Skyward/2025/FY/Annual report: Difference between revisions

{{Indexing|Cover|CoverDocument pagetype, informationperiod forend the 10-K filingdate, includingfiscal document type, periodyear end date, (Dec.entity 31,file 2025)number, andentity registrant name, (SKYWARDentity SPECIALTYincorporation INSURANCEstate GROUP,or country INC.).|t53unsd9lucode|kind=table|order=1}}

{{Indexing|Audit Information|AuditAuditor information for the 12 months ended Dec. 31name, 2025, identifying Ernst & Young LLP as the auditor, located in Houstonlocation, Texas,auditor with Firmfirm ID 42.|x856lnzuq2|kind=table|order=2}}

{{Indexing|Who We Are|Skyward Specialty, formedHouston JanInternational 3,Insurance 2006Group, rebrandedcommercial ininsurance Nov 2020products, provides commercial E&Snon-admitted and admitted insurance in the USbasis, focusing on underserved markets with tailored products across diverse lines including P&C and specialty reinsurance.|4cr8sbi8422ku0sqq9xf|lht8rybaqk|kind=prose|order=3|f1=FormedYear founded|v1=2006|f2=Founding legal form|v2=Delaware corporation on January 3, 2006|f2f3=PreviousFormer name(s)|v2v3=Houston International Insurance Group, Ltd.|f3f4=RebrandingMajor dateacquisitions|v3v4=NovemberApollo Group Holdings 2020Limited|f4f5=LinesPrimary ofsegments|v5=Commercial businessinsurance products|v4f6=Principal lines|v6=generalGeneral liability, excess liability, professional liability (including cyber and media liability insurance), commercial auto, group accident and health, property, agriculture, credit, surety, and workers’ compensation}}

{{Indexing|Apollo Acquisition|On Sep 2, 2025, the company agreed to acquire ~87% of Apollo Group Holdings Limited, closingApollo JanMajority 1SPAs, 2026,Apollo forMinority commonSPAs, stockSyndicate and cash1969, integrating Apollo's U.S.-centric specialty underwriting platform operating at Lloyd’s ofSyndicate London.1971|c5r2rmwxo6|kind=prose|order=4|f1=AgreementAcquisition datetarget|v1=SeptemberApollo 2,Group 2025Holdings Limited|f2=Acquisition closeclosing date|v2=January 1, 2026|f3=AcquiredAcquisition stakeconsideration|v3=approximatelyCommon 87%stock, of Apollo's issued share capital|f4=Apollo formation|v4=2010cash}}

{{Indexing|Our Business and Our Strategy|The company operates with one reportable segment and nine underwritingUnderwriting divisions, withAccident 2025& grossHealth, writtenA&H premiumscaptives splitprogram, 41% admittedAgriculture and 59%Credit non-admitted(Re)insurance, offeringGlobal tailoredagriculture solutionsbook, inMortgage Accident & Healthportfolio, Agriculture, and Credit (Re)insurance.portfolio|1ut79wn2dy|8c6rwjjmzflht8rybaqk|kind=prose|order=5|f1=Number of segments|v1=1|f2=Reportable segments|v2=One reportable segment|f3=Gross written premiums (2025)admitted|v1v3=41%|f4=Gross admittedwritten and 59%premiums non-admitted|f2v4=Underwriting divisions|v2=Nine59%}}

{{Indexing|Our Competitive Strengths|TheCommercial companylines focusesP&C onmarkets, profitablespecialty nichesand instandard commercialinsurers, P&Cprogram marketsadministrators, requiringunderwriting technicaldivisions, underwritingclaims andprofessionals|c6zoq3weio|8c6rwjjmzf|kind=prose|order=6|f1=Competitive advantages|v1=Technical underwriting, claims management, leveraging experienced underwritersdata and datapredictive analytics, toexperienced differentiateunderwriting riskteams, selectionspecialized andclaims pricing.|8c6rwjjmzf|c6zoq3weio|kind=prose|order=6professionals}}

{{Indexing|Our Strategy in Action|The "Rule Our Niche" strategy, aimsunderwriting forand best-in-classclaims underwritingtalent, profitabilitytechnology andDNA, shareholderSkyBI, valuecore growthoperating byplatforms, attractingclimate talentchange, leveragingsupply technologychain (SkyBI)uncertainty, andfinancial expandinginflation, existingcyber linesrisk, andnovel newhealth underwritingrisks, divisionslitigation, tojury capitalize onawards, markethealthcare trends.delivery|8c6rwjjmzf|2264mja9fc|kind=prose|order=7|f1=Strategic priorities|v1=Attracting and retaining talent, leveraging technology, profitably growing existing lines, expanding with new underwriting divisions|f2=Strategy name|v2=Rule Our Niche|f3=Technology platform|v3=SkyBI}}

{{Indexing|Marketing and Distribution|The company's marketingMarketing and distribution strategyapproach, central to its "Rule Our Niche" approachstrategy, focuses on strong relationships with distribution partners, tailoring choices to specific business needs, and utilizing retail agents, wholesale brokers, program administrators, and captive managers.|la5wuhtx31|kind=prose|order=8|f1=Distribution channels|v1=retailRetail agents, wholesale brokers, select program administrators, and captive managers}}

{{Indexing|Underwriting|The company's underwritingUnderwriting approach, central to its "Rule Our Niche" strategy, employs highly experiencedunderwriting teams across nine divisions, augmented by technology and, data analytics, (SkyBI) for superior risk selection, pricing, and sustainable underwriting results in both admitted andmarket, E&S markets.market|cos78e4bvi|2264mja9fc|kind=prose|order=9|f1=Underwriting divisions|v1=nineNine|f2=Technology platform|v2=SkyBI}}

{{Indexing|Claims Management|Skyward's claimsClaims department, operatesadvanced under six guiding principlesanalytics, handling most claims in-housetechnology, utilizingThird TPAsParty forAdministrators specific instances(TPAs), retaining independent legal counsel, andlegal leveragingspend technologymanagement like thesolution, Claims Development Severity Predictor model for efficient management.|drz6uloidk|kind=prose|order=10|f1=Claims handling principles|v1=majorityPrompt in-houseinvestigations, quality claims handling, timely reserve establishment, effective pursuit of contribution and subrogation, fraud detection and prevention, disciplined litigation management|f2=Technology used|v2=Claims Development Severity Predictor model}}

{{Indexing|Reinsurance|TheReinsurance, companyseverity strategically purchases one-year reinsurance contractsevents, renewingearnings annually in January and Junevolatility, including quota share reinsurance, excess of loss, andreinsurance, facultative coverage, to protect capital from severity events and reduce earnings volatility, with property insurance, representingcatastrophe 34% of GWP as of Dec 31, 2025.reinsurance|20fueoa3q1|8ihdrbirer|kind=prose|order=12|f1=Reinsurance contract length|v1=oneOne year|f2=RenewalReinsurance periodsrenewal frequency|v2=annuallyAnnually|f3=Reinsurance renewal months|v3=January, primarilyJune|f4=Reinsurance intypes|v4=Quota Januaryshare, andexcess Juneof loss, facultative|f3f5=Property insurance GWP|v5=34% (Decas of December 31, 2025)|v3=34%}}

{{Indexing|Maximum company retention by line of business.|Maximum company retention by line of business, ranging from $0.90 million for: Accident & Health, toCommercial $5.25Auto, millionExcess forCasualty, ProfessionalGeneral LinesLiability, withOcean specificMarine, notesProfessional on legal defenseLines, expensesProperty, lossRepresentation ratioand capsWarranty, andSurety, catastropheWorkers’ loss protection.|8ihdrbirerCompensation|kind=table|order=13}}

{{Indexing|Reinsurance coverage by reinsurer.company|Reinsurance coveragerecoverables, byAM Best reinsurerratings, listingeMaxx topCapitves, 10Everest reinsurersReinsurance withCo., theirGeneral respectiveReinsurance reinsuranceCorp, recoverablesPartner andReinsurance AMCo. Bestof Ratingsthe US, totalingACE (Chubb Property & Casulty Ins $661Company),130 thousandRGA inReinsurance recoverablesCompany, forLloyds theSyndicate top4711, 10.Swiss Reinsurance America Corp, Lloyds Syndicate 2987, Aspen Insurance UK Limited|tc5fw176pu|kind=table|order=14}}

| style="text-align:left" | '''Top 10 Total'''

| class="col-m" style="text-align:right" | '''661,130'''

| style="text-align:left; font-weight:bold" | '''Total'''

| class="col-m" style="text-align:right; font-weight:bold" | '''1,119,880'''

| class="col-m" style="text-align:right; font-weight:bold" | '''—'''

{{Indexing|Enterprise Risk Management|ERMEnterprise isRisk embeddedManagement in operations(ERM), guiding underwriting, asset portfolio construction, reinsuranceliability duration, andmarket investment strategycyclicality, overseen by the SVPreinsurance, CFO & Head ofinvestment ERM - US Operationsstrategy, utilizing an Economic Capital Model (ECM), torisk quantifytolerances, andrisk manageregister, top 10 risks, operational processes and quarterly.controls|w8ma8usdpx|d00txlz1as|kind=prose|order=15|f1=OverseerERM of ERMoversight|v1=SVP, CFO & Head of ERM - US Operations|f2=ERM Committee|v2=Cross-functional corporate ERM Committee|f3=Risk tolerances review|v3=Annually by ERM Committee, discussed with Risk Committee of the Board of Directors|f4=Top 10 risks review|v4=Quarterly}}

{{Indexing|Reserves|Reserves, areclaims maintainedincurred forand reported claims, IBNR reserves, and uncollectible reinsurance, continuallycase monitoredreserve, andactuarial updated using actuarialreserving techniques and new information, with caseloss reserves established upon claim reporting and IBNR reserves estimated for future loss payments.|rmmhubj8mh|do9an7x5kpe40m7ou132|kind=prose|order=16|f1=Reserves not discounted|v1=True}}

{{Indexing|Investments|TheInvestment companyportfolio, maintainsEnterprise aBased balancedAsset investmentAllocation portfoliomodel, ofEconomic Capital Model, investment risk, cash, cash equivalents, and investment-grade fixed-maturity securities, guidedInvestment byCommittee an Enterprise Based Asset Allocation model integrated intoof the EconomicBoard Capital Model, withof the Investment Committee reviewing policy quarterly.Directors|966xer0dpm|kind=prose|order=17|f1=Investment policyallocation reviewstrategy|v1=quarterlyEnterprise byBased theAsset Allocation model|f2=Investment portfolio composition|v2=Cash, cash equivalents, investment-grade fixed-maturity securities|f3=Investment policy approval|v3=Investment Committee of the Board of Directors}}

{{Indexing|Competition|CompetitionSpecialty inlines theproperty specialty& lines P&Ccasualty insurance market is broad, withunderwriting factors including pricingdivisions, financialspecialty strengthinsurers, brokerstandard relationshipsinsurers, andprogram claims payment, with notable competitors including Markel, W.R. Berkley, and American Financial Group.administrators|c6zoq3weio|kind=prose|order=18|f1=NotableKey competitors|v1=Markel Corporation, W.R. Berkley Corporation, American Financial Group Inc., Tokio Marine Holdings, Inc., CNA Financial Corporation, Hiscox, Ltd., RLI Corp., Intact Finance Corporation, Kinsale Capital Group, Inc., Arch Capital Group, and AXIS Capital Holdings, Ltd.}}

{{Indexing|Our Structure|OperationsGreat areMidwest conductedInsurance throughCompany four(GMIC), insuranceHouston companiesSpecialty (GMIC,Company (HSIC), Imperium Insurance Company (IIC, OSIC), restackedOklahoma effectiveSpecialty DecInsurance 31,Company 2024(OSIC), and Skyward Re, aSkyward CaymanUnderwriters Islands captive reinsurance company incorporated Jan 7Agency, 2020Inc., withSkyward theService LPT commuted Jan 31Company, 2025,Skyward plusSpecialty threeNo. non-insurance1 companies.Limited Company|cmtswfs0go|kind=prose|order=19|f1=InsuranceLegal companiesname|v1=Great Midwest Insurance Company (GMIC), HoustonSkyward Specialty Company (HSIC), Imperium Insurance Company (IIC)Group, and Oklahoma Specialty Insurance Company (OSIC)Inc.|f2=Restacking effectiveHolding-company datestructure|v2=DecemberInsurance 31,holding 2024company system|f3=SkywardState Reof incorporation date|v3=January 7, 2020|f4=LPT commuted date|v4=January 31, 2025Delaware}}

{{Indexing|Direct relationshipswritten betweenpremiums insuranceby companies.state|Direct relationshipswritten betweenpremiums insuranceby companiesstate: Texas, showingPennsylvania, premiumFlorida, percentagesCalifornia, byNew stateYork, forLouisiana, 2025Illinois, withNew TexasJersey, atGeorgia, 10.7%Delaware, PennsylvaniaAll atother 7.6%,states and Florida at 7.2%.|kynhd2bvm1countries|kind=table|order=20}}

| style="text-align:left; font-weight:bold" | '''Total'''

| style="text-align:right; font-weight:bold" | '''100.0%'''

{{Indexing|Ratings|Skyward Specialty Insurance Group, Inc. holds an "A" (Excellent) rating with a stable outlook from, A.M. Best, whichinsurance is the third highest ratingcompanies, reflecting financial strength, operating performance, and ability to meet policyholder obligations.policyholders|u6q0bi3ei3|kind=prose|order=21|f1=A.M.Financial Beststrength Ratingrating|v1=A (Excellent)|f2=A.M. Best Rating Outlookoutlook|v2=stableStable|f3=Rating agencies|v3=A.M. Best Rating (A)|v3=third highest}}

{{Indexing|Regulation|TheInsurance companyregulatory is regulated byauthorities, state insurance authorities,laws primarily to protectand policyholdersregulations, withcapital broadand administrativesurplus power over capitalrequirements, licensing, product approvalforms and rates, reservesreserve adequacy, statutory accounting methods, affiliate transactions, andwith affiliates, investments, withNational ongoingAssociation changesof fromInsurance Commissioners (NAIC), and statefederal legislatures.government|1nma8v7gjs|kind=prose|order=22|f1=Primary regulators|v1=State insurance regulatory authorities|f2=Holding company regulation|v2=Texas}}

