operating activities</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Net Cash Provided by (Used in) Operating Activities [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:to="lab_us-gaap_NetCashProvidedByUsedInOperatingActivitiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock_a1d60c15-4630-4744-b55b-5ab81752b557_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Accumulated Other Comprehensive Income (Loss)</link:label>
    <link:label id="lab_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Accumulated Other Comprehensive Income (Loss) [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfAccumulatedOtherComprehensiveIncomeLossTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_MeasurementInputIncrementalCostOfCapitalMember_eae92f63-7c74-441c-b282-91a2702eed66_terseLabel_en-US" xlink:label="lab_skwd_MeasurementInputIncrementalCostOfCapitalMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measurement Input, Incremental Cost of Capital</link:label>
    <link:label id="lab_skwd_MeasurementInputIncrementalCostOfCapitalMember_label_en-US" xlink:label="lab_skwd_MeasurementInputIncrementalCostOfCapitalMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measurement Input, Incremental Cost of Capital [Member]</link:label>
    <link:label id="lab_skwd_MeasurementInputIncrementalCostOfCapitalMember_documentation_en-US" xlink:label="lab_skwd_MeasurementInputIncrementalCostOfCapitalMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Measurement Input, Incremental Cost of Capital</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_MeasurementInputIncrementalCostOfCapitalMember" xlink:href="skwd-20241231.xsd#skwd_MeasurementInputIncrementalCostOfCapitalMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_MeasurementInputIncrementalCostOfCapitalMember" xlink:to="lab_skwd_MeasurementInputIncrementalCostOfCapitalMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ProceedsFromPortfolioTransfer_bb51f14b-fc49-4926-ba16-17337ce67fda_terseLabel_en-US" xlink:label="lab_skwd_ProceedsFromPortfolioTransfer" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Proceeds from portfolio transfer</link:label>
    <link:label id="lab_skwd_ProceedsFromPortfolioTransfer_label_en-US" xlink:label="lab_skwd_ProceedsFromPortfolioTransfer" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Portfolio Transfer</link:label>
    <link:label id="lab_skwd_ProceedsFromPortfolioTransfer_documentation_en-US" xlink:label="lab_skwd_ProceedsFromPortfolioTransfer" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Proceeds from Portfolio Transfer</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ProceedsFromPortfolioTransfer" xlink:href="skwd-20241231.xsd#skwd_ProceedsFromPortfolioTransfer"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ProceedsFromPortfolioTransfer" xlink:to="lab_skwd_ProceedsFromPortfolioTransfer" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardTmgMethodTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AwardTmgMethodTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Timing Method</link:label>
    <link:label id="lab_ecd_AwardTmgMethodTextBlock_label_en-US" xlink:label="lab_ecd_AwardTmgMethodTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Timing Method [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardTmgMethodTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_AwardTmgMethodTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardTmgMethodTextBlock" xlink:to="lab_ecd_AwardTmgMethodTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract_477417b5-5bd3-4838-87b1-fbe90c9d8eda_terseLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Available-for-sale and held-to-maturity, fair value</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract_label_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Unrealized Loss Position [Abstract]</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract_documentation_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Unrealized Loss Position</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract" xlink:href="skwd-20241231.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract" xlink:to="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TradingArrByIndTable_terseLabel_en-US" xlink:label="lab_ecd_TradingArrByIndTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Trading Arrangements, by Individual</link:label>
    <link:label id="lab_ecd_TradingArrByIndTable_label_en-US" xlink:label="lab_ecd_TradingArrByIndTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangements, by Individual [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TradingArrByIndTable" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_TradingArrByIndTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TradingArrByIndTable" xlink:to="lab_ecd_TradingArrByIndTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNet_77add343-2e90-4e6b-9fcc-0efd2815cb02_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 ALAE</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNet_9a2d3bfa-323c-412b-8f1c-42f844a67f3f_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>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNet_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNet" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNet" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNet" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityCommonStockSharesOutstanding_fd8dd27f-2a45-4e5e-98f9-61e4ccd02c6d_terseLabel_en-US" xlink:label="lab_dei_EntityCommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Common Stock, Shares Outstanding</link:label>
    <link:label id="lab_dei_EntityCommonStockSharesOutstanding_label_en-US" xlink:label="lab_dei_EntityCommonStockSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Common Stock, Shares Outstanding</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityCommonStockSharesOutstanding" xlink:href="https://xbrl.sec.gov/dei/2024/dei-2024.xsd#dei_EntityCommonStockSharesOutstanding"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityCommonStockSharesOutstanding" xlink:to="lab_dei_EntityCommonStockSharesOutstanding" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_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/2024/ecd-2024.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_us-gaap_UseOfEstimates_6bba289f-5435-4565-945b-32cb18d363de_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/2024/elts/us-gaap-2024.xsd#us-gaap_UseOfEstimates"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_UseOfEstimates" xlink:to="lab_us-gaap_UseOfEstimates" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AdjToCompAmt_terseLabel_en-US" xlink:label="lab_ecd_AdjToCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adjustment to Compensation, Amount</link:label>
    <link:label id="lab_ecd_AdjToCompAmt_label_en-US" xlink:label="lab_ecd_AdjToCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Adjustment to Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AdjToCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_AdjToCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AdjToCompAmt" xlink:to="lab_ecd_AdjToCompAmt" 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/2024/ecd-2024.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_ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember_terseLabel_en-US" xlink:label="lab_ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aggregate Change in Present Value of Accumulated Benefit for All Pension Plans Reported in Summary Compensation Table</link:label>
    <link:label id="lab_ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember_label_en-US" xlink:label="lab_ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Aggregate Change in Present Value of Accumulated Benefit for All Pension Plans Reported in Summary Compensation Table [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_AggtChngPnsnValInSummryCompstnTblForAplblYrMember"/>
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    <link:label id="lab_dei_EntitySmallBusiness_115285fc-29d2-48b2-ac2c-003012385f81_terseLabel_en-US" xlink:label="lab_dei_EntitySmallBusiness" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Small Business</link:label>
    <link:label id="lab_dei_EntitySmallBusiness_label_en-US" xlink:label="lab_dei_EntitySmallBusiness" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Small Business</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntitySmallBusiness" xlink:href="https://xbrl.sec.gov/dei/2024/dei-2024.xsd#dei_EntitySmallBusiness"/>
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    <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>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_CoSelectedMeasureAmt" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_CoSelectedMeasureAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_CoSelectedMeasureAmt" xlink:to="lab_ecd_CoSelectedMeasureAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredTaxAssetsCapitalLossCarryforwards_ff17f28c-8359-4d9f-85f6-679db705ff61_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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxAssetsCapitalLossCarryforwards" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_DeferredTaxAssetsCapitalLossCarryforwards"/>
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    <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/2024/elts/us-gaap-2024.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_skwd_EnergyMember_30cb2ada-632f-4553-833a-555f8ab612c3_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>
    <link:label id="lab_skwd_EnergyMember_documentation_en-US" xlink:label="lab_skwd_EnergyMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Energy</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_EnergyMember" xlink:href="skwd-20241231.xsd#skwd_EnergyMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_EnergyMember" xlink:to="lab_skwd_EnergyMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_IndustrialPortfolioSegmentMember_cc080499-3086-48dc-97ca-958d947a63a2_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-20241231.xsd#skwd_IndustrialPortfolioSegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_IndustrialPortfolioSegmentMember" xlink:to="lab_skwd_IndustrialPortfolioSegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_HospitalityPortfolioSegmentMember_2500f507-a08d-40e5-a646-ce9121a812f1_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>
    <link:label id="lab_skwd_HospitalityPortfolioSegmentMember_label_en-US" xlink:label="lab_skwd_HospitalityPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Hospitality Portfolio Segment [Member]</link:label>
    <link:label id="lab_skwd_HospitalityPortfolioSegmentMember_documentation_en-US" xlink:label="lab_skwd_HospitalityPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Hospitality Portfolio Segment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_HospitalityPortfolioSegmentMember" xlink:href="skwd-20241231.xsd#skwd_HospitalityPortfolioSegmentMember"/>
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    <link:label id="lab_skwd_UnderwritingExpense_e914d525-1e42-48f8-84a0-7424e367b478_terseLabel_en-US" xlink:label="lab_skwd_UnderwritingExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total underwriting expenses</link:label>
    <link:label id="lab_skwd_UnderwritingExpense_label_en-US" xlink:label="lab_skwd_UnderwritingExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Underwriting Expense</link:label>
    <link:label id="lab_skwd_UnderwritingExpense_documentation_en-US" xlink:label="lab_skwd_UnderwritingExpense" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Underwriting Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_UnderwritingExpense" xlink:href="skwd-20241231.xsd#skwd_UnderwritingExpense"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_UnderwritingExpense" xlink:to="lab_skwd_UnderwritingExpense" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTableTextBlock_759d658e-c47d-4cb2-8d13-069e4c8c6023_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/2024/elts/us-gaap-2024.xsd#us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTableTextBlock" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_StockUnitsMember_b93530eb-aba8-4df6-beff-aa9e098d300c_terseLabel_en-US" xlink:label="lab_skwd_StockUnitsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stock units</link:label>
    <link:label id="lab_skwd_StockUnitsMember_label_en-US" xlink:label="lab_skwd_StockUnitsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Stock Units [Member]</link:label>
    <link:label id="lab_skwd_StockUnitsMember_documentation_en-US" xlink:label="lab_skwd_StockUnitsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Stock Units</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_StockUnitsMember" xlink:href="skwd-20241231.xsd#skwd_StockUnitsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_StockUnitsMember" xlink:to="lab_skwd_StockUnitsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EmployeeStockOptionMember_fe08dce8-8a7d-439d-9995-08ca9847b764_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">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">Share-Based Payment Arrangement, Option [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EmployeeStockOptionMember" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.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_FinancingReceivablePortfolioSegmentAxis_eef28fd4-435c-4c1f-ad2a-57edcee13436_terseLabel_en-US" xlink:label="lab_us-gaap_FinancingReceivablePortfolioSegmentAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Financing Receivable Portfolio Segment [Axis]</link:label>
    <link:label id="lab_us-gaap_FinancingReceivablePortfolioSegmentAxis_label_en-US" xlink:label="lab_us-gaap_FinancingReceivablePortfolioSegmentAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Financing Receivable Portfolio Segment [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FinancingReceivablePortfolioSegmentAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_FinancingReceivablePortfolioSegmentAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FinancingReceivablePortfolioSegmentAxis" xlink:to="lab_us-gaap_FinancingReceivablePortfolioSegmentAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleTable_f6ea31f8-84a5-416b-95f7-43befe61721a_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/2024/elts/us-gaap-2024.xsd#us-gaap_DebtSecuritiesAvailableForSaleTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleTable" xlink:to="lab_us-gaap_DebtSecuritiesAvailableForSaleTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PreferredStockDividendsAndOtherAdjustmentsAbstract_5beef4cf-5369-4eae-9164-6229ef07006c_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>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockDividendsAndOtherAdjustmentsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_PreferredStockDividendsAndOtherAdjustmentsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PreferredStockDividendsAndOtherAdjustmentsAbstract" xlink:to="lab_us-gaap_PreferredStockDividendsAndOtherAdjustmentsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_Depreciation_4acb9874-d15d-401d-a61f-724dd766f0b9_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/2024/elts/us-gaap-2024.xsd#us-gaap_Depreciation"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_Depreciation" xlink:to="lab_us-gaap_Depreciation" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition_6c4b211a-edb7-4d0b-a24b-c187d7bd8768_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>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition_label_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Unrealized Loss Position</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPosition" xlink:href="skwd-20241231.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_LesseeOperatingLeaseLiabilityPaymentsDueNextTwelveMonths_1a769884-443f-4e77-a412-82521b0f8222_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">2025</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueNextTwelveMonths" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.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_LicenseMember_3dd36bf5-5d0b-4fd1-a349-c62a6dc3446d_terseLabel_en-US" xlink:label="lab_us-gaap_LicenseMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Licenses</link:label>
    <link:label id="lab_us-gaap_LicenseMember_label_en-US" xlink:label="lab_us-gaap_LicenseMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">License [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LicenseMember" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_LicenseMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LicenseMember" xlink:to="lab_us-gaap_LicenseMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherExpenses_50d2ef97-ac25-404d-8a73-2982ae2c7893_terseLabel_en-US" xlink:label="lab_us-gaap_OtherExpenses" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other expenses</link:label>
    <link:label id="lab_us-gaap_OtherExpenses_label_en-US" xlink:label="lab_us-gaap_OtherExpenses" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Expenses</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherExpenses" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_OtherExpenses"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherExpenses" xlink:to="lab_us-gaap_OtherExpenses" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable_8e6ad453-adbf-4a52-8d9a-e3e81b6995da_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable" 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 [Table]</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable" xlink:to="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTable" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ShortTermInvestmentFairValueDisclosure_8e83eba7-cd5b-4e90-9a83-774635d5e1f5_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-20241231.xsd#skwd_ShortTermInvestmentFairValueDisclosure"/>
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    <link:label id="lab_us-gaap_ComprehensiveIncomeNetOfTax_c0d67a1b-daa2-4aee-b611-d39fefa1ad12_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/2024/elts/us-gaap-2024.xsd#us-gaap_ComprehensiveIncomeNetOfTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ComprehensiveIncomeNetOfTax" xlink:to="lab_us-gaap_ComprehensiveIncomeNetOfTax" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationOtherAdjustments_8c6bc692-d9b5-4952-a350-dd5dfe3074f8_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>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationOtherAdjustments_label_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationOtherAdjustments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effective Income Tax Rate Reconciliation, Other Adjustments, Percent</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EffectiveIncomeTaxRateReconciliationOtherAdjustments" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_EffectiveIncomeTaxRateReconciliationOtherAdjustments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EffectiveIncomeTaxRateReconciliationOtherAdjustments" xlink:to="lab_us-gaap_EffectiveIncomeTaxRateReconciliationOtherAdjustments" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtInstrumentFixedInterestRatePeriodOneMember_bb1e476d-cb67-41d9-b5be-f781e8b2ecb8_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-20241231.xsd#skwd_DebtInstrumentFixedInterestRatePeriodOneMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtInstrumentFixedInterestRatePeriodOneMember" xlink:to="lab_skwd_DebtInstrumentFixedInterestRatePeriodOneMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_HudsonVenturesFund2LPMember_5449a1e1-ecdc-468c-9ac3-690ff4003f95_terseLabel_en-US" xlink:label="lab_skwd_HudsonVenturesFund2LPMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Hudson Ventures Fund II LP units</link:label>
    <link:label id="lab_skwd_HudsonVenturesFund2LPMember_label_en-US" xlink:label="lab_skwd_HudsonVenturesFund2LPMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Hudson Ventures Fund 2, L.P. [Member]</link:label>
    <link:label id="lab_skwd_HudsonVenturesFund2LPMember_documentation_en-US" xlink:label="lab_skwd_HudsonVenturesFund2LPMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" 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-20241231.xsd#skwd_HudsonVenturesFund2LPMember"/>
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    <link:label id="lab_us-gaap_MunicipalBondsMember_b371b2e4-8092-4c65-854e-a018eb10043e_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/2024/elts/us-gaap-2024.xsd#us-gaap_MunicipalBondsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MunicipalBondsMember" xlink:to="lab_us-gaap_MunicipalBondsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract_8c631ae2-edb9-42f3-8920-7d01c6f7f737_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity securities, held-to-maturity:</link:label>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale and Held-to-Maturity, Fair Value to Amortized Cost, after Allowance for Credit Loss [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleAndHeldToMaturityFairValueToAmortizedCostAfterAllowanceForCreditLossAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.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_InvestmentsClassifiedByContractualMaturityDateTableTextBlock_30fef35b-fb8e-4925-815c-11eb35dfdc2d_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/2024/elts/us-gaap-2024.xsd#us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock" xlink:to="lab_us-gaap_InvestmentsClassifiedByContractualMaturityDateTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestAfterAllowanceForCreditLoss_804fdf1d-2ef6-4b20-92f8-ff7e5467cc8e_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_f9570551-86b8-4bbe-bdf4-8f8100f100fa_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">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/2024/elts/us-gaap-2024.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_AwardTypeAxis_5e237d64-9be8-49e0-b84a-ae614572927b_terseLabel_en-US" xlink:label="lab_us-gaap_AwardTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Type [Axis]</link:label>
    <link:label id="lab_us-gaap_AwardTypeAxis_label_en-US" xlink:label="lab_us-gaap_AwardTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AwardTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_AwardTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AwardTypeAxis" xlink:to="lab_us-gaap_AwardTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CorporateDebtSecuritiesMember_39f74a24-9752-4ff4-b978-70064f0c578a_terseLabel_en-US" xlink:label="lab_us-gaap_CorporateDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Corporate securities and miscellaneous</link:label>
    <link:label id="lab_us-gaap_CorporateDebtSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_CorporateDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Corporate Debt Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CorporateDebtSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_CorporateDebtSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CorporateDebtSecuritiesMember" xlink:to="lab_us-gaap_CorporateDebtSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CreditRatingAMBestDomain_23febcce-c8bf-480a-ac50-aa290b5aed75_terseLabel_en-US" xlink:label="lab_srt_CreditRatingAMBestDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Credit Rating, AM Best [Domain]</link:label>
    <link:label id="lab_srt_CreditRatingAMBestDomain_label_en-US" xlink:label="lab_srt_CreditRatingAMBestDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Credit Rating, AM Best [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_CreditRatingAMBestDomain" xlink:href="https://xbrl.fasb.org/srt/2024/elts/srt-2024.xsd#srt_CreditRatingAMBestDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_CreditRatingAMBestDomain" xlink:to="lab_srt_CreditRatingAMBestDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CumulativeEffectPeriodOfAdoptionAdjustmentMember_08639932-ec3e-4f78-887b-c8a43ccda90f_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/2024/elts/srt-2024.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_skwd_LongTermIncentivePlanMember_a2d368e9-7118-4253-af04-0e157c193df6_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-20241231.xsd#skwd_LongTermIncentivePlanMember"/>
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    <link:label id="lab_us-gaap_CashAndCashEquivalentsRestrictedCashAndCashEquivalentsPolicy_ff7b5c56-df4b-4365-b9d1-d7bccf866ab1_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>
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    <link:label id="lab_us-gaap_CededCreditRiskLineItems_98ca4dcc-10b5-4cae-a838-96ab2942b435_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/2024/elts/us-gaap-2024.xsd#us-gaap_CededCreditRiskLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CededCreditRiskLineItems" xlink:to="lab_us-gaap_CededCreditRiskLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PaymentsForProceedsFromLongtermInvestments_5d9ec378-6f88-4b0b-85c6-225b9d72b356_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsForProceedsFromLongtermInvestments" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Sales of and distributions from equity method and other long-term investments</link:label>
    <link:label id="lab_us-gaap_PaymentsForProceedsFromLongtermInvestments_label_en-US" xlink:label="lab_us-gaap_PaymentsForProceedsFromLongtermInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments for (Proceeds from) Long-Term Investments</link:label>
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    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersAmortizationOfDeferredPolicyAcquisitionCosts_5315274c-040a-4811-b558-35bdcc6d8b93_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersAmortizationOfDeferredPolicyAcquisitionCosts" 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_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersAmortizationOfDeferredPolicyAcquisitionCosts_label_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersAmortizationOfDeferredPolicyAcquisitionCosts" 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, Amortization of Deferred Policy Acquisition Cost</link:label>
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    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentNet_db0e5d3d-dae7-4428-a715-d8907f240694_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>
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    <link:label id="lab_us-gaap_Liabilities_af2b6af4-e6b9-4bc7-a7db-71931bdfbe18_totalLabel_en-US" xlink:label="lab_us-gaap_Liabilities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total liabilities</link:label>
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    <link:label id="lab_us-gaap_CommonStockParOrStatedValuePerShare_154b67e1-6177-4a13-ad22-e0e0a8b12cc7_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockParOrStatedValuePerShare" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Common stock, par value (in dollar per share)</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ScheduleOfShareBasedCompensationArrangementsByShareBasedPaymentAwardTable"/>
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    <link:label id="lab_us-gaap_RevolvingCreditFacilityMember_41f42ed7-1748-4bb3-9cfe-85c523988d82_terseLabel_en-US" xlink:label="lab_us-gaap_RevolvingCreditFacilityMember" 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_us-gaap_RevolvingCreditFacilityMember_label_en-US" xlink:label="lab_us-gaap_RevolvingCreditFacilityMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Revolving Credit Facility [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RevolvingCreditFacilityMember" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_RevolvingCreditFacilityMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RevolvingCreditFacilityMember" xlink:to="lab_us-gaap_RevolvingCreditFacilityMember" xlink:type="arc" order="1"/>
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    <link:label id="lab_ecd_TrdArrExpirationDate_label_en-US" xlink:label="lab_ecd_TrdArrExpirationDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement Expiration Date</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrExpirationDate" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_TrdArrExpirationDate"/>
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    <link:label id="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract_955c22a4-d6e3-4f9b-8176-197f13d8eaee_terseLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash flows from investing activities:</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Net Cash Provided by (Used in) Investing Activities [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_NetCashProvidedByUsedInInvestingActivitiesAbstract"/>
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    <link:label id="lab_us-gaap_CededCreditRiskAxis_dd646a3b-10f2-4247-830f-5cdaa2445f4f_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/2024/elts/us-gaap-2024.xsd#us-gaap_CededCreditRiskAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CededCreditRiskAxis" xlink:to="lab_us-gaap_CededCreditRiskAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_FHLBLoanMember_8482821f-6247-46a2-b36f-e17defabe592_terseLabel_en-US" xlink:label="lab_skwd_FHLBLoanMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">FHLB Loan</link:label>
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    <link:label id="lab_skwd_FHLBLoanMember_documentation_en-US" xlink:label="lab_skwd_FHLBLoanMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">FHLB Loan</link:label>
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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_us-gaap_IncomeTaxExpenseBenefitContinuingOperationsIncomeTaxReconciliationAbstract_c97a1428-b05a-4e20-b5c9-6ae29cc0fbcd_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxExpenseBenefitContinuingOperationsIncomeTaxReconciliationAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Amount</link:label>
    <link:label id="lab_us-gaap_IncomeTaxExpenseBenefitContinuingOperationsIncomeTaxReconciliationAbstract_label_en-US" xlink:label="lab_us-gaap_IncomeTaxExpenseBenefitContinuingOperationsIncomeTaxReconciliationAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income Tax Expense (Benefit), Effective Income Tax Rate Reconciliation, Amount [Abstract]</link:label>
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    <link:label id="lab_skwd_ContingentlyIssuableInstrumentsCommonSharesMember_e6add369-adee-4c3c-8c5c-f895467cd77a_terseLabel_en-US" xlink:label="lab_skwd_ContingentlyIssuableInstrumentsCommonSharesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Common shares</link:label>
    <link:label id="lab_skwd_ContingentlyIssuableInstrumentsCommonSharesMember_label_en-US" xlink:label="lab_skwd_ContingentlyIssuableInstrumentsCommonSharesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Contingently Issuable Instruments, Common Shares [Member]</link:label>
    <link:label id="lab_skwd_ContingentlyIssuableInstrumentsCommonSharesMember_documentation_en-US" xlink:label="lab_skwd_ContingentlyIssuableInstrumentsCommonSharesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Contingently Issuable Instruments, Common Shares</link:label>
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    <link:label id="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2020Member_ee8daca1-7fd2-4ddd-a7ba-599c6269251a_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>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsFairValue_39debe95-1b7f-4f8f-9499-1e00252625e4_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>
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    <link:label id="lab_us-gaap_OtherShortTermInvestments_d87ff5f9-d846-4d48-9e55-71eb0ec0b5a5_terseLabel_en-US" xlink:label="lab_us-gaap_OtherShortTermInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Short-term investments, at fair value</link:label>
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    <link:label id="lab_us-gaap_UndistributedEarningsLossAllocatedToParticipatingSecuritiesBasic_4a0cdd5d-b0ba-4ac3-abb8-c15a0f171618_terseLabel_en-US" xlink:label="lab_us-gaap_UndistributedEarningsLossAllocatedToParticipatingSecuritiesBasic" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net income attributable to participating securities</link:label>
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    <link:label id="lab_skwd_GainOnSaleOfOtherInvestments_documentation_en-US" xlink:label="lab_skwd_GainOnSaleOfOtherInvestments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Gain on Sale of Other Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_GainOnSaleOfOtherInvestments" xlink:href="skwd-20241231.xsd#skwd_GainOnSaleOfOtherInvestments"/>
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    <link:label id="lab_us-gaap_DeferredTaxAssetsOperatingLossCarryforwards_c6d78a79-e161-4494-885d-6bf140927873_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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxAssetsOperatingLossCarryforwards" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_DeferredTaxAssetsOperatingLossCarryforwards"/>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedGain_97b53265-6beb-4b8f-8c22-3fe92dc8c9c9_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedGain" 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_DebtSecuritiesAvailableForSaleRealizedGain_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleRealizedGain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Realized Gain</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleRealizedGain" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_DebtSecuritiesAvailableForSaleRealizedGain"/>
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    <link:label id="lab_us-gaap_IncomeTaxReconciliationOtherReconcilingItems_6942b311-2a68-49cf-ba01-80530187128c_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeTaxReconciliationOtherReconcilingItems" 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_IncomeTaxReconciliationOtherReconcilingItems_label_en-US" xlink:label="lab_us-gaap_IncomeTaxReconciliationOtherReconcilingItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Effective Income Tax Rate Reconciliation, Other Reconciling Items, Amount</link:label>
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    <link:label id="lab_us-gaap_EquipmentMember_70c24e5d-8b63-4b66-8c3d-4973aa9b313f_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/2024/elts/us-gaap-2024.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_SubsequentEventLineItems_3ca4510d-2d8b-4d38-87b5-9c1fbc590e30_terseLabel_en-US" xlink:label="lab_us-gaap_SubsequentEventLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subsequent Event [Line Items]</link:label>
