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

| archive_filesummary_md = File:Skyward<!-2025-FY ARCHIVE_MD_LINK_HERE --Annual_report.md>

* The company operated under the name Houston International Insurance Group, Ltd. until rebrandingre-branding as Skyward Specialty in November 2020 ^{p. 1}.

* ''Lines of business'' include general liability, excess liability, professional liability (including cyber and media liability insurance), commercial auto, group accident and health, property, agriculture, credit, surety, and workers’ compensation ^{p. 1}.

* The business mix is principally primary insurance and, balanced between E&S and admitted markets ^{p. 1}.

* A portion of the business is ''specialty reinsurance'', primarily property, agriculture, and credit ^{p. 1}.

* Specialty reinsurance focuses on attractive specialty classes where approaching through reinsurance is more efficient due to factors like cost of entry and geographic expansion costs ^{p. 1}.

* This diversificationDiversification, including businesses not typically aligned with traditional P&C pricing cycles, combined with underwriting and claims expertise, aims to consistently produce strongconsistent growth and profitability across all insurance pricing cycles ^{p. 1}.

* High-quality leadership, underwriting and claims teams, technology DNA, advanced analytics capabilities, diversified book of business, and strong competitive position in chosen market niches are believed to position the company for continued profitable growth ^{p. 1}.

* All insurance company subsidiaries are group rated and have financial strength ratings of "A" (Excellent) from A.M. Best Company, with a stable outlook ^{p. 1}.

* On September 2, 2025, the company entered into two share purchase agreements (the "Apollo Majority SPAs") with institutional and management shareholders (the "Majority Sellers") of Apollo Group Holdings Limited ("Apollo") (the "Majority Sellers") ^{p. 2}.

* Apollo is a leading U.S.-centric specialty underwriting platform operating at Lloyd’s of London, characterized by low volatility, high growth, and a capital-light business model ^{p. 2}.

* Apollo's grossbusiness writtenmodel premiumis hascharacterized grownby consistentlylow sincevolatility, itshigh formationgrowth, inand 2010capital efficiency ^{p. 2}.

* Through Syndicate 1971, Apollo provides aan innovative platform liability product for the digital and sharing economy ^{p. 2}.

* Apollo earns managing agency fees and profit commissions for beingas the managing agent tofor its own syndicates and tofor innovative third-party syndicates (platform partners) ^{p. 2}.

* The acquisition aligns with Skyward Specialty’s strategy by introducingbringing new specialty niches, a distinctive new economy offering, accelerating innovation, and adding Apollo’s advanced technology capabilities ^{p. 2}.

* David Ibeson will continue as CEO of Apollo, leading Apollo'sits growth as a subsidiary of Skyward Specialty, along with Apollo’s management team ^{p. 2}.

* The company operates with one reportable segment, offering a broad range of insurance coverages across various market niches ^{p. 3}.

* This structure aims to effectively serve customerscustomer needs, partner with distributors, and achieve attractive risk-adjusted returns ^{p. 3}.

* The A&H division targets small and medium-sized enterprises seeking to control healthcare costs bythrough self-insuringinsurance ^{p. 3}.

* A&H products are written on an admitted basis and distributed throughvia retail and wholesale brokers ^{p. 3}.

* ''Agriculture and Credit (Re)insurance'' underwriting division provides specialty risk-transfer solutions across a global portfolioglobally ^{p. 3}.

* This division's portfolio includesspans agriculture, dairy and livestock revenue protection, and mortgage and credit product lines ^{p. 3}.

* The divisionIt supports insurers, MGAs, and other risk originators with tailored treaty protection using proportional and excess of loss structures ^{p. 3}.

* The ''Globalglobal agriculture book'' covers weather and, natural peril volatility, production, and other production/yield risks, helping toclients manage catastrophe exposure and seasonal earnings variability ^{p. 3}.

* The ''Mortgagemortgage portfolio'' supports government-sponsored entities and private mortgage insurers against default and loss severity volatility due to macroeconomic stress, structured to manage tail risk ^{p. 3}.

* The ''Creditcredit portfolio'' protects against losses from default risk for single obligors and multi-buyer trade credit across diverse regions and industries ^{p. 3}.

* The ''Dairydairy and livestock business'' provides producers withoffers revenue protection against price volatility in milk, cattle, and hog markets ^{p. 3}.

* These instruments are used solely for managing adverse price movements, with positions adjusted throughoutbased on market conditions and therisk yearprofile ^{p. 3}.

* ''Construction & Energy Solutions'' underwriting division focuses on high-severity exposures, withoffering tailored multi-line solutions including general liability, excess liability, commercial auto, and workers’ compensation ^{p. 3}.

* ''Global Property'' underwriting division provides comprehensive property insurance and reinsurance solutions for commercial clients worldwide ^{p. 3}.

* ''Professional Lines'' underwriting division includes three units: management liability, professional liability (including cyber), and allied health (including life sciences) ^{p. 3}.

* Management/Professional liability and allied health provide primary and excess claims-made liability products on E&S and admitted bases ^{p. 3}.

* TheseDistribution productsfor areProfessional offeredLines onis E&Sthrough wholesale and admittedretail basesbrokers, distributeddepending throughon wholesalethe and retail brokersproduct ^{p. 3}.

* This partnership model is used towhen participateprogram profitablyadministrators orhave extenda reachcompetitive inadvantage certain(scale markets,or leveragingproprietary administrators'technology) competitivethat advantageswould likebe scaledifficult orfor proprietarythe technologycompany to replicate ^{p. 3}.