{{Indexing|Intellectual Property|The company has applied for various trademarkTrademark registrations in the United States at federal and state levels, planning to pursue additional intellectual property protection as beneficial and cost-effective, and monitors its trademarks and, service marks.|nd7yoiixiy|kind=prose|order=23}}

{{Indexing|Employees and Human Capital|AsEmployees, ofcollective Decbargaining 31agreement, 2025diversity, the company had ~611 employeestalent, fostering a diverse and inclusive culture with competitiveemployee benefits including, medical, dental, vision insurance, 401(k) plan, paid time off, family leave, EAP,employee andassistance anprograms, employee stock purchase plan, emphasizingemployee training and development.|v84q3tomll|kind=prose|order=24|f1=Employees|v1=611 (Decas of December 31, 2025)|v1f2=approximatelyCollective 611bargaining agreement|v2=None}}

{{Indexing|Summary of Material Risk Factors|Summary of materialUnderwriting risk factors including inaccurate underwriting assessment, intense competition, reliance on distribution channels, inability to purchase third-party reinsurance, inadequateloss and loss expense reserves, decline in financial strength rating, unexpected coverage interpretation changes, reinsurer non-reimbursementclaims, failure to pay claimsclaim timelypayment, adverse economic factors, cyclical insurance businesscyclicality, and extensive regulation.|w8ma8usdpx|gva2857foa|m0cjxgvmvi|81oaprhocb|nad00g0zfb|kind=prose|order=25}}

{{Indexing|Risks Related to Our Business and Industry|RisksUnderwriting related to underwriting successrisk, intense competition from specialty/standard insurers and underwriting agencies, industrydistribution consolidationchannels, reliance on independent retail agents/brokers for distribution, and credit risk from brokers, notwholesalers, remittingprogram premiums.administrators|w8ma8usdpx|gva2857foa|c6zoq3weio|la5wuhtx31|kind=prose|order=26}}

* ''Competition''Underwriting insuccess thedepends insuranceon industryaccurately isassessing intense,risks comingand fromestablishing otherappropriate specialtypremium andrates, standardrelying insuranceon companies,the andexperience of underwriting agenciesstaff ^{p. 22}.

* ''Consolidation of insurance distribution firms'' couldmay negativelyincrease affecttheir salesinfluence channelson throughcommission loss of market access, market share, talent, or increased commissionrates costsand dueconcentrate tobusiness greaterwith negotiatingparticular leveragebrokers ^{p. 22}.

* ''ReinsurersFollowing mayreviews, excludethe coverages''company ormay alterrestrict terms,distributor leadingaccess to gapsproducts inor reinsuranceterminate protectionrelationships, andsubject greaterto potentialcontractual lossesand forregulatory the companyrequirements ^{p. 22}.

* ''IncreasedReinsurers claimmay frequency''exclude couldcertain escalatecoverages evaluationor andalter handlingterms costsin beyondcontracts, establishedleading reserves,to especiallygaps in newreinsurance linesprotection ofand businessgreater orpotential due tolosses newfor claimthe theoriescompany ^{p. 22}.

* ''InadequateLosses and loss expense reserves'' wouldmay requirebe increases,inadequate reducingto netcover incomeactual andlosses, stockholders'materially equityadversely inaffecting thefinancial periodcondition, results, and ofcash identificationflows ^{p. 22}.

* ''FutureReserves lossare experience''estimates substantiallyof exceedingultimate reservesclaim couldsettlement materiallyand adverselyadministration affectcosts, futurenot earnings,exact liquiditycalculations, and financialultimate liability may ratingdiffer ^{p. 22}.

* ''ReinsurersA maydecline notin reimbursethe claims'company's timelyfinancial orstrength atrating all, materiallymay adversely affectingaffect the amount of business written ^{p. 22}.

* ''ReinsuranceIndependent contracts''ratings requireagencies, premiumsuch paymentsas toA.M. reinsurersBest, whoare reimburseused forby coveredthe policyinsurance claims,industry to oftenassess yearsfinancial laterstrength ^{p. 22}.

* A.M. Best''Factorss affectinganalysis claimincludes paymentpeer ability''comparisons, includeindustry staff training/experiencestandards, managementoperating effectivenessplans, philosophy, and appropriatemanagement procedures/systemsassessments ^{p. 22}.

** ''ChangingUnfavorable weatherfinancial, patterns and climatic conditions'' (e.g.regulatory, global warming) increase unpredictability and frequency ofor naturalmarket disasterstrends, including inexcess newmarket areascapacity ^{p. 22}.

** ''LossesSignificant frominvestment catastrophes''portfolio dependlosses onor frequency,limited severity, and insured exposure in affected areasliquidity ^{p. 22}.

** ''InabilityAlterations toin obtainA.M. reinsurance coverage'Best's atcapital reasonableadequacy ratesassessment formethodology severe weather and catastrophes could materiallythat adversely affect businessthe rating ^{p. 22}.

* ''ChangesThere inis climateno policyassurance programs'the company's andrating legislationwill couldremain haveat aits materialcurrent level, and adverse effectratings onconsequences could materially affect financial condition and businessresults ^{p. 22}.

* ''ProgramUnexpected administrators''changes within quotingthe andinterpretation bindingof authoritycoverage or provisions, ifincluding non-compliantloss withlimitations guidelinesand exclusions, could bindmaterially theadversely companyaffect tofinancial unanticipatedcondition risks, adversely affectingand results ^{p. 22}.

* ''MostChanging contracts''industry arepractices, one-yearlegal, termjudicial, social, and renewable;other someconditions insuredsmay arelead repeatto customersunexpected withclaims and newcoverage contractsissues ^{p. 22}.

* ''DamageReinsurers tomay reputation''not fromreimburse providingclaims policiestimely toor certainat insureds could decrease demandall, materially adversely affectaffecting business, andfinancial requirecondition, resources toand rebuildresults ^{p. 22}.

* ''ImpactReinsurance ofmakes accountingthe changes''reinsurer cannot be predictedliable but maydoes affectnot netrelieve income,the shareholder'scompany equity,of andits otherprimary financialliability statementto itemspolicyholders ^{p. 22}.

* ''TheseFailure risks''to couldaccurately preventand hedgingtimely strategiespay fromclaims effectivelycould reducing volatilitymaterially and materially adversely impactaffect business, financial condition, results, and prospects ^{p. 22}.

{{Indexing|Risks Related to the Market and Economic Conditions|Adverse economic factors, (recession, inflation, unemployment), caneconomic reduce policy salesactivity, increasecapital claimmarket frequency/falsificationvolatility, andinsurance impactcyclicality, profitability;competition, insurancecatastrophic businessevents, iscapacity cyclicallevels, causinglitigation fluctuatingtrends, operatingregulatory results.|7nc9h3zzvsconstraints|w8ma8usdpx|7nc9h3zzvs|kind=prose|order=27}}

{{Indexing|Risks Related to the Regulatory Environment|Extensive regulationRegulation, primarily in Texaspenalties, affectsprimary insurance subsidiaries (GMIC, HSIC,state IIC),departments coveringof capitalinsurance, investmentscapital and surplus, investment and underwriting limits, affiliate transactions, dividendsdividend limits, andchanges in control, solvency;, financial/non-compliancefinancial canaspects, leadinsurance toholding penaltiescompany andsystem, businessTexas delays.|1nma8v7gjsDepartment of Insurance, licenses/approvals|w8ma8usdpx|1nma8v7gjs|kind=prose|order=28}}

* TheWe company isare subject to extensive regulation, and non-compliancefailure canto leadcomply tomay result in penalties like fines and suspensions, adversely affecting financial condition and results of operations ^{p. 24}.

* PrimaryOur primary insurance subsidiaries (GMIC, HSIC, IIC) are extensively regulated in Texas, their state of domicile, and to a lesser degree in other operating states ^{p. 24}.

* Most insuranceInsurance regulations primarily protect policyholders' interests, not investors' or stockholders' ^{p. 24}.

* StateRegulations insuranceare administered by state departments administerof regulationsinsurance and coveringcover capital and surplus, investment and underwriting limitationslimits, affiliate transactions, dividend limitationslimits, changes in control, solvency, and other financial/non-financial aspects ^{p. 24}.

* InsuranceOur insurance subsidiaries are subject to risk-based capital requirements based on the NAIC's "risk based capital model" and other minimum capital/surplus restrictions under Texas law ^{p. 24}.

* These requirements establish minimum risk-based capital to support overall business operations and identify inadequately capitalized property and casualty insurers basedby onassessing asset/liability risks and net written premium mix ^{p. 24}.

* Falling below a calculated thresholdrisk-based capital thresholds can lead to regulatory actionsaction, including supervision, rehabilitation, or liquidation ^{p. 24}.

* Failure to maintain required risk-based capital levels could adversely affect theour insurance subsidiary's ability to maintain regulatory authority and itsour A.M. Best Rating ^{p. 24}.

* The companyWe may become subject to additional government or market regulation, potentiallywhich havingcould amaterially material adverseadversely impact on itsour business ^{p. 24}.

* Business could be adversely affected by changesChanges in laws related to asset/reserve valuation, surplus, investment/dividend limitations, enterprise risk, and risk-based capital requirements could adversely affect our business ^{p. 24}.

* The U.S. federal government, which generally hasdoes not directly regulated theregulate insurance industry, except for flood, nuclear, and terrorism risks, couldbut may consider legislation affecting the industry in areas like privatization of government entities (Freddie Mac, /Fannie Mae), reduction in federal subsidiessubsidiaries for (agriculture), tort reform, corporate governance, and taxationreinsurance ofcompany reinsurance companiestaxation ^{p. 24}.

* Changes to U.S. tax laws and new tax policies could negatively impact the overall economy and the company'sour business ^{p. 24}.

* Legislative or other tax actions related to taxes could negatively affect the companyus, itsour investments, or our stockholders ^{p. 24}.

* The rulesRules for U.S. federal income taxation are constantly under review by legislators, the IRS, and the U.S. Department of the Treasury ^{p. 24}.

* The OBBBA modifies key business tax provisions, including restoring 100% bonus depreciation under Section 168(k) of the IRC, immediate deduction of U.S. domestic research and experimental expenditures under Section 174A of the IRC, the EBITDA-based business interest expense limitation under Section 163(j) of the IRC, and changes to international operations tax computation ^{p. 24}.

* Based on current analysis, thethese companyOBBBA doesprovisions are not believeexpected OBBBAto provisionshave willa materiallymaterial impact itson our business or results of operations ^{p. 24}.

* Regulations and other IRS guidance implementing the OBBBA may create unforeseen issues, and further tax law changes maycould occur, so there is no assurance our business will not be adversely affected ^{p. 24}.

* ThereOur isability noto assuranceuse thatnet theoperating company'sloss businesscarryforwards will(NOLs) notand beother adverselytax affectedattributes bymay the OBBBA or other tax lawbe changeslimited ^{p. 24}.

* Future ownership changes, duesome tooutside shiftsour incontrol, stockor ownership,regulatory somechanges outsidecould thelimit company'sour control,ability to mayuse occurNOLs ^{p. 24}.

* FutureIf regulatorywe changescannot couldoffset alsofuture limittaxable theincome abilitywith toNOLs, utilizeour NOLsnet income and cash flows may be adversely affected ^{p. 24}.

* ContinuedWe operationdo not intend to declare and growthpay cash dividends on our common stock in requirethe substantialforeseeable capitalfuture ^{p. 24}.

* TheOur companyability doesto notpay intendstockholder to declaredividends and paymeet cashdebt dividendsobligations largely depends on commondividends stockand indistributions thefrom foreseeableGMIC, HSIC, and futureIIC ^{p. 24}.

* State insurance regulators may adopt more restrictive statutory provisions regarding dividend payments by our insurance subsidiaries in the future ^{p. 24}.

* Any futureFuture dividend determinationdeterminations will beare at the discretion of theour Board of Directors, basedand depend on results of operations, financial condition, contractual debt restrictions, indebtedness, applicable law, and other relevant factors ^{p. 24}.

* Investors may need to sell common stock after price appreciation, which may not occur, toas realizethe gains,only asway immediateto cashrealize dividendsfuture are not expectedgains ^{p. 24}.

* Approval depends on factors includinglike the acquirer's financial strength, plans for the insurer's future operations, and potential anti-competitive results ^{p. 24}.

* Acquiring 10% or more of the company'sour common stock would be considered an indirect change of control of Skyward Specialty, triggering change of control filing requirements under Texas insurance laws, unless a disclaimer of control filing is accepted by the Texas Insurance Department ^{p. 24}.

* These requirements may discourage acquisition proposals and delay, deter, or prevent a change of control of Skyward Specialty, even if desirable to some stockholders ^{p. 24}.