    <link:label id="lab_us-gaap_SubsequentEventLineItems_label_en-US" xlink:label="lab_us-gaap_SubsequentEventLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsequent Event [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsequentEventLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_SubsequentEventLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsequentEventLineItems" xlink:to="lab_us-gaap_SubsequentEventLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve_34908125-1ad3-4b1d-8f08-8a799a84002b_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>
    <link:label id="lab_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Liability for Claims and Claims Adjustment Expense Reserve</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve" xlink:to="lab_us-gaap_IncreaseDecreaseInLiabilityForClaimsAndClaimsAdjustmentExpenseReserve" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentLineItems_5cfccfd5-9cd4-43fa-bc8b-537efe1ac228_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/2024/elts/us-gaap-2024.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_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>
    <link:label id="lab_ecd_NamedExecutiveOfficersFnTextBlock_label_en-US" xlink:label="lab_ecd_NamedExecutiveOfficersFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Named Executive Officers, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NamedExecutiveOfficersFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_NamedExecutiveOfficersFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NamedExecutiveOfficersFnTextBlock" xlink:to="lab_ecd_NamedExecutiveOfficersFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_GoodwillAndIntangibleAssetsPolicyTextBlock_55999441-3540-43fb-aaa3-84032693720a_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/2024/elts/us-gaap-2024.xsd#us-gaap_GoodwillAndIntangibleAssetsPolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillAndIntangibleAssetsPolicyTextBlock" xlink:to="lab_us-gaap_GoodwillAndIntangibleAssetsPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherAssets_a642b6f7-5e04-490c-b00b-02b561bf3ee7_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/2024/elts/us-gaap-2024.xsd#us-gaap_OtherAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherAssets" xlink:to="lab_us-gaap_OtherAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsNumberOfReportedClaims_9b0e2756-d5ba-405f-9656-f507704f437b_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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsNumberOfReportedClaims" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ShortdurationInsuranceContractsNumberOfReportedClaims"/>
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    <link:label id="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock_91cc1654-3464-485a-b88b-c94db3c8af2d_terseLabel_en-US" xlink:label="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Basis of Presentation</link:label>
    <link:label id="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Basis of Accounting, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_BasisOfAccountingPolicyPolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:to="lab_us-gaap_BasisOfAccountingPolicyPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_7cc98091-d429-4b1b-b1da-2c89143b1b2e_terseLabel_en-US" xlink:label="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Diluted (in shares)</link:label>
    <link:label id="lab_us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding_6047bc01-c696-4459-bdf2-970faa2e97f9_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>
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    <link:label id="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccountsWriteOffsAgainstAllowance_60370e85-5fbb-4ee3-80b2-fde14b9afbb9_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_StockholdersEquity_97b32eec-6ee2-4b7e-91e1-b235abd49d15_totalLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquity" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total stockholders&#8217; equity</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockholdersEquity" xlink:to="lab_us-gaap_StockholdersEquity" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredTaxAssetsGross_2fc13e81-55dd-4108-ac61-4e50e4800260_totalLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsGross" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total deferred tax assets</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxAssetsGross" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_DeferredTaxAssetsGross"/>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue_a7b7ea08-0603-44d2-918a-771221a6feee_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>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Fair Value, Maturity, Allocated and Single Maturity Date, Year One</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearFairValue"/>
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    <link:label id="lab_us-gaap_ScheduleOfGoodwillTextBlock_73b1229a-b16a-4181-91f6-94928590b4ea_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfGoodwillTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Goodwill</link:label>
    <link:label id="lab_us-gaap_ScheduleOfGoodwillTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfGoodwillTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Goodwill [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfGoodwillTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ScheduleOfGoodwillTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfGoodwillTextBlock" xlink:to="lab_us-gaap_ScheduleOfGoodwillTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConcentrationRiskTypeDomain_a60195b7-efef-490b-90dc-a65d4fbc511f_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskTypeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Concentration Risk Type [Domain]</link:label>
    <link:label id="lab_us-gaap_ConcentrationRiskTypeDomain_label_en-US" xlink:label="lab_us-gaap_ConcentrationRiskTypeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Concentration Risk Type [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConcentrationRiskTypeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ConcentrationRiskTypeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConcentrationRiskTypeDomain" xlink:to="lab_us-gaap_ConcentrationRiskTypeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ProceedsFromPaymentsForDepositAccounting_32e7f412-08c7-47ab-8291-5bb1fc2b4a8a_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-20241231.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_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost_e40df04c-0288-46ba-a030-cbd26f668749_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Without single maturity date</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Maturity, without Single Maturity Date, Amortized Cost</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateAmortizedCost"/>
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    <link:label id="lab_skwd_LoansHeldForInvestmentTerm_e9d623b4-33ad-4315-b4a1-cc513b347ee0_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-20241231.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_DefinedContributionPlanCostRecognized_fd8f9f3a-81fa-4f66-a07f-073c55b2e276_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/2024/elts/us-gaap-2024.xsd#us-gaap_DefinedContributionPlanCostRecognized"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DefinedContributionPlanCostRecognized" xlink:to="lab_us-gaap_DefinedContributionPlanCostRecognized" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesReportableDataLineItems_3d99766d-b27a-44c4-a9fc-04408235d947_terseLabel_en-US" xlink:label="lab_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesReportableDataLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-15, Insurance Companies, Summary of Investments, Other than Investments in Related Parties [Line Items]</link:label>
    <link:label id="lab_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesReportableDataLineItems_label_en-US" xlink:label="lab_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesReportableDataLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-15, Insurance Companies, Summary of Investments, Other than Investments in Related Parties [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesReportableDataLineItems" xlink:href="https://xbrl.fasb.org/srt/2024/elts/srt-2024.xsd#srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesReportableDataLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesReportableDataLineItems" xlink:to="lab_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesReportableDataLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_UnsecuredSubordinatedNotesDue2039Member_bccc90f6-9701-4928-82bf-2e23a81fd051_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-20241231.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_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAuthorized_da7609c5-546b-474b-8f1d-02778a52d279_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_d88bc25e-47aa-415a-8b6d-b6b58eb34033_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">Target Stock and Stock Units (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/2024/elts/us-gaap-2024.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAuthorized"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAuthorized" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardNumberOfSharesAuthorized" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SaleOfStockNameOfTransactionDomain_9f8c4f9f-fff6-436b-ac49-d8e01d1ae9c9_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/2024/elts/us-gaap-2024.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_dei_DocumentFiscalPeriodFocus_58a4145a-7dd1-4af7-a149-067772059e5e_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/2024/dei-2024.xsd#dei_DocumentFiscalPeriodFocus"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentFiscalPeriodFocus" xlink:to="lab_dei_DocumentFiscalPeriodFocus" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearSix_07a7830b-401d-45ef-b074-718722183be6_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>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearSix_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearSix" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contracts, Historical Claims Duration, Year Six</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearSix" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearSix"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearSix" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearSix" xlink:type="arc" order="1"/>
    <link:label id="lab_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>
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    <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_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements_26ce6afb-67c4-419e-a0fe-f3bd8ec651d5_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">Diluted effect of awards (in shares)</link:label>
    <link:label id="lab_us-gaap_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements_label_en-US" xlink:label="lab_us-gaap_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Incremental Common Shares Attributable to Dilutive Effect of Share-Based Payment Arrangements</link:label>
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    <link:label id="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities_435af54c-561b-4b3e-b68e-ed36e7ee53ba_negatedTerseLabel_en-US" xlink:label="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Change in receivable/payable for securities</link:label>
    <link:label id="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities_label_en-US" xlink:label="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments For (Proceeds From) Sale and Collection of Securities</link:label>
    <link:label id="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities_documentation_en-US" xlink:label="lab_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Payments For (Proceeds From) Sale and Collection of Securities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities" xlink:href="skwd-20241231.xsd#skwd_PaymentsForProceedsFromSaleAndCollectionOfSecurities"/>
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    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsScheduleOfHistoricalClaimsDurationTableTextBlock_1677db0d-1b1e-4b79-8e94-6718045bbdd0_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:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsScheduleOfHistoricalClaimsDurationTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ShortdurationInsuranceContractsScheduleOfHistoricalClaimsDurationTableTextBlock"/>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTable" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ShortdurationInsuranceContractsReconciliationOfClaimsDevelopmentToLiabilityTable"/>
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    <link:label id="lab_us-gaap_EquitySecuritiesMember_2d14365a-5944-4ece-9f91-c91667b6d993_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/2024/elts/us-gaap-2024.xsd#us-gaap_EquitySecuritiesMember"/>
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    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearTwo_69fd6972-c6c3-4698-ad7d-02001fec61a9_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearTwo" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2026</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearTwo_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearTwo" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Finite-Lived Intangible Asset, Expected Amortization, Year Two</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearTwo" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearTwo"/>
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    <link:label id="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardOptionsOutstandingWeightedAverageRemainingContractualTerm2_25b32102-06d4-4580-9c6c-357747d8f334_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: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>
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    <link:label id="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock_8492c55f-5401-4c06-a57e-5b60585a100e_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfSegmentReportingInformationBySegmentTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Segment Reporting Information, by Segment</link:label>
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    <link:label id="lab_skwd_EverestReinsuranceCoMember_e319e9a7-3d65-41c5-8580-37aeeef423cc_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>
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    <link:label id="lab_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet_1bc6e48a-0a85-4a1c-9641-807e903c455a_terseLabel_en-US" xlink:label="lab_us-gaap_MortgageLoansOnRealEstateCommercialAndConsumerNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mortgage loans, at fair value</link:label>
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    <link:label id="lab_skwd_AgencyAgreementMember_12717853-16fb-488b-bb27-699e62df6a39_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_us-gaap_OtherIncomeAndExpensesAbstract_label_en-US" xlink:label="lab_us-gaap_OtherIncomeAndExpensesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Income and Expenses [Abstract]</link:label>
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    <link:label id="lab_us-gaap_ContractWithCustomerAssetAndLiabilityTableTextBlock_9826de08-4560-4748-b03d-9b4cc05a66b7_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">Contract with Customer, Contract Asset, Contract Liability, and Receivable</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_srt_ParentCompanyMember" xlink:href="https://xbrl.fasb.org/srt/2024/elts/srt-2024.xsd#srt_ParentCompanyMember"/>
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    <link:label id="lab_srt_MaximumMember_33a8e881-8086-485f-8cb3-8de52c96b0ed_terseLabel_en-US" xlink:label="lab_srt_MaximumMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">High</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_srt_MaximumMember" xlink:href="https://xbrl.fasb.org/srt/2024/elts/srt-2024.xsd#srt_MaximumMember"/>
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    <link:label id="lab_us-gaap_ReinsuranceRecoverablesAllowance_3097b0f4-dbea-41ac-9ea0-fd8b6a39f6ec_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">Reinsurance Recoverables, Net, beginning balance</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesAllowance_183b2e63-b6ca-436e-bd46-4209414c1cc3_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_9e21ba49-e420-4132-a1ea-680354b84731_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/2024/elts/us-gaap-2024.xsd#us-gaap_ReinsuranceRecoverablesAllowance"/>
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    <link:label id="lab_us-gaap_GoodwillImpairedAccumulatedImpairmentLoss_35a43695-6c59-4da2-873e-310c2036b892_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>
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    <link:label id="lab_skwd_DeferredIncomeTaxExpenseBenefitTemporaryDifferences_d36db715-6653-468e-87f2-a4c2d679de62_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 (benefit) expense related to temporary differences</link:label>
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    <link:label id="lab_skwd_DeferredIncomeTaxExpenseBenefitTemporaryDifferences_documentation_en-US" xlink:label="lab_skwd_DeferredIncomeTaxExpenseBenefitTemporaryDifferences" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Deferred Income Tax Expense (Benefit), Temporary Differences</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DeferredIncomeTaxExpenseBenefitTemporaryDifferences" xlink:href="skwd-20241231.xsd#skwd_DeferredIncomeTaxExpenseBenefitTemporaryDifferences"/>
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    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsNet_fb7a6b46-6361-4620-994d-aaf27419a6de_periodEndLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsNet" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Net, ending balance</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsNet_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Finite-Lived Intangible Assets, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsNet" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_FiniteLivedIntangibleAssetsNet"/>
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    <link:label id="lab_us-gaap_ScheduleOfLiabilityForUnpaidClaimsAndClaimsAdjustmentExpense_8cab84a9-621c-4af3-94eb-dbcec996fbed_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_skwd_FixedMaturitiesHeldToMaturityMember_28d9ff7f-39ca-4576-a798-b49d30ca26dc_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_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease_b0906ec0-dc6e-482a-b809-f54e8ad58458_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpensePeriodIncreaseDecrease" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Liability for unpaid claims and claims adjustment expense, period increase (decrease)</link:label>
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    <link:label id="lab_skwd_ArenaSOPLPMember_1b098ce1-0d5c-48c0-a28c-1348e3ad8d64_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>
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    <link:label id="lab_us-gaap_InvestmentTypeAxis_e796a9e7-df3e-487b-8763-84d6426ee209_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment Type [Axis]</link:label>
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    <link:label id="lab_us-gaap_ReinsuranceTextBlock_a1df1173-4241-4d9a-8f1a-dbf128b7c1d0_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>
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    <link:label id="lab_us-gaap_LeaseCost_58235097-d8d2-44a6-b9c2-b432ff8dee67_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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustmentAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.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_srt_RangeAxis_bb780ae0-79b7-4d03-ba42-d0b3bd3c76ad_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/2024/elts/srt-2024.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_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>
    <link:label id="lab_ecd_NonRule10b51ArrTrmntdFlag_label_en-US" xlink:label="lab_ecd_NonRule10b51ArrTrmntdFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-Rule 10b5-1 Arrangement Terminated [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonRule10b51ArrTrmntdFlag" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_NonRule10b51ArrTrmntdFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonRule10b51ArrTrmntdFlag" xlink:to="lab_ecd_NonRule10b51ArrTrmntdFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_AAndAboveMember_3b5d6645-7356-499a-ad9c-c0a3587f5fdf_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-20241231.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_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_09685762-1a27-4c6a-aad1-58f46940ee67_totalLabel_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Income before income taxes</link:label>
    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_cede86dc-8b1d-4189-981b-4b5c6265c7a3_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Income before income taxes</link:label>
    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_label_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Income (Loss) from Continuing Operations before Income Taxes, Noncontrolling Interest</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:to="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccounts_7d629af5-c926-4a59-9dbd-a8b2c160af8e_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_2ff4b83c-dbc0-4c10-9f8e-4776d3cbf7d8_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>
    <link:label id="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccounts_58bd0216-b60d-4c72-bbf4-85265b6685ea_periodEndLabel_en-US" xlink:label="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccounts" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Allowance for Estimated Uncollectible Premiums, ending balance</link:label>
    <link:label id="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccounts_label_en-US" xlink:label="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccounts" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Premium Receivable, Allowance for Credit Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccounts" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_PremiumsReceivableAllowanceForDoubtfulAccounts"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccounts" xlink:to="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccounts" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_NonPeoNeoAvgTotalCompAmt_terseLabel_en-US" xlink:label="lab_ecd_NonPeoNeoAvgTotalCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-PEO NEO Average Total Compensation Amount</link:label>
    <link:label id="lab_ecd_NonPeoNeoAvgTotalCompAmt_label_en-US" xlink:label="lab_ecd_NonPeoNeoAvgTotalCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-PEO NEO Average Total Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_NonPeoNeoAvgTotalCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_NonPeoNeoAvgTotalCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_NonPeoNeoAvgTotalCompAmt" xlink:to="lab_ecd_NonPeoNeoAvgTotalCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CapitalizationOfDeferredPolicyAcquisitionCostsPolicy_55af55e8-36e5-454e-a3e1-c7e685bdef5c_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/2024/elts/us-gaap-2024.xsd#us-gaap_CapitalizationOfDeferredPolicyAcquisitionCostsPolicy"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CapitalizationOfDeferredPolicyAcquisitionCostsPolicy" xlink:to="lab_us-gaap_CapitalizationOfDeferredPolicyAcquisitionCostsPolicy" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredTaxLiabilitiesPropertyPlantAndEquipment_6a8118a1-1d79-445c-b262-f486ed2660c3_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/2024/elts/us-gaap-2024.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_ecd_OutstandingRecoveryIndName_terseLabel_en-US" xlink:label="lab_ecd_OutstandingRecoveryIndName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Name</link:label>
    <link:label id="lab_ecd_OutstandingRecoveryIndName_label_en-US" xlink:label="lab_ecd_OutstandingRecoveryIndName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Outstanding Recovery, Individual Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_OutstandingRecoveryIndName" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_OutstandingRecoveryIndName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_OutstandingRecoveryIndName" xlink:to="lab_ecd_OutstandingRecoveryIndName" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_SubordinatedDebtNetMember_78ac6a90-d09e-4080-ae54-b995fef9ef06_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-20241231.xsd#skwd_SubordinatedDebtNetMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_SubordinatedDebtNetMember" xlink:to="lab_skwd_SubordinatedDebtNetMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisaggregationOfRevenueLineItems_47437603-d7af-4b61-9e68-2da48060b1a4_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/2024/elts/us-gaap-2024.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_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock_e005278b-5b2b-4e82-a42a-9c09ad573366_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>
    <link:label id="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Antidilutive Securities Excluded from Computation of Earnings Per Share [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock" xlink:to="lab_us-gaap_ScheduleOfAntidilutiveSecuritiesExcludedFromComputationOfEarningsPerShareTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InsuranceCommissionsAndFees_9cb8ffd1-3c70-491d-82d4-061dfd5b03a2_terseLabel_en-US" xlink:label="lab_us-gaap_InsuranceCommissionsAndFees" 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_InsuranceCommissionsAndFees_label_en-US" xlink:label="lab_us-gaap_InsuranceCommissionsAndFees" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insurance Commissions and Fees</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InsuranceCommissionsAndFees" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_InsuranceCommissionsAndFees"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InsuranceCommissionsAndFees" xlink:to="lab_us-gaap_InsuranceCommissionsAndFees" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_TitleOfIndividualAxis_5b055213-e820-4335-81b1-772b9a3a8c14_terseLabel_en-US" xlink:label="lab_srt_TitleOfIndividualAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Title of Individual [Axis]</link:label>
    <link:label id="lab_srt_TitleOfIndividualAxis_label_en-US" xlink:label="lab_srt_TitleOfIndividualAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Title and Position [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_TitleOfIndividualAxis" xlink:href="https://xbrl.fasb.org/srt/2024/elts/srt-2024.xsd#srt_TitleOfIndividualAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_TitleOfIndividualAxis" xlink:to="lab_srt_TitleOfIndividualAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract_e30038c1-cfa7-4623-9e60-9816f17c7a7e_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>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract_label_en-US" xlink:label="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Unpaid Claims and Claims Adjustment Expense, Claims Paid [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseClaimsPaidAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardTmgPredtrmndFlag_terseLabel_en-US" xlink:label="lab_ecd_AwardTmgPredtrmndFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Timing Predetermined</link:label>
    <link:label id="lab_ecd_AwardTmgPredtrmndFlag_label_en-US" xlink:label="lab_ecd_AwardTmgPredtrmndFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Timing Predetermined [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardTmgPredtrmndFlag" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_AwardTmgPredtrmndFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardTmgPredtrmndFlag" xlink:to="lab_ecd_AwardTmgPredtrmndFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubsequentEventTypeDomain_a6652a0a-457d-494b-903a-b84b063bf876_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/2024/elts/us-gaap-2024.xsd#us-gaap_SubsequentEventTypeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsequentEventTypeDomain" xlink:to="lab_us-gaap_SubsequentEventTypeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AssumedPremiumsEarned_6074e82a-4a51-4a38-884e-2a149d26c948_terseLabel_en-US" xlink:label="lab_us-gaap_AssumedPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Assumed premiums</link:label>
    <link:label id="lab_us-gaap_AssumedPremiumsEarned_label_en-US" xlink:label="lab_us-gaap_AssumedPremiumsEarned" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Assumed Premiums Earned</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssumedPremiumsEarned" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_AssumedPremiumsEarned"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AssumedPremiumsEarned" xlink:to="lab_us-gaap_AssumedPremiumsEarned" xlink:type="arc" order="1"/>
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    <link:label id="lab_skwd_CreditLossTable_documentation_en-US" xlink:label="lab_skwd_CreditLossTable" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Credit Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_CreditLossTable" xlink:href="skwd-20241231.xsd#skwd_CreditLossTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_CreditLossTable" xlink:to="lab_skwd_CreditLossTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedPeriodForRecognition1_34cf917f-d34e-4832-81f5-8444286b6701_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/2024/elts/us-gaap-2024.xsd#us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedPeriodForRecognition1"/>
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    <link:label id="lab_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax_56bdd8fa-3ff4-408a-bbb8-a2321082387d_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>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax" xlink:to="lab_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FinancingReceivablePortfolioSegmentDomain_dd639999-8d15-4884-8224-bdd67c5d815b_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/2024/elts/us-gaap-2024.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_PaymentsToAcquireIntangibleAssets_e42ad78f-694a-4f78-9575-8793734abfdb_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireIntangibleAssets" 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_PaymentsToAcquireIntangibleAssets_label_en-US" xlink:label="lab_us-gaap_PaymentsToAcquireIntangibleAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments to Acquire Intangible Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireIntangibleAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_PaymentsToAcquireIntangibleAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PaymentsToAcquireIntangibleAssets" xlink:to="lab_us-gaap_PaymentsToAcquireIntangibleAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentOther_3400a857-9e61-4d3b-bd83-3c1428a206f1_terseLabel_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentOther" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Property, equipment and other, gross</link:label>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentOther_label_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentOther" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Property, Plant and Equipment, Other, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentOther" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_PropertyPlantAndEquipmentOther"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentOther" xlink:to="lab_us-gaap_PropertyPlantAndEquipmentOther" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_JuniorSubordinatedNotesDue2036CapitalSecuritiesMember_43a53d4d-8322-433f-b3e8-5d25c703f659_terseLabel_en-US" xlink:label="lab_skwd_JuniorSubordinatedNotesDue2036CapitalSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Junior Subordinated Notes Due 2036, Capital Securities</link:label>
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    <link:label id="lab_skwd_JuniorSubordinatedNotesDue2036CapitalSecuritiesMember_documentation_en-US" xlink:label="lab_skwd_JuniorSubordinatedNotesDue2036CapitalSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Junior Subordinated Notes Due 2036, Capital Securities</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_JuniorSubordinatedNotesDue2036CapitalSecuritiesMember" xlink:to="lab_skwd_JuniorSubordinatedNotesDue2036CapitalSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities_c6b53f3e-f43f-4abf-9cea-b1ed24d7085f_totalLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net cash used in investment activities</link:label>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities_label_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Net Cash Provided by (Used in) Investing Activities</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_NetCashProvidedByUsedInInvestingActivities"/>
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    <link:label id="lab_us-gaap_InterestExpense_17874a52-2909-44cf-891c-13388aac6570_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, Operating and Nonoperating</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.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_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/2024/ecd-2024.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_skwd_UniversaBlackSwanProtectionProtocolLIVLPMember_deca9a7a-7cec-45e7-b61e-b90c8b0da480_terseLabel_en-US" xlink:label="lab_skwd_UniversaBlackSwanProtectionProtocolLIVLPMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Universa Black Swan LP units</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_UniversaBlackSwanProtectionProtocolLIVLPMember" xlink:to="lab_skwd_UniversaBlackSwanProtectionProtocolLIVLPMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentsTextBlock_23034b21-6e50-4063-b9cb-0400f0e99cf6_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>