* FocusThe focus is on small to medium-sized enterprises with aggregate bond programs up to approximately ''$100.0 million'' for contract and ''$125.0 million'' for commercial and transactional ^{p. 3}.

* ThisSurety business is written on an admitted basis and distributed through retail agents and brokers ^{p. 3}.

* EmphasisThis isdivision onemphasizes risks considered hard- to-place risksplace due to complexity, loss history, or limited operating history (e.g., startups) ^{p. 3}.

* AccessMarket toaccess thefor marketTransactional in this divisionE&S is exclusively through wholesale brokers ^{p. 3}.

* This strategy is referred to as "Rule“Rule Our Niche"Niche” and aims to build a strong defensible market position and competitive moat ^{p. 3}.

* The company focuses on profitable niches in the market that require technical underwriting and claims management, which act as barriers to entry ^{p. 4}.

* The selectedcompany nichetargets areasunderserved, withindislocated, or complex commercial lines P&C markets arewhere consideredstandard attractiveproducts for generating risk-adjustedare returnsinsufficient ^{p. 4}.

* TheRisks companyin targets underserved, dislocatedcore markets orrequire those whereefficient, standardindividual productsunderwriting areto insufficientgenerate forsustainable customerunderwriting needsprofit ^{p. 4}.

* Underwriting teams are knowledgeable, experienced, and empowered, which is crucialcritical for operatingcomplex, in markets withnon-automatable risks difficult to automate ^{p. 4}.

* The company avoids strict underwriting rules, allowingallows professionals freedom to use their expertise and judgment in evaluating and pricing risks, rather than imposing strict underwriting rules ^{p. 4}.

* The company has a specialized team of claims professionals knowledgeable inabout thetheir niches and lines of business served ^{p. 4}.

* Analytics capabilities provide senior leadership and claims teams with real-time, detailed information on open claims and benchmarks against closed claims for senior leadership and claims teams ^{p. 4}.

* SkyBI, the company's business intelligence platform, provides real-time intelligence for superior decision-making to senior leadership and technical teams for decision-making ^{p. 4}.

* SkyBI incorporatesreflects best practices learned from the management team's experience in P&C insurance and technology sectors ^{p. 4}.

* SkyBI provides information and performance metrics across the company in aan easy-to-consume visualized format ^{p. 4}.

* Data in SkyBI can be filtered by categories such as distributor, customer segment, line of business, industry, individual underwriter, and specific risk feature ^{p. 4}.

* The company believes thatevery underwriting and claims decision can be augmented with new types of risk data and advanced technology can augment underwriting and claims decisions ^{p. 4}.

* Underwriting decisions are supportedbacked by historical data and in-depth risk evaluation from intentional investment in data collection and processing capabilities ^{p. 4}.

* Underwriting and claims capabilities are amplified by combining historical data with new forms of risk data and predictive analytics ^{p. 4}.

* GenerativeThe artificialcompany intelligenceutilizes isgenerative usedartificial intelligence in underwriting and claims handling to enhanceaid effectiveness and efficiency, while still relying on employee expertise ^{p. 4}.

* ThisThe diversificationdiversified business includes businessoperations not typically aligned with traditional P&C cycles ^{p. 4}.

* The company aims to evolve with and adapt to the market by, growing certain lines in favorablewhen conditions are favorable and limiting exposure inwhen conditions are less favorable conditions ^{p. 4}.

* The company has a distinctive winning culture, evidenced by internal surveys, public information (Glassdoor, LinkedIn), and selection as a "Best Places to Work in Insurance" ^{p. 4}.

* TheKey cultureto andthe operatingculture approach featureis a flat structure of communication and decision-making structure ^{p. 4}.

* Staff are trusted to make decisions that achieveproduce or exceed desired financial results and are supported by a clear system of performance measurement system ^{p. 4}.

* The company adopted a hybrid work schedule, offeringproviding flexibilityemployees forwith remote working flexibility ^{p. 4}.

* The company maintains an entrepreneurial environment that encourages and rewards a proactive approach to capitalize on market disruption ^{p. 4}.

* The leadership team, is led by Chairman and CEO, Andrew Robinson, is experienced, innovative, and entrepreneurial ^{p. 4}.

* The executiveSenior leadership teamcompensation hasis astructured trackto recordalign ofwith successshareholders, inwith seniora managementmaterial rolesportion atin industrylong-leadingterm P&Cand companiesshort-term andincentives intied to delivering buildingsustainable newunderwriting businessesreturns ^{p. 4}.

* SeniorExecutive leadership compensationhas isadditional structuredlong-term incentive targets tied directly to aligngrowth in book value withper shareholdersshare ^{p. 4}.

* The company's "Rule Our Niche" strategy aimsguides toall generateactivities best-in-classfrom underwritingrecruiting profitability within its niches and create superior long-term shareholder value through growth in book valueto perclaims shareresolution ^{p. 5}.

* CoreThe tenetsstrategy ofaims theto "Ruleachieve Ourbest-in-class Niche"underwriting strategyprofitability includewithin attractingniches and retainingcreate bluesuperior long-chipterm underwritingshareholder andvalue claimsthrough talentgrowth toin expand andbook enhancevalue marketper positionshare ^{p. 5}.

* TheCore companytenets seeksof tothe hire"Rule andOur retainNiche" technicalstrategy underwritinginclude professionalsattracting withand longretaining blue-standingchip industry relationshipsunderwriting and claims professionals with expertise in specific nichestalent ^{p. 5}.

* TheseThe company seeks to hire technical underwriting professionals with long-standing industry relationships areand claims professionals with expertise in their niches crucialto forensure consistentsteady access to preferred business ^{p. 5}.