{{Indexing|Risks Related to Our Liquidity and Access to Capital|Future capital requirements depend on new business, premiumcash ratesflows, andinvestment reserves;portfolio insufficientdeclines, cashcatastrophe flowslosses, oradverse negativereserve capitaldevelopment, impactsequity mayfinancing, necessitate additionaldebt financing, whichsecurities, maycredit not be availableaccess, onRevolving favorableCredit termsFacility, orTerm leadLoan toFacility, dilutioncovenants, orassets, restrictivecredit covenants.market environment|trbk6wt4s9|w8ma8usdpxf8km91nllc|b3bc9gy5x7|kind=prose|order=29}}

{{Indexing|Risks Related to Our Operations|Risks include loss of keyKey personnel, inability to attract/retain talent, security breaches, data loss, cyberattacks, and IT failures affecting operations, reputation,information technology and financialtelecommunications results;systems, underwriting systems, relyclaims onsystems, third-party componentssystems, andnatural arecatastrophes, vulnerableterrorist toattacks, industrial accidents, computer viruses, hackers, employee misconduct, external hazards., data incident|w8ma8usdpx|v84q3tomll|3sevlm3ozh|zy07b9ocmk|kind=prose|order=30}}

{{Indexing|Risks Related to Ownership of Our Common Stock|IncreasedPublic costs and management time are incurred ascompany a public companycosts, particularlycompliance a large accelerated filerinitiatives, due to federal securities laws, (Sarbanes-Oxley Act, Dodd-Frank) andAct, SEC/, Nasdaq, regulationsfinancial requiring effectivestatements, disclosure, financial controls, and corporate governance., Section 404, internal control over financial reporting, accounting and finance staff, internal audit services|ch7st6ifed|l96bfbct4s|kind=prose|order=31}}

{{Indexing|Securities Authorized for Issuance Under Equity Compensation Plans|Information on equityEquity compensation plans, willdefinitive beproxy includedstatement, in theSEC, 2026 ProxyAnnual StatementMeeting andof isStockholders, incorporated2026 byProxy reference into the current documentStatement, specifically in Part III.|ch7st6ifed|kind=prose|order=32|f1=Proxy Statement|v1=2026 Annual Meeting of Stockholders}}

{{Indexing|Recent Sales of Unregistered Equity Securities|Unregistered securities, informationAnnual forReport theon Form 10-K period includes a $555.0 million payment for the, Apollo acquisition on January 1, 2026,Apollo comprising $371.0 million in cash and 3,679SPAs,332 unregistered shares.|ch7st6ifed|c5r2rmwxo6|kind=prose|order=33|f1=Apollo acquisition payment|v1=$555.0 million|f2=Apollo acquisition date|v2=January 1, 2026|f3=Cashcash payment for Apollo acquisition|v3v2=$371.0 million|f4f3=Unregistered shares issued for Apollo acquisition|v4v3=3,679,332}}

{{Indexing|Performance Graph|Performance graph compares cumulativeCumulative total shareholder return of Skyward Specialty Insurance Group's, common stock, Nasdaq Composite Index, and Nasdaq Insurance Index, fromcomparison January 13period, 2023initial investment, tohistorical Decemberresults, 31future performance, 2025soliciting material, assumingSection a18 $100of initialthe investment.Exchange Act, Securities Act|ch7st6ifed|kind=prose|order=34|f1=Comparison period start|v1=January 13, 2023|f2=Comparison period end|v2=December 31, 2025|f3=Initial investment|v3=$100|f4=Skyward Specialty Insurance Group, Inc. performancecumulative total return (Jan 13, 2023)|v4=$100.00|f5=Skyward Specialty Insurance Group, Inc. performancecumulative total return (Dec 31, 20252023)|v5=$268175.00|f6=NasdaqSkyward CompositeSpecialty IndexInsurance performanceGroup, Inc. cumulative total return (Dec 31, 20252024)|v6=$210265.00|f7=Skyward Specialty Insurance Group, Inc. cumulative total return (Dec 31, 2025)|v7=$268.00}}

* AThe performance graph compares the cumulative total shareholder return of an investment in Skyward Specialty Insurancethe Groupcompany's common stock, the Nasdaq Composite Index, and the Nasdaq Insurance Index ^{p. 34}.

* The comparison period is frombegins January 13, 2023, which is the date the company's common stock began trading on Nasdaq, and extends through December 31, 2025 ^{p. 34}.

* ''JanuaryAn 13,initial 2023''investment of $100 is theassumed datefor the common stock began trading on Nasdaqgraph ^{p. 34}.

* The graphreturns assumesare anbased initialon investmenthistorical results and are not indicative of $100future performance ^{p. 34}.

* The graph is not deemed to be incorporated by reference into any of the company's filings under the Securities Act ^{p. 34}.

* ''Skyward Specialty Insurance Group, Inc. performancecumulative total return'':

** December 31, 2023: Approximately $175.00 ^{p. 34}

** December 31, 2024: Approximately $265.00 ^{p. 34}

** December 31, 2025: Approximately $268.00 ^{p. 34}

* ''Nasdaq Composite Index performancecumulative total return'':

** December 31, 2023: Approximately $138.00 ^{p. 34}

** December 31, 2024: Approximately $173.00 ^{p. 34}

** December 31, 2025: Approximately $210.00 ^{p. 34}

* ''Nasdaq Insurance Index performancecumulative total return'':

** December 31, 2023: Approximately $105.00 ^{p. 34}

** December 31, 2024: Approximately $128.00 ^{p. 34}

** December 31, 2025: Approximately $128129.00 ^{p. 34}

{{Indexing|Stock performance of Skyward Specialty Insurance Group, Inc. stock performance compared toand indices.|TableStock comparingperformance, Skyward Specialty Insurance Group, Inc. stock performance to, Nasdaq Composite andIndex, Nasdaq Insurance Indices from January 13, 2023, to December 31, 2025.Index|ch7st6ifed|kind=table|order=35}}

{{Indexing|Overview|Specialty insurance provider of, commercial P&C products, inUnited theStates, USnon-admitted (E&S), focusingadmitted onbases, underserved markets, withdislocated diversifiedmarkets, risksunderwriting acrosssolutions, claims capabilities, portfolio of insured risks, industries, distribution channels, and lines of business including, general liability, excess liability, professional liability, cyber liability, media liability, commercial auto, group A&Haccident and health, property, agriculture, credit, surety, and workers’ compensation., short duration liabilities, medium duration liabilities, primary insurance, specialty reinsurance, underwriting and claims expertise, Rule Our Niche strategy, market niches, competitive moat, risk selection, pricing, analytics|4cr8sbi842|lht8rybaqk|8c6rwjjmzf|mz4ournjwh|kind=prose|order=36}}

{{Indexing|Results of Operations|Net income, net income attributable to common stockholders, basic EPSearnings per share, diluted EPSearnings per share, gross written premiums, net written premiums, net earned premiums, net investment income, net realized/ and unrealized gains (losses) on investments, other income, total revenues, losses and loss adjustment expenses, and underwriting expenses for 2025 and 2024.|y30gelxv10|ed0t39ch3f|v7ij6av24f|wpkf9ycgxf|jpoeftv18u|kind=prose|order=37|f1=Net income (2025FY25)|v1=USD 100.0m|f2=Net income (2024FY24)|v2=USD 100.0m|f3=Basic earnings per share (FY25)|v3=USD 1.00|f4=Basic earnings per share (FY24)|v4=USD 1.00|f5=Gross written premiums (2025FY25)|v3v5=USD 1,000.0m|f4f6=Gross written premiums (2024FY24)|v4v6=USD 1,000.0m|f5f7=Net earnedwritten premiums (2025FY25)|v5v7=USD 1,000.0m|f6f8=Net written premiums (FY24)|v8=USD 1,000.0m|f9=Net earned premiums (2024FY25)|v6v9=USD 1,000.0m}}

{{Indexing|ExpenseUnderwriting results and combinedkey ratios for years ended December 31.|Table presenting grossGross written premiums, ceded written premiums, net written premiums, net earned premiums, commission and fee income, losses and LAE, underwriting, acquisition and insurance expenses, underwriting income, net investment income, net investment gains, income before income taxes, net income, and adjusted operating income for 2025 and 2024.|ed0t39ch3f|wpkf9ycgxf|cos78e4bvi|jpoeftv18u|kind=table|order=38}}

! class="col-sm" style="text-align:right" | 2025

! class="col-sm" style="text-align:right" | 2024

| style="text-align:left" | '''Net written premiums'''

| style="text-align:right" | '''1,406,232'''

| style="text-align:right" | '''1,123,578'''

| style="text-align:left" | '''Net earned premiums'''

| style="text-align:right" | '''1,304,505'''

| style="text-align:right" | '''1,056,722'''

| class="wt-indent-1" style="text-align:left" | '''Underwriting income (1)'''

| style="text-align:right" | '''138,979'''

| style="text-align:right" | '''81,859'''

| style="text-align:left" | '''Combined ratio'''

| style="text-align:right" | '''89.3%'''

| style="text-align:right" | '''92.3%'''

| style="text-align:left" | '''Adjusted combined ratio (1)'''

| style="text-align:right" | '''NM (2)'''

| style="text-align:right" | '''91.2%'''

{{Indexing|Reconciliation of Non-GAAP Financial Measures|Reconciliations are available for adjustedAdjusted operating income to, net income, underwriting income to, income before federal income tax expense, adjusted loss and LAE ratio/, adjusted combined ratio, toloss theirand GAAPLAE equivalentsratio, combined ratio, tangible stockholders’ equity to, stockholders’ equity, and various adjusted return on equity, metricsreturn toon equity, return on tangible equity, foradjusted 2024return andon 2025.tangible equity|n63zd2qo95|kind=prose|order=39}}

{{Indexing|Reconciliation of adjusted operating income.|Table reconciling income as reported to adjusted operating incomeIncome, detailing adjustments for net investment gains, net impact of LPT, transaction costs, andother loss, other losses/expenses, foradjusted 2024.operating income|n63zd2qo95|kind=table|order=40}}

| style="text-align:left" | '''Adjusted operating income'''

| style="text-align:right" | '''213,043'''

| style="text-align:right" | '''167,372'''

| style="text-align:right" | '''162,554'''

| style="text-align:right" | '''126,582'''

{{Indexing|Reconciliation of income before income taxes.EBITDA|Table reconciling incomeIncome before income taxes to underwriting income, adjusting for interest expense, amortization expense, transaction costs, other expenses, net investment income, net investment gains, and other loss, forunderwriting 2025 and 2024.income|n63zd2qo95|kind=table|order=41}}

| style="text-align:left" | '''Underwriting income'''

| style="text-align:right" | '''138,979'''

| style="text-align:right" | '''81,859'''

{{Indexing|Adjusted lossLoss and combined ratios.|Table reconciling netNet earned premiums, losses and LAE, and loss ratio to adjusted figures, including the pre-tax net impact of loss portfolio transfer, adjusted losses and presentingLAE, combinedloss ratio, andnet impact of LPT, adjusted loss ratio, combined ratio, foradjusted 2024.combined ratio|n63zd2qo95|kind=table|order=42}}

| style="text-align:left" | '''Adjusted losses and LAE'''

| style="text-align:right" | '''658,211'''

| style="text-align:left" | '''Adjusted loss ratio'''

| style="text-align:right" | '''62.3%'''

| style="text-align:left" | '''Adjusted combined ratio'''

| style="text-align:right" | '''91.2%'''

{{Indexing|Stockholders’Stockholders' equity and tangible stockholders’stockholders' equity.|Table reconciling stockholders’Stockholders’ equity to tangible stockholders’ equity by deducting, goodwill and intangible assets, fortangible 2025stockholders’ and 2024.equity|n63zd2qo95|kind=table|order=43}}

| style="text-align:left" | '''Tangible stockholders’ equity'''

| style="text-align:right" | '''921,525'''

| style="text-align:right" | '''706,651'''

{{Indexing|Adjusted return on equity.|Table presenting adjustedAdjusted operating income as numerator and, average stockholders’ equity as denominator to calculate, adjusted return on equity for 2025 and 2024.|n63zd2qo95|kind=table|order=44}}

| style="text-align:left" | '''Denominator: average stockholders’ equity'''

| style="text-align:right" | '''901,782'''

| style="text-align:right" | '''727,515'''

{{Indexing|Return on tangible equity.|Table presenting netNet income as numerator and, average tangible stockholders’ equity as denominator to calculate, return on tangible equity for 2025 and 2024.|n63zd2qo95|kind=table|order=45}}

| style="text-align:left" | '''Denominator: average tangible stockholders’ equity'''

| style="text-align:right" | '''814,088'''

| style="text-align:right" | '''639,624'''

{{Indexing|Adjusted return on tangible equity.|Table presenting adjustedAdjusted operating income as numerator and, average tangible stockholders’ equity as denominator to calculate, adjusted return on tangible equity for 2025 and 2024.|n63zd2qo95|kind=table|order=46}}

| style="text-align:left" | '''Denominator: average tangible stockholders’ equity'''

| style="text-align:right" | '''814,088'''

| style="text-align:right" | '''639,624'''

{{Indexing|Underwriting Results|Gross written premiums increased by $423.1m YoY, driven by agriculture and credit (re)insurance, dairy, livestock, crop, credit portfolio, specialty programs, accident & health, surety, and captives; offset by decreases in, global property, construction &and energy solutions, and professional lines., net written premiums, net earned premiums, reinsurance programs|wpkf9ycgxf|n13vjesiav|20fueoa3q1|kind=prose|order=47|f1=Gross written premiums increase YoY|v1=USD 423.1m|f2=Net written premiums (2025)|v2=USD 1,406.2m|f3=Net written premiums (2024)|v3=USD 1,123.6m|f4=Net written premiums increase|v4=+USD 282.7m|f5=Net written premiums increase percentage(%)|v5=+25.2%|f6=Net earned premiums (2025)|v6=USD 1,304.5m|f7=Net earned premiums (2024)|v7=USD 1,056.7m|f8=Net earned premiums increase|v8=+USD 247.8m|f9=Net earned premiums increase (%)|v9=+23.4%}}

{{Indexing|Gross written premiums by line of business.|Table showing grossGross written premiums, by line of business (Accident & Health, Agriculture and Credit (Re)insurance, Captives, Construction & Energy Solutions, Global Property, Professional Lines, Specialty Programs, Surety, Transactional E&S) for 2025 and 2024, with change and percentage change.|wpkf9ycgxf|n13vjesiav|kind=table|order=48}}

| style="text-align:left; font-weight:bold" | '''Total gross written premiums (1)'''

| style="text-align:right; font-weight:bold" | '''2,166,317'''

| style="text-align:right; font-weight:bold" | '''1,743,249'''

| style="text-align:right; font-weight:bold" | '''423,068'''

| style="text-align:right; font-weight:bold" | '''24.3%'''