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    <link:label id="lab_us-gaap_AdditionalPaidInCapital_009262e1-bdff-4448-a5c7-2d2cc1a781cd_terseLabel_en-US" xlink:label="lab_us-gaap_AdditionalPaidInCapital" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Additional paid-in capital</link:label>
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    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLoss_09efed5b-9b0c-4120-8c98-b8a2cb36c36d_negatedTotalLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLoss" xlink:role="http://www.xbrl.org/2009/role/negatedTotalLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLoss" xlink:href="skwd-20241231.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLoss"/>
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    <link:label id="lab_skwd_EffectiveIncomeTaxRateReconciliationAdvantagedInvestmentsPercent_74929392-4427-4f50-938b-b3a5df8687fc_terseLabel_en-US" xlink:label="lab_skwd_EffectiveIncomeTaxRateReconciliationAdvantagedInvestmentsPercent" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Tax advantaged investments</link:label>
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    <link:label id="lab_us-gaap_ScheduleOfPropertyPlantAndEquipmentTable_label_en-US" xlink:label="lab_us-gaap_ScheduleOfPropertyPlantAndEquipmentTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" 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_ConcentrationRiskTable" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ConcentrationRiskTable"/>
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    <link:label id="lab_srt_CondensedFinancialInformationOfParentCompanyOnlyDisclosureAbstract_label_en-US" xlink:label="lab_srt_CondensedFinancialInformationOfParentCompanyOnlyDisclosureAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Condensed Financial Information Disclosure [Abstract]</link:label>
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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>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeTaxPolicyTextBlock" xlink:to="lab_us-gaap_IncomeTaxPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_PeerGroupIssuersFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_PeerGroupIssuersFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Peer Group Issuers, Footnote</link:label>
    <link:label id="lab_ecd_PeerGroupIssuersFnTextBlock_label_en-US" xlink:label="lab_ecd_PeerGroupIssuersFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Peer Group Issuers, Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeerGroupIssuersFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_PeerGroupIssuersFnTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_PeerGroupIssuersFnTextBlock" xlink:to="lab_ecd_PeerGroupIssuersFnTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OtherIncome_372401a2-0c21-4208-b3e4-73e6d1e9d5bc_terseLabel_en-US" xlink:label="lab_us-gaap_OtherIncome" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Other (loss) income</link:label>
    <link:label id="lab_us-gaap_OtherIncome_label_en-US" xlink:label="lab_us-gaap_OtherIncome" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Other Income</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherIncome" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_OtherIncome"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OtherIncome" xlink:to="lab_us-gaap_OtherIncome" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SegmentDomain_b2ed43e4-a611-4198-98c9-0f850ca14f81_terseLabel_en-US" xlink:label="lab_us-gaap_SegmentDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Segments [Domain]</link:label>
    <link:label id="lab_us-gaap_SegmentDomain_label_en-US" xlink:label="lab_us-gaap_SegmentDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segments [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SegmentDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_SegmentDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SegmentDomain" xlink:to="lab_us-gaap_SegmentDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromLinesOfCredit_71e81510-136f-4175-a145-2ca2a0f0228b_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">Proceeds from long term borrowings</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/2024/elts/us-gaap-2024.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_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>
    <link:label id="lab_ecd_PeoMember_label_en-US" xlink:label="lab_ecd_PeoMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">PEO [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeoMember" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_PeoMember"/>
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    <link:label id="lab_us-gaap_IncreaseDecreaseInPremiumsReceivable_35edabf1-2b43-447c-9721-ca2edb0406d2_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>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInPremiumsReceivable" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_IncreaseDecreaseInPremiumsReceivable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInPremiumsReceivable" xlink:to="lab_us-gaap_IncreaseDecreaseInPremiumsReceivable" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_TrdArrIndName_terseLabel_en-US" xlink:label="lab_ecd_TrdArrIndName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Name</link:label>
    <link:label id="lab_ecd_TrdArrIndName_label_en-US" xlink:label="lab_ecd_TrdArrIndName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement, Individual Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrIndName" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_TrdArrIndName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrIndName" xlink:to="lab_ecd_TrdArrIndName" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentByTypeAxis_3d3164c6-10bd-46e5-871e-944c47303071_terseLabel_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentByTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Long-Lived Tangible Asset [Axis]</link:label>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentByTypeAxis_label_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentByTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Long-Lived Tangible Asset [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentByTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_PropertyPlantAndEquipmentByTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentByTypeAxis" xlink:to="lab_us-gaap_PropertyPlantAndEquipmentByTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityPublicFloat_49f288d1-2edc-443e-bff2-bf2a0c3d80d4_terseLabel_en-US" xlink:label="lab_dei_EntityPublicFloat" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Public Float</link:label>
    <link:label id="lab_dei_EntityPublicFloat_label_en-US" xlink:label="lab_dei_EntityPublicFloat" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Public Float</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityPublicFloat" xlink:href="https://xbrl.sec.gov/dei/2024/dei-2024.xsd#dei_EntityPublicFloat"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityPublicFloat" xlink:to="lab_dei_EntityPublicFloat" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseRemainingLeaseTerm_1a3db43b-30bc-42d0-a67e-b7a6d80989e7_terseLabel_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseRemainingLeaseTerm" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Remaining lease term</link:label>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseRemainingLeaseTerm_label_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseRemainingLeaseTerm" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Lessee, Operating Lease, Remaining Lease Term</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeaseRemainingLeaseTerm" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_LesseeOperatingLeaseRemainingLeaseTerm"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LesseeOperatingLeaseRemainingLeaseTerm" xlink:to="lab_us-gaap_LesseeOperatingLeaseRemainingLeaseTerm" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments_1dd132f6-b08a-4773-8b21-ce98f493a2c4_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/2024/elts/us-gaap-2024.xsd#us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments" xlink:to="lab_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2023Member_feabced9-7112-4fff-8a77-d2eb287e14b5_terseLabel_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2023Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accident Year 2023</link:label>
    <link:label id="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2023Member_label_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2023Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contract, Accident Year 2023 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortDurationInsuranceContractAccidentYear2023Member" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ShortDurationInsuranceContractAccidentYear2023Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortDurationInsuranceContractAccidentYear2023Member" xlink:to="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2023Member" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodFairValue_fd3c0649-e866-415e-b726-e1e48a6b052b_terseLabel_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Shares granted, value</link:label>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodFairValue_label_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Grants in Period, Fair Value</link:label>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodFairValue_documentation_en-US" xlink:label="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodFairValue" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Equity Instruments Other than Options, Grants in Period, Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodFairValue" xlink:href="skwd-20241231.xsd#skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodFairValue" xlink:to="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsGrantsInPeriodFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardsCloseToMnpiDiscTableTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AwardsCloseToMnpiDiscTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Awards Close in Time to MNPI Disclosures, Table</link:label>
    <link:label id="lab_ecd_AwardsCloseToMnpiDiscTableTextBlock_label_en-US" xlink:label="lab_ecd_AwardsCloseToMnpiDiscTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Awards Close in Time to MNPI Disclosures [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardsCloseToMnpiDiscTableTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_AwardsCloseToMnpiDiscTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardsCloseToMnpiDiscTableTextBlock" xlink:to="lab_ecd_AwardsCloseToMnpiDiscTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RevenueRecognitionPremiumsEarnedPolicy_66625f55-4ff4-430e-a9d3-a0605a92ca60_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>
    <link:label id="lab_us-gaap_RevenueRecognitionPremiumsEarnedPolicy_label_en-US" xlink:label="lab_us-gaap_RevenueRecognitionPremiumsEarnedPolicy" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Revenue Recognition, Premiums Earned, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RevenueRecognitionPremiumsEarnedPolicy" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_RevenueRecognitionPremiumsEarnedPolicy"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_RevenueRecognitionPremiumsEarnedPolicy" xlink:to="lab_us-gaap_RevenueRecognitionPremiumsEarnedPolicy" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ValuationAndQualifyingAccountsAbstract_label_en-US" xlink:label="lab_srt_ValuationAndQualifyingAccountsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-09, Valuation and Qualifying Accounts [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ValuationAndQualifyingAccountsAbstract" xlink:href="https://xbrl.fasb.org/srt/2024/elts/srt-2024.xsd#srt_ValuationAndQualifyingAccountsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ValuationAndQualifyingAccountsAbstract" xlink:to="lab_srt_ValuationAndQualifyingAccountsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember_terseLabel_en-US" xlink:label="lab_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Prior Year End Fair Value of Equity Awards Granted in Any Prior Year that Fail to Meet Applicable Vesting Conditions During Covered Year</link:label>
    <link:label id="lab_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember_label_en-US" xlink:label="lab_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Prior Year End Fair Value of Equity Awards Granted in Any Prior Year that Fail to Meet Applicable Vesting Conditions During Covered Year [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_FrValAsOfPrrYrEndOfEqtyAwrdsGrntdInPrrYrsFldVstngCondsDrngCvrdYrMember"/>
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    <link:label id="lab_us-gaap_ReinsuranceRecoverables_ba3b166b-259d-4575-9a1e-f20d45ff8c38_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>
    <link:label id="lab_us-gaap_ReinsuranceRecoverables_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverables" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverables, Including Reinsurance Premium Paid</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverables" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ReinsuranceRecoverables"/>
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    <link:loc xlink:type="locator" xlink:label="loc_ecd_AggtErrCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_AggtErrCompAmt"/>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesCarryingAmount" xlink:to="lab_us-gaap_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesCarryingAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_FollowOnOfferingSharesFromCompanyMember_0e383250-6744-4e3b-a5a4-c2ba3fa649af_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-20241231.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_CommonStockMember_349d9972-b464-4d45-ae03-c44be0e26100_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_189b549f-de6a-4101-aac5-010d330f99da_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Common stocks:</link:label>
    <link:label id="lab_us-gaap_CommonStockMember_e27a2c30-2c55-4c02-9668-33a697ed1453_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/2024/elts/us-gaap-2024.xsd#us-gaap_CommonStockMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommonStockMember" xlink:to="lab_us-gaap_CommonStockMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInPrepaidReinsurancePremiums_04ec2914-96cc-496a-93c5-707aff52a866_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>
    <link:label id="lab_us-gaap_IncreaseDecreaseInPrepaidReinsurancePremiums_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInPrepaidReinsurancePremiums" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Prepaid Reinsurance Premiums</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInPrepaidReinsurancePremiums" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_IncreaseDecreaseInPrepaidReinsurancePremiums"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInPrepaidReinsurancePremiums" xlink:to="lab_us-gaap_IncreaseDecreaseInPrepaidReinsurancePremiums" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearEight_91d9bac9-559b-4d58-89b4-2b986de019c0_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearEight" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Year 8</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearEight_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearEight" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contracts, Historical Claims Duration, Year Eight</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearEight" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearEight"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearEight" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearEight" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockholdersEquityNoteStockSplitConversionRatio1_5e109426-7ed1-4aed-b630-f72a045f6bbb_terseLabel_en-US" xlink:label="lab_us-gaap_StockholdersEquityNoteStockSplitConversionRatio1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity conversion ratio</link:label>
    <link:label id="lab_us-gaap_StockholdersEquityNoteStockSplitConversionRatio1_label_en-US" xlink:label="lab_us-gaap_StockholdersEquityNoteStockSplitConversionRatio1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Stockholders' Equity Note, Stock Split, Conversion Ratio</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquityNoteStockSplitConversionRatio1" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_StockholdersEquityNoteStockSplitConversionRatio1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockholdersEquityNoteStockSplitConversionRatio1" xlink:to="lab_us-gaap_StockholdersEquityNoteStockSplitConversionRatio1" xlink:type="arc" order="1"/>
    <link:label id="lab_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/2024/ecd-2024.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_FairValueLiabilitiesMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock_d372c0cc-d072-47cb-a78b-a4e8c43ee7a2_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueLiabilitiesMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value, Liabilities Measured on Recurring Basis, Unobservable Input Reconciliation</link:label>
    <link:label id="lab_us-gaap_FairValueLiabilitiesMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock_label_en-US" xlink:label="lab_us-gaap_FairValueLiabilitiesMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Liabilities Measured on Recurring Basis, Unobservable Input Reconciliation [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueLiabilitiesMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.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_EffectsOfReinsuranceTableTextBlock_9266907c-6ea5-4e88-965f-57c11db20757_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/2024/elts/us-gaap-2024.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_LineOfCreditMember_20f1df72-4b15-4b6e-9544-44b9c54b6ee5_terseLabel_en-US" xlink:label="lab_us-gaap_LineOfCreditMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Line of Credit</link:label>
    <link:label id="lab_us-gaap_LineOfCreditMember_label_en-US" xlink:label="lab_us-gaap_LineOfCreditMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Line of Credit [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LineOfCreditMember" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_LineOfCreditMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LineOfCreditMember" xlink:to="lab_us-gaap_LineOfCreditMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract_8e883bea-613c-4c34-9c9f-8733924a3701_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Earned</link:label>
    <link:label id="lab_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract_label_en-US" xlink:label="lab_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Premiums Earned, Net [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract" xlink:to="lab_us-gaap_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentNetAmountAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_GrossRealizedInvestmentLossesAbstract_c7582b65-65f1-42bc-8c98-270b23533af3_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>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_GrossRealizedInvestmentLossesAbstract" xlink:href="skwd-20241231.xsd#skwd_GrossRealizedInvestmentLossesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_GrossRealizedInvestmentLossesAbstract" xlink:to="lab_skwd_GrossRealizedInvestmentLossesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SegmentReportingAbstract_label_en-US" xlink:label="lab_us-gaap_SegmentReportingAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segment Reporting [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SegmentReportingAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_SegmentReportingAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SegmentReportingAbstract" xlink:to="lab_us-gaap_SegmentReportingAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityCentralIndexKey_25edbb23-06d6-4813-90e5-4d8e71f5cacb_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/2024/dei-2024.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_EquityMethodInvestmentsAndJointVenturesAbstract_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentsAndJointVenturesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investments and Joint Ventures [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentsAndJointVenturesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_EquityMethodInvestmentsAndJointVenturesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentsAndJointVenturesAbstract" xlink:to="lab_us-gaap_EquityMethodInvestmentsAndJointVenturesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_IncreaseDecreaseInDeferredCedingCommission_f91ca2b7-dc40-400d-8901-af8a8cd4c39a_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>
    <link:label id="lab_skwd_IncreaseDecreaseInDeferredCedingCommission_label_en-US" xlink:label="lab_skwd_IncreaseDecreaseInDeferredCedingCommission" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Deferred Ceding Commission</link:label>
    <link:label id="lab_skwd_IncreaseDecreaseInDeferredCedingCommission_documentation_en-US" xlink:label="lab_skwd_IncreaseDecreaseInDeferredCedingCommission" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" 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-20241231.xsd#skwd_IncreaseDecreaseInDeferredCedingCommission"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_IncreaseDecreaseInDeferredCedingCommission" xlink:to="lab_skwd_IncreaseDecreaseInDeferredCedingCommission" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ClaimsDevelopmentLineItems_34f2b8b6-c604-4dfb-96fc-4d8b99b7d367_terseLabel_en-US" xlink:label="lab_us-gaap_ClaimsDevelopmentLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Claims Development [Line Items]</link:label>
    <link:label id="lab_us-gaap_ClaimsDevelopmentLineItems_label_en-US" xlink:label="lab_us-gaap_ClaimsDevelopmentLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Claims Development [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ClaimsDevelopmentLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ClaimsDevelopmentLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ClaimsDevelopmentLineItems" xlink:to="lab_us-gaap_ClaimsDevelopmentLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaims1_319c4681-e2a3-41cd-a802-c847469adc53_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/2024/elts/us-gaap-2024.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_ecd_NonPeoNeoAvgCompActuallyPaidAmt_terseLabel_en-US" xlink:label="lab_ecd_NonPeoNeoAvgCompActuallyPaidAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Non-PEO NEO Average Compensation Actually Paid Amount</link:label>
    <link:label id="lab_ecd_NonPeoNeoAvgCompActuallyPaidAmt_label_en-US" xlink:label="lab_ecd_NonPeoNeoAvgCompActuallyPaidAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Non-PEO NEO Average Compensation Actually Paid Amount</link:label>
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    <link:label id="lab_us-gaap_CededCreditRiskReinsurerDomain_771651da-b746-4164-9797-80b127f0469b_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>
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    <link:label id="lab_us-gaap_FundsHeldUnderReinsuranceAgreementsLiability_501bb9a3-295c-4a05-82a2-057174e70ebc_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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FundsHeldUnderReinsuranceAgreementsLiability" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_FundsHeldUnderReinsuranceAgreementsLiability"/>
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    <link:label id="lab_us-gaap_StockholdersEquityNoteDisclosureTextBlock_ac2db93f-fd8b-40be-8a8e-24fdb96991d9_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/2024/elts/us-gaap-2024.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_IncreaseDecreaseInAccountsPayableAndAccruedLiabilities_99262260-5092-4cd5-9a52-364e613215a0_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>
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    <link:label id="lab_ecd_AwardTmgHowMnpiCnsdrdTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AwardTmgHowMnpiCnsdrdTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Timing, How MNPI Considered</link:label>
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    <link:label id="lab_us-gaap_FinancialInstrumentAxis_f7be8f4c-94dc-468e-98d5-40573d032a90_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>
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    <link:label id="lab_us-gaap_RestrictedStockMember_64447bc7-29c3-46b6-b385-929f724c5810_terseLabel_en-US" xlink:label="lab_us-gaap_RestrictedStockMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Restricted Stock</link:label>
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    <link:label id="lab_us-gaap_FairValueByMeasurementBasisAxis_b50c2771-a520-4ce0-a966-6c62f46f692c_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueByMeasurementBasisAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measurement Basis [Axis]</link:label>
    <link:label id="lab_us-gaap_FairValueByMeasurementBasisAxis_label_en-US" xlink:label="lab_us-gaap_FairValueByMeasurementBasisAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measurement Basis [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueByMeasurementBasisAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_FairValueByMeasurementBasisAxis"/>
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    <link:label id="lab_skwd_MortgageLoansMember_de6f3a22-54cb-44c2-9a4e-da570e7dba10_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>
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    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearThree_a7253b61-54c3-4236-a393-9701dfc0ac8f_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>
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    <link:label id="lab_us-gaap_LoansReceivableFairValueDisclosure_4a30f817-0e22-4df7-9c47-6317c942c056_terseLabel_en-US" xlink:label="lab_us-gaap_LoansReceivableFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mortgage loans</link:label>
    <link:label id="lab_us-gaap_LoansReceivableFairValueDisclosure_label_en-US" xlink:label="lab_us-gaap_LoansReceivableFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Loans Receivable, Fair Value Disclosure</link:label>
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    <link:label id="lab_srt_ConsolidatedEntitiesAxis_18cdc51b-ed70-4ef6-89d6-e78cfb34fbef_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>
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    <link:label id="lab_skwd_DeferredTaxAssetsOperatingLossCarryforwardsSubjectToExpirationTaxEffected_be17d0d9-7445-486f-8ce1-ec3a692f5c00_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_us-gaap_OtherLongTermInvestments_f70e3a51-5ca7-469c-be52-6ebafe21b36a_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>
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    <link:label id="lab_skwd_EquityMethodInvestmentDifferenceInNetAssetsAmortizationPeriod_1f3ec139-95c8-4f1f-b6df-66cb7ac97e3d_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_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>
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    <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_EquitySecuritiesFvNiUnrealizedGainLoss_d643342f-a85a-41ff-ba23-ccb3d9504f7e_verboseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGainLoss" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Equity securities</link:label>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGainLoss_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiUnrealizedGainLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Securities, FV-NI, Unrealized Gain (Loss)</link:label>
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    <link:label id="lab_ecd_TrdArrSecuritiesAggAvailAmt_label_en-US" xlink:label="lab_ecd_TrdArrSecuritiesAggAvailAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trading Arrangement, Securities Aggregate Available Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_TrdArrSecuritiesAggAvailAmt" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_TrdArrSecuritiesAggAvailAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_TrdArrSecuritiesAggAvailAmt" xlink:to="lab_ecd_TrdArrSecuritiesAggAvailAmt" xlink:type="arc" order="1"/>
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    <link:loc xlink:type="locator" xlink:label="loc_ecd_EqtyAwrdsAdjsMember" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_EqtyAwrdsAdjsMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_EqtyAwrdsAdjsMember" xlink:to="lab_ecd_EqtyAwrdsAdjsMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OperatingLeaseLiability_3724217e-ebb4-41d2-a013-4bc34e72a55c_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingLeaseLiability" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Operating lease liabilities</link:label>
    <link:label id="lab_us-gaap_OperatingLeaseLiability_label_en-US" xlink:label="lab_us-gaap_OperatingLeaseLiability" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Operating Lease, Liability</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseLiability" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_OperatingLeaseLiability"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OperatingLeaseLiability" xlink:to="lab_us-gaap_OperatingLeaseLiability" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AwardUndrlygSecuritiesAmt_terseLabel_en-US" xlink:label="lab_ecd_AwardUndrlygSecuritiesAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Underlying Securities</link:label>
    <link:label id="lab_ecd_AwardUndrlygSecuritiesAmt_label_en-US" xlink:label="lab_ecd_AwardUndrlygSecuritiesAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Underlying Securities Amount</link:label>
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    <link:label id="lab_us-gaap_PerformanceSharesMember_82f6c44e-b40c-4fc1-9e47-592be3ce66c9_terseLabel_en-US" xlink:label="lab_us-gaap_PerformanceSharesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Performance condition awards</link:label>
    <link:label id="lab_us-gaap_PerformanceSharesMember_label_en-US" xlink:label="lab_us-gaap_PerformanceSharesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Performance Shares [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PerformanceSharesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_PerformanceSharesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PerformanceSharesMember" xlink:to="lab_us-gaap_PerformanceSharesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ShareBasedCompensationArrangementByShareBasedPaymentAwardPurchasePeriod_5fe58000-163e-47dd-af86-b2d9dec6bfdc_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>
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    <link:label id="lab_us-gaap_CarryingReportedAmountFairValueDisclosureMember_09d06189-af62-4225-ba68-0e359c630544_terseLabel_en-US" xlink:label="lab_us-gaap_CarryingReportedAmountFairValueDisclosureMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Carrying Value</link:label>
    <link:label id="lab_us-gaap_CarryingReportedAmountFairValueDisclosureMember_label_en-US" xlink:label="lab_us-gaap_CarryingReportedAmountFairValueDisclosureMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reported Value Measurement [Member]</link:label>
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    <link:label id="lab_skwd_ProceedsFromRepaymentsOfReceivableFromShareholdersOrAffiliatesForIssuanceOfCapitalStock_56c0c37c-a57b-46bf-8cf0-f88a1ab40882_terseLabel_en-US" xlink:label="lab_skwd_ProceedsFromRepaymentsOfReceivableFromShareholdersOrAffiliatesForIssuanceOfCapitalStock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Repayment of stock notes receivable</link:label>
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    <link:label id="lab_us-gaap_SubordinatedDebtMember_48d8dcdd-cb0e-4207-b1d8-91fb15e67039_terseLabel_en-US" xlink:label="lab_us-gaap_SubordinatedDebtMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Subordinated debt, net of debt issuance costs</link:label>
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    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationTable_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationTable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contracts, Historical Claims Duration [Table]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationTable" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationTable"/>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockAppreciationRightsSARSMember" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_StockAppreciationRightsSARSMember"/>
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    <link:label id="lab_skwd_TotalIntangibleAssetsRollForward_7136e3fb-fc1f-4f90-b8a5-0d7537192795_terseLabel_en-US" xlink:label="lab_skwd_TotalIntangibleAssetsRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total</link:label>
    <link:label id="lab_skwd_TotalIntangibleAssetsRollForward_label_en-US" xlink:label="lab_skwd_TotalIntangibleAssetsRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Total Intangible Assets [Roll Forward]</link:label>
    <link:label id="lab_skwd_TotalIntangibleAssetsRollForward_documentation_en-US" xlink:label="lab_skwd_TotalIntangibleAssetsRollForward" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Total Intangible Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_TotalIntangibleAssetsRollForward" xlink:href="skwd-20241231.xsd#skwd_TotalIntangibleAssetsRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_TotalIntangibleAssetsRollForward" xlink:to="lab_skwd_TotalIntangibleAssetsRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SubsequentEventsAbstract_label_en-US" xlink:label="lab_us-gaap_SubsequentEventsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Subsequent Events [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsequentEventsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_SubsequentEventsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsequentEventsAbstract" xlink:to="lab_us-gaap_SubsequentEventsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_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/2024/elts/srt-2024.xsd#srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesAbstract" xlink:to="lab_srt_SummaryOfInvestmentsOtherThanInvestmentsInRelatedPartiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi_61be315a-e6e7-4735-b786-aa314da848fa_verboseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Proceeds from the sales of equity securities</link:label>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfEquitySecuritiesFvNi_e985e72d-b76e-4823-9de3-3478d30592e3_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/2024/elts/us-gaap-2024.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_us-gaap_SaleOfStockNumberOfSharesIssuedInTransaction_a295e2ea-2fdf-4f85-8a2b-4a49b5382530_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/2024/elts/us-gaap-2024.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_DeferredFinanceCostsNet_3d13f00b-e1a0-43a6-af5a-cf2aa32e13ea_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredFinanceCostsNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt issuance costs</link:label>