* The company aimsbelieves it is a preferred employer for top talent in the industry and plans to grow its market position by recruiting world-class talent in chosen markets ^{p. 5}.

* Another core tenet is leveraging technology DNA to differentiate from competitors ^{p. 5}.

* The company has demonstrated an ability to use new forms of risk data forms and advanced technology in complex, higherhigh-severity risk categories within the specialty P&C insurance market categories ^{p. 5}.

* SkyBI enablesallows for prompt sensing and quick response to market changes ^{p. 5}.

* Core operating platforms allowenable efficient entry into new markets without complex orsystem burdensome systemsburdens ^{p. 5}.

* The company believes its's technological advantage supportsis believed to position it for profitable growth and expansion into additional specialty market niches ^{p. 5}.

* TheA strategyfurther alsotenet includesis profitably growing existing lines of business and expanding with new underwriting divisions ^{p. 5}.

* The company is positioned to capitalize on trends impactingaffecting customers in the U.S. and globally, such as increased demand for specialized insurance due to rising and complex risks ^{p. 5}.

* TheseOne trend is the rising demand for specialized insurance due to increasing and complex risks includefrom climate change/, severe weather, supply chain uncertainty, financial inflation, cyber risk, novel health risks, increased litigation, attorney involvement, jury awards, and healthcare delivery/cost ^{p. 5}.

* Another notable market trend is the emergence of "micro cycles and micro dislocations" where different P&C insurance market segments experience hardening and softening at varyingdifferent times ^{p. 5}.

* The company has reactedresponded quickly to these trends by launching new underwriting units (manysome not aligned with P&C cycles), entering underserved markets, partnering on advanced technology, and launching new captive solutions ^{p. 5}.

* Meeting long-term goals, including best-in-class underwriting returns and book value per share growth, depends on execution of day-to-day operationsoperational execution across all functional departments (underwriting, product management, claims management) ^{p. 5}.

* SkyBI provides asenior foundationmanagement forwith seniora managementfoundation to monitor performance, including renewal rates, new business pricing, portfolio performance for underwriters, and claims aging/, reserving practices, and outcomes for adjusters ^{p. 5}.

* Cross-functional collaboration ensures regular review of performance and trends by underwriting, claims, actuarial, and product management teams regularly review performance and trends to implement portfolio, pricing, and coverage changes quickly ^{p. 5}.

* The company's practice is to maintain incurred but not reported reserves (IBNR) that, combined with case reserves, are aboveexceed the actuarial central estimate ^{p. 5}.

* The company's marketing'Marketing and distribution approach'' mirrors its underwriting strategyapproach and is centrala key facet toof itsthe "Rule Our Niche" strategy ^{p. 6}.

* ''Underwriting teams'' and the companyCompany maintainhave strong relationships and reputations with distribution partners and strong reputations, facilitatingwhich newhelps establish affiliations with new partners ^{p. 6}.

* The''Distribution company attributes itspartners'' successare withattracted distribution partners toby deep expertise in niche markets, high-caliber underwriters, a culture of innovation, thoughtful product lineupline-up and design, and responsivespeed and quality of serviceresponsiveness ^{p. 6}.

* All underwriting''Underwriting divisions'' dedicateinvest significant time and effort to maintainingsustain and expandingexpand distribution partner loyalty and long-term relationships ^{p. 6}.

* The company tailors its choice''Choice of distribution partners'' is tailored to access specific business, similarthe toCompany how it tailors underwritingseeks to insureds' needswrite ^{p. 6}.

* ''Products are distributed'' through retail agents, wholesale brokers, select program administrators, and captive managers ^{p. 6}.

* This distribution''Distribution approach'' enablesallows effective and efficient access to targeted business based on market niche needs and dynamics ^{p. 6}.

* The company's underwriting approach is centralintegral to its "Rule Our Niche" strategy and market success ^{p. 7}.

* Within its nine divisions, the company further specializes underwriting teams to focus on specific niches within their respective markets ^{p. 7}.

* The underwriting approach reliesis built on hiring highly experienced, best-in-class, and diverse teams of technical underwriters with proven track records in specific specialty niche markets ^{p. 7}.

* Underwriters' skillsskill sets are enhanced with advanced technology and data analytics, and they are empowered withgiven appropriate decision-making authority ^{p. 7}.

* This approach aimsis forconsidered key to superior risk selection and, pricing, leadingand toachieving sustainable best-in-class underwriting results across market cycles ^{p. 7}.

* The company augmentsaims to improve underwriting professionals' capabilities usingand newexperience formsusing ofnew data and analytics for risk selection and pricing ^{p. 7}.

* Underwriting data is captured in the company's business intelligence platform, SkyBI, which serves as a comprehensive data repository for reporting, analytics, and other data capabilities ^{p. 7}.

* SkyBI serves as a comprehensive data repository for reporting, analytics, and other data capabilities, and is a key tool for senior management and business leaders ^{p. 7}.

* The company is highly selective in bindingthe policies it binds ^{p. 7}.

* Underwriters are encouraged to move on quickly from prospective opportunities quickly if they cannot reasonably expect to bind coverage at premium and coverage terms meetingthat meet company standards ^{p. 7}.

* When accepting risks, the company carefully establishes terms and prices suited to the underlying exposure ^{p. 7}.

* In the admitted market, the company ensures approved forms and filed rates are appropriate and adequate for accepted risks, while allowing flexibility for specific or /unique exposures ^{p. 7}.