{{Indexing|Losses and LAE by type.|2025:Losses Non-catand $786.9mLAE (60.3%),by Cat $15.5m (1.2%)type, Prior dev -$7.5m (-0.6%); Total $795.0m (60.9%). 2024: Non-cat $640.3mloss (60.6%)and LAE, Cat $18.0mloss (1.7%)and LAE, Prior devaccident $11.6myear (1.1%); Total $669.8m (63.4%).development|cos78e4bvi|drz6uloidkcaxaby4jlv|kind=table|order=49}}

| class="wt-indent-1" style="text-align:left" | Non-cat loss and LAE

| class="wt-indent-1" style="text-align:left" | Cat loss and LAE (1)

| style="text-align:left; font-weight:bold" | '''Total losses and LAE'''

| style="text-align:right; font-weight:bold" | '''795,022'''

| style="text-align:right; font-weight:bold" | '''60.9%'''

| style="text-align:right; font-weight:bold" | '''669,809'''

| style="text-align:right; font-weight:bold" | '''63.4%'''

| style="text-align:left; font-weight:bold" | '''Total'''

| style="text-align:right; font-weight:bold" | '''-7,475'''

| style="text-align:right; font-weight:bold" | '''25,728'''

| style="text-align:left" | '''Reserve development on losses subject to LPT'''

| style="text-align:right" | '''—'''

| style="text-align:right" | '''25,300'''

| style="text-align:left" | '''Reserve development on losses excluding losses subject to LPT'''

| style="text-align:right" | -'''(7,475)'''

| style="text-align:right" | '''428'''

{{Indexing|Net expenses for underwritingUnderwriting, acquisition, and insurance. expenses|2025: Acquisition $195.4m (15.0%)Underwriting, Otheracquisition $181.9mand (13.9%),insurance Total exp $377.4m (28.9%)expenses, Net $370.5mpolicy (28.4%).acquisition 2024: Acquisition $150.0m (14.2%)expenses, Other $161.8moperating (15.3%),and Totalgeneral expexpenses, $311.8mCommission (29.5%),and Netfee $305.1m (28.9%).income|irxh3hcbqz|cos78e4bvi|kind=table|order=51}}

| style="text-align:left" | '''Underwriting, acquisition and insurance expenses'''

| style="text-align:right" | '''377,359'''

| style="text-align:right" | '''28.9%'''

| style="text-align:right" | '''311,757'''

| style="text-align:right" | '''29.5%'''

| style="text-align:left; font-weight:bold" | '''Total net expenses'''

| style="text-align:right; font-weight:bold" | '''370,504'''

| style="text-align:right; font-weight:bold" | '''28.4%'''

| style="text-align:right; font-weight:bold" | '''305,054'''

| style="text-align:right; font-weight:bold" | '''28.9%'''

{{Indexing|Net investment income and gains.|2025:Net Fixedinvestment income $77.9m,and Equities $1.4mgains, Alt Short-$11.5m;term Net income $83.6minvestments, UnrealizedFixed -$1.6mincome, Realized $23.7mEquities, NetAlternative gainsand $22.1m.strategic 2024: Fixed income $57.6minvestments, Equities $2.7m, Alt $2.6m; Net incomeunrealized $80.6m,(losses) Unrealizedgains $7.9m,on Realized -$1.6msecurities, Net realized gains $6.3m.(losses)|jpoeftv18u|j8uunnd14x|kind=table|order=52}}

| style="text-align:left" | '''Net investment income'''

| style="text-align:right" | '''83,619'''

| style="text-align:right" | '''80,600'''

| style="text-align:left" | '''Net unrealized (losses) gains on securities still held'''

| style="text-align:right" | -'''(1,555)'''

| style="text-align:right" | '''7,921'''

| style="text-align:left" | '''Net investment gains'''

| style="text-align:right" | '''22,149'''

| style="text-align:right" | '''6,342'''

{{Indexing|Investments|Fixed income: A+ (2025)portfolio, AA-Commercial (2024), duration 3.60ymortgage (2025)loans, 4.34y (2024). Equities: 100% publicportfolio, soldAlternative Q3investments, 2025Strategic retaining preferreds. Alt: floating rate senior secured loans.investments, Market risk:, creditCredit risk, interestInterest rate; FX/commodity not significant.risk|ooly7l7133966xer0dpm|p7k94aok7u|m0cjxgvmvi|utnmaoxh50|gp3o3dfk95|kind=prose|order=53|f1=Fixed income portfolio credit rating 2025|v1=A+|f2=Fixed (Decincome 31,portfolio 2025)credit rating 2024|f2v2=AA-|f3=Fixed income portfolio average duration 2025|v2v3=3.60 years|f4=Fixed (Decincome 31,portfolio 2025)average duration 2024|f3v4=4.34 years|f5=Equities portfolio public tradedtrading|v3v5=100.0%|f6=Equities portfolio sale|v6=third quarter of 2025}}

{{Indexing|Investment portfolio by asset class.|2025:Investment Cash $168.5m (6.8%),portfolio STby $264.3masset (10.7%)class, FixedCash $1,866.2m (75.6%), Equitiesand $1.2mcash (0.1%)equivalents, AltShort-term $168.8m (6.8%); Total $2,469.1m. 2024: Cash $121.6m (6.1%), ST $274.9m (13.8%)investments, Fixed $1,318.7m (66.2%)income, Equities $106.3m (5.3%), AltAlternative $170.9mand (8.6%);strategic Total $1,992.4m.investments|966xer0dpm|1f87rdfb5o|kind=table|order=54}}

| style="text-align:left; font-weight:bold" | '''Total portfolio'''

| style="text-align:right; font-weight:bold" | '''2,469,059'''

| style="text-align:right; font-weight:bold" | '''100.0%'''

| style="text-align:right; font-weight:bold" | '''1,992,423'''

| style="text-align:right; font-weight:bold" | '''100.0%'''

{{Indexing|Fixed income portfolio by security type.|2025:Fixed USincome Govportfolio $44.5mby (2.4%),security Corp $636.4m (34.1%)type, Muni $102U.1m (5S.5%), RMBSgovernment $486.6m (26.1%)securities, CMBSCorporate $73.1m (3.9%)securities, ABS $513.7m (27.5%); TotalMunicipal $1securities,856.3m. 2024:Residential USmortgage-backed Gov $26.5m (2.0%)securities, CorpCommercial $425.6mmortgage-backed (32.3%)securities, MuniOther $84.7masset-backed (6.4%)securities, RMBSCommercial $393.8mmortgage (29.9%), CMBS $69.4m (5.2%), ABS $292.2m (22.2%); Total $1,292.2m.loans|utnmaoxh50|966xer0dpm|kind=table|order=55}}

| style="text-align:left; font-weight:bold" | '''Total fixed income portfolio, available-for-sale'''

| style="text-align:right; font-weight:bold" | '''1,856,303'''

| style="text-align:right; font-weight:bold" | '''99.5%'''

| style="text-align:right; font-weight:bold" | '''1,292,218'''

| style="text-align:right; font-weight:bold" | '''98.0%'''

| style="text-align:left" | '''Commercial mortgage loans'''

| style="text-align:right" | '''9,902'''

| style="text-align:right" | '''0.5%'''

| style="text-align:right" | '''26,490'''

| style="text-align:right" | '''2.0%'''

| style="text-align:left; font-weight:bold" | '''Total fixed income portfolio'''

| style="text-align:right; font-weight:bold" | '''1,866,205'''

| style="text-align:right; font-weight:bold" | '''100.0%'''

| style="text-align:right; font-weight:bold" | '''1,318,708'''

| style="text-align:right; font-weight:bold" | '''100.0%'''

{{Indexing|Fixed income portfolio by credit rating.|2025:Fixed AAAincome $286.6mportfolio (15.4%),by AA $548.0mcredit (29.6%)rating, A $620.8m (33.5%), BBB $379.6m (20.4%), BB+ $21.3m (1.1%); Total $1,856.3m. 2024: AAA $483.1m (37.3%), AA $141.2m (10.9%), A $429.7m (33.3%), BBB $216.6m (16.8%), BB+ $21.6mand (1.7%); Total $1,292.2m.Lower|ooly7l7133|utnmaoxh50|kind=table|order=56}}

| style="text-align:left; font-weight:bold" | '''Total fixed income portfolio, available-for-sale'''

| style="text-align:right; font-weight:bold" | '''1,856,303'''

| style="text-align:right; font-weight:bold" | '''100.0%'''

| style="text-align:right; font-weight:bold" | '''1,292,218'''

| style="text-align:right; font-weight:bold" | '''100.0%'''

{{Indexing|Equities portfolio by type.|2025:Equities Domesticportfolio commonby $0type, Int'l common $0, Preferred $1.2m (100%); Total $1.2m. 2024: Domestic common $70.7m (66.5%)equities, Int'lInternational common $34.4m (32.4%)equities, Preferred $1.2m (1.1%); Total $106.3m.stock|966xer0dpm|kind=table|order=57}}

| style="text-align:left" | '''Equities'''

| style="text-align:right" | '''1,174'''

| style="text-align:right" | '''100.0%'''

| style="text-align:right" | '''106,254'''

| style="text-align:right" | '''100.0%'''

{{Indexing|Estimated change inSensitivity fairof valueinvestment dueportfolio to interest rate changes.|300bpSensitivity up:of -$201.8minvestment (-10.9%);portfolio 200bpto up:interest -$134.5mrate (-7.2%);changes, 100bpEstimated up:Fair -$67.2mValue, (-3.6%).Estimated 100bpChange down:in +$67.1mFair (3.6%);Value, 200bpEstimated down:% +$134.2mIncrease (7.2%Decrease); 300bpin down:Fair +$201.2m (10.8%). Base: $1,856.3m.Value|p7k94aok7u|966xer0dpm|kind=table|order=58}}

{{Indexing|Other Items|2025:Income Taxtax expense $46.4m, ETREffective 21.4%. 2024: Taxtax expense $33.9mrate, ETRFederal 22.2%.income Reconciliationtax inexpense Note 13.reconciliation|kmocop7wiu|kind=prose|order=59|f1=Income tax expense 2025|v1=FY25:USD $46.4m|f2=EffectiveIncome tax rateexpense 2024|v2=FY25:USD 33.9m|f3=Effective tax rate 2025|v3=21.4%|f4=Effective tax rate 2024|v4=22.2%}}

{{Indexing|Liquidity and Capital Resources|Holding cocompany with subsidiaries GMICstructure, HSIC,Operating IIC (TX)subsidiaries, OSIC (OK). Funding:Corporate service fees, Consolidated tax allocallocation agreement, Subsidiary dividends, Bank loans, equity/debt.Revolving Dividendsloan restrictedagreement, byEquity stateand laws;debt surplussecurities limitsissuance, apply.State Noinsurance assurancelaws, maxStatutory dividendscapital permitted.and surplus|trbk6wt4s9|75shp9ailk|trbk6wt4s9cmtswfs0go|kind=prose|order=60|f1=Subsidiaries|v1=GMIC, HSIC, IIC, OSIC|f2=IIC domicile|v2=Texas|f3=OSIC domicile|v3=Oklahoma}}

{{Indexing|Cash Flows|Sources:Cash premiumsflows, investmentPremiums, income.Claims, Uses:Investment claimssecurities, Operating expenses, capex.Capital 2025expenditures, opsReinsurance, cash up due to insurance inflows. InvestingNet cash used for fixed maturity purchases. Reinsurancein affectsinvesting timing.activities|cs6p6hop55|kind=prose|order=61}}

{{Indexing|Cash flows fromby operating,activity|Cash flows by investingactivity, and financingOperating activities.|2025:, OpsInvesting $408.1mactivities, InvFinancing -$366.9mactivities, Fin $0.4m; Change $41.6m.in 2024:cash Opsand $305.1m,cash Invequivalents -$243.7m,and Fin -$4.2m; Changerestricted $57.2m.cash|cs6p6hop55|kind=table|order=62}}

| style="text-align:left" | '''Change in cash and cash equivalents and restricted cash'''

| style="text-align:right" | '''41,589'''

| style="text-align:right" | '''57,189'''

{{Indexing|Credit Agreements|Credit Agreements, FHLB Loan: $57.0m, 4.5y,Term 4.00%Loan fixedFacility, AugUnsecured 2024.senior Termdelayed Loan:draw $150mterm Trancheloan Afacility, +Apollo $150mGroup TrancheHoldings BLimited DDTLacquisition, Q4Interest 2025rate calculation, forSOFR, ApolloBase acquisition.rate, SOFR+150-190bpsUndrawn oramounts Base+50-90bps. Fee 0.20-0.35%.fee|bhnpa5y4f0|b3bc9gy5x7|bhnpa5y4f0|kind=prose|order=63|f1=FHLB Loan principaldate|v1=$57.0August million30, 2024|f2=FHLB Loan term|v2=4.5 years-year|f3=FHLB Loan interest rateprincipal|v3=4$57.00%0 million|f4=FHLB Loan dateinterest rate|v4=Aug 30, 20244.00%|f5=Term Loan Facility Tranche A DDTL|v5=$150.0 million|f6=Term Loan Facility Tranche B DDTL|v6=$150.0 million}}

{{Indexing|Share Repurchase Program|OctShare 2024:Repurchase $50.0mProgram, buybackCommon programstock approved.repurchase, Methods: openOpen market, blockpurchases, 10b5Privately-1.negotiated Notransactions, sharesBlock repurchasedpurchases, asAccelerated ofshare Decrepurchase 31agreements, 2025.Rule 10b5-1 trading plans|70zdwfnrmi|f7q5tvbfqm|kind=prose|order=64|f1=BuybackProgram authorizationapproval date|v1=$50.0October million2024|f2=ProgramAuthorized repurchase approvedamount|v2=Oct$50.0 2024million|f3=Shares repurchased|v3=0 (as of Dec 31, 2025)|v3=None}}

{{Indexing|Contractual Obligations and Commitments|Reserves:Contractual bestObligations estimateand ofCommitments, ultimateReserves cost.for Reinsurancelosses recoverables:and $1LAE,119.9m (2025),Reinsurance $857.9mbalances (2024).recoverable, ReportedClaims separatelypayment as assets.estimation, TimingActuarial uncertain.assumptions|wugbjvah7b|rmmhubj8mh|tc5fw176pu|kind=prose|order=65|f1=Reinsurance recoverablesbalances recoverable 2025|v1=$1,119.9 million|f2=Reinsurance (Decbalances 31,recoverable 2025)2024|v2=$857.9 million}}

{{Indexing|Reinsurance balances recoverable onand reservesdebt for losses and LAE.obligations|2025:Reinsurance Lossbalances reservesrecoverable $2,318.9mand (<1y:debt $524.3mobligations, >1y:Reserves $1,794.6m),for Debtlosses $548.5mand (>1y)LAE, InterestLong-term $107.1m (<1y: $26.8mdebt, >1y:Interest $80.2m);on Totaldebt $2,974.5m.|bhnpa5y4f0obligations|rmmhubj8mh|b3bc9gy5x7|tc5fw176pu|kind=table|order=66}}

| style="text-align:left; font-weight:bold" | '''Total'''

| style="text-align:right; font-weight:bold" | '''2,974,464'''

| style="text-align:right; font-weight:bold" | '''551,157'''

| style="text-align:right; font-weight:bold" | '''2,423,307'''

{{Indexing|Critical Accounting Policies|Critical Accounting Policies, Critical accounting estimates:, Consolidated financial statements, reservesReserves for unpaid losses/LAE (largest/complex).and Not discounted.LAE, Methods:Individual case-basis valuations, statisticalStatistical analyses, actuarial.Actuarial Adjustedprocedures, asHistorical information, Industry and peer group information, experienceFuture develops.trends|ie3cmfrol3|rmmhubj8mh|e40m7ou132|kind=prose|order=67}}

* ''Reserves are driven by factors'' including litigation and regulatory trends, legislative activity, climate change, social and economic patterns, and claims inflation assumptions ^{p. 46}.