    <link:label id="lab_us-gaap_DeferredFinanceCostsNet_label_en-US" xlink:label="lab_us-gaap_DeferredFinanceCostsNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Issuance Costs, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredFinanceCostsNet" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_DeferredFinanceCostsNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredFinanceCostsNet" xlink:to="lab_us-gaap_DeferredFinanceCostsNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithinOneYearAmortizedCost_332d8236-5948-4a9e-9431-02ed67fd72fb_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/2024/elts/us-gaap-2024.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_us-gaap_DebtDisclosureTextBlock_47fbd145-54f7-41c6-b160-1a19da74fbd2_verboseLabel_en-US" xlink:label="lab_us-gaap_DebtDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Notes Payable</link:label>
    <link:label id="lab_us-gaap_DebtDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_DebtDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_DebtDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtDisclosureTextBlock" xlink:to="lab_us-gaap_DebtDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CondensedIncomeStatementTable_098e2731-81aa-422e-b897-0f39ca2906b1_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/2024/elts/srt-2024.xsd#srt_CondensedIncomeStatementTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_CondensedIncomeStatementTable" xlink:to="lab_srt_CondensedIncomeStatementTable" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain_1bb6067f-11d8-4005-b732-d2607c9d35ab_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value Hierarchy and NAV [Domain]</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Hierarchy and NAV [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementsFairValueHierarchyDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_FairValueMeasurementsFairValueHierarchyDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementsFairValueHierarchyDomain" xlink:to="lab_us-gaap_FairValueMeasurementsFairValueHierarchyDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_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>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_RecoveryOfErrCompDisclosureLineItems" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_RecoveryOfErrCompDisclosureLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_RecoveryOfErrCompDisclosureLineItems" xlink:to="lab_ecd_RecoveryOfErrCompDisclosureLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentFaceAmount_0b1b1173-f303-4b89-aff3-f90d780ba0a5_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/2024/elts/us-gaap-2024.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_FollowOnOfferingMember_4bd33703-4ecf-4b80-90ae-864e06787d0a_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-20241231.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_srt_CondensedCashFlowStatementsCaptionsLineItems_da9e5c2a-ff7c-4fe4-bcdf-c6f0a4177e9a_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/2024/elts/srt-2024.xsd#srt_CondensedCashFlowStatementsCaptionsLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_CondensedCashFlowStatementsCaptionsLineItems" xlink:to="lab_srt_CondensedCashFlowStatementsCaptionsLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityAddressPostalZipCode_2ebd0c2b-34c3-42c7-84f4-db6e59cdc5da_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/2024/dei-2024.xsd#dei_EntityAddressPostalZipCode"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityAddressPostalZipCode" xlink:to="lab_dei_EntityAddressPostalZipCode" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ScheduleOfSupplementalInformationForPropertyCasualtyInsuranceUnderwritersTextBlock_57460c0f-8abd-4ab9-83b5-4bfce9e0fb26_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>
    <link:loc xlink:type="locator" xlink:label="loc_srt_ScheduleOfSupplementalInformationForPropertyCasualtyInsuranceUnderwritersTextBlock" xlink:href="https://xbrl.fasb.org/srt/2024/elts/srt-2024.xsd#srt_ScheduleOfSupplementalInformationForPropertyCasualtyInsuranceUnderwritersTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ScheduleOfSupplementalInformationForPropertyCasualtyInsuranceUnderwritersTextBlock" xlink:to="lab_srt_ScheduleOfSupplementalInformationForPropertyCasualtyInsuranceUnderwritersTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtInstrumentFixedRatePeriodAxis_63c2421b-f80b-45d9-9566-726570299d3c_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>
    <link:label id="lab_skwd_DebtInstrumentFixedRatePeriodAxis_label_en-US" xlink:label="lab_skwd_DebtInstrumentFixedRatePeriodAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Fixed Rate, Period [Axis]</link:label>
    <link:label id="lab_skwd_DebtInstrumentFixedRatePeriodAxis_documentation_en-US" xlink:label="lab_skwd_DebtInstrumentFixedRatePeriodAxis" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Instrument, Fixed Rate, Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtInstrumentFixedRatePeriodAxis" xlink:href="skwd-20241231.xsd#skwd_DebtInstrumentFixedRatePeriodAxis"/>
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    <link:label id="lab_us-gaap_IncreaseDecreaseInReinsurancePayables_121e01d2-e7d8-4f38-ad84-f29334476827_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/2024/elts/us-gaap-2024.xsd#us-gaap_IncreaseDecreaseInReinsurancePayables"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInReinsurancePayables" xlink:to="lab_us-gaap_IncreaseDecreaseInReinsurancePayables" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersEarnedPremiums_476ba268-a993-4eaa-9f27-f937d5186dd7_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersEarnedPremiums" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net earned premium</link:label>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersEarnedPremiums_label_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersEarnedPremiums" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-18, Supplemental Information, Property-Casualty Insurance Underwriters, Earned Premium</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersEarnedPremiums" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersEarnedPremiums"/>
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    <link:label id="lab_skwd_SuretyMember_3c42cfa4-4f12-4af3-8ba0-339390e8834b_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-20241231.xsd#skwd_SuretyMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_SuretyMember" xlink:to="lab_skwd_SuretyMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_AgentRelationshipMember_19e89143-1f6f-4efa-b2fb-675ca5b9f47b_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>
    <link:label id="lab_skwd_AgentRelationshipMember_label_en-US" xlink:label="lab_skwd_AgentRelationshipMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Agent Relationship [Member]</link:label>
    <link:label id="lab_skwd_AgentRelationshipMember_documentation_en-US" xlink:label="lab_skwd_AgentRelationshipMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Agent Relationship</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_AgentRelationshipMember" xlink:href="skwd-20241231.xsd#skwd_AgentRelationshipMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_AgentRelationshipMember" xlink:to="lab_skwd_AgentRelationshipMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_USGovernmentDebtSecuritiesMember_3cfc6ee8-bd07-444e-9646-ca09394b40ae_terseLabel_en-US" xlink:label="lab_us-gaap_USGovernmentDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">U.S. government securities</link:label>
    <link:label id="lab_us-gaap_USGovernmentDebtSecuritiesMember_label_en-US" xlink:label="lab_us-gaap_USGovernmentDebtSecuritiesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">US Government Debt Securities [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_USGovernmentDebtSecuritiesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_USGovernmentDebtSecuritiesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_USGovernmentDebtSecuritiesMember" xlink:to="lab_us-gaap_USGovernmentDebtSecuritiesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CashAndCashEquivalentsAtCarryingValue_0b212194-b449-4642-98a6-b5585f4fe327_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>
    <link:label id="lab_us-gaap_CashAndCashEquivalentsAtCarryingValue_label_en-US" xlink:label="lab_us-gaap_CashAndCashEquivalentsAtCarryingValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash and Cash Equivalents, at Carrying Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashAndCashEquivalentsAtCarryingValue" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_CashAndCashEquivalentsAtCarryingValue"/>
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    <link:label id="lab_ecd_ChngInFrValOfOutsdngAndUnvstdEqtyAwrdsGrntdInPrrYrsMember_terseLabel_en-US" xlink:label="lab_ecd_ChngInFrValOfOutsdngAndUnvstdEqtyAwrdsGrntdInPrrYrsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Year-over-Year Change in Fair Value of Equity Awards Granted in Prior Years That are Outstanding and Unvested</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_ecd_ChngInFrValOfOutsdngAndUnvstdEqtyAwrdsGrntdInPrrYrsMember" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_ChngInFrValOfOutsdngAndUnvstdEqtyAwrdsGrntdInPrrYrsMember"/>
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    <link:label id="lab_dei_AuditorName_1d51ddd6-283b-42f4-b347-a863ca55bf27_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/2024/dei-2024.xsd#dei_AuditorName"/>
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    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeituresWeightedAverageGrantDateFairValue_904c393d-a61b-423d-9530-98e8d12d42b0_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsForfeituresWeightedAverageGrantDateFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Forfeited (in dollars per share)</link:label>
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    <link:label id="lab_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember_terseLabel_en-US" xlink:label="lab_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Year-end Fair Value of Equity Awards Granted in Covered Year that are Outstanding and Unvested</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_YrEndFrValOfEqtyAwrdsGrntdInCvrdYrOutsdngAndUnvstdMember"/>
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    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestBeforeAllowanceForCreditLoss_d174b54f-c37c-45fe-905d-f32b669c3868_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">Amortized Cost</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestBeforeAllowanceForCreditLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_DebtSecuritiesHeldToMaturityExcludingAccruedInterestBeforeAllowanceForCreditLoss"/>
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    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentUsefulLife_4c96c3ad-3ede-4593-ae73-d0407cadaaab_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>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentUsefulLife_label_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentUsefulLife" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Property, Plant and Equipment, Useful Life</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentUsefulLife" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_PropertyPlantAndEquipmentUsefulLife"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentUsefulLife" xlink:to="lab_us-gaap_PropertyPlantAndEquipmentUsefulLife" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingRollForward_8a2b4a1d-ed93-461a-aa41-7f90883345c1_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stock</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingRollForward_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingRollForward" 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 [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingRollForward"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingRollForward" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsOutstandingRollForward" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EmployeeStockMember_43e68645-05c6-4419-995d-a67d535103ed_terseLabel_en-US" xlink:label="lab_us-gaap_EmployeeStockMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Employee Stock</link:label>
    <link:label id="lab_us-gaap_EmployeeStockMember_label_en-US" xlink:label="lab_us-gaap_EmployeeStockMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Employee Stock [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EmployeeStockMember" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_EmployeeStockMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EmployeeStockMember" xlink:to="lab_us-gaap_EmployeeStockMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueDisclosureItemAmountsDomain_69aee5cd-fa0b-4976-8556-a708c793858d_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueDisclosureItemAmountsDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value Measurement [Domain]</link:label>
    <link:label id="lab_us-gaap_FairValueDisclosureItemAmountsDomain_label_en-US" xlink:label="lab_us-gaap_FairValueDisclosureItemAmountsDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Measurement [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueDisclosureItemAmountsDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_FairValueDisclosureItemAmountsDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueDisclosureItemAmountsDomain" xlink:to="lab_us-gaap_FairValueDisclosureItemAmountsDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis_e0eb669e-24a1-4e50-94df-139e86a20c86_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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.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_ProceedsFromStockPlans_174d13ce-aae9-4ca8-a61b-8865489791c7_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>
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    <link:label id="lab_skwd_RelatedPartyOwnershipInterest_6788fc27-f019-4787-ae9f-663f83e11cb9_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>
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    <link:loc xlink:type="locator" xlink:label="loc_skwd_RelatedPartyOwnershipInterest" xlink:href="skwd-20241231.xsd#skwd_RelatedPartyOwnershipInterest"/>
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    <link:label id="lab_us-gaap_DeferredTaxAssetsTaxDeferredExpenseReservesAndAccrualsUnearnedPremiumsReserve_7adca687-10d2-4bb3-a759-c28d05c31f0e_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsTaxDeferredExpenseReservesAndAccrualsUnearnedPremiumsReserve" 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_NetIncomeLossAvailableToCommonStockholdersBasic_6be36c93-e40e-49f7-8c16-e4917f88bbf0_verboseLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Net loss before equity in earnings of subsidiaries</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic"/>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock_b0acef02-7699-4cfd-bb91-3f05ad6136dc_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Unrealized Loss Position, Fair Value</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionFairValueTableTextBlock"/>
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    <link:label id="lab_skwd_RealizedInvestmentLosses_documentation_en-US" xlink:label="lab_skwd_RealizedInvestmentLosses" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Realized Investment Losses</link:label>
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    <link:label id="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2024Member_cc0a4360-e3fb-45c7-aafe-5fd4c7d9ffca_terseLabel_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2024Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accident Year 2024</link:label>
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    <link:label id="lab_us-gaap_Assets_1b992458-e035-4058-bdbf-479fbb865acb_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:label id="lab_skwd_DebtInstrumentFixedInterestRatePeriodTwoMember_b4c86d83-fed7-4718-b548-384cbb39a9f9_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_skwd_TransactionalESMember_68569496-c79a-479d-94c3-d952f109abc6_terseLabel_en-US" xlink:label="lab_skwd_TransactionalESMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Transactional E&amp;S</link:label>
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    <link:label id="lab_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment_84559122-811f-4aa3-ac2b-4d56b1929477_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>
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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:label id="lab_srt_CumulativeEffectPeriodOfAdoptionAxis_58340850-a0a5-4187-a268-28c206b8a865_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:label id="lab_us-gaap_ShareBasedCompensationOptionAndIncentivePlansPolicy_7b71e316-8ced-43ca-b203-017c89f12384_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>
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    <link:label id="lab_skwd_FixedMaturitiesAvailableForSaleMember_1f0f66d3-6c6a-40d1-b240-896a3afc088f_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_skwd_FixedMaturitiesAvailableForSaleMember_documentation_en-US" xlink:label="lab_skwd_FixedMaturitiesAvailableForSaleMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Fixed Maturities, Available-For-Sale</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_FixedMaturitiesAvailableForSaleMember" xlink:href="skwd-20241231.xsd#skwd_FixedMaturitiesAvailableForSaleMember"/>
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    <link:label id="lab_us-gaap_ScheduleOfRelatedPartyTransactionsByRelatedPartyTable_7f146b6e-6d67-4bc3-9959-e98f0595f9e0_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfRelatedPartyTransactionsByRelatedPartyTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Related Party Transactions, by Related Party [Table]</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfRelatedPartyTransactionsByRelatedPartyTable" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ScheduleOfRelatedPartyTransactionsByRelatedPartyTable"/>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_FairValueAssetsAndLiabilitiesMeasuredOnRecurringAndNonrecurringBasisLineItems"/>
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    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearTwo_1829fd3d-54ca-4bdb-9825-012af9709fd7_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">2026</link:label>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearTwo_label_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearTwo" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Lessee, Operating Lease, Liability, to be Paid, Year Two</link:label>
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    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAbstract_b8f7bfb9-e30f-492a-9a23-cbecb859c9c8_terseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Held-to-maturity, fair value</link:label>
    <link:label id="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAbstract_label_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Continuous Unrealized Loss Position [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionAbstract"/>
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    <link:label id="lab_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest_9116853b-b4f4-4271-b238-2341130f4443_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_90d78d2d-a10a-41bf-be4c-873730e89e74_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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_DebtSecuritiesHeldToMaturityAllowanceForCreditLossExcludingAccruedInterest"/>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsFairValue_e06b13a0-9de6-48ba-a77f-af8c9147fbcd_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>
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    <link:label id="lab_skwd_CaptivesMember_175c1120-2103-480c-ad0d-452d8bfeb9ca_terseLabel_en-US" xlink:label="lab_skwd_CaptivesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Captives</link:label>
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    <link:label id="lab_us-gaap_DebtInstrumentAxis_1d6f6a50-c47c-4a19-8863-7295ca371c83_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Instrument [Axis]</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_DebtInstrumentAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentAxis" xlink:to="lab_us-gaap_DebtInstrumentAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ReinsuranceRecoverableForLossPortfolioTransfer_e81a7af6-3b73-4d6a-ab06-608ee1be0e49_terseLabel_en-US" xlink:label="lab_skwd_ReinsuranceRecoverableForLossPortfolioTransfer" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Loss portfolio transfer</link:label>
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    <link:label id="lab_skwd_ShortTailMonolineSpecialtyMember_fb2ec934-7796-4b26-98ac-49c05a5c47aa_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 Lines</link:label>
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    <link:label id="lab_us-gaap_ReinsurancePayable_4f459c1e-eece-4d66-a5a4-737717e8e051_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>
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    <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) Attributable to Parent</link:label>
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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>
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    <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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingGain" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingGain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingGain" xlink:to="lab_us-gaap_HeldToMaturitySecuritiesAccumulatedUnrecognizedHoldingGain" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_StockNotesMember_1f45f89f-3187-4467-b94d-2acae0015538_terseLabel_en-US" xlink:label="lab_skwd_StockNotesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stock Notes</link:label>
    <link:label id="lab_skwd_StockNotesMember_label_en-US" xlink:label="lab_skwd_StockNotesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Stock Notes [Member]</link:label>
    <link:label id="lab_skwd_StockNotesMember_documentation_en-US" xlink:label="lab_skwd_StockNotesMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Stock Notes</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_StockNotesMember" xlink:href="skwd-20241231.xsd#skwd_StockNotesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_StockNotesMember" xlink:to="lab_skwd_StockNotesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember_terseLabel_en-US" xlink:label="lab_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Awards Adjustments, Excluding Value Reported in Compensation Table</link:label>
    <link:label id="lab_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember_label_en-US" xlink:label="lab_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Awards Adjustments, Excluding Value Reported in the Compensation Table [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember" xlink:to="lab_ecd_EqtyAwrdsAdjsExclgValRprtdInSummryCompstnTblMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost_b8fcb607-8d56-4401-a6e4-4dd5d2a564c8_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/2024/elts/us-gaap-2024.xsd#us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost" xlink:to="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterTenYearsAmortizedCost" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract_503e8c12-56fb-4f42-a590-b89d09dbe7d4_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity securities, available-for-sale:</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Fair Value to Amortized Cost, after Allowance for Credit Loss [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleSecuritiesFairValueToAmortizedCostBasisAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.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_BenefitsLossesAndExpenses_9e2591b9-db65-4b2f-bf8e-7401f32b4583_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_124e2264-b3c3-4135-8c0e-79321675140f_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>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_BenefitsLossesAndExpenses" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_BenefitsLossesAndExpenses"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_BenefitsLossesAndExpenses" xlink:to="lab_us-gaap_BenefitsLossesAndExpenses" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_BookValuePerShare_1cff1e90-ec11-4ec1-908c-c025eac9b78c_terseLabel_en-US" xlink:label="lab_skwd_BookValuePerShare" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Book value per share (in dollars per share)</link:label>
    <link:label id="lab_skwd_BookValuePerShare_label_en-US" xlink:label="lab_skwd_BookValuePerShare" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Book Value, Per Share</link:label>
    <link:label id="lab_skwd_BookValuePerShare_documentation_en-US" xlink:label="lab_skwd_BookValuePerShare" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Book Value, Per Share</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_BookValuePerShare" xlink:href="skwd-20241231.xsd#skwd_BookValuePerShare"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_BookValuePerShare" xlink:to="lab_skwd_BookValuePerShare" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityFileNumber_cdd96b63-c402-4b8d-a5ea-655038b8b79a_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>
    <link:label id="lab_dei_EntityFileNumber_label_en-US" xlink:label="lab_dei_EntityFileNumber" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity File Number</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityFileNumber" xlink:href="https://xbrl.sec.gov/dei/2024/dei-2024.xsd#dei_EntityFileNumber"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityFileNumber" xlink:to="lab_dei_EntityFileNumber" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ConsolidatedEntitiesDomain_03c2200e-c1a5-4f86-a7e6-48b1abf54a40_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/2024/elts/srt-2024.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_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/2024/elts/us-gaap-2024.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_dei_EntityAddressAddressLine1_7101a105-e18c-4bda-b2b0-5720b443aa85_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/2024/dei-2024.xsd#dei_EntityAddressAddressLine1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityAddressAddressLine1" xlink:to="lab_dei_EntityAddressAddressLine1" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ExitedLinesMember_584834ab-3704-4042-8408-67dd93b16465_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-20241231.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_de5d868e-29bc-4a2c-9787-7f62b0d90a0e_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-20241231.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_dei_EntityAddressAddressLine2_a0070894-840c-4058-976f-dad0a44fdb95_terseLabel_en-US" xlink:label="lab_dei_EntityAddressAddressLine2" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Address, Address Line Two</link:label>
    <link:label id="lab_dei_EntityAddressAddressLine2_label_en-US" xlink:label="lab_dei_EntityAddressAddressLine2" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Address, Address Line Two</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityAddressAddressLine2" xlink:href="https://xbrl.sec.gov/dei/2024/dei-2024.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_ecd_ForgoneRecoveryIndName_terseLabel_en-US" xlink:label="lab_ecd_ForgoneRecoveryIndName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Name</link:label>
    <link:label id="lab_ecd_ForgoneRecoveryIndName_label_en-US" xlink:label="lab_ecd_ForgoneRecoveryIndName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Forgone Recovery, Individual Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_ForgoneRecoveryIndName" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_ForgoneRecoveryIndName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_ForgoneRecoveryIndName" xlink:to="lab_ecd_ForgoneRecoveryIndName" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_OperatingLeaseWeightedAverageRemainingLeaseTerm1_1fb766d4-8680-490e-a5f5-124a855510da_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingLeaseWeightedAverageRemainingLeaseTerm1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Operating lease weighted-average remaining lease term</link:label>
    <link:label id="lab_us-gaap_OperatingLeaseWeightedAverageRemainingLeaseTerm1_label_en-US" xlink:label="lab_us-gaap_OperatingLeaseWeightedAverageRemainingLeaseTerm1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Operating Lease, Weighted Average Remaining Lease Term</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseWeightedAverageRemainingLeaseTerm1" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_OperatingLeaseWeightedAverageRemainingLeaseTerm1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OperatingLeaseWeightedAverageRemainingLeaseTerm1" xlink:to="lab_us-gaap_OperatingLeaseWeightedAverageRemainingLeaseTerm1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInDeferredIncomeTaxes_3642da42-3bb5-4b6b-ba34-2d27a2eb6442_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInDeferredIncomeTaxes" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Federal income taxes</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInDeferredIncomeTaxes_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInDeferredIncomeTaxes" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Deferred Income Taxes</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInDeferredIncomeTaxes" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_IncreaseDecreaseInDeferredIncomeTaxes"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInDeferredIncomeTaxes" xlink:to="lab_us-gaap_IncreaseDecreaseInDeferredIncomeTaxes" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentPolicyTextBlock_fb607346-5ff2-47c3-8625-0634ea90f3dd_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/2024/elts/us-gaap-2024.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_ecd_AwardTmgMnpiCnsdrdFlag_terseLabel_en-US" xlink:label="lab_ecd_AwardTmgMnpiCnsdrdFlag" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Award Timing MNPI Considered</link:label>
    <link:label id="lab_ecd_AwardTmgMnpiCnsdrdFlag_label_en-US" xlink:label="lab_ecd_AwardTmgMnpiCnsdrdFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Award Timing MNPI Considered [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AwardTmgMnpiCnsdrdFlag" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_AwardTmgMnpiCnsdrdFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AwardTmgMnpiCnsdrdFlag" xlink:to="lab_ecd_AwardTmgMnpiCnsdrdFlag" xlink:type="arc" order="1"/>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateFairValue_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesWithoutSingleMaturityDateFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Maturity, without Single Maturity Date, Fair Value</link:label>
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    <link:label id="lab_us-gaap_ComponentsOfDeferredTaxLiabilitiesAbstract_0dea7aa1-0932-4e0b-b78d-36d5328b1056_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/2024/elts/us-gaap-2024.xsd#us-gaap_ComponentsOfDeferredTaxLiabilitiesAbstract"/>
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    <link:label id="lab_us-gaap_ReinsuranceRecoverableCreditLossExpenseReversal_b2386052-d2cb-4f24-9871-981e9f968230_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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverableCreditLossExpenseReversal" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ReinsuranceRecoverableCreditLossExpenseReversal"/>
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    <link:label id="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccountsRollForward_7b4ea2a7-a01a-4d73-8ba6-17762ecae5e4_terseLabel_en-US" xlink:label="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccountsRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Premium Receivable, Allowance for Credit Loss [Roll Forward]</link:label>
    <link:label id="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccountsRollForward_label_en-US" xlink:label="lab_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccountsRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Premium Receivable, Allowance for Credit Loss [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PremiumsReceivableAllowanceForDoubtfulAccountsRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_PremiumsReceivableAllowanceForDoubtfulAccountsRollForward"/>
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    <link:label id="lab_us-gaap_EquitySecuritiesFvNiRealizedGain_36f151dc-2974-4c41-9a93-ab382c11e7d3_terseLabel_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiRealizedGain" 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_EquitySecuritiesFvNiRealizedGain_label_en-US" xlink:label="lab_us-gaap_EquitySecuritiesFvNiRealizedGain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Securities, FV-NI, Realized Gain</link:label>
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    <link:label id="lab_skwd_DeferredTaxLiabilitiesUnrealizedGainsOnEquitySecurities_98ba8a1e-f8bb-4bd5-a108-862049618c79_terseLabel_en-US" xlink:label="lab_skwd_DeferredTaxLiabilitiesUnrealizedGainsOnEquitySecurities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Unrealized gains on equity securities</link:label>