* In the E&S market, the company uses freedom of rate and form to matchensure risk and coverage toare theappropriate for unique needs and exposures of that market ^{p. 7}.

* PoliciesThe arecompany craftedendeavors to craft policies that offer affordable and appropriate protection for insureds' exposures, withwhile coveragestructuring structuredcoverage to make potential losses more predictable and claims costs manageable ^{p. 7}.

* This collaboration ensures timely analysis and action onthat trends in business, legal and tort developments, and competitor and regulatory actions are analyzed, shared, and acted upon promptly ^{p. 7}.

* Underwriters are consideredviewed as central to the company, with all support functions incentivized and measured to help achieve underwriting profitability targets ^{p. 7}.

* This structure helps identify opportunities and issues early, contributing to the company's nimbleness and ability to leveragecapitalize on market disruptions ^{p. 7}.

* Underwriting controls and procedures are regularly reviewed to ensure underwriters operate with clear visibility to profitably underwrite in each market served ^{p. 7}.

* Skyward's claims department operates under six guiding principles: prompt and comprehensive claim investigations using advanced analytics and technology; quality claims handling andservice with customer engagement; timely establishment of reserves based onreflecting best estimates of ultimate loss; effective pursuit of contribution and subrogation; detection and prevention of fraud; and disciplined litigation management for superior legal defense and cost monitoring ^{p. 8}.

* Continuous training is provided to claim staff on claim evaluation, strategy, litigation management, good-faith claims handling, and best practices to achieve timely and optimal claim outcomes ^{p. 8}.

* Third Party Administrators (TPAs) are utilized for specificcertain instances, such as programs, captives, occupational accident, workers' compensation, and runoff claims ^{p. 8}.

* TPAs are actively managed, overseen, and regularly auditedmonitored to ensure compliance with Skyward's claims handling and reserving guidelines and best practices ^{p. 8}.

* LitigationFor guidelinesliability haveclaims beenagainst developedan forinsured, claimsindependent professionalslegal andcounsel outsideis counselretained tobased ensureon appropriategeographical defenselocation forand insuredsexpertise ^{p. 8}.

* ALitigation legalguidelines spendhave managementbeen solutiondeveloped isfor usedclaims toprofessionals analyzeand legaloutside invoicescounsel forto adherenceensure toappropriate case handlingdefense and billing practice standards, ensuring reasonable and customary legal costs ^{p. 8}.

* A "quick strike" program has been implemented for commercial auto claims, deployingto experienced investigators and vendorsrespond to accident scenes within two hours, regardless ofclaim locationreports ^{p. 8}.

* The "quick strike" program assistsdeploys inexperienced evaluatinginvestigators and vendors to accident scenes, ideally within two hours, to evaluate facts and circumstances and resolvingfacilitate quick resolution of third-party claims quicklyif appropriate ^{p. 8}.

* ManagersClaims managers and adjusters collaborate closely with underwriting partners to inform them of legal trends and emerging claims issues, educating underwriters on loss experience for risk selection ^{p. 8}.

* ''Technology'' is central to Skywardthe Specialty Insurance Groupcompany's operations and decision-making, aiming forto drive long-term competitive advantagessuccess ^{p. 9}.

* ''SkyBI'', incorporatesthe bestcompany's practicesbusiness fromintelligence theplatform, managementprovides team'sreal-time experienceintelligence into P&Csenior insuranceleadership and technologytechnical teams for sectorsdecision-making ^{p. 9}.

* SkyBI isincorporates abest single,practices comprehensivefrom enterprise-widethe datamanagement repositoryteam's forexperience reporting,in businessthe intelligence,P&C analytics,insurance and advancedtechnology data capabilitiessectors ^{p. 9}.

* ''Predictive analytics technology'' augmentsis used to augment employee capabilities usingdaily, utilizing new risk data and predictiveartificial analytics, including AI,intelligence for risk selection, pricing, and claims handling ^{p. 9}.

* UnderwritingWithin divisionseach intentionallyunderwriting division, actions are intentional to "Rule Our Niche" through constant innovation tailored to specific divisions/markets ^{p. 9}.

* The core platform organization is used for all business except for accident & health, global property, agriculture, and credit (re)insurance, and surety, which require dedicated core processing components due to their unique features ^{p. 9}.

* Data from all divisions' core operating platforms flows to the SkyBI platform with comparable data quality and granularity ^{p. 9}.

* AdvancedThe use of advanced technology for underwriting and claims, SkyBI, and core operating platforms createcreates a flywheel effect, enabling underwriters to better select risk, claims professionals to adjudicate claims, unit leaders to communicate with partners, and senior leadership to evaluate business trends ^{p. 9}.

* TheThese companytools facesalso externalenable threatsmore toaccurate, itseffective, informationand technologyefficient systems,communication includingwith systemdistribution failurepartners, data theft attemptsreinsurers, and ransomwareother third-party attackspartners ^{p. 9}.

* Data is replicated in real-time to a third-party cloud disaster recovery site for use during major system failures ^{p. 9}.

* Actions to prevent system and data disruptions include: actively monitoring Cybersecurity and Infrastructure Security Agency’s (“CISA”) cybersecurity directives and taking immediate action on identified vulnerabilities ^{p. 9}.

** ConductingTwo-factor monthlyauthentication vulnerabilityis scansrequired onfor allaccess network-attached devices atto all locations, with patching as neededsystems ^{p. 9}.

** RequiringMonthly two-factorsecurity authenticationtraining is provided for systemall accessemployees ^{p. 9}.

** ConductingEndpoint monthlydetection securityagents trainingare implemented for allthreat detection and employeesresponse ^{p. 9}.