* The impact of potential changes in the regulatory or legislative environment is difficult to quantify without specific, significant new regulation or legislation ^{p. 46}.

* Development is ''Unfavorable developmentunfavorable'' occurs when losses settle for more than reserved or subsequent estimates indicate reserve increases ^{p. 46}.

* Development is ''Favorable developmentfavorable'' occurs when losses settle for less than reserved or subsequent estimates indicate reserve reductions ^{p. 46}.

* Favorable or unfavorable development of loss reserves is reflected in the results of operations in the period the estimates are changed ^{p. 46}.

{{Indexing|Impact of a 5% change in net IBNR on reserves, income, and equity.|2025:Impact Caseof $625.7ma (27.05%), IBNRchange $1,693.2min (73.0%);net GrossIBNR $2,318.9m.on Net: Case $362.3m (25.9%)reserves, IBNR $1income,035.4m (74.1%);and Net $1equity,397.7m. 2024: Case $567.2m (31.8%)reserves, IBNR $1,215.2m (68.2%); Gross $1,782.4m.|rmmhubj8mh|e40m7ou132|kind=table|order=68}}

| style="text-align:left; font-weight:bold" | '''Total'''

| style="text-align:right; font-weight:bold" | '''2,318,894'''

| style="text-align:right; font-weight:bold" | '''100.0%'''

| style="text-align:right; font-weight:bold" | '''1,397,729'''

| style="text-align:right; font-weight:bold" | '''100.0%'''

| style="text-align:right; font-weight:bold" | '''1,782,383'''

| style="text-align:right; font-weight:bold" | '''100.0%'''

| style="text-align:right; font-weight:bold" | '''1,111,537'''

| style="text-align:right; font-weight:bold" | '''100.0%'''

{{Indexing|Recent Accounting Pronouncements|Recent Accounting Pronouncements, ASU 2023-09, (DecIncome 2023):Tax EnhancedDisclosures, taxASU disclosures2024-03, effectiveIncome FY2025.statement expenses, ASU 20242025-0301|ie3cmfrol3|kind=prose|order=69|f1=ASU (Nov2023-09 2024):issuance|v1=December Disaggregated2023|f2=ASU expense2023-09 disclosureeffective date|v2=fiscal years beginning after December 15, effective2024|f3=ASU FY2027.2024-03 issuance|v3=November 2024|f4=ASU 2025-01 (Janissuance|v4=January 2025): Clarifies |f5=ASU 2024-03 effective date.|ie3cmfrol3|kindv5=prose|order=69first annual reporting period beginning after December 15, 2026}}

{{Indexing|Report of Independent Registered Public Accounting Firm|Opinion:Report Fairof presentationIndependent forRegistered 2023/2022.Public ICFRAccounting effectiveFirm, DecConsolidated 31financial statements, 2023Internal (COSOControl 2013).Over PCAOBFinancial standards.Reporting, NoBasis criticalfor auditOpinion, Responsibilities of the Auditor, Audit Scope, Critical Audit matters.Matters|x856lnzuq2|l96bfbct4s|kind=prose|order=70|f1=Financial statements as of|v1=December 31, 2023 and 2022|f2=Internal Control Over Financial Reporting as of|v2=December 31, 2023|f3=Auditor|v3=public accounting firm registered with the PCAOB|f4=Critical Audit Matters|v4=None}}

{{Indexing|Opinion on Internal Control Over Financial Reporting|ICFROpinion effectiveon DecInternal 31Control Over Financial Reporting, 2025Internal (COSOcontrol 2013).over Unqualifiedfinancial opinionreporting, onConsolidated financialsbalance forsheets, 2025/2024.Consolidated Reportstatements datedof Marchoperations 2and comprehensive income, 2026.Stockholders’ equity, Cash flows|l96bfbct4s|x856lnzuq2|kind=prose|order=71|f1=ICFRInternal effectivecontrol dateaudit as of|v1=DecDecember 31, 2025|f2=AuditCOSO report datecriteria|v2=2013 framework|f3=Consolidated balance sheets as of|v3=December 31, 2025 and 2024|f4=Report dated|v4=March 2, 2026}}

{{Indexing|Basis for Opinion|Management responsibleBasis for ICFR.Opinion, Management's responsibility, Auditor:'s responsibility, PCAOB registeredstandards, independent. Audit: assessscope, Material weakness riskassessment, testInternal control design/effectiveness. Reasonableand assuranceoperating obtained.effectiveness|x856lnzuq2|l96bfbct4s|kind=prose|order=72}}

{{Indexing|Definition and Limitations of Internal Control Over Financial Reporting|Internal control over financial reporting, providesfinancial reasonablestatement assurance of reliable financial reportingreliability, accurate transaction recordsrecording, andasset authorized expendituresdisposition, buteffectiveness has inherent limitations and may not prevent or detect all misstatements.evaluations|l96bfbct4s|x856lnzuq2|kind=prose|order=73|f1=Report date|v1=March 2, 2026}}

{{Indexing|Report of Independent Registered Public Accounting Firm|The independent auditor issued an unqualified opinion on the consolidatedConsolidated financial statements and the effectiveness of, internal control over financial reporting, asaudit ofscope, Decemberaudit 31procedures, 2023,auditor based on PCAOB standards and COSO framework.responsibilities|x856lnzuq2|l96bfbct4s|kind=prose|order=74|f1=Financial position as ofAuditor|v1=DecemberErnst 31,& 2023Young and 2022LLP|f2=Audit opinion|v2=unqualified|f3=Internal control opinion|v3=effective as of|v2f4=DecemberInternal 31,control 2023framework|f3=Framework|v3v4=Internal Control—Integrated Framework (2013) issued by theCOSO|f5=Audit Committee of Sponsoring Organizations of the Treadway Commission (COSO)standards|v5=PCAOB}}

{{Indexing|Opinion on the Financial Statements|The consolidatedConsolidated financial statements as of December 31, 2025audit and 2024scope, and for the three years ended December 31, 2025, were audited and present fairly the Company's financial position and, operational results, incash conformity with U.S. GAAPflows, with an unqualified opinion on internal control over financial reporting.|x856lnzuq2|l96bfbct4s|kind=prose|order=75|f1=AuditedAudit as ofopinion|v1=December 31, 2025 and 2024unqualified|f2=AuditedInternal forcontrol three years endedopinion|v2=December 31, 2025unqualified|f3=Internal control audited as offramework|v3=December 31, 2025|f4=Framework|v4=2013 framework of Internal Control—Integrated Framework issued by the Committee of Sponsoring Organizations of the Treadway Commission|f5f4=ReportAudit datedstandards|v5v4=March 2, 2026PCAOB}}

{{Indexing|Basis for Opinion|The auditor's responsibility is to express an opinion on the financialFinancial statements, conductedauditor inresponsibilities, accordance with PCAOBaudit standards, providingmaterial reasonablemisstatement, assuranceaudit that financial statements are free of material misstatement.procedures|x856lnzuq2|kind=prose|order=76|f1=Audit standards|v1=PCAOB}}

{{Indexing|Critical Audit Matter|A criticalCritical audit matter, involving challenging judgments and material to the financial statements, was communicated to the audit committee communication, but does not alter the overall opinion on the consolidated financial statements.judgments|x856lnzuq2|kind=prose|order=77}}

{{Indexing|Valuation of Reserves for Unpaid Losses and Loss Adjustment Expenses|Auditing management's estimate of USD 2.3bn in reservesReserves for unpaid losses and LAE,loss includingadjustment IBNRexpenses, wasincurred complexbut duenot toreported significantreserves (IBNR), estimation uncertainty in evaluating methods, andactuarial assumptionsprocedures, like loss development factors and expected lossinternal ratios.controls|rmmhubj8mh|e40m7ou132gva2857foa|do9an7x5kpe40m7ou132|kind=prose|order=78|f1=Reserves for unpaid losses and LAE|v1=USD 2.3bn at December 31, 2025}}

{{Indexing|Consolidated balance sheets|TheConsolidated balance sheets, accompanying notes are an integral part of the consolidated financial statements.|offa7is5x7|kind=prose|order=79}}

{{Indexing|Consolidated balance sheets for assets.|Consolidated balance sheets for assets, including fixed maturity securities, equity securities, mortgage loans, equity method investments, other long-term investments, and short-term investments, as of December 31, 2025 and 2024.|offa7is5x7|1f87rdfb5o|966xer0dpm|kind=table|order=80}}

| class="wt-indent-1" style="text-align:left" | Fixed maturity securities, available-for-sale, at fair value (net of allowance for credit losses of $ 7,000 and $ 0 , respectively) (amortized cost of $ 1,848,755 and $ 1,320,266 , respectively)

| class="wt-indent-1" style="text-align:left" | Fixed maturity securities, held-to-maturity, at amortized cost (net of allowance for credit losses of $ 468 and $ 243 , respectively)

| style="text-align:left; font-weight:bold" | '''Total investments'''

| style="text-align:right; font-weight:bold" | '''2,300,515'''

| style="text-align:right; font-weight:bold" | '''1,870,820'''

| style="text-align:left; font-weight:bold" | '''Total assets'''

| style="text-align:right; font-weight:bold" | '''4,791,852'''

| style="text-align:right; font-weight:bold" | '''3,729,478'''

| style="text-align:left" | '''Liabilities and stockholders’ equity'''

| style="text-align:left; font-weight:bold" | '''Total liabilities'''

| style="text-align:right; font-weight:bold" | '''3,782,287'''

| style="text-align:right; font-weight:bold" | '''2,935,479'''

| style="text-align:left" | '''Stockholders’ equity'''

| class="wt-indent-1" style="text-align:left" | Common stock, $ 0.01 par value, 500,000,000 shares authorized, 40,511,222 and 40,127,908 shares issued and outstanding, respectively

| style="text-align:left; font-weight:bold" | '''Total stockholders’ equity'''

| style="text-align:right; font-weight:bold" | '''1,009,565'''

| style="text-align:right; font-weight:bold" | '''793,999'''

| style="text-align:left; font-weight:bold" | '''Total liabilities and stockholders’ equity'''

| style="text-align:right; font-weight:bold" | '''4,791,852'''

| style="text-align:right; font-weight:bold" | '''3,729,478'''

{{Indexing|Consolidated statements of operations and comprehensive income|TheConsolidated accompanyingstatements notesof areoperations, ancomprehensive integralincome, partaccompanying of the consolidated financial statements.notes|ed0t39ch3f|utcfjac7ow|kind=prose|order=81}}

{{Indexing|Consolidated statements of income for revenues and expenses.operations|Consolidated statements of income for revenues (net earned premiums, commission and fee income, net investment income, net investment gains) and expenses (losses and loss adjustment expenses, underwriting, acquisition and insurance expenses) for years ended December 31, 2025, 2024, and 2023.|ed0t39ch3f|wpkf9ycgxf|qfq1t7e6o0|jpoeftv18u|irxh3hcbqz|qfq1t7e6o0|kind=table|order=82}}

! class="col-sm" style="text-align:right" | —

! class="col-sm" style="text-align:right" | —

! class="col-sm" style="text-align:right" | —

| style="text-align:left; font-weight:bold" | '''Total revenues'''

| style="text-align:right; font-weight:bold" | '''1,416,541'''

| style="text-align:right; font-weight:bold" | '''1,150,200'''

| style="text-align:right; font-weight:bold" | '''885,969'''

| style="text-align:left; font-weight:bold" | '''Total expenses'''

| style="text-align:right; font-weight:bold" | '''1,200,117'''

| style="text-align:right; font-weight:bold" | '''997,461'''

| style="text-align:right; font-weight:bold" | '''775,867'''

| style="text-align:left" | '''Income before income taxes'''

| style="text-align:right" | '''216,424'''

| style="text-align:right" | '''152,739'''

| style="text-align:right" | '''110,102'''

| style="text-align:left" | '''Net income'''

| style="text-align:right" | '''170,028'''

| style="text-align:right" | '''118,828'''

| style="text-align:right" | '''85,984'''

| style="text-align:left" | '''Net income attributable to participating securities'''

| style="text-align:left; font-weight:bold" | '''Total other comprehensive income'''

| style="text-align:right; font-weight:bold" | '''33,577'''

| style="text-align:right; font-weight:bold" | '''833'''

| style="text-align:right; font-weight:bold" | '''20,532'''

| style="text-align:left" | '''Comprehensive income'''

| style="text-align:right" | '''203,605'''

| style="text-align:right" | '''119,661'''

| style="text-align:right" | '''106,516'''

| style="text-align:left" | '''Diluted earnings per share'''

| style="text-align:right" | '''4.07'''

| style="text-align:right" | '''2.87'''

| style="text-align:right" | '''2.24'''

| style="text-align:left" | '''Weighted-average common shares outstanding'''

| style="text-align:left" | '''Diluted'''

| style="text-align:right" | '''41,808,046'''

| style="text-align:right" | '''41,377,460'''

| style="text-align:right" | '''38,317,534'''