    <link:label id="lab_skwd_DeferredTaxLiabilitiesUnrealizedGainsOnEquitySecurities_label_en-US" xlink:label="lab_skwd_DeferredTaxLiabilitiesUnrealizedGainsOnEquitySecurities" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Tax Liabilities, Unrealized Gains on Equity Securities</link:label>
    <link:label id="lab_skwd_DeferredTaxLiabilitiesUnrealizedGainsOnEquitySecurities_documentation_en-US" xlink:label="lab_skwd_DeferredTaxLiabilitiesUnrealizedGainsOnEquitySecurities" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Deferred Tax Liabilities, Unrealized Gains on Equity Securities</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DeferredTaxLiabilitiesUnrealizedGainsOnEquitySecurities" xlink:to="lab_skwd_DeferredTaxLiabilitiesUnrealizedGainsOnEquitySecurities" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ContractWithCustomerAssetNet_2de1da00-3370-45bd-ba82-99ef2ce0cfd6_terseLabel_en-US" xlink:label="lab_us-gaap_ContractWithCustomerAssetNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Contract asset after allowance for credit loss</link:label>
    <link:label id="lab_us-gaap_ContractWithCustomerAssetNet_label_en-US" xlink:label="lab_us-gaap_ContractWithCustomerAssetNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Contract with Customer, Asset, after Allowance for Credit Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ContractWithCustomerAssetNet" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.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_ShortdurationInsuranceContractsHistoricalClaimsDurationYearTwo_dcffaeb4-b5e1-4bcb-808f-913a3431e086_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearTwo" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Year 2</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearTwo_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearTwo" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contracts, Historical Claims Duration, Year Two</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearTwo" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearTwo"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearTwo" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearTwo" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_OutstandingAggtErrCompAmt_terseLabel_en-US" xlink:label="lab_ecd_OutstandingAggtErrCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Outstanding Aggregate Erroneous Compensation Amount</link:label>
    <link:label id="lab_ecd_OutstandingAggtErrCompAmt_label_en-US" xlink:label="lab_ecd_OutstandingAggtErrCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Outstanding Aggregate Erroneous Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_OutstandingAggtErrCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_OutstandingAggtErrCompAmt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_OutstandingAggtErrCompAmt" xlink:to="lab_ecd_OutstandingAggtErrCompAmt" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_SECSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersDeferredCedingCommission_09063e46-9496-44d9-a463-1f67a5aa376f_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>
    <link:label id="lab_skwd_SECSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersDeferredCedingCommission_label_en-US" xlink:label="lab_skwd_SECSchedule1218SupplementalInformationPropertyCasualtyInsuranceUnderwritersDeferredCedingCommission" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-18, Supplemental Information, Property-Casualty Insurance Underwriters, Deferred Ceding Commission</link:label>
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    <link:label id="lab_ecd_PeoActuallyPaidCompAmt_terseLabel_en-US" xlink:label="lab_ecd_PeoActuallyPaidCompAmt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">PEO Actually Paid Compensation Amount</link:label>
    <link:label id="lab_ecd_PeoActuallyPaidCompAmt_label_en-US" xlink:label="lab_ecd_PeoActuallyPaidCompAmt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">PEO Actually Paid Compensation Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeoActuallyPaidCompAmt" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_PeoActuallyPaidCompAmt"/>
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    <link:label id="lab_us-gaap_ShortDurationInsuranceContractsAccidentYear2018Member_7f215c56-5597-49ce-a479-c4c01803fb0e_terseLabel_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractsAccidentYear2018Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accident Year 2018</link:label>
    <link:label id="lab_us-gaap_ShortDurationInsuranceContractsAccidentYear2018Member_label_en-US" xlink:label="lab_us-gaap_ShortDurationInsuranceContractsAccidentYear2018Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contracts, Accident Year 2018 [Member]</link:label>
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    <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>
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    <link:loc xlink:type="locator" xlink:label="loc_ecd_AdjToCompAxis" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_AdjToCompAxis"/>
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    <link:label id="lab_us-gaap_ReinsuranceLossOnUncollectibleAccountsInPeriodAmount_b0f2b7cc-50bd-481f-952a-e078c92ef022_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceLossOnUncollectibleAccountsInPeriodAmount" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Write-offs of uncollectible reinsurance recoverables</link:label>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterOneThroughFiveYearsAmortizedCost_a3e37bf7-d76e-4ce2-b61e-5173a9bb092f_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:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax_ef81d194-abf8-4867-af5e-00d0d829bd91_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>
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    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases_f40ed3b5-2a9e-4a18-ac28-2158faff3007_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetPurchases" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Purchases</link:label>
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    <link:label id="lab_us-gaap_PropertyLiabilityAndCasualtyInsuranceSegmentMember_12654ad1-0e80-4c32-9453-1737c67ab942_terseLabel_en-US" xlink:label="lab_us-gaap_PropertyLiabilityAndCasualtyInsuranceSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Property &amp; Casualty</link:label>
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    <link:label id="lab_us-gaap_LeaseCostTableTextBlock_38135869-4b46-4266-8798-d817eeedcb14_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>
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    <link:label id="lab_us-gaap_ReinsurerConcentrationRiskMember_e3ff21ae-073e-400a-92ff-aa4bcde6b3cc_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>
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    <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_CommissionsPolicy_d64c9a55-f551-4936-b168-6cbb9c6b351f_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_srt_DirectorMember_d7ff5a3f-0080-4ad7-b2b9-69b16c64199e_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>
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    <link:label id="lab_skwd_CashAndCashEquivalentsAndOtherAssetsMember_8af11b3c-4d2a-4a5b-9c7a-c58cae9c0960_terseLabel_en-US" xlink:label="lab_skwd_CashAndCashEquivalentsAndOtherAssetsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cash and Cash Equivalents and Other Assets</link:label>
    <link:label id="lab_skwd_CashAndCashEquivalentsAndOtherAssetsMember_label_en-US" xlink:label="lab_skwd_CashAndCashEquivalentsAndOtherAssetsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cash and Cash Equivalents and Other Assets [Member]</link:label>
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    <link:label id="lab_skwd_RestrictedStockAwardsAndUnitsMember_8b49f540-2e18-4290-93ad-4a0f2950796a_terseLabel_en-US" xlink:label="lab_skwd_RestrictedStockAwardsAndUnitsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Restricted Stock Awards And Units</link:label>
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    <link:label id="lab_skwd_RestrictedStockAwardsAndUnitsMember_documentation_en-US" xlink:label="lab_skwd_RestrictedStockAwardsAndUnitsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Restricted Stock Awards And Units</link:label>
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    <link:label id="lab_us-gaap_MutualFundMember_aaa57fee-8ff4-4538-b114-d421ed320b30_terseLabel_en-US" xlink:label="lab_us-gaap_MutualFundMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Mutual funds:</link:label>
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    <link:label id="lab_us-gaap_MutualFundMember_label_en-US" xlink:label="lab_us-gaap_MutualFundMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Mutual Fund [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MutualFundMember" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_MutualFundMember"/>
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    <link:label id="lab_us-gaap_EquitySecuritiesFvNiRealizedLoss_279fbb11-03cc-497c-bc21-1db0bc5d7b1c_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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquitySecuritiesFvNiRealizedLoss" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_EquitySecuritiesFvNiRealizedLoss"/>
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    <link:label id="lab_us-gaap_SegmentReportingInformationLineItems_dcb44949-e2d8-48fe-a8b8-385600b285a7_terseLabel_en-US" xlink:label="lab_us-gaap_SegmentReportingInformationLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Segment Reporting Information [Line Items]</link:label>
    <link:label id="lab_us-gaap_SegmentReportingInformationLineItems_label_en-US" xlink:label="lab_us-gaap_SegmentReportingInformationLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segment Reporting Information [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SegmentReportingInformationLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_SegmentReportingInformationLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SegmentReportingInformationLineItems" xlink:to="lab_us-gaap_SegmentReportingInformationLineItems" xlink:type="arc" order="1"/>
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    <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>
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    <link:label id="lab_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock_5268e20b-882c-47c0-a581-2f7492cf72ee_terseLabel_en-US" xlink:label="lab_us-gaap_ScheduleOfEarningsPerShareBasicAndDilutedTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Schedule of Earnings Per Share, Basic and Diluted</link:label>
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    <link:label id="lab_us-gaap_ShortDurationInsuranceContractsAccidentYear2017Member_a60701fd-fe69-49b2-8111-bc6e3200cd12_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>
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    <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>
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    <link:label id="lab_us-gaap_IncomeTaxesPaidNet_94fcb02d-2d1a-4b62-93f7-1a213f7fa09b_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>
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    <link:label id="lab_us-gaap_SecuritiesHeldAsCollateralAtFairValue_eae73705-568c-4d7f-b60d-9434be1e500f_terseLabel_en-US" xlink:label="lab_us-gaap_SecuritiesHeldAsCollateralAtFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Securities held as collateral, at fair value</link:label>
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    <link:label id="lab_us-gaap_ResidentialMortgageBackedSecuritiesMember_6f5e5b88-b498-47b0-ad8e-7b7ae801d486_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_AllowanceForReinsuranceRecoverableMember_857a976e-7a69-4c6a-82c9-51d5c7fc6c12_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>
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    <link:label id="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill_9ebae8d2-daaf-44e5-9e6c-0abc5b671cce_terseLabel_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetIncludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Goodwill and intangible assets, net</link:label>
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    <link:label id="lab_skwd_IndirectLoansAndLoanCollateralMember_f11ee58a-1838-4567-a724-49d60d7d6cb9_verboseLabel_en-US" xlink:label="lab_skwd_IndirectLoansAndLoanCollateralMember" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Indirect loans</link:label>
    <link:label id="lab_skwd_IndirectLoansAndLoanCollateralMember_863375b0-ab3c-4142-bb30-2efbef8d59f6_terseLabel_en-US" xlink:label="lab_skwd_IndirectLoansAndLoanCollateralMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment in indirect loans and loan collateral</link:label>
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    <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>
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    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearThree_e796c819-7d4d-48ef-867a-3597d0b5ba61_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearThree" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">2027</link:label>
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    <link:label id="lab_us-gaap_LesseeOperatingLeasesTextBlock_03a46d13-c999-42ad-a0c9-9b853a934282_terseLabel_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeasesTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Leases</link:label>
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    <link:label id="lab_us-gaap_OperatingLeaseCost_8f6e5540-ec5f-4242-b1c4-d25a7b894421_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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetValue"/>
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    <link:label id="lab_us-gaap_DirectPremiumsEarned_3c051dff-e145-4dc1-98ce-a3238abe0425_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>
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    <link:label id="lab_us-gaap_InvestmentTypeCategorizationMember_a396e1f6-412f-4f0f-9b22-fcd334aee050_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/2024/elts/us-gaap-2024.xsd#us-gaap_InvestmentTypeCategorizationMember"/>
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    <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>
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    <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/2024/elts/us-gaap-2024.xsd#us-gaap_CreditLossAbstract"/>
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    <link:label id="lab_us-gaap_ValuationAllowancesAndReservesRecoveries_6a80a650-ae78-4cc0-a03c-5203a690327f_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_ProceedsFromMaturitiesPrepaymentsAndCallsOfAvailableForSaleSecurities_8429c237-8f3d-483b-a31c-9ed274c5b0a0_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfAvailableForSaleSecurities" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Maturities, calls, transfers and paydowns of fixed maturity securities, available-for-sale</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfAvailableForSaleSecurities" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ProceedsFromMaturitiesPrepaymentsAndCallsOfAvailableForSaleSecurities"/>
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    <link:label id="lab_us-gaap_DeferredTaxAssetsLiabilitiesNet_dbbcd21b-ccfe-4e79-af86-a3658260ebd2_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/2024/elts/us-gaap-2024.xsd#us-gaap_DeferredTaxAssetsLiabilitiesNet"/>
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    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFive_e00a4a93-61b2-4361-8efb-da00380dec5c_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">2029</link:label>
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    <link:label id="lab_ecd_EqtyAwrdsInSummryCompstnTblForAplblYrMember_terseLabel_en-US" xlink:label="lab_ecd_EqtyAwrdsInSummryCompstnTblForAplblYrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aggregate Grant Date Fair Value of Equity Award Amounts Reported in Summary Compensation Table</link:label>
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    <link:label id="lab_us-gaap_LesseeLeaseDescriptionLineItems_03b57038-3c8e-4079-957e-b1bd417ffd85_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>
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    <link:label id="lab_us-gaap_IncomeLossFromContinuingOperations_4c038c13-f0a8-44d0-afd2-6e16efe8be8f_terseLabel_en-US" xlink:label="lab_us-gaap_IncomeLossFromContinuingOperations" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net income</link:label>
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    <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>
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    <link:label id="lab_us-gaap_ShortTermLeaseCost_98c513d6-6aaf-4379-9897-64bfab6654fb_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>
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    <link:label id="lab_us-gaap_RealizedInvestmentGainsLosses_014f7351-a132-4a53-9d31-d70ceca8bff2_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_RealizedInvestmentGainsLosses" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Net investment (gains) losses</link:label>
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    <link:label id="lab_us-gaap_PrepaidReinsurancePremiums_label_en-US" xlink:label="lab_us-gaap_PrepaidReinsurancePremiums" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Prepaid Reinsurance Premiums</link:label>
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    <link:label id="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales_1dcfac4d-eea6-4907-b3ad-8ef65dbabde9_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementWithUnobservableInputsReconciliationRecurringBasisAssetSales" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Sales/Disposals</link:label>
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    <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>
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    <link:label id="lab_us-gaap_LineOfCreditFacilityMaximumBorrowingCapacity_704e8c8d-d0eb-404d-8fd5-7c7d0ecfb086_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>
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    <link:label id="lab_us-gaap_AllowanceForUncollectiblePremiumsReceivableMember_cc92a1bb-70ee-454d-b17f-df78e3d99757_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>
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    <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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedDepreciationDepletionAndAmortizationPropertyPlantAndEquipment" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_AccumulatedDepreciationDepletionAndAmortizationPropertyPlantAndEquipment"/>
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    <link:label id="lab_us-gaap_IndefiniteLivedIntangibleAssetsRollForward_7eda2fb3-924f-4d16-97ba-5c4b3ef1d1b7_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_us-gaap_CommonStockSharesAuthorized_36682b5d-362e-420e-bc2f-67dd37a6a025_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockSharesAuthorized" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Common stock, shares authorized (in shares)</link:label>
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    <link:label id="lab_skwd_MortgageLoansNotProducingIncomeAmount_1a51bdd8-8b63-476b-a5dc-cdf29d28f6af_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>
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    <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>
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    <link:label id="lab_us-gaap_InsuranceAbstract_label_en-US" xlink:label="lab_us-gaap_InsuranceAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insurance [Abstract]</link:label>
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    <link:label id="lab_us-gaap_LongtermDebtTypeAxis_1fa517b0-bd66-459a-b26b-16ef08e5482f_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_us-gaap_RelatedPartyMember_c5d2d9dc-781a-4093-9080-51e8522899f8_terseLabel_en-US" xlink:label="lab_us-gaap_RelatedPartyMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Related Party</link:label>
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    <link:label id="lab_us-gaap_IncrementalCommonSharesAttributableToContingentlyIssuableShares_4b757996-97ed-48d4-9ab0-cb28c3098a36_verboseLabel_en-US" xlink:label="lab_us-gaap_IncrementalCommonSharesAttributableToContingentlyIssuableShares" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Diluted effect of stock notes (in shares)</link:label>
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    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossNetOfTaxPortionAttributableToParent_64704b99-3636-4037-8dbc-0aa93aee2daa_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_skwd_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsNet_6c4b6f1e-231d-4765-af41-794a21c25322_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>
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    <link:label id="lab_us-gaap_SubordinatedDebt_455de0bc-eead-4141-8d71-6327266913d7_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>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger_57a93147-ead8-4812-8015-4fdec149f6d8_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/2024/elts/us-gaap-2024.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger"/>
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    <link:label id="lab_ecd_PnsnAdjsPrrSvcCstMember_terseLabel_en-US" xlink:label="lab_ecd_PnsnAdjsPrrSvcCstMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Pension Adjustments Prior Service Cost</link:label>
    <link:label id="lab_ecd_PnsnAdjsPrrSvcCstMember_label_en-US" xlink:label="lab_ecd_PnsnAdjsPrrSvcCstMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Pension Adjustments Prior Service Cost [Member]</link:label>
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    <link:label id="lab_us-gaap_OperatingLeaseLiabilityStatementOfFinancialPositionExtensibleList_afee57a7-b125-410a-8cc9-8de1054e49b2_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>
    <link:label id="lab_us-gaap_OperatingLeaseLiabilityStatementOfFinancialPositionExtensibleList_label_en-US" xlink:label="lab_us-gaap_OperatingLeaseLiabilityStatementOfFinancialPositionExtensibleList" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Operating Lease, Liability, Statement of Financial Position [Extensible Enumeration]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseLiabilityStatementOfFinancialPositionExtensibleList" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_OperatingLeaseLiabilityStatementOfFinancialPositionExtensibleList"/>
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    <link:label id="lab_skwd_ReportableSegmentMember_ca573a01-ab59-4e46-931e-46e5be818c9e_terseLabel_en-US" xlink:label="lab_skwd_ReportableSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reportable Segment</link:label>
    <link:label id="lab_skwd_ReportableSegmentMember_label_en-US" xlink:label="lab_skwd_ReportableSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reportable Segment [Member]</link:label>
    <link:label id="lab_skwd_ReportableSegmentMember_documentation_en-US" xlink:label="lab_skwd_ReportableSegmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Reportable Segment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ReportableSegmentMember" xlink:href="skwd-20241231.xsd#skwd_ReportableSegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ReportableSegmentMember" xlink:to="lab_skwd_ReportableSegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable_b5f2b673-c0f6-4ef1-989e-3156b0009b04_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/2024/elts/us-gaap-2024.xsd#us-gaap_ScheduleOfInvestmentIncomeReportedAmountsByCategoryTable"/>
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    <link:label id="lab_us-gaap_InvestmentIncomeInvestmentExpense_bea20475-6d59-4525-8a1d-f88d3ca9eb81_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_InvestmentIncomeInvestmentExpense" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Investment expenses</link:label>
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    <link:label id="lab_us-gaap_InvestmentsInAffiliatesSubsidiariesAssociatesAndJointVentures_e1636c88-92bb-40ff-a8d5-896304af8155_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_AmortizationOfIntangibleAssets_6467911b-1378-42e3-8c31-9a01ce50b1aa_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_851d9ae1-b133-4c50-b5af-7d0ceb3ada2c_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/2024/elts/us-gaap-2024.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_skwd_CreditLossLineItems_1ca43aac-b75d-456d-8219-10d3418f9251_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-20241231.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_MovementInValuationAllowancesAndReservesRollForward_2d9d5caf-e172-4671-840f-e9edcede8612_terseLabel_en-US" xlink:label="lab_us-gaap_MovementInValuationAllowancesAndReservesRollForward" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-09, Movement in Valuation Allowances and Reserves [Roll Forward]</link:label>
    <link:label id="lab_us-gaap_MovementInValuationAllowancesAndReservesRollForward_label_en-US" xlink:label="lab_us-gaap_MovementInValuationAllowancesAndReservesRollForward" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-09, Movement in Valuation Allowances and Reserves [Roll Forward]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MovementInValuationAllowancesAndReservesRollForward" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_MovementInValuationAllowancesAndReservesRollForward"/>
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    <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/2024/elts/us-gaap-2024.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_LiabilitiesAbstract_023d7b34-de87-44e3-b7be-7099045a2313_terseLabel_en-US" xlink:label="lab_us-gaap_LiabilitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Liabilities:</link:label>
    <link:label id="lab_us-gaap_LiabilitiesAbstract_label_en-US" xlink:label="lab_us-gaap_LiabilitiesAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liabilities [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_LiabilitiesAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilitiesAbstract" xlink:to="lab_us-gaap_LiabilitiesAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RevenuesAbstract_bae4510c-22ad-444a-a01b-1c92e31760e1_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/2024/elts/us-gaap-2024.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_LeaseholdImprovementsMember_59982570-24f2-4c70-a23c-b724f87b5f94_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/2024/elts/us-gaap-2024.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_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue_a2589e20-0365-4ba3-9a5d-c759be491b95_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/2024/elts/us-gaap-2024.xsd#us-gaap_HeldToMaturitySecuritiesContinuousUnrealizedLossPositionTwelveMonthsOrLongerFairValue"/>
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    <link:label id="lab_us-gaap_FairValueMeasurementPolicyPolicyTextBlock_aeadb2e1-36f8-4a65-9637-d4a0e8bb03bb_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasurementPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value</link:label>
    <link:label id="lab_us-gaap_FairValueMeasurementPolicyPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_FairValueMeasurementPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Measurement, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasurementPolicyPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_FairValueMeasurementPolicyPolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasurementPolicyPolicyTextBlock" xlink:to="lab_us-gaap_FairValueMeasurementPolicyPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_CurrentFiscalYearEndDate_2813237f-54b5-4948-85dc-3db19a7f646e_terseLabel_en-US" xlink:label="lab_dei_CurrentFiscalYearEndDate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Current Fiscal Year End Date</link:label>
    <link:label id="lab_dei_CurrentFiscalYearEndDate_label_en-US" xlink:label="lab_dei_CurrentFiscalYearEndDate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Current Fiscal Year End Date</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_CurrentFiscalYearEndDate" xlink:href="https://xbrl.sec.gov/dei/2024/dei-2024.xsd#dei_CurrentFiscalYearEndDate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_CurrentFiscalYearEndDate" xlink:to="lab_dei_CurrentFiscalYearEndDate" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ValuationAllowancesAndReservesBalance_5c79517f-6559-49d6-94f7-4110c28f480b_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_aeaca35a-89b2-4a32-bc93-f1a88ca16638_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/2024/elts/us-gaap-2024.xsd#us-gaap_ValuationAllowancesAndReservesBalance"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ValuationAllowancesAndReservesBalance" xlink:to="lab_us-gaap_ValuationAllowancesAndReservesBalance" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityUndiscountedExcessAmount_f14da9e5-009e-4132-80e4-0203b9139501_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityUndiscountedExcessAmount" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Less imputed interest</link:label>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityUndiscountedExcessAmount_label_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityUndiscountedExcessAmount" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Lessee, Operating Lease, Liability, Undiscounted Excess Amount</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeaseLiabilityUndiscountedExcessAmount" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_LesseeOperatingLeaseLiabilityUndiscountedExcessAmount"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LesseeOperatingLeaseLiabilityUndiscountedExcessAmount" xlink:to="lab_us-gaap_LesseeOperatingLeaseLiabilityUndiscountedExcessAmount" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersReservesForUnpaidClaimsAndClaimsAdjustmentExpense_867dfe83-4907-408e-9659-e6faecb29251_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersReservesForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reserve for losses and loss adjustment expenses</link:label>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersReservesForUnpaidClaimsAndClaimsAdjustmentExpense_label_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersReservesForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-18, Supplemental Information, Property-Casualty Insurance Underwriters, Reserve for Unpaid Claim and Claim Adjustment Expense</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersReservesForUnpaidClaimsAndClaimsAdjustmentExpense" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersReservesForUnpaidClaimsAndClaimsAdjustmentExpense"/>
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    <link:label id="lab_ecd_PeoName_terseLabel_en-US" xlink:label="lab_ecd_PeoName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">PEO Name</link:label>
    <link:label id="lab_ecd_PeoName_label_en-US" xlink:label="lab_ecd_PeoName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">PEO Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_PeoName" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_PeoName"/>
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    <link:label id="lab_skwd_BrewerLaneVenturesFundIILPMember_cd97fbf4-cc61-4d2f-af70-f7ad998cb40e_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>
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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_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod_0a703b8b-6425-4884-a023-fef2c9b4a1b9_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod" 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, shares issues in period (in shares)</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardSharesIssuedInPeriod" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementsByShareBasedPaymentAwardAwardTypeAndPlanNameDomain_93c795c9-4402-4b77-b9e0-e33422ffc4f8_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/2024/elts/us-gaap-2024.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_us-gaap_StockIssuedDuringPeriodSharesShareBasedCompensation_1196e303-977c-4d93-bc75-dbeacc7ca99b_terseLabel_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodSharesShareBasedCompensation" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Issuance of shares (in shares)</link:label>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodSharesShareBasedCompensation_label_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodSharesShareBasedCompensation" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Shares Issued, Shares, Share-Based Payment Arrangement, after Forfeiture</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockIssuedDuringPeriodSharesShareBasedCompensation" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_StockIssuedDuringPeriodSharesShareBasedCompensation"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockIssuedDuringPeriodSharesShareBasedCompensation" xlink:to="lab_us-gaap_StockIssuedDuringPeriodSharesShareBasedCompensation" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredTaxAssetsTaxDeferredExpenseCompensationAndBenefitsShareBasedCompensationCost_54e4355b-a117-45c7-9244-ff8e62cd128e_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsTaxDeferredExpenseCompensationAndBenefitsShareBasedCompensationCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stock options/awards</link:label>