* TheReinsurance companyis strategically purchases reinsurancepurchased from third parties to protect capital from severity events (large single event losses or catastrophes) and reduce earnings volatility ^{p. 10}.

* AnnualFactors renewalinfluencing considerationsreinsurance forpurchase reinsurancechanges purchasesat annual renewal include changesplans to change underlying insurance coverage, updated loss activity, capital and surplus levels, changes in risk appetite, and the cost and availability of reinsurance treaties ^{p. 10}.

* The company purchases quota share, excess of loss, and facultative reinsurance coverage to limit exposure from losses on any one occurrence ^{p. 10}.

* The mix of reinsurance purchased is based onconsiders efficiency, cost, risk appetite, and specific factors of the underlying risks underwritten ^{p. 10}.

* ''Quota share reinsurance'' involves athe reinsurer assuming a specified percentage of the ceding company’s losses from a defined class of business class in exchange for a corresponding percentage of premiums, net of a ceding commission ^{p. 10}.

* ''Excess of loss reinsurance'' involves athe reinsurer assuming all or a portion of the ceding company’s losses for an individual claim or event above a specified amount, in exchange for a negotiated premium, and includesincluding the catastrophe reinsurance program ^{p. 10}.

* The company actively manages and monitors property writings aggregation by geographic area to limit potential loss aggregation from severe events like hurricanes, convective storms, and earthquakes ^{p. 10}.

* Catastrophe reinsurance is purchased to further mitigate property loss aggregation duelosses tofrom single or series of events ^{p. 10}.

* Third-party stochastic and proprietaryinternal deterministic models are used to analyze theaggregation risk of loss aggregation from such events and informfor catastrophe reinsurance purchases ^{p. 10}.

* These models provide a quantitative view of PML (Probable Maximum Loss) events, which estimate the expectedestimating loss levellevels for a given return period ^{p. 10}.

* Based on modeling, an event beyond a 1 in 250-year PML would be required to exhaust the company's'property catastrophe coverage'' of $36.0 million property catastrophe coverage'' ^{p. 10}.

* The company aims to expose no more than 3.0% of stockholders’ equity to a catastrophic loss that is less than a 1 in 250-year event ^{p. 10}.

* The company seeks to purchase reinsurance from reinsurers rated at least "A“A-"” ("Excellent"“Excellent”) or better by A.M. Best ^{p. 10}.

* As of December 31, 2025, ''98% of reinsurance recoverables'' were from reinsurers rated "A“A-"” (Excellent) or better by A.M. Best, or were collateralized ^{p. 10}.

* TheIf companyreinsurers retainsfail primaryto liabilitypay toclaims, policyholdersthe ifcompany reinsurersretains failprimary liability to pay claimspolicyholders, leadingpotentially toresulting potentialin losses ^{p. 10}.

* Allowances for uncollectible reinsurance are established due to the risk of reinsurer defaultfailure ^{p. 10}.

* The ''allowance for uncollectible reinsurance'' was $2.3 million at December 31, 2025, and December 31, 2024 ^{p. 10}.

* ''Enterprise Risk Management (ERM)'' is embeddedintegrated ininto nearly every aspect of the company and guides day-to-daydaily activities ^{p. 11}.

* ''The ERM approach'' aims to ensureachieve an acceptable risk-adjusted return for shareholders while maintaining trust and reliability for those served ^{p. 11}.

* ''UnderwritingThe company is intentional in its underwriting and asset portfolio construction'' are intentional ^{p. 11}.

* ''LiabilityAn example of ERM application is balancing liability duration and market cyclicality'' of the underwriting portfolio are balanced ^{p. 11}.

* ''Reinsurance'' is used to manage volatility outside of defined risk tolerances ^{p. 11}.

* The ''Investmentinvestment strategy'' targetsfocuses on a diversified target portfolio that balances yield, liquidity, volatility, and potential for principal loss ^{p. 11}.

* The ''Senior Vice President (SVP), Chief Financial Officer (CFO) & Head of ERM - US Operations'' oversees critical ERM processes and chairs the cross-functional corporate ERM Committee ^{p. 11}.

* ''EconomicThe Capital Model (ECM)''company formalizes the company'sits view of risk and solvency inusing termsan of''Economic Capital Model (ECM)'' to measure potential economic loss ^{p. 11}.

* ''The ECM output'' measuresis used to measure potential earnings and capital loss foracross various scenarios ^{p. 11}.

* These outputs are measured against ''Riskrisk tolerances'' are set and updated annually by the ERM Committee and discussed with the Risk Committee of the Board of Directors ^{p. 11}.

* ''The ECM'' provides a probabilistic modeled view of earnings and capital loss, integratingincorporating potential losses from catastrophes, reserving, underwriting, market, credit risk, strategic, and operational risks ^{p. 11}.

* ''The SVP, CFO & Head of ERM'', worksin collaboration with the ERM Committee, to reviewreviews and maintainmaintains a ''comprehensive risk register'' with accountabilities for mitigationsmitigation and monitoring ^{p. 11}.

* The ''Toptop 10 risks'' are identified, quantified by the SVP, CFO & Head of ERM and the ERM Committee, and reviewed quarterly ^{p. 11}.

* ''Reports'' on topthese risks are submitted to the Risk Committee regularly by the SVP, CFO & Head of ERM and the ERM Committee ^{p. 11}.

* The ''Underwriting Committee'' overseesis responsible for overseeing changes in risk appetite, product line, and division expansion ^{p. 11}.