{{Indexing|Consolidated statements of stockholders’ equity|TheConsolidated accompanying notes are an integral partstatements of thestockholders’ consolidatedequity, financialaccompanying statements.notes|0lk0pqg9zhz6dk9e62ik|kind=prose|order=83}}

{{Indexing|Consolidated statements of changes in shareholders' equity for preferred and common shares.|Consolidated statements of changes in shareholders' equity, detailing preferred and common shares, including conversions and issuances, for the years ended December 31, 2025, 2024, and 2023.|z6dk9e62ik|0lk0pqg9zh|z6dk9e62ik|kind=table|order=84}}

! class="col-sm" style="text-align:right" | —

! class="col-sm" style="text-align:right" | —

! class="col-sm" style="text-align:right" | —

| style="text-align:left" | '''Balance at December 31'''

| style="text-align:right" | '''—'''

| style="text-align:right" | '''—'''

| style="text-align:right" | '''—'''

| style="text-align:left" | '''Balance at December 31'''

| style="text-align:right" | '''40,511,222'''

| style="text-align:right" | '''40,127,908'''

| style="text-align:right" | '''39,863,756'''

| style="text-align:left" | '''Balance at December 31'''

| style="text-align:right" | '''—'''

| style="text-align:right" | '''—'''

| style="text-align:right" | '''—'''

| style="text-align:left" | '''Common stock:'''

| style="text-align:left" | '''Balance at December 31'''

| style="text-align:right" | '''405'''

| style="text-align:right" | '''401'''

| style="text-align:right" | '''399'''

| style="text-align:left" | '''Balance at December 31'''

| style="text-align:right" | '''—'''

| style="text-align:right" | '''—'''

| style="text-align:right" | '''—'''

| style="text-align:left" | '''Additional paid-in capital:'''

| style="text-align:left" | '''Balance at December 31'''

| style="text-align:right" | '''730,555'''

| style="text-align:right" | '''718,598'''

| style="text-align:right" | '''710,855'''

| style="text-align:left" | '''Stock notes receivable:'''

| style="text-align:left" | '''Balance at December 31'''

| style="text-align:right" | '''—'''

| style="text-align:right" | '''—'''

| style="text-align:right" | '''( 5,562 )'''

| style="text-align:left" | '''Accumulated other comprehensive income (loss):'''

| style="text-align:left" | '''Balance at December 31'''

| style="text-align:right" | '''11,457'''

| style="text-align:right" | '''( 22,120 )'''

| style="text-align:right" | '''( 22,953 )'''

| style="text-align:left" | '''Retained earnings (accumulated deficit):'''

| style="text-align:left" | '''Balance at December 31'''

| style="text-align:right" | '''267,148'''

| style="text-align:right" | '''97,120'''

| style="text-align:right" | '''( 21,708 )'''

| style="text-align:left; font-weight:bold" | '''Total stockholders’ equity'''

| style="text-align:right; font-weight:bold" | '''1,009,565'''

| style="text-align:right; font-weight:bold" | '''793,999'''

| style="text-align:right; font-weight:bold" | '''661,031'''

{{Indexing|Consolidated statements of cash flows|TheConsolidated accompanying notes are an integral partstatements of thecash consolidatedflows, financialaccompanying statements.notes|cs6p6hop55|kind=prose|order=85}}

! class="col-sm" style="text-align:right" | —

! class="col-sm" style="text-align:right" | —

! class="col-sm" style="text-align:right" | —

| style="text-align:left" | '''Net cash provided by operating activities'''

| style="text-align:right" | '''408,076'''

| style="text-align:right" | '''305,115'''

| style="text-align:right" | '''338,187'''

| style="text-align:left" | '''Net cash used in investment activities'''

| style="text-align:right" | '''( 366,898 )'''

| style="text-align:right" | '''( 243,694 )'''

| style="text-align:right" | '''( 493,809 )'''

| style="text-align:left" | '''Net cash provided by (used in) financing activities'''

| style="text-align:right" | '''411'''

| style="text-align:right" | '''( 4,232 )'''

| style="text-align:right" | '''130,947'''

| style="text-align:left" | '''Net increase (decrease) in cash and cash equivalents and restricted cash'''

| style="text-align:right" | '''41,589'''

| style="text-align:right" | '''57,189'''

| style="text-align:right" | '''( 24,675 )'''

| style="text-align:left" | '''Cash and cash equivalents and restricted cash at end of period (1)'''

| style="text-align:right" | '''199,114'''

| style="text-align:right" | '''157,525'''

| style="text-align:right" | '''100,336'''

| style="text-align:left" | '''Supplemental disclosure of cash flow information:'''

{{Indexing|A. Description of Business|Skyward Specialty Insurance Group, Inc., ainsurance Delawareholding corporationcompany, formedunderwriting in 2006divisions, operatesGreat asMidwest aInsurance specialtyCompany, P&CHouston insurerSpecialty throughInsurance its subsidiariesCompany, includingImperium GMIC,Insurance HSICCompany, IIC,Oklahoma OSICSpecialty Insurance Company, Skyward Re, SUASkyward Underwriters Agency, Inc., Skyward Service Company, and Skyward Specialty No. 1 Limited, and acquired Apollo Group on January 1,Holdings 2026.|4cr8sbi842|2ku0sqq9xfLimited|cmtswfs0go|lht8rybaqk|20fueoa3q1|kind=prose|order=87|f1=FormedLegal name|v1=DelawareSkyward corporationSpecialty Insurance Group, 2006Inc.|f2=AcquisitionState of incorporation|v2=Delaware|f3=Year founded|v3=2006|f4=Subsidiaries|v4=Great Midwest Insurance Company, Houston Specialty Insurance Company, Imperium Insurance Company, Oklahoma Specialty Insurance Company, Skyward Re, Skyward Underwriters Agency, Inc., Skyward Service Company, Skyward Specialty No. 1 Limited|f5=Acquisition|v5=Apollo Group (Holdings Limited on January 1, 2026)}}

* ''Skyward Specialty Insurance Group, Inc.'' (the "Company") is a Delaware corporation organized in 2006, operating as an insurance holding company ^{p. 62}.

* The Company operates as a specialty insurance company in one segment, providingdelivering commercial property and casualty insurance products through its underwriting divisions ^{p. 62}.

* The Company has four wholly owned U.S.-based insurance company subsidiaries based in the United States ^{p. 62}.

** ''Great Midwest Insurance Company'' ("GMIC")'' underwrites insurance on an admitted basis and is a certified surety bond company listed with the U.S. Department of the Treasury ^{p. 62}.

** ''Houston Specialty Insurance Company'' ("HSIC")'', a subsidiary of GMIC, underwrites insurance on a non-admitted basis ^{p. 62}.

** ''Imperium Insurance Company'' ("IIC")'', a subsidiary of HSIC, underwrites insurance on an admitted basis ^{p. 62}.

** ''Oklahoma Specialty Insurance Company'' ("OSIC")'', a subsidiary of IIC, underwrites insurance on a non-admitted basis ^{p. 62}.

** Skyward Re assumed net reserves for certain divisions, related to a retroactive reinsurance contract, from the Company’sCompany's insurance companies and retroceded these net reserves to a third-party reinsurer ^{p. 62}.

** ''Skyward Underwriters Agency, Inc.'' ("SUA")'' is a managing general insurance agent and reinsurance broker for property and casualty risks in specialty niche markets ^{p. 62}.

** ''Skyward Service Company'' provides various administrative services to the Company’sCompany's subsidiaries ^{p. 62}.

** ''Skyward Specialty No. 1 Limited'' is a Lloyd’sLloyd's corporate member authorized to invest in Lloyd’sLloyd's syndicates ^{p. 62}.

** Additional information regardingon thethis acquisition is provided in Note 24 ^{p. 62}.

{{Indexing|B.     Basis of Presentation|The Company's consolidatedConsolidated financial statements, areGenerally preparedAccepted underAccounting U.S.Principles (GAAP), differingintercompany from insurance regulatory principlestransactions, and include estimates and assumptions that may vary from actual results.|ow7tevuxxr|ie3cmfrol3|kind=prose|order=88}}

{{Indexing|C.    Consolidation|TheConsolidation, Companyvariable consolidatesinterest entitiesentity that are VIEs where it is the(VIE), primary beneficiary, or entities it controls through voting interest, withrelated assessmentsparty involvinganalysis, subjectivityfair andvalue reassessmentsof at eachassets, reportingfinancial period.performance|ow7tevuxxr|kind=prose|order=89}}

{{Indexing|D.     Cash and Cash Equivalents|Cash and cash equivalents include cash on hand and, fixed maturity securities with original maturities of three months or less, with carrying value approximating fair value.|1f87rdfb5ocs6p6hop55|kind=prose|order=90}}

{{Indexing|E.    Restricted Cash|Restricted cash, withlegal carryingrestriction, value approximating fair valueSUA, includes unremitted insurance premiums held by SUA for third-party insurers and cash held for, state regulations or as, collateral for reinsurance balances.|1f87rdfb5ocs6p6hop55|kind=prose|order=91}}

{{Indexing|F.    Investments|Available- for-sale Sale fixed maturities, arefair carriedvalue, atunrealized fairloss valueposition, withamortized unrealizedcost, losses assessedallowance for credit losses, credit-related factors or intent to sell, and held-to-maturity fixed maturitiesmaturity aresecurities, carriedhistorical atloss amortizedrate, costMoody’s netmulti-year ofcumulative anloss allowance for credit lossesrates, with changes recognized in net investment gains as ofasset-backed 2025.securities|966xer0dpm|j8uunnd14x|m0cjxgvmvi|kind=prose|order=92|f1=Credit loss allowance change recognition|v1=As of 2025, in net investment gains (prior periods updated)}}

{{Indexing|G.    Derivatives|The Company uses commodityCommodity derivatives, accounted for at fair value per FASB ASC Topic 815, withDerivatives changesand reflectedHedging, infair value, current earnings, and nettednet assets/liabilities includedand in "other assets";liabilities, exchange-traded futures and, forward contractspurchase areand consideredsale effectivecontracts, economic hedges without, hedge accounting. treatment, valuation models|s22xbq0z1h|kind=prose|order=93|f1=Accounting standard|v1=FASB ASC Topic 815, Derivatives and Hedging}}

{{Indexing|H.    Reinsurance|TheProspective Companyreinsurance, purchases prospectiveproportional reinsurance (proportional, excess of loss reinsurance, facultative) and retroactive reinsurance (loss portfolio transfers, adverse development covers), reporting ceded unearned premium, andreinsurance recoverablesbalances as assetsrecoverable, andretroactive presentingreinsurance, netloss earnedportfolio premiums,transfers losses(LPT), andadverse expensesdevelopment net of reinsurance ceded.covers|20fueoa3q1|8ihdrbirer|tc5fw176pu|kind=prose|order=94}}

{{Indexing|I.     Concentration of Credit Risk|ConcentrationsFinancial instruments, concentrations of credit risk, incash financialand instrumentscash equivalents, restricted (cash, investments, premiums receivable), areU.S. limitedgovernment bysecurities, diversificationmoney acrossmarket industriesfunds, andcredit geographiesexposure, with no significant concentration believed tocustomer existbase, though failure by distribution sources to remit premiums could lead to losses.|m0cjxgvmvi|966xer0dpm|kind=prose|order=95|f1=Premiums receivable as of|v1=December 31, 2025 and 2024}}

{{Indexing|J.     Deferred Policy Acquisition Costs|Policy acquisition costs, (commissions, premium taxes), areceding deferred and amortized proportionally with earned premium; acommissions, premium deficiency, if expected losses, LAE,loss andadjustment unamortized costs exceedexpenses, unearned premiums, is recognized by charging unamortized costs to expense or accruing a liability, with no deficiency existing as of December 31, 2025anticipated andinvestment 2024.income|or43xxg565|kind=prose|order=96|f1=Premium deficiency|v1=Nonenone as of December 31, 2025, and 2024}}

{{Indexing|K.    Goodwill and Intangible Assets|Goodwill and, intangible assets are recorded post-business combination, with goodwill being the excess purchase price over fair value of acquired assets. The company reviews purchase price allocation for up to one year, amortizes finite-lived intangible assetsamortization, and annually reviews goodwill and identifiable intangible assets for recoverability, with no impairment in 2024 and 2025.review|hekiequlv1|ie3cmfrol3|kind=prose|order=97|f1=Goodwill impairment|v1=no goodwill impairment for the years ended December 31, 2025, and 2024}}

{{Indexing|L.    Property and Equipment|Property and equipment, includeddepreciation in other assets on Consolidated Balance Sheetsexpense, is recorded at cost less accumulated depreciation, with depreciation expense recognized on a straight-line basis over three to seven years.periods|ie3cmfrol3|1f87rdfb5o|kind=prose|order=98|f1=Depreciation periods|v1=three to seven years}}

{{Indexing|M.     Reserves for Losses and Loss Adjustment Expenses|Reserves for unpaid losses and, loss adjustment expenses (LAE) represent the estimated ultimate cost of all unreported and reported but unpaid insured claims, estimated using individual case-basis valuations, statistical analyses, and actuarial procedures, andhistorical areinformation, regularlyindustry reviewedinformation, peer group andinformation, future trends, loss severity, loss frequency, adjusted.inflation|rmmhubj8mh|ie3cmfrol3|kind=prose|order=99}}

* ''Reserves for unpaid losses and loss adjustment expenses (LAE)'' represent the Company's estimated ultimate cost offor all unreported and reported but unpaid insured claims, and the cost to adjust these losses incurred as of the balance sheet date ^{p. 74}.