    <link:label id="lab_us-gaap_DeferredTaxAssetsTaxDeferredExpenseCompensationAndBenefitsShareBasedCompensationCost_label_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsTaxDeferredExpenseCompensationAndBenefitsShareBasedCompensationCost" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Tax Assets, Tax Deferred Expense, Compensation and Benefits, Share-Based Compensation Cost</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxAssetsTaxDeferredExpenseCompensationAndBenefitsShareBasedCompensationCost" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_DeferredTaxAssetsTaxDeferredExpenseCompensationAndBenefitsShareBasedCompensationCost"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredTaxAssetsTaxDeferredExpenseCompensationAndBenefitsShareBasedCompensationCost" xlink:to="lab_us-gaap_DeferredTaxAssetsTaxDeferredExpenseCompensationAndBenefitsShareBasedCompensationCost" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfCededCreditRiskByReinsurerTextBlock_0d977d2b-503b-47bc-b395-a8efd6b4f4f5_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/2024/elts/us-gaap-2024.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_skwd_GrossInvestmentIncomeExpenseOperating_5f46c75a-9318-4afe-bd61-a0209e2ca461_terseLabel_en-US" xlink:label="lab_skwd_GrossInvestmentIncomeExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total investment income</link:label>
    <link:label id="lab_skwd_GrossInvestmentIncomeExpenseOperating_label_en-US" xlink:label="lab_skwd_GrossInvestmentIncomeExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gross Investment Income (Expense), Operating</link:label>
    <link:label id="lab_skwd_GrossInvestmentIncomeExpenseOperating_documentation_en-US" xlink:label="lab_skwd_GrossInvestmentIncomeExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Gross Investment Income (Expense), Operating</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_GrossInvestmentIncomeExpenseOperating" xlink:href="skwd-20241231.xsd#skwd_GrossInvestmentIncomeExpenseOperating"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_GrossInvestmentIncomeExpenseOperating" xlink:to="lab_skwd_GrossInvestmentIncomeExpenseOperating" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock_terseLabel_en-US" xlink:label="lab_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Company Selected Measure</link:label>
    <link:label id="lab_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock_label_en-US" xlink:label="lab_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Compensation Actually Paid vs. Company Selected Measure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock" xlink:to="lab_ecd_CompActuallyPaidVsCoSelectedMeasureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock_c4e4136e-7c48-4059-a774-df9ec7fd074d_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>
    <link:label id="lab_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock_label_en-US" xlink:label="lab_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Schedule of Intangible Assets and Goodwill [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfIntangibleAssetsAndGoodwillTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredIncomeTaxAssetsNet_60709614-a41b-4b71-8759-3ad1190a97ab_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredIncomeTaxAssetsNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Deferred income taxes</link:label>
    <link:label id="lab_us-gaap_DeferredIncomeTaxAssetsNet_label_en-US" xlink:label="lab_us-gaap_DeferredIncomeTaxAssetsNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Income Tax Assets, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredIncomeTaxAssetsNet" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_DeferredIncomeTaxAssetsNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredIncomeTaxAssetsNet" xlink:to="lab_us-gaap_DeferredIncomeTaxAssetsNet" xlink:type="arc" order="1"/>
    <link:label id="lab_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/2024/ecd-2024.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_skwd_UnderwritingIncomeNet_df48c12a-a68c-472b-85c4-8adea4b1055f_terseLabel_en-US" xlink:label="lab_skwd_UnderwritingIncomeNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net underwriting income</link:label>
    <link:label id="lab_skwd_UnderwritingIncomeNet_label_en-US" xlink:label="lab_skwd_UnderwritingIncomeNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Underwriting Income, Net</link:label>
    <link:label id="lab_skwd_UnderwritingIncomeNet_documentation_en-US" xlink:label="lab_skwd_UnderwritingIncomeNet" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Underwriting Income, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_UnderwritingIncomeNet" xlink:href="skwd-20241231.xsd#skwd_UnderwritingIncomeNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_UnderwritingIncomeNet" xlink:to="lab_skwd_UnderwritingIncomeNet" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetUsefulLife_88f0cbe4-90d3-4dce-b143-b5045763c3f5_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/2024/elts/us-gaap-2024.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_InvestmentsFairValueDisclosure_430f91ab-d932-43a6-b14e-1ad695721e9d_terseLabel_en-US" xlink:label="lab_us-gaap_InvestmentsFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investments, fair value disclosure</link:label>
    <link:label id="lab_us-gaap_InvestmentsFairValueDisclosure_label_en-US" xlink:label="lab_us-gaap_InvestmentsFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Investments, Fair Value Disclosure</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InvestmentsFairValueDisclosure" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_InvestmentsFairValueDisclosure"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_InvestmentsFairValueDisclosure" xlink:to="lab_us-gaap_InvestmentsFairValueDisclosure" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AdditionalPaidInCapitalMember_18e0fc34-c304-4f10-ac3e-d42a4d284f02_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/2024/elts/us-gaap-2024.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_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTextBlock_64628e8a-66da-4bff-b5ed-34e239e0e3ba_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/2024/elts/us-gaap-2024.xsd#us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTextBlock" xlink:to="lab_us-gaap_ScheduleOfAccountsNotesLoansAndFinancingReceivableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_PaymentsForContributionsToSubsidiaries_af3d2010-dcbb-4674-a7e8-bc1ca5f5da64_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>
    <link:label id="lab_skwd_PaymentsForContributionsToSubsidiaries_label_en-US" xlink:label="lab_skwd_PaymentsForContributionsToSubsidiaries" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Payments For Contributions To Subsidiaries</link:label>
    <link:label id="lab_skwd_PaymentsForContributionsToSubsidiaries_documentation_en-US" xlink:label="lab_skwd_PaymentsForContributionsToSubsidiaries" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Payments For Contributions To Subsidiaries</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_PaymentsForContributionsToSubsidiaries" xlink:href="skwd-20241231.xsd#skwd_PaymentsForContributionsToSubsidiaries"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_PaymentsForContributionsToSubsidiaries" xlink:to="lab_skwd_PaymentsForContributionsToSubsidiaries" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtInstrumentVariableRate_a3105790-4a62-47de-8050-87d291a03411_terseLabel_en-US" xlink:label="lab_skwd_DebtInstrumentVariableRate" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Six-month SOFR</link:label>
    <link:label id="lab_skwd_DebtInstrumentVariableRate_label_en-US" xlink:label="lab_skwd_DebtInstrumentVariableRate" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Variable Rate</link:label>
    <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-20241231.xsd#skwd_DebtInstrumentVariableRate"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtInstrumentVariableRate" xlink:to="lab_skwd_DebtInstrumentVariableRate" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PensionAndOtherPostretirementBenefitsDisclosureTextBlock_71bd6a40-406f-4ddb-9d12-369567ce06bb_terseLabel_en-US" xlink:label="lab_us-gaap_PensionAndOtherPostretirementBenefitsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Employee Benefit Plans</link:label>
    <link:label id="lab_us-gaap_PensionAndOtherPostretirementBenefitsDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_PensionAndOtherPostretirementBenefitsDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Retirement Benefits [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PensionAndOtherPostretirementBenefitsDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_PensionAndOtherPostretirementBenefitsDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PensionAndOtherPostretirementBenefitsDisclosureTextBlock" xlink:to="lab_us-gaap_PensionAndOtherPostretirementBenefitsDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NotesPayable_b84c89aa-40d1-4876-aff4-a681de4d29ba_terseLabel_en-US" xlink:label="lab_us-gaap_NotesPayable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Notes payable</link:label>
    <link:label id="lab_us-gaap_NotesPayable_label_en-US" xlink:label="lab_us-gaap_NotesPayable" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Notes Payable</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NotesPayable" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_NotesPayable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NotesPayable" xlink:to="lab_us-gaap_NotesPayable" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating_6311e141-800c-4e24-8fb6-3481f816191d_terseLabel_en-US" xlink:label="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Underwriting, acquisition and insurance expenses</link:label>
    <link:label id="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating_517d650e-3ada-4c13-8845-dd799991151d_totalLabel_en-US" xlink:label="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total underwriting, acquisition and insurance expenses</link:label>
    <link:label id="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating_label_en-US" xlink:label="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Policy Acquisition Costs, Amortization Expense And Other Cost And Expense, Operating</link:label>
    <link:label id="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating_documentation_en-US" xlink:label="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Deferred Policy Acquisition Costs, Amortization Expense And Other Cost And Expense, Operating</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating" xlink:href="skwd-20241231.xsd#skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating" xlink:to="lab_skwd_DeferredPolicyAcquisitionCostsAmortizationExpenseAndOtherCostAndExpenseOperating" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NewAccountingPronouncementsPolicyPolicyTextBlock_e092e8be-9ac8-4391-be92-0dc4cd0644a4_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 Pronouncements</link:label>
    <link:label id="lab_us-gaap_NewAccountingPronouncementsPolicyPolicyTextBlock_label_en-US" xlink:label="lab_us-gaap_NewAccountingPronouncementsPolicyPolicyTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">New Accounting Pronouncements, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NewAccountingPronouncementsPolicyPolicyTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_NewAccountingPronouncementsPolicyPolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NewAccountingPronouncementsPolicyPolicyTextBlock" xlink:to="lab_us-gaap_NewAccountingPronouncementsPolicyPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPremiumsWritten_615ef37d-2227-4891-9e8c-fc84c2060011_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>
    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPremiumsWritten_label_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">SEC Schedule, 12-18, Supplemental Information, Property-Casualty Insurance Underwriters, Premium Written</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPremiumsWritten" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPremiumsWritten"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPremiumsWritten" xlink:to="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersPremiumsWritten" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PremiumReceivableCreditLossExpenseReversal_84630237-9995-4f88-a6bb-a702b64a30cd_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/2024/elts/us-gaap-2024.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_srt_TitleOfIndividualWithRelationshipToEntityDomain_47f0f743-e227-4a01-81d2-0ff87a7b4aee_terseLabel_en-US" xlink:label="lab_srt_TitleOfIndividualWithRelationshipToEntityDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Title of Individual [Domain]</link:label>
    <link:label id="lab_srt_TitleOfIndividualWithRelationshipToEntityDomain_label_en-US" xlink:label="lab_srt_TitleOfIndividualWithRelationshipToEntityDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Title and Position [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_TitleOfIndividualWithRelationshipToEntityDomain" xlink:href="https://xbrl.fasb.org/srt/2024/elts/srt-2024.xsd#srt_TitleOfIndividualWithRelationshipToEntityDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_TitleOfIndividualWithRelationshipToEntityDomain" xlink:to="lab_srt_TitleOfIndividualWithRelationshipToEntityDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsByMajorClassAxis_6a95f074-7183-4624-ab1c-79bc92ef4d22_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/2024/elts/us-gaap-2024.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_FiniteLivedIntangibleAssetsAccumulatedAmortization_6a281966-8555-4f4d-a673-022a4017c564_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Accumulated amortization</link:label>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Finite-Lived Intangible Assets, Accumulated Amortization</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsAccumulatedAmortization" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_MeasureName_terseLabel_en-US" xlink:label="lab_ecd_MeasureName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Name</link:label>
    <link:label id="lab_ecd_MeasureName_label_en-US" xlink:label="lab_ecd_MeasureName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measure Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_MeasureName" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_MeasureName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_MeasureName" xlink:to="lab_ecd_MeasureName" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_RealizedInvestmentGains_fd9a3d28-c406-4b0c-bcbb-928087873c06_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>
    <link:label id="lab_skwd_RealizedInvestmentGains_label_en-US" xlink:label="lab_skwd_RealizedInvestmentGains" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Realized Investment Gains</link:label>
    <link:label id="lab_skwd_RealizedInvestmentGains_documentation_en-US" xlink:label="lab_skwd_RealizedInvestmentGains" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Realized Investment Gains</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RealizedInvestmentGains" xlink:href="skwd-20241231.xsd#skwd_RealizedInvestmentGains"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_RealizedInvestmentGains" xlink:to="lab_skwd_RealizedInvestmentGains" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityInteractiveDataCurrent_7ac3f7a7-eba5-490d-b5a3-8d0cf5e27749_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>
    <link:label id="lab_dei_EntityInteractiveDataCurrent_label_en-US" xlink:label="lab_dei_EntityInteractiveDataCurrent" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Interactive Data Current</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityInteractiveDataCurrent" xlink:href="https://xbrl.sec.gov/dei/2024/dei-2024.xsd#dei_EntityInteractiveDataCurrent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityInteractiveDataCurrent" xlink:to="lab_dei_EntityInteractiveDataCurrent" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_SupplementalScheduleOfReinsurancePremiumsForInsuranceCompaniesTextBlock_b0ce16d2-5786-43d2-98de-c322e9d52a7f_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/2024/elts/srt-2024.xsd#srt_SupplementalScheduleOfReinsurancePremiumsForInsuranceCompaniesTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_SupplementalScheduleOfReinsurancePremiumsForInsuranceCompaniesTextBlock" xlink:to="lab_srt_SupplementalScheduleOfReinsurancePremiumsForInsuranceCompaniesTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments_767e3cdb-e8d4-4f14-bbe0-c341bd608e71_terseLabel_en-US" xlink:label="lab_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Investment in direct and indirect loans</link:label>
    <link:label id="lab_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments_label_en-US" xlink:label="lab_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds From (Payments To Acquire) Equity Method Investments</link:label>
    <link:label id="lab_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments_documentation_en-US" xlink:label="lab_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Proceeds From (Payments To Acquire) Equity Method Investments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments" xlink:href="skwd-20241231.xsd#skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments" xlink:to="lab_skwd_ProceedsFromPaymentsToAcquireEquityMethodInvestments" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt_481bd62c-2c1c-4b24-a76d-820dd792503d_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fixed maturity securities, available-for sale</link:label>
    <link:label id="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt_label_en-US" xlink:label="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Sale of Debt Securities, Available-for-Sale</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt" xlink:to="lab_us-gaap_ProceedsFromSaleOfAvailableForSaleSecuritiesDebt" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NumberOfOperatingSegments_901a5562-0258-45b9-b8f5-ecb00369fa6d_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>
    <link:label id="lab_us-gaap_NumberOfOperatingSegments_label_en-US" xlink:label="lab_us-gaap_NumberOfOperatingSegments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Number of Operating Segments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NumberOfOperatingSegments" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_NumberOfOperatingSegments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NumberOfOperatingSegments" xlink:to="lab_us-gaap_NumberOfOperatingSegments" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger_495b3246-7066-4fe2-89bb-fefc0759bebe_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>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger_label_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Continuous Unrealized Loss Position, 12 Months or Longer</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger_documentation_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Continuous Unrealized Loss Position, 12 Months or Longer</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPosition12MonthsOrLonger" xlink:href="skwd-20241231.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_ComponentsOfDeferredTaxAssetsAbstract_3e7b7f3a-b7bd-4e54-89ed-b8d959c6c70f_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/2024/elts/us-gaap-2024.xsd#us-gaap_ComponentsOfDeferredTaxAssetsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ComponentsOfDeferredTaxAssetsAbstract" xlink:to="lab_us-gaap_ComponentsOfDeferredTaxAssetsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfFairValueAssetsAndLiabilitiesMeasuredOnRecurringBasisTableTextBlock_2e7f188f-1a9f-4188-8bd6-fb0a342ed64b_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/2024/elts/us-gaap-2024.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_DisaggregationOfRevenueTable_3c4c030d-a113-4795-812c-fb18938bf8c9_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/2024/elts/us-gaap-2024.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_FundsHeldUnderReinsuranceAgreementsAsset_abab0559-4237-42cc-a2a1-45e43e8af705_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/2024/elts/us-gaap-2024.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_skwd_ReturnOnEquityPercentage_00a3753c-190f-46d2-9f0b-9b0ad30f730e_terseLabel_en-US" xlink:label="lab_skwd_ReturnOnEquityPercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Return on equity</link:label>
    <link:label id="lab_skwd_ReturnOnEquityPercentage_label_en-US" xlink:label="lab_skwd_ReturnOnEquityPercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Return on Equity, Percentage</link:label>
    <link:label id="lab_skwd_ReturnOnEquityPercentage_documentation_en-US" xlink:label="lab_skwd_ReturnOnEquityPercentage" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Return on Equity, Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ReturnOnEquityPercentage" xlink:href="skwd-20241231.xsd#skwd_ReturnOnEquityPercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ReturnOnEquityPercentage" xlink:to="lab_skwd_ReturnOnEquityPercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensation_5ecd4df5-a1fb-4f5a-90ce-3f206567b869_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/2024/elts/us-gaap-2024.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_skwd_RISCOMMember_7878092a-35a2-4e1b-93eb-7ec3783af139_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-20241231.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_DeferredTaxAssetsNet_7161183c-aaf0-41d9-ad4d-2cddc08829df_totalLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsNet" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total deferred tax assets after valuation allowance</link:label>
    <link:label id="lab_us-gaap_DeferredTaxAssetsNet_label_en-US" xlink:label="lab_us-gaap_DeferredTaxAssetsNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Deferred Tax Assets, Net of Valuation Allowance</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DeferredTaxAssetsNet" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_DeferredTaxAssetsNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DeferredTaxAssetsNet" xlink:to="lab_us-gaap_DeferredTaxAssetsNet" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_BToBMember_8cd1c331-c5e9-43f7-bbaf-2d5907716dd0_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-20241231.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_FairValueMeasuredAtNetAssetValuePerShareMember_b1d917f4-88b7-40f9-aa97-74edf62c63a4_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value Measured at Net Asset Value Per Share</link:label>
    <link:label id="lab_us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember_label_en-US" xlink:label="lab_us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value Measured at Net Asset Value Per Share [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember" xlink:to="lab_us-gaap_FairValueMeasuredAtNetAssetValuePerShareMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_CreditSpreadAdjustmentMember_24f12cc2-8166-4511-97da-6847a4ed43dd_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-20241231.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_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months_000c209a-64b2-4630-b10b-6232b850fd6e_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>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months_documentation_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Continuous Unrealized Loss Position, Less than 12 Months</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months" xlink:href="skwd-20241231.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months" xlink:to="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityContinuousUnrealizedLossPositionLessThan12Months" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage_8da62a6f-eef6-43fe-8ba8-1e2ec4437bed_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Stated interest rate</link:label>
    <link:label id="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage_label_en-US" xlink:label="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Interest Rate, Stated Percentage</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_DebtInstrumentInterestRateStatedPercentage"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:to="lab_us-gaap_DebtInstrumentInterestRateStatedPercentage" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CededPremiumsWritten_81459a72-d53a-48e4-9b29-5a7ec3ecc601_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_CededPremiumsWritten" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Ceded premiums</link:label>
    <link:label id="lab_us-gaap_CededPremiumsWritten_label_en-US" xlink:label="lab_us-gaap_CededPremiumsWritten" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Ceded Premiums Written</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CededPremiumsWritten" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_CededPremiumsWritten"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CededPremiumsWritten" xlink:to="lab_us-gaap_CededPremiumsWritten" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SupplementalCashFlowInformationAbstract_838b906c-abc6-48ca-a2d5-7ef7c90f9b9f_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalCashFlowInformationAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Supplemental disclosure of cash flow information:</link:label>
    <link:label id="lab_us-gaap_SupplementalCashFlowInformationAbstract_label_en-US" xlink:label="lab_us-gaap_SupplementalCashFlowInformationAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Supplemental Cash Flow Information [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SupplementalCashFlowInformationAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_SupplementalCashFlowInformationAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SupplementalCashFlowInformationAbstract" xlink:to="lab_us-gaap_SupplementalCashFlowInformationAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent_68d2fd2c-4ed1-48d6-a2cb-040df7437cf8_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/2024/elts/us-gaap-2024.xsd#us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent" xlink:to="lab_us-gaap_EquitySecuritiesFvNiCurrentAndNoncurrent" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_JuniorSubordinatedNotesDue2036Member_df366ad7-9506-4183-aab3-a5131faaea01_terseLabel_en-US" xlink:label="lab_skwd_JuniorSubordinatedNotesDue2036Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Junior Subordinated Notes Due 2036</link:label>
    <link:label id="lab_skwd_JuniorSubordinatedNotesDue2036Member_label_en-US" xlink:label="lab_skwd_JuniorSubordinatedNotesDue2036Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Junior Subordinated Notes Due 2036 [Member]</link:label>
    <link:label id="lab_skwd_JuniorSubordinatedNotesDue2036Member_documentation_en-US" xlink:label="lab_skwd_JuniorSubordinatedNotesDue2036Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Junior Subordinated Notes Due 2036</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_JuniorSubordinatedNotesDue2036Member" xlink:href="skwd-20241231.xsd#skwd_JuniorSubordinatedNotesDue2036Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_JuniorSubordinatedNotesDue2036Member" xlink:to="lab_skwd_JuniorSubordinatedNotesDue2036Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted_14226d8a-174f-4e56-816c-6635d3caca35_terseLabel_en-US" xlink:label="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net income (numerator for diluted earnings per share under the two-class method)</link:label>
    <link:label id="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted_label_en-US" xlink:label="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Net Income (Loss) Available to Common Stockholders, Diluted</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted" xlink:to="lab_us-gaap_NetIncomeLossAvailableToCommonStockholdersDiluted" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConcentrationRiskBenchmarkDomain_604f563e-63f7-41bc-8686-eed04e2a6f57_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/2024/elts/us-gaap-2024.xsd#us-gaap_ConcentrationRiskBenchmarkDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConcentrationRiskBenchmarkDomain" xlink:to="lab_us-gaap_ConcentrationRiskBenchmarkDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ScheduleOfValuationAndQualifyingAccountsDisclosureTextBlock_41c657f5-9e7b-408c-bb14-315c678d9eff_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>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ScheduleOfValuationAndQualifyingAccountsDisclosureTextBlock" xlink:to="lab_srt_ScheduleOfValuationAndQualifyingAccountsDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInFundsHeldUnderReinsuranceAgreements_afe2917a-4d8d-4d36-b47c-e5d18d7e83ee_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/2024/elts/us-gaap-2024.xsd#us-gaap_IncreaseDecreaseInFundsHeldUnderReinsuranceAgreements"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInFundsHeldUnderReinsuranceAgreements" xlink:to="lab_us-gaap_IncreaseDecreaseInFundsHeldUnderReinsuranceAgreements" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_AuditorFirmId_adf1b4ab-7d16-4787-a4a9-e4e38141d477_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>
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    <link:loc xlink:type="locator" xlink:label="loc_dei_AuditorFirmId" xlink:href="https://xbrl.sec.gov/dei/2024/dei-2024.xsd#dei_AuditorFirmId"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_AuditorFirmId" xlink:to="lab_dei_AuditorFirmId" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperations_0f95d4e4-0a10-413e-989f-cb2611959796_totalLabel_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateContinuingOperations" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Total income tax expense</link:label>
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    <link:label id="lab_us-gaap_PremiumsPercentageAssumedToNet_a8a87a67-9d04-4430-914a-97679b18ba20_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>
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    <link:label id="lab_skwd_ManagingGeneralInsuranceAgentAndBrokerCommissionRevenueMember_0743fd26-56a9-4c28-a33c-f6fa487f5882_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_CededPremiumsEarned_5c01eb1f-36c7-4ea2-8680-96fff557de61_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>
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    <link:label id="lab_us-gaap_FairValueByFairValueHierarchyLevelAxis_09f700da-1e3f-413f-a3c1-3f4c848898cf_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>
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    <link:label id="lab_us-gaap_DeferredTaxLiabilitiesDeferredExpenseDeferredPolicyAcquisitionCost_a1991ecc-335d-4035-acbd-e519731b3c9b_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredTaxLiabilitiesDeferredExpenseDeferredPolicyAcquisitionCost" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Deferred policy acquisition costs</link:label>
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    <link:label id="lab_us-gaap_AmortizationOfDeferredCharges_0eacc5fc-e06e-456b-b634-136c860aafa8_verboseLabel_en-US" xlink:label="lab_us-gaap_AmortizationOfDeferredCharges" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Amortization expense</link:label>
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    <link:label id="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersUnearnedPremiums_89de7ede-d4bc-48ec-97e7-c834ed7b045d_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_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNetNotSeparatelyPresented_84018aa0-4ddf-47f0-b3fd-7c40d4f50938_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndAllocatedClaimAdjustmentExpenseNetNotSeparatelyPresented" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Net reserves for loss and ALAE before 2020</link:label>
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    <link:label id="lab_us-gaap_ReceivablesFromStockholderMember_69179bc5-1df8-44ac-b95e-2b08ae3ba52a_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>
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    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain_e11fa790-0432-44c5-a81f-dfef6c77533b_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsMajorClassNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Finite-Lived Intangible Assets, Major Class Name [Domain]</link:label>
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    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearNine_fb9a574a-135d-49b8-a300-d5dfd78b1d61_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>
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    <link:loc xlink:type="locator" xlink:label="loc_ecd_UndrlygSecurityMktPriceChngPct" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_UndrlygSecurityMktPriceChngPct"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_UndrlygSecurityMktPriceChngPct" xlink:to="lab_ecd_UndrlygSecurityMktPriceChngPct" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MeasurementInputTypeAxis_ab087575-73c9-4e91-9fa0-294a986a021f_terseLabel_en-US" xlink:label="lab_us-gaap_MeasurementInputTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measurement Input Type [Axis]</link:label>
    <link:label id="lab_us-gaap_MeasurementInputTypeAxis_label_en-US" xlink:label="lab_us-gaap_MeasurementInputTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measurement Input Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MeasurementInputTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_MeasurementInputTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MeasurementInputTypeAxis" xlink:to="lab_us-gaap_MeasurementInputTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_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/2024/ecd-2024.xsd#ecd_IndividualAxis"/>
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    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember_b60cab1b-f2bf-43a5-b8dc-4aa755c232cc_terseLabel_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accumulated other comprehensive loss:</link:label>