* Within ''Claims department'', monitorspractices handlingare practicesmonitored against guidelines viathrough regular internal audits, conducts monthly large loss reviews are conducted, and maintains a watchlist forof potential high severity claims is maintained ^{p. 11}.

* Within ''Actuarial department'' performs, quarterly reserve studies are performed, and the Reserve Committee meets quarterly to review and respond to trends in loss emergence ^{p. 11}.

* ''ReserveKey Committee''observations meetsfrom quarterlyActuarial toare reviewdiscussed andwith respondthe to trends in loss emergenceCEO ^{p. 11}.

* Reserves are maintained for specific claims incurred and reported, IBNR reserves, and uncollectible reinsurance when appropriate ^{p. 12}.

* The ultimate liability may differ from current reserves, and there is always a risk of inadequate reserves in the insurance industry ^{p. 12}.

* UponWhen a claim reportingis reported, a ''case reserve'' is established for the estimated ultimate payment after assessing coverage, damages, and investigationother investigations ^{p. 12}.

* Case reserve estimates are based on reserving practices and the claims adjuster's experience and knowledge of the claim's typenature and value ^{p. 12}.

* Case reserves are revised periodically based on subsequent developments for each claim ^{p. 12}.

* ''IBNR reserves'' are established forin theaccordance estimatedwith amountindustry ofpractice to cover estimated future loss payments on incurred butclaims not yet reported claims, and for potential development on reported claims ^{p. 12}.

* Reserve estimates are updated as historical loss experience develops, additional claims are reported and/or settled, and new information becomes available ^{p. 12}.

* AdditionalFor additional information on loss reserves, is availablerefer into Item 7 of Form 10-K, "Management’s Discussion and Analysis of Financial Condition and Results of Operations - “Results of Operations - Losses and LAE” and “Critical Accounting Policies” ^{p. 12}.

* The company aims to maintain a balanced investment portfolio primarily consisting of investments that provide predictable and stable returns, complemented by strategic investments for attractive risk-adjusted returns ^{p. 13}.

* TheAn portfolioEnterprise isBased augmentedAsset byAllocation strategicmodel investmentsis chosenused for attractivethe company's investment risk-adjustedallocation returnsstrategy ^{p. 13}.

* TheThis model is integrated into the Economic Capital Model, allowing the company to assess the impact of investment allocation strategydecisions useson ancapital, Enterpriseliquidity, Basedand Assetrisk Allocationprofile modelacross various market scenarios ^{p. 13}.

* The investment portfolio mainly consists of cash and cash equivalents and investment-grade fixed-maturity securities, with additional investments fitting the company's risk appetite ^{p. 13}.

* AdditionalThe investmentsInvestment areCommittee includedof ifthe theyBoard fitof Directors reviews and approves the company's riskinvestment policy and appetitestrategy ^{p. 13}.

* The portfolio is directed internally and includesmanaged both self-managed investmentsinternally and portfolios managed by selectselected third-party investment management firms ^{p. 13}.

* For furtherAdditional discussion on investments, includingand related market risks, refercan tobe found in Item 7 of this Form 10-K, "Management’s Discussion and Analysis of Financial Condition and Results of Operations—Investments" ^{p. 13}.

* The specialty lines property & casualty insurance market comprisesincludes numerousmany distinct markets and sub-markets, each with unique customer needs, products, services, and economic/structural features ^{p. 14}.

* Competition factors include pricing, general reputation, perceived financial strength, broker relationships, product terms and conditions, independent rating agency ratings, speed and reputation of claims payment, and the experience and /reputation of underwriting and claims teams ^{p. 14}.

* Due to the diversity of underwriting divisions, competition is broad, with some competitors specific to only a subset ofcertain divisions ^{p. 14}.

* Operations are conducted principally through four insurance companies: Great Midwest Insurance Company (GMIC), Houston Specialty Company (HSIC), Imperium Insurance Company (IIC), and Oklahoma Specialty Insurance Company (OSIC) ^{p. 15}.

* ''Great Midwest Insurance Company (GMIC)'', is the largest insurance subsidiary, underwritesunderwriting multiple lines of insurance on an admitted basis in all 50 states and the District of Columbia ^{p. 15}.

* ''Houston Specialty Company (HSIC)'', a subsidiary of GMIC, underwrites multiple lines of insurance on a surplus lines basis in 50 states, the District of Columbia, and select foreign countries ^{p. 15}.

* ''Imperium Insurance Company (IIC)'', a subsidiary of HSIC, underwrites on an admitted basis in all 50 states and the District of Columbia ^{p. 15}.

* ''Oklahoma Specialty Insurance Company (OSIC)'', a subsidiary of IIC, is an approved surplus lines company in 49 states and the District of Columbia ^{p. 15}.

* ''Skyward Re'' is a wholly-owned captive reinsurance company domiciled in the Cayman Islands, incorporated on January 7, 2020 ^{p. 15}.

* ''Skyward Service Company'' provides various administrative services to the subsidiaries ^{p. 15}.

* ''SkywardSKYWARD SpecialtySPECIALTY InsuranceINSURANCE GroupGROUP, IncINC.'' (Delaware corporation) is the parenttop companyentity ^{p. 15}.

* SkywardDirect Specialtysubsidiaries Insuranceof Group,SKYWARD Inc.SPECIALTY hasINSURANCE directGROUP, relationshipsINC. withinclude: SkywardSKYWARD ServiceSERVICE CompanyCOMPANY (Delaware corporation), GreatGREAT MidwestMIDWEST InsuranceINSURANCE CompanyCOMPANY (Texas stock insurance company), SkywardSKYWARD UnderwritersUNDERWRITERS AgencyAGENCY, IncINC. (Texas corporation), SkywardSKYWARD SpecialtySPECIALTY NoNO. 1 LimitedLIMITED (United Kingdom company), and SkywardSKYWARD ReRE (Cayman Islands corporation) ^{p. 15}.