* EstimatesThese estimates are based on the Company's historical information, industry and peer group information, and estimates of future trends in variable factors such as loss severity, loss frequency, and other factors like inflation ^{p. 74}.

* The Company regularly reviews and adjusts its estimates as experience develops or new information becomes known ^{p. 74}.

{{Indexing|N.    Premiums|Property and casualty andpremiums, surety premiums are recognized pro-rata over policy terms, while accident and health premiums, are earned as billed. Grossgross premiums written are reduced by, ceded premiums, and premiums receivable, aredeferred carried net of anpremiums, allowance for credit losses, withhistorical changesloss recognizedrate, inunearned underwritingpremiums, expenses.ceded unearned premiums|wpkf9ycgxf|ie3cmfrol3|kind=prose|order=100}}

{{Indexing|O.     Commission and Fee Income|SUA commission revenue, isSUA generatedfee from placingincome, insurance policies on, reinsurance programs, with the transaction price fixed at contract inception and recognized when the policy is placed. SUA fee income is generated from placing policies with third-party insurersinsurance company, with a variable transaction price, estimated using the expected value method and recognized upon policyperformance placement.obligation|qfq1t7e6o0|ie3cmfrol3|kind=prose|order=101}}

{{Indexing|P.     Income Taxes|Income tax expense, is accruedprovision for taxincome effects of transactionstaxes, consisting of current and deferred taxes., Atemporary differences, valuation allowance is established for unrealized, deferred tax assets, anddeferred atax liability forliabilities, uncertain tax positions, isnet recordedinterest whenincome, unlikelypenalties, toconsolidated befederal sustained.income Thetax company files consolidated federal andreturn, state tax returns, withpremium admitted insurance subsidiaries payingtaxes, premium taxes.tax expense|kmocop7wiu|ie3cmfrol3|kind=prose|order=102}}

{{Indexing|Q.     Fair Value of Financial Instruments|Fair value for, financial instruments is estimated using a framework maximizing, observable inputs and minimizing, unobservable inputs, withfair disclosures based on input quality. Thevalue hierarchy prioritizes, Level 1 measurements (quoted prices in active markets) and gives lowest priority to, Level 3 measurements, (unobservable inputs). Thirdthird-party pricing sources are used for fair value determination.|di0lc3m1jj|ie3cmfrol3|kind=prose|order=103|f1=Further details|v1=Note 4}}

{{Indexing|R.     Stock-Based Compensation|TheEmployee estimatedstock fair value of employeeoptions, stock-based optionscompensation, andequity similarinstrument awards is expensed, with compensation cost, measured at grant-date fair value and recognized over the vestingservice period., Taxtax effects are made through net earnings. The, Employee Stock Purchase Plan (ESPP) allows employees to purchase, common stock at a discount, with compensation cost recognized straight-line over the offering period.|ie3cmfrol3|kind=prose|order=104|f1=Further discussion|v1=note 18}}

{{Indexing|S.    Earnings Per Share|Basic earnings per share is calculated using the, two-class method, allocating undistributed earnings to, participating securities and dividing, net income, bycommon stockholders, weighted-average common shares, outstanding.common Dilutedshares, EPSpreferred includesshares, instrumentsdividends, convertibledistributions, intoinstruments commonawarded shares on an if-convertedto basisemployees, and contingently issuable instruments, aretreasury excludedstock frommethod, basicstock EPSnotes, ifinstruments vestingconvertible requirementsinto arecommon notshares, share-based met.awards|v7ij6av24f|ie3cmfrol3|kind=prose|order=105|f1=Impact of contingently issuable instruments on diluted EPS|v1=calculated using the treasury stock method for the year ended December 31, 2024|f2=Outstanding stock notes|v2=settled during 2024}}

{{Indexing|T.    Recent Accounting Pronouncements|ASU 2023-09, (DecASU 20232024-03, effectiveASU after Dec 152025-01, 2024) mandates enhanced income tax disclosures, including rate reconciliation and disaggregation ofdisclosures, income taxes paid., ASUincome 2024-03statement (Nov 2024expenses, effectiveexpense aftercaptions, Decnatural 15expenses, 2026)purchases requiresof disaggregatedinventory, incomeemployee statementcompensation, expensedepreciation, disclosuresintangible forasset public business entitiesamortization, clarifieddepletion by ASU 2025-01 (Jan 2025).expenses|ie3cmfrol3|kind=prose|order=106|f1=ASU 2023-09 issued|v1=December 2023|f2=ASU 2023-09 effective|v2=fiscal years beginning after December 15, 2024|f3=ASU 2024-03 issued|v3=November 2024|f4=ASU 2025-01 issued|v4=January 2025|f5=ASU 2024-03 effective|v5=first annual reporting period beginning after December 15, 2026|f6=Additional disclosures|v6=Note 13}}

{{Indexing|2. Goodwill and Intangible Assets|TheIndefinite-lived company'sintangible indefiniteassets, finite-lived intangible assets, includeamortization expense|hekiequlv1|kind=prose|order=107|f1=Indefinite-lived intangible assets|v1=insurance licenses and trademarks, while finitetrademarks|f2=Finite-lived assets likeintangible assets|v2=policy renewals, agency relationships, and non-compete/exclusivity agreements had a weighted average useful life of ~12 years as of December 31, 2025. Amortization expense was $1.3m in 2025, $1.1m in 2024, and $1.5m in 2023.|hekiequlv1|kind=prose|order=107|f1f3=Weighted average useful life of finite-lived intangible assets|v1v3=approximately 12 years as of December 31, 2025|f2f4=Amortization expense|v2v4=approximatelyFY25: $1.3m for the year ended December 31, 2025}}

{{Indexing|Goodwill by segment at December 31, 2025.|Goodwill by segment at December 31, 2025, showing gross balance, accumulated impairment, and net balance for Accident and Health, Surety, Construction and Energy Solutions, and Other segments.|hekiequlv1|kind=table|order=108}}

| style="text-align:left" | '''Net balance at December 31, 2025'''

| style="text-align:right" | '''46,756'''

| style="text-align:right" | '''6,781'''

| style="text-align:right" | '''10,204'''

| style="text-align:right" | '''1,993'''

| style="text-align:right" | '''65,734'''

{{Indexing|Goodwill by segment at December 31, 2024.|Goodwill by segment at December 31, 2024, showing gross balance, accumulated impairment, and net balance for Accident and Health, Surety, Construction and Energy Solutions, and Other segments.|hekiequlv1|kind=table|order=109}}

| style="text-align:left" | '''Net balance at December 31, 2024'''

| style="text-align:right" | '''46,756'''

| style="text-align:right" | '''6,781'''

| style="text-align:right" | '''10,204'''

| style="text-align:right" | '''1,993'''

| style="text-align:right" | '''65,734'''

{{Indexing|Other intangible assets at December 31, 2025.|Other intangible assets at December 31, 2025, showing gross balance, accumulated amortization, additions, amortization, and net balance for Agent Relationships, Non-competes, Trademarks, and Licenses.|hekiequlv1|kind=table|order=110}}

| style="text-align:left" | '''Net balance at December 31, 2025'''

| style="text-align:right" | '''7,288'''

| style="text-align:right" | '''—'''

| style="text-align:right" | '''999'''

| style="text-align:right" | '''14,019'''

| style="text-align:right" | '''22,306'''

{{Indexing|Other intangible assets at December 31, 2024.|Other intangible assets at December 31, 2024, showing gross balance, accumulated amortization, amortization, and net balance for Agent Relationships, Non-competes, Trademarks, and Licenses.|hekiequlv1|kind=table|order=111}}

| style="text-align:left" | '''Net balance at December 31, 2024'''

| style="text-align:right" | '''6,596'''

| style="text-align:right" | '''—'''

| style="text-align:right" | '''999'''

| style="text-align:right" | '''14,019'''

| style="text-align:right" | '''21,614'''

{{Indexing|Future amortizationAmortization of intangible assets.|Future amortizationAmortization of intangible assets, with amounts for years ending December 31, 2026, 2027, 2028, 2029, and 2030.|hekiequlv1|kind=table|order=112}}

{{Indexing|3. Investments|Fixed maturity securities, held-to-maturity, were entirely asset-backed at December 31securities, 2025. The company pledged $68.5m in U.S. government agencies mortgage-backed securitiesfixed formaturity ansecurities, FHLB loanLoan, andFederal $69.5mHome inLoan assetsBank of Dallas (includingFHLB), $57.8mpledged assets, reinsurance agreements, residential mortgage-backed securities, $9.5mcash and cash, $2.2mequivalents, short-term investments) for reinsurance. The company monitors, available-for-sale fixed maturity securities for, impairment, identifying credit impairments for two, corporate securities, at year-end 2025.miscellaneous|966xer0dpm|utnmaoxh50|m0cjxgvmvi|kind=prose|order=113|f1=Fixed maturity securities, held-to-maturity|v1=entirely asset-backed securities not due at a single maturity date at December 31, 2025|f2=U.S. government agencies mortgage-backed fixed maturity securities pledged|v2=approximately $68.5 million at December 31, 2025|f3=Assets with fair values pledged as collateral|v3=approximately $69.5 million at December 31, 2025|f4=Residential mortgage-backed securities pledged|v4=$57.8 million|f5=Cash and cash equivalents and other assets pledged|v5=$9.5 million|f6=Short-term investments pledged|v6=$2.2 million}}

{{Indexing|Fixed maturity securities at December 31, 2025.|Fixed maturity securities at December 31, 2025, showing amortized cost, gross unrealized gains, gross unrealized losses, allowance for credit losses, and fair value for U.S. government securities, corporate securities, municipal securities, residential mortgage-backed, andsecurities, commercial mortgage-backed securities.|966xer0dpm|kind=table|order=114}}

| style="text-align:left; font-weight:bold" | '''Total fixed maturity securities, available-for-sale'''

| style="text-align:right; font-weight:bold" | '''1,848,755'''

| style="text-align:right; font-weight:bold" | '''31,378'''

| style="text-align:right; font-weight:bold" | '''( 16,830 )'''

| style="text-align:right; font-weight:bold" | '''( 7,000 )'''

| style="text-align:right; font-weight:bold" | '''1,856,303'''

| style="text-align:left; font-weight:bold" | '''Total fixed maturity securities, held-to-maturity'''

| style="text-align:right; font-weight:bold" | '''33,290'''

| style="text-align:right; font-weight:bold" | '''829'''

| style="text-align:right; font-weight:bold" | '''( 48 )'''

| style="text-align:right; font-weight:bold" | '''( 468 )'''

| style="text-align:right; font-weight:bold" | '''33,603'''

{{Indexing|Fixed maturity securities at December 31, 2024.|Fixed maturity securities at December 31, 2024, showing amortized cost, gross unrealized gains, gross unrealized losses, allowance for credit losses, and fair value for U.S. government securities, corporate securities, municipal securities, residential mortgage-backed, andsecurities, commercial mortgage-backed securities.|966xer0dpm|kind=table|order=115}}

| style="text-align:left; font-weight:bold" | '''Total fixed maturity securities, available-for-sale'''

| style="text-align:right; font-weight:bold" | '''1,320,266'''

| style="text-align:right; font-weight:bold" | '''10,636'''

| style="text-align:right; font-weight:bold" | '''( 38,684 )'''

| style="text-align:right; font-weight:bold" | '''—'''

| style="text-align:right; font-weight:bold" | '''1,292,218'''

| style="text-align:left; font-weight:bold" | '''Total fixed maturity securities, held-to-maturity'''

| style="text-align:right; font-weight:bold" | '''39,396'''

| style="text-align:right; font-weight:bold" | '''—'''

| style="text-align:right; font-weight:bold" | '''( 436 )'''

| style="text-align:right; font-weight:bold" | '''( 243 )'''

| style="text-align:right; font-weight:bold" | '''38,717'''

{{Indexing|Maturity distribution of fixed maturity securities.|Maturity distribution of fixed maturity securities, showing amortized cost and fair value for maturities less than one year, one to five years, five to ten years, and after ten years, as well as mortgage-backed andsecurities, other asset-backed securities.|966xer0dpm|kind=table|order=116}}

| style="text-align:left; font-weight:bold" | '''Total'''

| style="text-align:right; font-weight:bold" | '''1,848,755'''

| style="text-align:right; font-weight:bold" | '''1,856,303'''

{{Indexing|Fixed maturity securities, available-for-sale, by contractual maturity at December 31, 2025.|Fixed maturity securities, available-for-sale, by contractual maturity at December 31, 2025, showing fair value and gross unrealized losses for maturities less than 12 months and 12 months or more, across U.S. government securities, corporate securities, and municipal securities.|966xer0dpm|kind=table|order=117}}

| style="text-align:left; font-weight:bold" | '''Total fixed maturity securities, available-for-sale'''

| style="text-align:right; font-weight:bold" | '''233,041'''

| style="text-align:right; font-weight:bold" | '''( 1,436 )'''

| style="text-align:right; font-weight:bold" | '''185,663'''

| style="text-align:right; font-weight:bold" | '''( 15,394 )'''

| style="text-align:right; font-weight:bold" | '''418,704'''

| style="text-align:right; font-weight:bold" | '''( 16,830 )'''

| style="text-align:left; font-weight:bold" | '''Total fixed maturity securities, held-to-maturity:'''

| style="text-align:right; font-weight:bold" | '''1,912'''

| style="text-align:right; font-weight:bold" | '''( 48 )'''

| style="text-align:right; font-weight:bold" | '''—'''

| style="text-align:right; font-weight:bold" | '''—'''

| style="text-align:right; font-weight:bold" | '''1,912'''

| style="text-align:right; font-weight:bold" | '''( 48 )'''

| style="text-align:left; font-weight:bold" | '''Total'''

| style="text-align:right; font-weight:bold" | '''234,953'''

| style="text-align:right; font-weight:bold" | '''( 1,484 )'''

| style="text-align:right; font-weight:bold" | '''185,663'''

| style="text-align:right; font-weight:bold" | '''( 15,394 )'''

| style="text-align:right; font-weight:bold" | '''420,616'''

| style="text-align:right; font-weight:bold" | '''( 16,878 )'''