    <link:label id="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember_label_en-US" xlink:label="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">AOCI Attributable to Parent [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_AccumulatedOtherComprehensiveIncomeMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:to="lab_us-gaap_AccumulatedOtherComprehensiveIncomeMember" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_ProductOrServiceAxis_54d21932-7f32-469a-a340-158c8acd60d5_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/2024/elts/srt-2024.xsd#srt_ProductOrServiceAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_ProductOrServiceAxis" xlink:to="lab_srt_ProductOrServiceAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentLineItems_19aae03a-d9a9-4206-8a0a-046961483c10_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>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentLineItems_label_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Property, Plant and Equipment [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_PropertyPlantAndEquipmentLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentLineItems" xlink:to="lab_us-gaap_PropertyPlantAndEquipmentLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StatementLineItems_9cb78241-351f-4e12-aeae-5a3840f4b6f5_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>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_StatementLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementLineItems" xlink:to="lab_us-gaap_StatementLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MeasurementInputTypeDomain_bbde3820-4033-47a7-8e3d-af84516490a9_terseLabel_en-US" xlink:label="lab_us-gaap_MeasurementInputTypeDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Measurement Input Type [Domain]</link:label>
    <link:label id="lab_us-gaap_MeasurementInputTypeDomain_label_en-US" xlink:label="lab_us-gaap_MeasurementInputTypeDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Measurement Input Type [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MeasurementInputTypeDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_MeasurementInputTypeDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_MeasurementInputTypeDomain" xlink:to="lab_us-gaap_MeasurementInputTypeDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ScheduleOfRelatedPartyTransactionsTableTextBlock_5aa814a7-bd41-43b6-9ddd-18a914af857b_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/2024/elts/us-gaap-2024.xsd#us-gaap_ScheduleOfRelatedPartyTransactionsTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ScheduleOfRelatedPartyTransactionsTableTextBlock" xlink:to="lab_us-gaap_ScheduleOfRelatedPartyTransactionsTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_MortgageLoansOnRealEstatePrincipalAmountPercentageOfPropertyAppraisalValue_96d1784f-e6a9-488f-b20b-41b4b905c8aa_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-20241231.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_PropertyPlantAndEquipmentTextBlock_9b9dabd3-f8a2-4da8-896b-40664ca96f24_terseLabel_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Property, Plant and Equipment</link:label>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentTextBlock_label_en-US" xlink:label="lab_us-gaap_PropertyPlantAndEquipmentTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Property, Plant and Equipment [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_PropertyPlantAndEquipmentTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentTextBlock" xlink:to="lab_us-gaap_PropertyPlantAndEquipmentTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_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/2024/ecd-2024.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_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersDeferredPolicyAcquisitionCosts_71fb09e2-475f-433a-9098-22e346418137_terseLabel_en-US" xlink:label="lab_us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersDeferredPolicyAcquisitionCosts" 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_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/2024/elts/us-gaap-2024.xsd#us-gaap_SupplementalInformationForPropertyCasualtyInsuranceUnderwritersDeferredPolicyAcquisitionCosts"/>
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    <link:label id="lab_us-gaap_IPOMember_8cc1db36-fe63-4eaf-ac9f-dfc5796c8d79_terseLabel_en-US" xlink:label="lab_us-gaap_IPOMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">IPO</link:label>
    <link:label id="lab_us-gaap_IPOMember_label_en-US" xlink:label="lab_us-gaap_IPOMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">IPO [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IPOMember" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_IPOMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IPOMember" xlink:to="lab_us-gaap_IPOMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearTen_b886b755-c31e-4ff2-9d3c-757be16d79ef_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearTen" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Year 10</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearTen_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearTen" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contracts, Historical Claims Duration, Year 10</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearTen" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearTen"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearTen" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearTen" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_SoftwareDevelopmentMember_19916c80-95ff-4c10-a980-2ed46e15a441_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/2024/elts/us-gaap-2024.xsd#us-gaap_SoftwareDevelopmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SoftwareDevelopmentMember" xlink:to="lab_us-gaap_SoftwareDevelopmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock_34e113c6-6a2c-40d0-9230-3f93e5191c9c_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:to="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CondensedCashFlowStatementTable_3a7cfe4e-54f5-4275-8ab7-0971c316e04d_terseLabel_en-US" xlink:label="lab_srt_CondensedCashFlowStatementTable" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Condensed Cash Flow Statement [Table]</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_srt_CondensedCashFlowStatementTable" xlink:href="https://xbrl.fasb.org/srt/2024/elts/srt-2024.xsd#srt_CondensedCashFlowStatementTable"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_CondensedCashFlowStatementTable" xlink:to="lab_srt_CondensedCashFlowStatementTable" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_MinimumMember_6b678e32-fdd6-4385-8568-f72dad7f35e5_terseLabel_en-US" xlink:label="lab_srt_MinimumMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Low</link:label>
    <link:label id="lab_srt_MinimumMember_label_en-US" xlink:label="lab_srt_MinimumMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Minimum [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_MinimumMember" xlink:href="https://xbrl.fasb.org/srt/2024/elts/srt-2024.xsd#srt_MinimumMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_MinimumMember" xlink:to="lab_srt_MinimumMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NotesPayableFairValueDisclosure_bae2e2b5-d9d3-4b4f-b35a-2aaac7d0a045_terseLabel_en-US" xlink:label="lab_us-gaap_NotesPayableFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Notes payable, fair value disclosure</link:label>
    <link:label id="lab_us-gaap_NotesPayableFairValueDisclosure_label_en-US" xlink:label="lab_us-gaap_NotesPayableFairValueDisclosure" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Notes Payable, Fair Value Disclosure</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NotesPayableFairValueDisclosure" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_NotesPayableFairValueDisclosure"/>
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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>
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    <link:label id="lab_us-gaap_RelatedPartyTransactionsAbstract_label_en-US" xlink:label="lab_us-gaap_RelatedPartyTransactionsAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Related Party Transactions [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RelatedPartyTransactionsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_RelatedPartyTransactionsAbstract"/>
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    <link:label id="lab_skwd_JVMFundsLLCMember_5734b9e8-aff6-4e23-93ef-a634878a5dbe_terseLabel_en-US" xlink:label="lab_skwd_JVMFundsLLCMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">JVM Funds LLC</link:label>
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    <link:label id="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense_07ab134a-18aa-458c-95e6-7508d8dba789_terseLabel_en-US" xlink:label="lab_us-gaap_DeferredPolicyAcquisitionCostAmortizationExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Amortization of policy acquisition costs</link:label>
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    <link:label id="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue_41c6433a-0810-4eb9-b23c-dbf7781b7fd3_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleSecuritiesDebtMaturitiesAfterFiveThroughTenYearsFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Due after five years through ten years</link:label>
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    <link:label id="lab_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded_07dce367-58e5-44d0-a176-600b2deadd46_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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ReinsuranceEffectOnClaimsAndBenefitsIncurredAmountCeded"/>
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    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAccumulatedUnallocatedClaimAdjustmentExpense_0ad34ea3-ecad-4e8a-9909-30f0667bf527_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsLiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseAccumulatedUnallocatedClaimAdjustmentExpense" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Unallocated LAE</link:label>
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    <link:label id="lab_us-gaap_StatementBusinessSegmentsAxis_53f54136-3be9-44cc-93ea-d03aeb98add7_terseLabel_en-US" xlink:label="lab_us-gaap_StatementBusinessSegmentsAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Segments [Axis]</link:label>
    <link:label id="lab_us-gaap_StatementBusinessSegmentsAxis_label_en-US" xlink:label="lab_us-gaap_StatementBusinessSegmentsAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Segments [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementBusinessSegmentsAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_StatementBusinessSegmentsAxis"/>
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    <link:label id="lab_ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember_terseLabel_en-US" xlink:label="lab_ecd_ChngInFrValAsOfVstngDtOfPrrYrEqtyAwrdsVstdInCvrdYrMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Change in Fair Value as of Vesting Date of Prior Year Equity Awards Vested in Covered Year</link:label>
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    <link:label id="lab_us-gaap_EffectiveIncomeTaxRateReconciliationAtFederalStatutoryIncomeTaxRate_e71c7e5c-ad46-4f8a-b02b-a6d5feedc517_terseLabel_en-US" xlink:label="lab_us-gaap_EffectiveIncomeTaxRateReconciliationAtFederalStatutoryIncomeTaxRate" 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_DebtInstrumentCarryingAmount_31f3683b-16d9-438f-a8f5-4f01b99c3af6_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/2024/elts/us-gaap-2024.xsd#us-gaap_DebtInstrumentCarryingAmount"/>
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    <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/2024/ecd-2024.xsd#ecd_AwardExrcPrice"/>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableforSaleUnrealizedLossPositionAbstract_fecdfdbc-889c-4724-821e-fe5e65be2bfc_terseLabel_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableforSaleUnrealizedLossPositionAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Available for sale, fair value</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableforSaleUnrealizedLossPositionAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_DebtSecuritiesAvailableforSaleUnrealizedLossPositionAbstract"/>
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    <link:label id="lab_us-gaap_ScheduleOfDeferredTaxAssetsAndLiabilitiesTableTextBlock_c83b51c2-df97-4982-b175-365dfc04ff76_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:label id="lab_ecd_TrdArrDuration_terseLabel_en-US" xlink:label="lab_ecd_TrdArrDuration" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Arrangement Duration</link:label>
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    <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/2024/elts/us-gaap-2024.xsd#us-gaap_GoodwillGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_GoodwillGross" xlink:to="lab_us-gaap_GoodwillGross" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_MortgageLoansUnrealizedGainLoss_02700322-b645-46a1-8b56-a52e4fa2b324_terseLabel_en-US" xlink:label="lab_skwd_MortgageLoansUnrealizedGainLoss" 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_MortgageLoansUnrealizedGainLoss_label_en-US" xlink:label="lab_skwd_MortgageLoansUnrealizedGainLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Mortgage Loans, Unrealized Gain (Loss)</link:label>
    <link:label id="lab_skwd_MortgageLoansUnrealizedGainLoss_documentation_en-US" xlink:label="lab_skwd_MortgageLoansUnrealizedGainLoss" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Mortgage Loans, Unrealized Gain (Loss)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_MortgageLoansUnrealizedGainLoss" xlink:href="skwd-20241231.xsd#skwd_MortgageLoansUnrealizedGainLoss"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_MortgageLoansUnrealizedGainLoss" xlink:to="lab_skwd_MortgageLoansUnrealizedGainLoss" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IntangibleAssetsNetExcludingGoodwill_cd2090b7-ee9c-4960-8110-de2b2345d719_periodEndLabel_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/periodEndLabel" xlink:type="resource" xml:lang="en-US">Gross intangible assets, ending balance</link:label>
    <link:label id="lab_us-gaap_IntangibleAssetsNetExcludingGoodwill_label_en-US" xlink:label="lab_us-gaap_IntangibleAssetsNetExcludingGoodwill" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Intangible Assets, Net (Excluding Goodwill)</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IntangibleAssetsNetExcludingGoodwill" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_IntangibleAssetsNetExcludingGoodwill"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IntangibleAssetsNetExcludingGoodwill" xlink:to="lab_us-gaap_IntangibleAssetsNetExcludingGoodwill" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableCreditQualityIndicatorTableTextBlock_5425b1e1-2cef-45da-8cc2-5386fc8a057f_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/2024/elts/us-gaap-2024.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_StatementOfStockholdersEquityAbstract_label_en-US" xlink:label="lab_us-gaap_StatementOfStockholdersEquityAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Statement of Stockholders' Equity [Abstract]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StatementOfStockholdersEquityAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_StatementOfStockholdersEquityAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StatementOfStockholdersEquityAbstract" xlink:to="lab_us-gaap_StatementOfStockholdersEquityAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsAccidentYear2015Member_d07acebc-afe5-40f5-a9e6-6434649b692a_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>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsAccidentYear2015Member_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsAccidentYear2015Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contracts, Accident Year 2015 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsAccidentYear2015Member" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ShortdurationInsuranceContractsAccidentYear2015Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsAccidentYear2015Member" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsAccidentYear2015Member" xlink:type="arc" order="1"/>
    <link:label id="lab_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/2024/elts/us-gaap-2024.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_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems_def126a1-fa85-4aed-bd77-bc7abb1de1dc_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>
    <link:label id="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems_label_en-US" xlink:label="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Liability for Claims and Claims Adjustment Expense [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems" xlink:to="lab_us-gaap_LiabilityForClaimsAndClaimsAdjustmentExpenseLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax_bee893c7-725a-4fa8-ab85-16686e582374_terseLabel_en-US" xlink:label="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gross Unrealized Gains</link:label>
    <link:label id="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax_label_en-US" xlink:label="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Accumulated Gross Unrealized Gain, before Tax</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax" xlink:to="lab_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions_0794fb89-e4eb-48ea-b8b8-a4a8ab525000_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/2024/elts/us-gaap-2024.xsd#us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions" xlink:to="lab_us-gaap_EmployeeServiceShareBasedCompensationNonvestedAwardsTotalCompensationCostNotYetRecognizedShareBasedAwardsOtherThanOptions" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverableMember_ba957b15-8926-40c6-87ea-bcc8a290b486_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/2024/elts/us-gaap-2024.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_ShortdurationInsuranceContractsIncurredButNotReportedIbnrClaimsLiabilityNet_0960266b-6037-4c3e-a3a1-c9ad8e7db101_terseLabel_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsIncurredButNotReportedIbnrClaimsLiabilityNet" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contracts, Incurred but Not Reported (IBNR) Claims Liability, Net</link:label>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsIncurredButNotReportedIbnrClaimsLiabilityNet_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsIncurredButNotReportedIbnrClaimsLiabilityNet" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contracts, Incurred but Not Reported (IBNR) Claims Liability, Net</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsIncurredButNotReportedIbnrClaimsLiabilityNet" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ShortdurationInsuranceContractsIncurredButNotReportedIbnrClaimsLiabilityNet"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsIncurredButNotReportedIbnrClaimsLiabilityNet" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsIncurredButNotReportedIbnrClaimsLiabilityNet" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_AuditInformationAbstract_label_en-US" xlink:label="lab_skwd_AuditInformationAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Audit Information [Abstract]</link:label>
    <link:label id="lab_skwd_AuditInformationAbstract_documentation_en-US" xlink:label="lab_skwd_AuditInformationAbstract" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Audit Information</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_AuditInformationAbstract" xlink:href="skwd-20241231.xsd#skwd_AuditInformationAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_AuditInformationAbstract" xlink:to="lab_skwd_AuditInformationAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract_491894c7-89ab-4594-a025-15d0ea784fe0_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/2024/elts/us-gaap-2024.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseIncurredClaimsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_RetailPortfolioSegmentMember_15d741e9-4e2c-488e-930d-2f26f24b95c4_terseLabel_en-US" xlink:label="lab_skwd_RetailPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Retail</link:label>
    <link:label id="lab_skwd_RetailPortfolioSegmentMember_label_en-US" xlink:label="lab_skwd_RetailPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Retail Portfolio Segment [Member]</link:label>
    <link:label id="lab_skwd_RetailPortfolioSegmentMember_documentation_en-US" xlink:label="lab_skwd_RetailPortfolioSegmentMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Retail Portfolio Segment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RetailPortfolioSegmentMember" xlink:href="skwd-20241231.xsd#skwd_RetailPortfolioSegmentMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_RetailPortfolioSegmentMember" xlink:to="lab_skwd_RetailPortfolioSegmentMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_RelatedPartyDomain_b635c0b8-92a4-42f6-b62c-9322f262ca38_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 and Nonrelated Parties [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RelatedPartyDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.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_ArenaSpecialOpportunitiesFundLPMember_a79303e8-90b7-4639-960e-d38db6187f30_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-20241231.xsd#skwd_ArenaSpecialOpportunitiesFundLPMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ArenaSpecialOpportunitiesFundLPMember" xlink:to="lab_skwd_ArenaSpecialOpportunitiesFundLPMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ProceedsFromRepaymentsOfLinesOfCredit_91eb1407-55f3-4075-8c9e-b9f4847de762_terseLabel_en-US" xlink:label="lab_us-gaap_ProceedsFromRepaymentsOfLinesOfCredit" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Proceeds from (repayments of) lines of credit</link:label>
    <link:label id="lab_us-gaap_ProceedsFromRepaymentsOfLinesOfCredit_label_en-US" xlink:label="lab_us-gaap_ProceedsFromRepaymentsOfLinesOfCredit" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from (Repayments of) Lines of Credit</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromRepaymentsOfLinesOfCredit" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ProceedsFromRepaymentsOfLinesOfCredit"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ProceedsFromRepaymentsOfLinesOfCredit" xlink:to="lab_us-gaap_ProceedsFromRepaymentsOfLinesOfCredit" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_MortgagesMember_67d8a5f9-52ae-467c-9202-03d47d06aa01_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/2024/elts/us-gaap-2024.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_ShortdurationInsuranceContractsHistoricalClaimsDurationLineItems_0b73930f-3dc2-4e65-b949-d34cffebb124_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>
    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationLineItems_label_en-US" xlink:label="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationLineItems" xlink:to="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_GainOnLossPortfolioTransfer_dfd42da2-b090-4a26-a4ae-5e81e70934e0_terseLabel_en-US" xlink:label="lab_skwd_GainOnLossPortfolioTransfer" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Gain on loss portfolio transfer</link:label>
    <link:label id="lab_skwd_GainOnLossPortfolioTransfer_label_en-US" xlink:label="lab_skwd_GainOnLossPortfolioTransfer" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Gain on Loss Portfolio Transfer</link:label>
    <link:label id="lab_skwd_GainOnLossPortfolioTransfer_documentation_en-US" xlink:label="lab_skwd_GainOnLossPortfolioTransfer" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Gain on Loss Portfolio Transfer</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_GainOnLossPortfolioTransfer" xlink:href="skwd-20241231.xsd#skwd_GainOnLossPortfolioTransfer"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_GainOnLossPortfolioTransfer" xlink:to="lab_skwd_GainOnLossPortfolioTransfer" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ProceedsFromDistributionsFromConsolidatedEntities_95359a14-9015-4a46-95e1-54159fe7898a_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-20241231.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_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardRequisiteServicePeriod1_a3a2e3d5-d699-48a8-a20c-9539aefc53e8_verboseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardRequisiteServicePeriod1" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Requisite service period</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardRequisiteServicePeriod1_aaf34468-86e1-4c41-b157-48630f5d4079_terseLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardRequisiteServicePeriod1" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Requisite Service Period</link:label>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardRequisiteServicePeriod1_label_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardRequisiteServicePeriod1" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Share-Based Compensation Arrangement by Share-Based Payment Award, Award Requisite Service Period</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardRequisiteServicePeriod1" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardRequisiteServicePeriod1"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardRequisiteServicePeriod1" xlink:to="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardAwardRequisiteServicePeriod1" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IncreaseDecreaseInOtherOperatingAssets_3d1c2539-9c3a-4a7f-a875-707f44918e3d_negatedTerseLabel_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInOtherOperatingAssets" xlink:role="http://www.xbrl.org/2009/role/negatedTerseLabel" xlink:type="resource" xml:lang="en-US">Other, net</link:label>
    <link:label id="lab_us-gaap_IncreaseDecreaseInOtherOperatingAssets_label_en-US" xlink:label="lab_us-gaap_IncreaseDecreaseInOtherOperatingAssets" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Increase (Decrease) in Other Operating Assets</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInOtherOperatingAssets" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_IncreaseDecreaseInOtherOperatingAssets"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_IncreaseDecreaseInOtherOperatingAssets" xlink:to="lab_us-gaap_IncreaseDecreaseInOtherOperatingAssets" xlink:type="arc" order="1"/>
    <link:label id="lab_srt_CumulativeEffectPeriodOfAdoptionDomain_b2381164-833c-4ab9-85bb-d539e5f360d1_terseLabel_en-US" xlink:label="lab_srt_CumulativeEffectPeriodOfAdoptionDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Cumulative Effect, Period of Adoption [Domain]</link:label>
    <link:label id="lab_srt_CumulativeEffectPeriodOfAdoptionDomain_label_en-US" xlink:label="lab_srt_CumulativeEffectPeriodOfAdoptionDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Cumulative Effect, Period of Adoption [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_CumulativeEffectPeriodOfAdoptionDomain" xlink:href="https://xbrl.fasb.org/srt/2024/elts/srt-2024.xsd#srt_CumulativeEffectPeriodOfAdoptionDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_CumulativeEffectPeriodOfAdoptionDomain" xlink:to="lab_srt_CumulativeEffectPeriodOfAdoptionDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_BrewerLaneVentureFundIILPMember_a2a4e879-1438-4f22-876f-43d5ebb6cc1a_terseLabel_en-US" xlink:label="lab_skwd_BrewerLaneVentureFundIILPMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Brewer Lane Ventures Fund II LP</link:label>
    <link:label id="lab_skwd_BrewerLaneVentureFundIILPMember_label_en-US" xlink:label="lab_skwd_BrewerLaneVentureFundIILPMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Brewer Lane Venture Fund II LP [Member]</link:label>
    <link:label id="lab_skwd_BrewerLaneVentureFundIILPMember_documentation_en-US" xlink:label="lab_skwd_BrewerLaneVentureFundIILPMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Brewer Lane Venture Fund II LP</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_BrewerLaneVentureFundIILPMember" xlink:href="skwd-20241231.xsd#skwd_BrewerLaneVentureFundIILPMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_BrewerLaneVentureFundIILPMember" xlink:to="lab_skwd_BrewerLaneVentureFundIILPMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesGross_cd388aac-7603-45da-950e-c451a385b621_terseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesGross" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverables, Gross, Amortized Cost</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesGross_e491a3ce-5dd2-4c6e-9193-a61b347ce368_verboseLabel_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesGross" xlink:role="http://www.xbrl.org/2003/role/verboseLabel" xlink:type="resource" xml:lang="en-US">Reinsurance recoverable</link:label>
    <link:label id="lab_us-gaap_ReinsuranceRecoverablesGross_label_en-US" xlink:label="lab_us-gaap_ReinsuranceRecoverablesGross" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Reinsurance Recoverables, Gross</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ReinsuranceRecoverablesGross" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ReinsuranceRecoverablesGross"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverablesGross" xlink:to="lab_us-gaap_ReinsuranceRecoverablesGross" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CashAndCashEquivalentsPolicyTextBlock_7419580e-a96b-484d-b3f0-2038e0e0da9a_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/2024/elts/us-gaap-2024.xsd#us-gaap_CashAndCashEquivalentsPolicyTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CashAndCashEquivalentsPolicyTextBlock" xlink:to="lab_us-gaap_CashAndCashEquivalentsPolicyTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock_3f504134-2a77-4983-8694-78c3a7c70644_terseLabel_en-US" xlink:label="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Commitments and Contingencies</link:label>
    <link:label id="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock_label_en-US" xlink:label="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Commitments and Contingencies Disclosure [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_CommitmentsAndContingenciesDisclosureTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" xlink:to="lab_us-gaap_CommitmentsAndContingenciesDisclosureTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_MultiFamilyPortfolioSegmentMember_9f045243-d69b-4542-9e5b-a948534f4b75_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-20241231.xsd#skwd_MultiFamilyPortfolioSegmentMember"/>
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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:loc xlink:type="locator" xlink:label="loc_ecd_MeasureAxis" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_MeasureAxis"/>
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    <link:label id="lab_us-gaap_UnearnedPremiums_dd813867-7f10-4343-a8b7-53a4e1770150_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>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_UnearnedPremiums" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_UnearnedPremiums"/>
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    <link:label id="lab_us-gaap_StockIssuedDuringPeriodValueShareBasedCompensation_d77798fb-3ddd-44b1-ac5b-a883cfa17f56_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/2024/elts/us-gaap-2024.xsd#us-gaap_StockIssuedDuringPeriodValueShareBasedCompensation"/>
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    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationByAssetClassDomain_48bec46c-18e7-4206-ba16-fe0efcd2f063_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>
    <link:label id="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationByAssetClassDomain_label_en-US" xlink:label="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationByAssetClassDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Asset Class [Domain]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationByAssetClassDomain" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationByAssetClassDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationByAssetClassDomain" xlink:to="lab_us-gaap_FairValueAssetsMeasuredOnRecurringBasisUnobservableInputReconciliationByAssetClassDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_InvestmentsAbstract_5c657bc9-3fd6-4fad-b881-1433bfa04eec_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/2024/elts/us-gaap-2024.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_us-gaap_PreferredStockSharesAuthorized_e17702e2-bf74-4a6a-9eb9-b6df52f2778d_terseLabel_en-US" xlink:label="lab_us-gaap_PreferredStockSharesAuthorized" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Preferred stock, shares authorized (in shares)</link:label>
    <link:label id="lab_us-gaap_PreferredStockSharesAuthorized_label_en-US" xlink:label="lab_us-gaap_PreferredStockSharesAuthorized" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Preferred Stock, Shares Authorized</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PreferredStockSharesAuthorized" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_PreferredStockSharesAuthorized"/>
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    <link:label id="lab_skwd_RevolvingLineOfCreditDueDecember2024Member_186c30ff-a5bb-4f5a-bc2c-c853a9064bdd_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>
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    <link:label id="lab_us-gaap_PaymentsForLossesAndLossAdjustmentExpense_73ad5c1d-0385-412a-b55b-2022a75c787f_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_AccumulatedOtherComprehensiveIncomeLossNetOfTaxAbstract_931b5fa0-305d-4c8d-8e08-744b31595a99_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:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearFour_ee31939b-4230-486b-bc57-b3c996e7052b_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">2028</link:label>
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    <link:label id="lab_us-gaap_OtherLongTermInvestmentsMember_b5debc57-523b-4323-b280-f434d4feccdb_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>
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    <link:label id="lab_us-gaap_OperatingLeaseWeightedAverageDiscountRatePercent_1ce4d3d6-4e94-4fb7-b9bd-d1a65e323617_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_NetCashProvidedByUsedInFinancingActivities_ad6f5c17-6a75-4fc8-a1f7-f6bffe1058a9_totalLabel_en-US" xlink:label="lab_us-gaap_NetCashProvidedByUsedInFinancingActivities" xlink:role="http://www.xbrl.org/2003/role/totalLabel" xlink:type="resource" xml:lang="en-US">Net cash (used in) provided by financing activities</link:label>
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    <link:label id="lab_us-gaap_CreditFacilityAxis_ef64a5d2-de38-4d76-8ec0-8c580cb24ea8_terseLabel_en-US" xlink:label="lab_us-gaap_CreditFacilityAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Credit Facility [Axis]</link:label>
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    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_CreditFacilityAxis" xlink:to="lab_us-gaap_CreditFacilityAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LongTermDebtFairValue_8d5e5968-3807-446b-a938-159cc6703a6f_terseLabel_en-US" xlink:label="lab_us-gaap_LongTermDebtFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Long-term debt</link:label>