* ''GreatGREAT MidwestMIDWEST InsuranceINSURANCE CompanyCOMPANY'' has(Texas astock directinsurance relationshipcompany) withhas HoustonHOUSTON SpecialtySPECIALTY InsuranceINSURANCE CompanyCOMPANY (Texas stock insurance company) as its direct subsidiary ^{p. 15}.

* ''HoustonHOUSTON SpecialtySPECIALTY InsuranceINSURANCE CompanyCOMPANY'' has(Texas astock directinsurance relationshipcompany) withhas ImperiumIMPERIUM InsuranceINSURANCE CompanyCOMPANY (Texas stock insurance company) as its direct subsidiary ^{p. 15}.

* ''ImperiumIMPERIUM InsuranceINSURANCE CompanyCOMPANY'' has(Texas astock directinsurance relationshipcompany) withhas OklahomaOKLAHOMA SpecialtySPECIALTY InsuranceINSURANCE CompanyCOMPANY (Oklahoma insurance corporation) as its direct subsidiary ^{p. 15}.

* ''Skyward Specialty Insurance Group, Inc.'' hasholds an "A" (Excellent) rating with a stable outlook from A.M. Best ^{p. 16}.

* ''A.M. Best'' rates insurance companies based on factors relevant to policyholders ^{p. 16}.

* ''A.M. Best'' assigns 13 ratings to insurance companies, ranging from "A++" (Superior) to "D" (Poor) ^{p. 16}.

* The ''"A" (Excellent) rating'' is the third highest rating assigned by A.M. Best ^{p. 16}.

* ''A.M. Best evaluates a company's evaluation''financial and operating performance by includesreviewing profitability, leverage, liquidity, book of business, reinsurance adequacy, assetand soundness, quality and estimated market value of assets, adequacy of losses and loss expense reserves, surplus adequacy, capital structure, management experience and competence, and market presence ^{p. 16}.

* ''A.M. Best's ratings'' reflect its opinion on an insurance company’s financial strength, operating performance, and ability to meet policyholder obligations to policyholders ^{p. 16}.

* ''Ratings''These ratings are based on factors relevant to policyholders, agents, insurance brokers, and intermediaries, and are not specifically related to securities issued by the company ^{p. 16}.

* State insurance laws and regulations are primarily designed to protect policyholders, consumers, and claimants, not stockholders or other investors ^{p. 17}.

* These statutes require each insurance company in the system to register with the insurance department of its state of domicile's insurance department ^{p. 17}.

* RegistrationRegistered involvescompanies furnishingmust provide information abouton operations within the holding company system that could materially affect the operations, management, or financial condition of domiciled insurers ^{p. 17}.

* The company plans towill pursue additional ''trademark registrations'' and other intellectual property protection if deemed beneficial and cost-effective ^{p. 18}.

* As of ''December 31, 2025Employees'',: theapproximately company611 hadas approximatelyof ''611December employees''31, 2025 ^{p. 19}.

* Employees are not subject to any collective bargaining agreement, and there are no known current efforts to implement such an agreementone ^{p. 19}.

* The company aims to be an employer of choice, fosteringincluding a culture committed to diversityoutside of thought, background,the andinsurance perspectivesector ^{p. 19}.

* The company strives to cultivatecreate ana exceptionalculture workforcethat tofosters perpetuatediversity itsof ownershipthought, culturebackground, and achieve superior business resultsperspective ^{p. 19}.

* The company offers a competitive benefits package to support employee well-being, including medical, dental, and vision insurance, a 401(k) plan, paid time off, family leave, employee assistance programs, and an employee stock purchase plan ^{p. 19}.

* Investing in the company's common stock carriesinvolves a high degree of risk ^{p. 20}.

* Investors should carefully consider the risks and uncertainties described in the report, including consolidated financial statements and related notes, and other SEC filings, before investing in common stock ^{p. 20}.

* The listeddescribed risks and uncertainties are not exhaustive; additional unstated, unknown, or currently immaterial risks may also affectbecome thesignificant companyfactors ^{p. 20}.

* TheIf occurrenceany of anythe identified riskrisks could materially harmoccur, the company's business, operating results, financial condition, and prospects could be materially harmed ^{p. 20}.

* Such events could lead to a decline in the price of the common stock price, potentially resulting in a loss of part or all of an investment ^{p. 20}.

* ''Financial condition and results of operations'' could be materially adversely affected byif inaccurateunderwriting assessmentrisk ofis underwritingnot riskaccurately assessed ^{p. 21}.

* ''Reliance on distribution channels'' (insurance retail agents and brokers, wholesalers, program administrators) exposes the business to certain risks that could adversely affect results ^{p. 21}.

* ''Inability to purchase third-party reinsurance'' on desired or commercially acceptable terms or terms that adequately protect the company maycould materially adversely affect the business, financial condition, and results of operations ^{p. 21}.

* ''LossesInadequate losses and loss expense reserves'' may be inadequate to cover actual losses,could materially adversely affectingaffect financial condition, results of operations, and cash flows ^{p. 21}.

* ''Reinsurers may not reimburse claims'' on a timely basis or at all, which may materially adversely affect the business, financial condition, and results of operations ^{p. 21}.