{{Indexing|Fixed maturity securities, available-for-sale, by contractual maturity at December 31, 2024.|Fixed maturity securities, available-for-sale, by contractual maturity at December 31, 2024, showing fair value and gross unrealized losses for maturities less than 12 months and 12 months or more, across U.S. government securities, corporate securities, and municipal securities.|966xer0dpm|kind=table|order=118}}

| style="text-align:left; font-weight:bold" | '''Total fixed maturity securities, available-for-sale'''

| style="text-align:right; font-weight:bold" | '''480,693'''

| style="text-align:right; font-weight:bold" | '''( 7,353 )'''

| style="text-align:right; font-weight:bold" | '''236,741'''

| style="text-align:right; font-weight:bold" | '''( 31,331 )'''

| style="text-align:right; font-weight:bold" | '''717,434'''

| style="text-align:right; font-weight:bold" | '''( 38,684 )'''

| style="text-align:left; font-weight:bold" | '''Total fixed maturity securities, held-to-maturity:'''

| style="text-align:right; font-weight:bold" | '''2,144'''

| style="text-align:right; font-weight:bold" | '''( 2 )'''

| style="text-align:right; font-weight:bold" | '''36,573'''

| style="text-align:right; font-weight:bold" | '''( 434 )'''

| style="text-align:right; font-weight:bold" | '''38,717'''

| style="text-align:right; font-weight:bold" | '''( 436 )'''

| style="text-align:left; font-weight:bold" | '''Total'''

| style="text-align:right; font-weight:bold" | '''482,837'''

| style="text-align:right; font-weight:bold" | '''( 7,355 )'''

| style="text-align:right; font-weight:bold" | '''273,314'''

| style="text-align:right; font-weight:bold" | '''( 31,765 )'''

| style="text-align:right; font-weight:bold" | '''756,151'''

| style="text-align:right; font-weight:bold" | '''( 39,120 )'''

{{Indexing|Allowance for credit losses on fixed maturity securities at December 31, 2025.|Allowance for credit losses on fixed maturity securities at December 31, 2025, detailing balances for available-for-sale and, held-to-maturity securities, including current period provision and recoveries of previously written-off amounts.|966xer0dpm|kind=table|order=119}}

| style="text-align:left" | '''Balance at December 31, 2025'''

| style="text-align:right" | '''7,000'''

| style="text-align:right" | '''468'''

{{Indexing|Allowance for credit losses on fixed maturity securities at December 31, 2024.|Allowance for credit losses on fixed maturity securities at December 31, 2024, detailing balances for held-to-maturity securities, including current period provision and recoveries of previously written-off amounts.|966xer0dpm|kind=table|order=120}}

| style="text-align:left" | '''Balance at December 31, 2024'''

| style="text-align:right" | '''243'''

{{Indexing|Net realized investment gains and losses.|Net realizedRealized investment gains and losses for 2023-2025, broken down by fixed maturity securities (available-for-sale), equity securities, and other investments.|jpoeftv18u|kind=table|order=121}}

| style="text-align:left; font-weight:bold" | '''Total'''

| style="text-align:right; font-weight:bold" | '''37,949'''

| style="text-align:right; font-weight:bold" | '''10,937'''

| style="text-align:right; font-weight:bold" | '''7,079'''

| style="text-align:left; font-weight:bold" | '''Total'''

| style="text-align:right; font-weight:bold" | '''( 14,245 )'''

| style="text-align:right; font-weight:bold" | '''( 12,516 )'''

| style="text-align:right; font-weight:bold" | '''( 7,155 )'''

| class="wt-indent-1" style="text-align:left" | '''Net investment gains'''

| style="text-align:right" | '''22,149'''

| style="text-align:right" | '''6,342'''

| style="text-align:right" | '''11,054'''

{{Indexing|ProceedsNet fromunrealized salesinvestment ofgains available-for-saleand securities.losses|ProceedsUnrealized frominvestment salesgains ofand available-for-sale securities for 2023-2025losses, including fixed maturity andsecurities, equity securities.|jpoeftv18uj8uunnd14x|kind=table|order=122}}

{{Indexing|Net investment income by investment type.source|Net investment income, byfixed investmentmaturity typesecurities, forequity 2023-2025securities, includingequity fixedmethod maturity, equityinvestments, mortgage loans, andindirect loans, short-term investments., cash|jpoeftv18u|kind=table|order=123}}

| style="text-align:left; font-weight:bold" | '''Total investment income'''

| style="text-align:right; font-weight:bold" | '''87,666'''

| style="text-align:right; font-weight:bold" | '''87,513'''

| style="text-align:right; font-weight:bold" | '''45,897'''

| style="text-align:left" | '''Net investment income'''

| style="text-align:right" | '''83,619'''

| style="text-align:right" | '''80,600'''

| style="text-align:right" | '''40,340'''

{{Indexing|Components of accumulated other comprehensivedeferred income (loss).taxes|Components of accumulated other comprehensiveDeferred income (loss) for 2023-2025taxes, including fixed maturity securities and deferred income taxes.|j8uunnd14xkmocop7wiu|kind=table|order=124}}

| style="text-align:left; font-weight:bold" | '''Total'''

| style="text-align:right; font-weight:bold" | '''33,577'''

| style="text-align:right; font-weight:bold" | '''833'''

| style="text-align:right; font-weight:bold" | '''20,532'''

{{Indexing|4. Fair Value Measurements|Fair value measurements, usefinancial instruments, market approach, third-partyfair value of datainvestments, andperiodic aanalyses, three-level hierarchy:|di0lc3m1jj|kind=prose|order=125|f1=Fair value hierarchy|v1=three-level hierarchy|f2=Level 1 for inputs|v2=U.S. government securities, mutual funds, and common stock; |f3=Level 2 for preferredinputs|v3=Preferred stocks, municipal securities, corporate securities, and miscellaneous; Level 3 for unobservable inputs.|di0lc3m1jj|kind=prose|order=125}}

* The Company's financial instruments include assets and liabilities carried at fair value, and those carried at cost or amortized cost but disclosed at fair value in consolidated financial statements ^{p. 84}.

* The ''market approach'' is generally usedapplied to determine fair value, utilizingusing prices and data from market transactions ofinvolving identical or comparable assets and liabilities ^{p. 84}.

* ''Fair value of investments'' is primarily determined using data from third-party investment managers or pricing vendors ^{p. 84}.

* ''Periodic analyses'' are conductedperformed on third-party prices to ensure they are reasonable estimates of fair value, including reviewing month-to-month fluctuations and comparing valuations from different pricing services for identical securities ^{p. 84}.

* FinancialThe instrumentsCompany areclassifies classifiedfinancial instruments into a ''three-level hierarchy'': ^{p. 84}.

** ''Level 1 inputs'': are unadjustedUnadjusted, quoted prices for identical assets or liabilities in active markets at the measurement date ^{p. 84}.

** ''Level 2 inputs'': are observable inputsInputs other than Level 1 quoted prices, corroboratedthat are observable for the asset or liability through corroboration with market data at the measurement date ^{p. 84}.

** ''Level 3 inputs'': are unobservableUnobservable inputs reflecting management's best estimate of what market participants would use in pricing the asset or liability at the measurement date ^{p. 84}.

* ''U.S. government securities, mutual funds, and common stock'' usefair value is measured using unadjusted quoted prices for identical instruments in an active exchange, representing Level 1 inputs ^{p. 84}.

* ''Preferred stocks, municipal securities, corporate securities, and miscellaneous'' usefair value is determined using a pricing model with market-based inputs likesuch as trades in illiquid markets for specific securities or active markets for similar securities, considering benchmark yields, issuer spreads, security terms, and other market data, representing Level 2 fair value inputs ^{p. 84}.

** ''Commercial mortgage-backed securities, residential mortgage-backed securities, and other asset-backed securities'' use a pricingThe model withconsiders market-basedbenchmark inputs such as dealer quotesyields, marketissuer spreads, and yield curves, and may evaluate individual tranches by determining cash flows using security terms, collateraland performanceconditions, creditand information,other benchmark yields, and estimatedmarket prepaymentsdata, representing Level 2 fair value inputs ^{p. 84}.

* The''Fixed discountmaturity ratesecurities, spreadavailable for sale classified as Level 3'', fixedinclude maturitycorporate securities representsand theother riskasset-backed associatedsecurities withmanaged futureby cashan flows,independent includingasset inflation, opportunitymanager cost,and andpriced timeby valuean ofindependent moneyprovider ^{p. 84}.

** Fair value of mortgage loans is determined using the income approach with observable and unobservable (Level 3) inputs ^{p. 84}.

** The unobservable input for mortgage loans is the spread applied to a prime rate for discounting cash flows, representing the incremental cost of capital based on borrower's ability to pay and collateral value relative to loan balance, subject to judgment and uncertainty ^{p. 84}.

* ''Derivatives'', included in other assets, consist of exchange-traded options contracts ^{p. 84}.

** Fair values of derivatives are measured using quoted prices in active markets on the relevant exchange, specifically the volume-weighted average price of trades in similar contracts or the last trade settlement price if no trades occur, representing Level 1 inputs ^{p. 84}.

* The Company disclosesmeasures faircertain valuesassets, ofincluding other''investments financialin instrumentsindirect whereloans practicableand toloan estimatecollateral, usingequity quotedmethod marketinvestments, prices orand other valuationinvested assets'', at fair value on a nonrecurring basis only when methodologiesimpaired ^{p. 84}.

* JudgmentsThe areCompany is required into estimatingdisclose fair valuevalues whenof quotedother marketfinancial pricesinstruments arewhere unavailable,practicable andto theseestimate estimatesfair may notvalue, indicateeven amountsif realizablecarried inat acost currentor marketamortized exchangecost ^{p. 84}.

** DifferentEstimated fair value amounts are determined using available market assumptionsinformation orand estimationother valuation methodologies, canbut affectconsiderable estimatedjudgment fairis valuerequired amountswhen quoted market prices are unavailable ^{p. 84}.

** As of December 31, 2025, thetheir fair value of held-to-maturity fixed maturity securities was determined using the income approach with unobservable inputs (Level 3) inputs ^{p. 84}.

* ''Investment in RedBird Capital Partners'' is included in other long-term investments, and is a limited partnership investingthat invests in Bishop Street Underwriters, LLC (MGA) ^{p. 84}.

** The investment had a fair value of ''$55.6 million'' at December 31, 2025, and ''$28.2 million'' at December 31, 2024, determined using the net asset value ^{p. 84}.

** Procedures to assess the reasonableness of the investment's fair value include obtaining and reviewing audited financial statements ^{p. 84}.

** The unfunded commitment related to the investment was ''$18.3 million'' at December 31, 2025, and ''$24.4 million'' at December 31, 2024 ^{p. 84}.

** The Company may sell its interest in the investment with prior written notice and general partner approval ^{p. 84}.

** ThisIn accordance with Accounting Standard Codification 820-10, this investment is measured at fair value using the net asset value per share practical expedient and is not classified in the fair value hierarchy, in accordance with Accounting Standard Codification 820-10 ^{p. 84}.

** Net earned premiums related to this agreement were ''$41.5 million'' for the year ended December 31, 2025, and ''$2.5 million'' for the year ended December 31, 2024 ^{p. 84}.

** Fair value for notes payable is determined using the income approach with observable inputs (Level 2) inputs ^{p. 84}.

** Fair value of subordinated debt is determined using the income approach with observable inputs (Level 2) inputs ^{p. 84}.

* Other financial instruments that qualify as ''insurance-related products'' and are exempt from fair value disclosure requirements ^{p. 84}.

{{Indexing|Fair value of subordinatedfinancial debt.instruments|Fair value of subordinatedfinancial debt for 2024 and 2025, showing high, low, and weighted average interest rates.instruments|di0lc3m1jj|b3bc9gy5x7|kind=table|order=126}}

{{Indexing|Weighted average interest rates for 2024 and 2025.|Weighted average interest rates for 2024 and 2025, showing high, low, and weighted average percentages.|di0lc3m1jj|kind=table|order=127}}

{{Indexing|Fixed maturity securities available-for-sale and held-to-maturity as of December 31, 2025.|Fixed maturity securities, available-for-saleU.S. andgovernment held-to-maturitysecurities, ascorporate ofsecurities, Decembermunicipal 31securities, 2025,residential categorizedmortgage-backed bysecurities, faircommercial valuemortgage-backed hierarchy levels (Level 1securities, Levelother 2,asset-backed Level 3) and security type.securities|di0lc3m1jj|utnmaoxh50|kind=table|order=128}}

| style="text-align:left; font-weight:bold" | '''Total fixed maturity securities, available-for-sale'''

| style="text-align:right; font-weight:bold" | '''44,468'''

| style="text-align:right; font-weight:bold" | '''1,660,918'''

| style="text-align:right; font-weight:bold" | '''150,917'''

| style="text-align:right; font-weight:bold" | '''1,856,303'''

| style="text-align:left; font-weight:bold" | '''Total fixed maturity securities, held-to-maturity'''

| style="text-align:right; font-weight:bold" | '''—'''

| style="text-align:right; font-weight:bold" | '''—'''

| style="text-align:right; font-weight:bold" | '''33,603'''

| style="text-align:right; font-weight:bold" | '''33,603'''

| style="text-align:left; font-weight:bold" | '''Total equity securities'''

| style="text-align:right; font-weight:bold" | '''—'''

| style="text-align:right; font-weight:bold" | '''1,174'''

| style="text-align:right; font-weight:bold" | '''—'''

| style="text-align:right; font-weight:bold" | '''1,174'''

| style="text-align:left" | '''Mortgage loans'''

| style="text-align:right" | '''—'''

| style="text-align:right" | '''—'''

| style="text-align:right" | '''9,902'''

| style="text-align:right" | '''9,902'''

| style="text-align:left" | '''Short-term investments'''

| style="text-align:right" | '''264,299'''

| style="text-align:right" | '''—'''

| style="text-align:right" | '''—'''

| style="text-align:right" | '''264,299'''

| style="text-align:left" | '''Derivatives'''