    <link:label id="lab_us-gaap_LongTermDebtFairValue_label_en-US" xlink:label="lab_us-gaap_LongTermDebtFairValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Long-Term Debt, Fair Value</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtFairValue" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_LongTermDebtFairValue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LongTermDebtFairValue" xlink:to="lab_us-gaap_LongTermDebtFairValue" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_EntityRegistrantName_24916c9b-6c37-4e30-beb6-491974b64721_terseLabel_en-US" xlink:label="lab_dei_EntityRegistrantName" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Entity Registrant Name</link:label>
    <link:label id="lab_dei_EntityRegistrantName_label_en-US" xlink:label="lab_dei_EntityRegistrantName" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Entity Registrant Name</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_EntityRegistrantName" xlink:href="https://xbrl.sec.gov/dei/2024/dei-2024.xsd#dei_EntityRegistrantName"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_EntityRegistrantName" xlink:to="lab_dei_EntityRegistrantName" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommercialMortgageBackedSecuritiesMember_e8959d07-9bc1-49a6-b42a-ab8aae4a9764_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/2024/elts/us-gaap-2024.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_AdjToNonPeoNeoCompFnTextBlock_terseLabel_en-US" xlink:label="lab_ecd_AdjToNonPeoNeoCompFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Adjustment to Non-PEO NEO Compensation Footnote</link:label>
    <link:label id="lab_ecd_AdjToNonPeoNeoCompFnTextBlock_label_en-US" xlink:label="lab_ecd_AdjToNonPeoNeoCompFnTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Adjustment to Non-PEO NEO Compensation Footnote [Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_AdjToNonPeoNeoCompFnTextBlock" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.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_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments_1b7966a2-d462-42ce-9c90-2e5c18d79631_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_eece98bd-6735-4761-9083-c1cdeac95f08_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_82a5a1ac-c063-42c0-9dfc-f1d2bb1174b5_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">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/2024/elts/us-gaap-2024.xsd#us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:to="lab_us-gaap_ReinsuranceRecoverableForUnpaidClaimsAndClaimsAdjustments" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_NumberOfUnderwritingDivisions_604495ac-dfb9-4fd1-8f4e-ab72a0cb0f34_terseLabel_en-US" xlink:label="lab_skwd_NumberOfUnderwritingDivisions" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Number of underwriting divisions</link:label>
    <link:label id="lab_skwd_NumberOfUnderwritingDivisions_label_en-US" xlink:label="lab_skwd_NumberOfUnderwritingDivisions" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Number of Underwriting Divisions</link:label>
    <link:label id="lab_skwd_NumberOfUnderwritingDivisions_documentation_en-US" xlink:label="lab_skwd_NumberOfUnderwritingDivisions" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Number of Underwriting Divisions</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_NumberOfUnderwritingDivisions" xlink:href="skwd-20241231.xsd#skwd_NumberOfUnderwritingDivisions"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_NumberOfUnderwritingDivisions" xlink:to="lab_skwd_NumberOfUnderwritingDivisions" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeOrGroupOfInvesteesMember_d6eab7a7-cb13-46a6-a1e6-a66e043a1c00_terseLabel_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeOrGroupOfInvesteesMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Nonconsolidated Investee or Group of Investees</link:label>
    <link:label id="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeOrGroupOfInvesteesMember_label_en-US" xlink:label="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeOrGroupOfInvesteesMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investment, Nonconsolidated Investee or Group of Investees [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeOrGroupOfInvesteesMember" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeOrGroupOfInvesteesMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeOrGroupOfInvesteesMember" xlink:to="lab_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeOrGroupOfInvesteesMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract_2330b887-f831-4d7e-a3f9-ef9ca81a1e15_terseLabel_en-US" xlink:label="lab_skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Held-to-maturity, gross unrealized losses</link:label>
    <link:label id="lab_skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract_label_en-US" xlink:label="lab_skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Continuous Unrealized Loss Position, Accumulated Loss [Abstract]</link:label>
    <link:label id="lab_skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract_documentation_en-US" xlink:label="lab_skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Held-to-Maturity, Continuous Unrealized Loss Position, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:href="skwd-20241231.xsd#skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:to="lab_skwd_DebtSecuritiesHeldToMaturityContinuousUnrealizedLossPositionAccumulatedLossAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_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/2024/ecd-2024.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_AffiliatedEntityMember_125d7620-75c6-42d6-9d61-e1d6ff964508_terseLabel_en-US" xlink:label="lab_srt_AffiliatedEntityMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Affiliated entity</link:label>
    <link:label id="lab_srt_AffiliatedEntityMember_label_en-US" xlink:label="lab_srt_AffiliatedEntityMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Affiliated Entity [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_srt_AffiliatedEntityMember" xlink:href="https://xbrl.fasb.org/srt/2024/elts/srt-2024.xsd#srt_AffiliatedEntityMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_srt_AffiliatedEntityMember" xlink:to="lab_srt_AffiliatedEntityMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardOptionsVestedAndExpectedToVestOutstandingAggregateIntrinsicValue_b522fd7d-2855-45b1-880b-12e2c1b422ec_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/2024/elts/us-gaap-2024.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_FairValueInputsLevel2Member_a304b066-69ed-4d9a-8781-e84333f7f0f8_terseLabel_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel2Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Level 2</link:label>
    <link:label id="lab_us-gaap_FairValueInputsLevel2Member_label_en-US" xlink:label="lab_us-gaap_FairValueInputsLevel2Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Fair Value, Inputs, Level 2 [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FairValueInputsLevel2Member" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_FairValueInputsLevel2Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FairValueInputsLevel2Member" xlink:to="lab_us-gaap_FairValueInputsLevel2Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DisaggregationOfRevenueTableTextBlock_c5131850-af71-41a0-b925-a275f2b5dd32_terseLabel_en-US" xlink:label="lab_us-gaap_DisaggregationOfRevenueTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Disaggregation of Revenue</link:label>
    <link:label id="lab_us-gaap_DisaggregationOfRevenueTableTextBlock_label_en-US" xlink:label="lab_us-gaap_DisaggregationOfRevenueTableTextBlock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Disaggregation of Revenue [Table Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisaggregationOfRevenueTableTextBlock" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_DisaggregationOfRevenueTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisaggregationOfRevenueTableTextBlock" xlink:to="lab_us-gaap_DisaggregationOfRevenueTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodValueNewIssues_b1151e3d-8cef-405c-9071-a7af116879c3_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>
    <link:label id="lab_us-gaap_StockIssuedDuringPeriodValueNewIssues_label_en-US" xlink:label="lab_us-gaap_StockIssuedDuringPeriodValueNewIssues" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Stock Issued During Period, Value, New Issues</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockIssuedDuringPeriodValueNewIssues" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_StockIssuedDuringPeriodValueNewIssues"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_StockIssuedDuringPeriodValueNewIssues" xlink:to="lab_us-gaap_StockIssuedDuringPeriodValueNewIssues" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtInstrumentFixedRatePeriodDomain_cfe46437-7520-4c80-901c-be9095801572_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>
    <link:label id="lab_skwd_DebtInstrumentFixedRatePeriodDomain_label_en-US" xlink:label="lab_skwd_DebtInstrumentFixedRatePeriodDomain" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Instrument, Fixed Rate, Period [Domain]</link:label>
    <link:label id="lab_skwd_DebtInstrumentFixedRatePeriodDomain_documentation_en-US" xlink:label="lab_skwd_DebtInstrumentFixedRatePeriodDomain" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" 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-20241231.xsd#skwd_DebtInstrumentFixedRatePeriodDomain"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtInstrumentFixedRatePeriodDomain" xlink:to="lab_skwd_DebtInstrumentFixedRatePeriodDomain" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_RestatementDateAxis_terseLabel_en-US" xlink:label="lab_ecd_RestatementDateAxis" 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_RestatementDateAxis_label_en-US" xlink:label="lab_ecd_RestatementDateAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Restatement Determination Date [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_ecd_RestatementDateAxis" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_RestatementDateAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_RestatementDateAxis" xlink:to="lab_ecd_RestatementDateAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_dei_Security12bTitle_21a08a0f-f0d1-4871-9ea7-6a80e70fc928_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/2024/dei-2024.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_ConcentrationRiskByTypeAxis_2e7ee6ab-1d42-48a1-af8c-a464f89ce04b_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskByTypeAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Concentration Risk Type [Axis]</link:label>
    <link:label id="lab_us-gaap_ConcentrationRiskByTypeAxis_label_en-US" xlink:label="lab_us-gaap_ConcentrationRiskByTypeAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Concentration Risk Type [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConcentrationRiskByTypeAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ConcentrationRiskByTypeAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConcentrationRiskByTypeAxis" xlink:to="lab_us-gaap_ConcentrationRiskByTypeAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_CommonStockValue_ab0ca754-8990-4220-a320-627215081e82_terseLabel_en-US" xlink:label="lab_us-gaap_CommonStockValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Common stock, $0.01 par value, 500,000,000 shares authorized, 40,127,908 and 39,863,756 shares issued and outstanding, respectively</link:label>
    <link:label id="lab_us-gaap_CommonStockValue_label_en-US" xlink:label="lab_us-gaap_CommonStockValue" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Common Stock, Value, Issued</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockValue" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_CommonStockValue"/>
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    <link:label id="lab_dei_DocumentFinStmtErrorCorrectionFlag_a2d694d4-9938-4a97-995a-0615c91f0ec3_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>
    <link:label id="lab_dei_DocumentFinStmtErrorCorrectionFlag_label_en-US" xlink:label="lab_dei_DocumentFinStmtErrorCorrectionFlag" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Document Financial Statement Error Correction [Flag]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentFinStmtErrorCorrectionFlag" xlink:href="https://xbrl.sec.gov/dei/2024/dei-2024.xsd#dei_DocumentFinStmtErrorCorrectionFlag"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_dei_DocumentFinStmtErrorCorrectionFlag" xlink:to="lab_dei_DocumentFinStmtErrorCorrectionFlag" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ProgramsMember_dc67266e-6821-4229-8bfe-7a1b633b0391_terseLabel_en-US" xlink:label="lab_skwd_ProgramsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Programs</link:label>
    <link:label id="lab_skwd_ProgramsMember_label_en-US" xlink:label="lab_skwd_ProgramsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Programs [Member]</link:label>
    <link:label id="lab_skwd_ProgramsMember_documentation_en-US" xlink:label="lab_skwd_ProgramsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Programs</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ProgramsMember" xlink:href="skwd-20241231.xsd#skwd_ProgramsMember"/>
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    <link:label id="lab_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock_f1ebfc14-83b1-4326-b685-c04d3ec92278_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>
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    <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>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock" xlink:href="skwd-20241231.xsd#skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock" xlink:to="lab_skwd_ScheduleOfUnderwritingAcquisitionAndInsuranceExpensesTableTextBlock" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_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>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract" xlink:to="lab_us-gaap_DisclosureOfCompensationRelatedCostsSharebasedPaymentsAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract_cbb1c2a5-2470-4dc6-96b2-eef136a4119d_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/2024/elts/us-gaap-2024.xsd#us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract" xlink:to="lab_us-gaap_LiabilityForUnpaidClaimsAndClaimsAdjustmentExpenseNetAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract_312de00d-d76e-44db-888f-111949e5edcb_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>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract_label_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Unrealized Loss Position, Accumulated Loss [Abstract]</link:label>
    <link:label id="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract_documentation_en-US" xlink:label="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale And Held-to-Maturity, Unrealized Loss Position, Accumulated Loss</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract" xlink:href="skwd-20241231.xsd#skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract" xlink:to="lab_skwd_DebtSecuritiesAvailableForSaleAndHeldToMaturityUnrealizedLossPositionAccumulatedLossAbstract" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_IndefinitelivedIntangibleAssetsAcquired_35438d15-151f-4073-8690-827fabbea1a4_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/2024/elts/us-gaap-2024.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_skwd_AccidentHealthMember_696c86a0-24b7-4e74-8f8f-4260f10c9a50_terseLabel_en-US" xlink:label="lab_skwd_AccidentHealthMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Accident &amp; Health</link:label>
    <link:label id="lab_skwd_AccidentHealthMember_label_en-US" xlink:label="lab_skwd_AccidentHealthMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Accident &amp; Health [Member]</link:label>
    <link:label id="lab_skwd_AccidentHealthMember_documentation_en-US" xlink:label="lab_skwd_AccidentHealthMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Accident &amp; Health</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_AccidentHealthMember" xlink:href="skwd-20241231.xsd#skwd_AccidentHealthMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_AccidentHealthMember" xlink:to="lab_skwd_AccidentHealthMember" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_RevolvingLineOfCreditDueDecember2023Member_7ec9af99-a62a-4f4d-98a0-f1f746993af3_terseLabel_en-US" xlink:label="lab_skwd_RevolvingLineOfCreditDueDecember2023Member" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Revolving Line Of Credit Due December 2023</link:label>
    <link:label id="lab_skwd_RevolvingLineOfCreditDueDecember2023Member_label_en-US" xlink:label="lab_skwd_RevolvingLineOfCreditDueDecember2023Member" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Revolving Line Of Credit Due December 2023 [Member]</link:label>
    <link:label id="lab_skwd_RevolvingLineOfCreditDueDecember2023Member_documentation_en-US" xlink:label="lab_skwd_RevolvingLineOfCreditDueDecember2023Member" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Revolving Line Of Credit Due December 2023</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_RevolvingLineOfCreditDueDecember2023Member" xlink:href="skwd-20241231.xsd#skwd_RevolvingLineOfCreditDueDecember2023Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_RevolvingLineOfCreditDueDecember2023Member" xlink:to="lab_skwd_RevolvingLineOfCreditDueDecember2023Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_DeferredTaxAssetsOther_34c77052-89f9-4550-a9a6-c6c28c2f9ac0_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/2024/elts/us-gaap-2024.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_FiniteLivedIntangibleAssetsLineItems_d1dc5de7-84c7-43c8-bcf5-0198c810d706_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>
    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsLineItems_label_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Finite-Lived Intangible Assets [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_FiniteLivedIntangibleAssetsLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_FiniteLivedIntangibleAssetsLineItems" xlink:to="lab_us-gaap_FiniteLivedIntangibleAssetsLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_EquityMethodInvestmentsUnfundedCommitment_604be9bb-c216-4723-ab17-c6be29c3d463_terseLabel_en-US" xlink:label="lab_skwd_EquityMethodInvestmentsUnfundedCommitment" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Equity method investments, unfunded commitment</link:label>
    <link:label id="lab_skwd_EquityMethodInvestmentsUnfundedCommitment_label_en-US" xlink:label="lab_skwd_EquityMethodInvestmentsUnfundedCommitment" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Equity Method Investments, Unfunded Commitment</link:label>
    <link:label id="lab_skwd_EquityMethodInvestmentsUnfundedCommitment_documentation_en-US" xlink:label="lab_skwd_EquityMethodInvestmentsUnfundedCommitment" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Equity Method Investments, Unfunded Commitment</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_EquityMethodInvestmentsUnfundedCommitment" xlink:href="skwd-20241231.xsd#skwd_EquityMethodInvestmentsUnfundedCommitment"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_skwd_EquityMethodInvestmentsUnfundedCommitment" xlink:to="lab_skwd_EquityMethodInvestmentsUnfundedCommitment" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_UnpaidPolicyClaimsAndClaimsAdjustmentExpensePolicy_3b0c0629-3759-45c7-a9a1-d671dad6952b_terseLabel_en-US" xlink:label="lab_us-gaap_UnpaidPolicyClaimsAndClaimsAdjustmentExpensePolicy" 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_UnpaidPolicyClaimsAndClaimsAdjustmentExpensePolicy_label_en-US" xlink:label="lab_us-gaap_UnpaidPolicyClaimsAndClaimsAdjustmentExpensePolicy" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Unpaid Policy Claims and Claims Adjustment Expense, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_UnpaidPolicyClaimsAndClaimsAdjustmentExpensePolicy" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_UnpaidPolicyClaimsAndClaimsAdjustmentExpensePolicy"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_UnpaidPolicyClaimsAndClaimsAdjustmentExpensePolicy" xlink:to="lab_us-gaap_UnpaidPolicyClaimsAndClaimsAdjustmentExpensePolicy" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract_7393e11e-b47d-4ebc-a3fe-de2247691df1_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/2024/elts/us-gaap-2024.xsd#us-gaap_NetCashProvidedByUsedInFinancingActivitiesAbstract"/>
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    <link:label id="lab_us-gaap_ConcentrationRiskLineItems_24cae42a-531d-4142-968d-12b918c3d332_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskLineItems" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Concentration Risk [Line Items]</link:label>
    <link:label id="lab_us-gaap_ConcentrationRiskLineItems_label_en-US" xlink:label="lab_us-gaap_ConcentrationRiskLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Concentration Risk [Line Items]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConcentrationRiskLineItems" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ConcentrationRiskLineItems"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConcentrationRiskLineItems" xlink:to="lab_us-gaap_ConcentrationRiskLineItems" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ReportingUnitDomain_242addf2-7575-4e2f-bcf3-7806189ac914_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/2024/elts/us-gaap-2024.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_us-gaap_DeferredIncomeTaxLiabilities_f46f94a6-ddc6-4292-8604-94aa0606e8cd_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/2024/elts/us-gaap-2024.xsd#us-gaap_DeferredIncomeTaxLiabilities"/>
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    <link:label id="lab_us-gaap_EarningsPerShareBasic_687cad34-6921-4b22-91f3-b6fe3d0a50aa_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 dollar per share)</link:label>
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    <link:label id="lab_us-gaap_ProceedsFromIssuanceOfCommonStock_label_en-US" xlink:label="lab_us-gaap_ProceedsFromIssuanceOfCommonStock" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Proceeds from Issuance of Common Stock</link:label>
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    <link:label id="lab_us-gaap_OperatingLeasePayments_4b4012a3-68da-486c-a525-32f9015d0330_terseLabel_en-US" xlink:label="lab_us-gaap_OperatingLeasePayments" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Operating cash outflows from operating leases</link:label>
    <link:label id="lab_us-gaap_OperatingLeasePayments_label_en-US" xlink:label="lab_us-gaap_OperatingLeasePayments" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Operating Lease, Payments</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeasePayments" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_OperatingLeasePayments"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_OperatingLeasePayments" xlink:to="lab_us-gaap_OperatingLeasePayments" xlink:type="arc" order="1"/>
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    <link:label id="lab_srt_ReinsurancePremiumsForInsuranceCompaniesByProductSegmentLineItems_9519fc1e-4559-4512-a0a4-0581fe19e42c_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>
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    <link:label id="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardExpirationPeriod_2c793804-44bc-43fa-9146-3675ba4a2701_terseLabel_en-US" xlink:label="lab_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardExpirationPeriod" 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, expiration period</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardExpirationPeriod" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_SharebasedCompensationArrangementBySharebasedPaymentAwardExpirationPeriod"/>
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    <link:label id="lab_us-gaap_TrademarksMember_24919e50-2922-4ad9-bf80-ad190abf73cc_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>
    <link:label id="lab_us-gaap_TrademarksMember_label_en-US" xlink:label="lab_us-gaap_TrademarksMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Trademarks [Member]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_TrademarksMember" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_TrademarksMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_TrademarksMember" xlink:to="lab_us-gaap_TrademarksMember" xlink:type="arc" order="1"/>
    <link:label id="lab_ecd_AggtPnsnAdjsSvcCstMember_terseLabel_en-US" xlink:label="lab_ecd_AggtPnsnAdjsSvcCstMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Aggregate Pension Adjustments Service Cost</link:label>
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    <link:loc xlink:type="locator" xlink:label="loc_ecd_AggtPnsnAdjsSvcCstMember" xlink:href="https://xbrl.sec.gov/ecd/2024/ecd-2024.xsd#ecd_AggtPnsnAdjsSvcCstMember"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_ecd_AggtPnsnAdjsSvcCstMember" xlink:to="lab_ecd_AggtPnsnAdjsSvcCstMember" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_PropertyPlantAndEquipmentPolicyTextBlock_a3c3e95f-8d03-42ec-9820-bd27065dd5ba_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/2024/elts/us-gaap-2024.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_ShortDurationInsuranceContractAccidentYear2019Member_bafa1d91-e2a0-4fd4-88cc-3c4e216dd0c7_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/2024/elts/us-gaap-2024.xsd#us-gaap_ShortDurationInsuranceContractAccidentYear2019Member"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ShortDurationInsuranceContractAccidentYear2019Member" xlink:to="lab_us-gaap_ShortDurationInsuranceContractAccidentYear2019Member" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ConcentrationRiskCreditRisk_b8ec12bd-1a76-4bd3-92e9-facaa37419e0_terseLabel_en-US" xlink:label="lab_us-gaap_ConcentrationRiskCreditRisk" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Concentration of Credit Risk</link:label>
    <link:label id="lab_us-gaap_ConcentrationRiskCreditRisk_label_en-US" xlink:label="lab_us-gaap_ConcentrationRiskCreditRisk" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Concentration Risk, Credit Risk, Policy [Policy Text Block]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ConcentrationRiskCreditRisk" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_ConcentrationRiskCreditRisk"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_ConcentrationRiskCreditRisk" xlink:to="lab_us-gaap_ConcentrationRiskCreditRisk" xlink:type="arc" order="1"/>
    <link:label id="lab_skwd_ServiceConditionAwardsMember_a6a78c7e-2403-47e4-a723-9de985f63697_terseLabel_en-US" xlink:label="lab_skwd_ServiceConditionAwardsMember" 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_skwd_ServiceConditionAwardsMember_label_en-US" xlink:label="lab_skwd_ServiceConditionAwardsMember" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Service Condition Awards [Member]</link:label>
    <link:label id="lab_skwd_ServiceConditionAwardsMember_documentation_en-US" xlink:label="lab_skwd_ServiceConditionAwardsMember" xlink:role="http://www.xbrl.org/2003/role/documentation" xlink:type="resource" xml:lang="en-US">Service Condition Awards</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_skwd_ServiceConditionAwardsMember" xlink:href="skwd-20241231.xsd#skwd_ServiceConditionAwardsMember"/>
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    <link:label id="lab_us-gaap_PremiumsWrittenGrossAbstract_3377448a-672b-4079-92a2-23e8e84cfa21_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>
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    <link:label id="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseNextTwelveMonths_d58100e1-6dd8-4ace-b008-e5e3345cad52_terseLabel_en-US" xlink:label="lab_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseNextTwelveMonths" 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_us-gaap_EquityMethodInvestmentNonconsolidatedInvesteeDomain_81d2fb70-648f-4288-bb6b-bb4c94897660_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>
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    <link:label id="lab_skwd_MultiLineSolutionsMember_9e23db47-9cbb-4a64-a660-87974366a6f7_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_HeldToMaturitySecuritiesFairValue_65917efd-35d5-4e1c-a164-cbf208fa0036_terseLabel_en-US" xlink:label="lab_us-gaap_HeldToMaturitySecuritiesFairValue" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Total fixed maturity securities, held-to-maturity</link:label>
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    <link:label id="lab_us-gaap_CommercialPortfolioSegmentMember_a94698f2-628f-49c3-a0ba-9835f9e20918_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/2024/elts/us-gaap-2024.xsd#us-gaap_CommercialPortfolioSegmentMember"/>
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    <link:label id="lab_us-gaap_RevenueFromContractWithCustomerTextBlock_eb55c1e7-2067-4b7b-b60f-85799c60fb9c_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>
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    <link:label id="lab_us-gaap_DebtInstrumentNameDomain_0586f26d-7a29-4d90-bab2-36a34f22bd87_terseLabel_en-US" xlink:label="lab_us-gaap_DebtInstrumentNameDomain" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Debt Instrument, Name [Domain]</link:label>
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    <link:label id="lab_us-gaap_AssetsFairValueDisclosure_2d269417-962a-4cdd-931f-17d5ae866675_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</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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFive" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_FiniteLivedIntangibleAssetsAmortizationExpenseYearFive"/>
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    <link:loc xlink:type="locator" xlink:label="loc_dei_DocumentPeriodEndDate" xlink:href="https://xbrl.sec.gov/dei/2024/dei-2024.xsd#dei_DocumentPeriodEndDate"/>
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    <link:label id="lab_us-gaap_SubsidiarySaleOfStockAxis_d0dc3c51-350b-4344-8f81-9a90bc9a7be2_terseLabel_en-US" xlink:label="lab_us-gaap_SubsidiarySaleOfStockAxis" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Sale of Stock [Axis]</link:label>
    <link:label id="lab_us-gaap_SubsidiarySaleOfStockAxis_label_en-US" xlink:label="lab_us-gaap_SubsidiarySaleOfStockAxis" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Sale of Stock [Axis]</link:label>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SubsidiarySaleOfStockAxis" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_SubsidiarySaleOfStockAxis"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_SubsidiarySaleOfStockAxis" xlink:to="lab_us-gaap_SubsidiarySaleOfStockAxis" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue_4877678d-f256-4c5c-b335-c8c38e38d14e_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:loc xlink:type="locator" xlink:label="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue"/>
    <link:labelArc xlink:arcrole="http://www.xbrl.org/2003/arcrole/concept-label" xlink:from="loc_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue" xlink:to="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDue" xlink:type="arc" order="1"/>
    <link:label id="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber_07a9a75a-a1f1-442e-8e1b-f5d80e72218c_periodStartLabel_en-US" xlink:label="lab_us-gaap_ShareBasedCompensationArrangementByShareBasedPaymentAwardEquityInstrumentsOtherThanOptionsNonvestedNumber" xlink:role="http://www.xbrl.org/2003/role/periodStartLabel" xlink:type="resource" xml:lang="en-US">Non-vested, beginning period (in shares)</link:label>
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    <link:label id="lab_us-gaap_ShortdurationInsuranceContractsHistoricalClaimsDurationYearOne_65ba6d9a-4033-4708-be69-a0c0c3444496_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>
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    <link:label id="lab_us-gaap_FairValueByAssetClassAxis_2e4575cf-cfb9-48f7-ba07-ecab1f1f3f8c_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/2024/elts/us-gaap-2024.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_ecd_InsiderTradingArrLineItems_label_en-US" xlink:label="lab_ecd_InsiderTradingArrLineItems" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Insider Trading Arrangements [Line Items]</link:label>
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    <link:label id="lab_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax_12ab0153-67aa-4e4d-a977-9b9892f20486_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>
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    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax" xlink:href="https://xbrl.fasb.org/us-gaap/2024/elts/us-gaap-2024.xsd#us-gaap_OtherComprehensiveIncomeLossAvailableForSaleSecuritiesAdjustmentBeforeReclassificationAdjustmentsNetOfTax"/>
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    <link:label id="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss_label_en-US" xlink:label="lab_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestBeforeAllowanceForCreditLoss" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Debt Securities, Available-for-Sale, Amortized Cost, Excluding Accrued Interest, before Allowance for Credit Loss</link:label>
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    <link:label id="lab_us-gaap_MaterialReconcilingItemsMember_0e38e6a9-74da-4cd4-9bda-0054da95b382_terseLabel_en-US" xlink:label="lab_us-gaap_MaterialReconcilingItemsMember" xlink:role="http://www.xbrl.org/2003/role/terseLabel" xlink:type="resource" xml:lang="en-US">Segment Reporting, Reconciling Item, Excluding Corporate Nonsegment</link:label>
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    <link:label id="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearThree_892c3be4-c09c-485c-bf36-5215f4a61175_terseLabel_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearThree" 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_LesseeOperatingLeaseLiabilityPaymentsDueYearThree_label_en-US" xlink:label="lab_us-gaap_LesseeOperatingLeaseLiabilityPaymentsDueYearThree" xlink:role="http://www.xbrl.org/2003/role/label" xlink:type="resource" xml:lang="en-US">Lessee, Operating Lease, Liability, to be Paid, Year Three</link:label>
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