* ''Failure to accurately and timely pay claims'' could materially and adversely affect the business, financial condition, results of operations, and prospects ^{p. 21}.

* ''InsuranceCyclical businessnature isof cyclicalthe insurance business'', which may affect financial performance and cause operating results to vary quarter-to-quarterquarterly, not indicative of future performance ^{p. 21}.

* ''Extensive regulation'' may adversely affect the ability to achieve business objectives; non-compliance could result in penalties (fines, suspensions) adversely affecting financial condition and results of operations ^{p. 21}.

* ''Costs will increase significantly'' due to operating as a public company, requiring substantial management time for compliance with public company regulations ^{p. 21}.

* ''Integration of Apollo'' may present unforeseen challenges, including difficulties with technology systems, business processes, and risk management frameworks, potentially causingleading to operational disruptions, increased costs, or delays in realizing anticipated strategic benefits ^{p. 21}.

* Underwriting''Employee successdecisions'', dependsincluding on accurately assessing risksmanagement and establishing appropriate premium ratesunderwriters, relying onexpose the experience ofcompany underwritingto staffrisk ^{p. 22}.

* The''Consolidation business relies onof insurance retaildistribution agents,firms'' brokers,may wholesalers,increase andtheir programinfluence administrators,on exposingcommission itrates toand risksconcentrate frombusiness thesewith distributionparticular channelsbrokers ^{p. 22}.

* Consolidation''Restrictions ofor insurancetermination distributionof firmsdistributor relationships'' may increaseoccur theirif influencethey ondo commissionnot ratesmeet andprofitability concentratestandards or business withobjectives, subject to contractual and particularregulatory brokersrequirements ^{p. 22}.

* Failure''Distributors byexceeding brokersauthority'', failing to remittransfer collected premiums, hasor notbreaching beenobligations materialcould to date, butexpose the company may be required to provide coverage despite unpaid premiumsliability ^{p. 22}.

** ReinsurersTime mayrequired excludeto certainfully coveragesassess orcovered alter terms in contractslosses, leading to gapspotential increases in reinsuranceloss protectionestimates and greater potential losses for theinadequate companyreserves ^{p. 22}.

** ReservesVolatility arein estimatesfinancial ofmarkets, ultimateeconomic claim settlementevents, and administrationinflation costs,increasing notclaim exact calculations,frequency/severity and ultimateloss liability may differcosts ^{p. 22}.

** Time''Decline requiredin tofinancial fullystrength appreciaterating'' coveredmay lossadversely extent,affect leadingthe toamount increasedof lossbusiness estimates over timewritten ^{p. 22}.

* ''A rating downgrade or withdrawal of the rating'' could cause distribution partners and insureds to choose higher-rated competitors, increase reinsurance costs or reduce availability, or severely limit/prevent writing new and renewal insurance contracts ^{p. 22}.

* There''Unexpected ischanges noin assuranceinterpretation theof companycoverage''s ratingor willpolicy remainprovisions at(including itsloss current level,limitations and adverse ratings consequencesexclusions) could materially adversely affect financial condition and results of operations ^{p. 22}.

* Unexpected changes in the interpretation''Enforceability of coverage or provisions, including loss limitations andor exclusions,'' couldis materiallynot adverselyassured, affectas financialindustry conditionpractices and resultslegal/judicial/social conditions change ^{p. 22}.

* There''Courts isor noregulatory assuranceauthorities'' thatcould lossnullify limitations/exclusions, or exclusionslegislation could modify/bar their use, leading into policieshigher willthan beanticipated enforceablelosses asand intendedLAE ^{p. 22}.

* Governmental''Reinsurers actionsmay couldnot resultreimburse inclaims highertimely than anticipatedor lossesat and LAEall'', materially adversely affecting business, financial condition, orand results of operations ^{p. 22}.

* Disputes''Severe withweather reinsurersconditions'', couldclimate bechange time-consumingeffects, costlycatastrophes, pandemics, and uncertain of success,man-made leadingevents tomay increasedadversely netaffect lossesbusiness ^{p. 22}.

* Failure''Changing toweather accuratelypatterns and timelyclimatic payconditions'' claimsincrease could materiallyunpredictability and adverselyfrequency affectof businessnatural disasters, financialincluding condition,in results,new areas and prospectsexisting markets ^{p. 22}.

* Decreased quality''Extent of claimslosses workfrom couldcatastrophes'' adverselydepends affecton operatingfrequency/severity marginsof andinsured potentiallyevents and requiretotal slowinginsured growthexposure in affected marketsareas ^{p. 22}.

* Severe''Unpredictability weather conditions, climate change effects,of catastrophes, pandemics,'' and man-madesevere eventsweather may adversely affect business, results, and financial conditionconditions ^{p. 22}.

* Climate''Inability changeto mayobtain increasereinsurance thecoverage'' frequencyat andreasonable severityrates offor extremesevere weather events,and leadingcatastrophes tocould conditionsmaterially that increase hurricane activity andadversely wildfireaffect risksbusiness ^{p. 22}.

* A''Exposure naturalto disasterrisk orfrom catastrophepandemics, lossoutbreaks, couldpublic materiallyhealth adversely affect businesscrises, financialand condition, andgeopolitical/social resultsevents'' ^{p. 22}.

* Catastrophes''Policy canterms impactand theconditions'' companyare evenexpected withoutto direct insurancepreclude coverage, suchfor asvirus-related theclaims, 2025but Californiacourt wildfires,decisions asand affectedgovernmental policyholdersactions may cancel otherchallenge policiesexclusions ^{p. 22}.

* The incidence''Marketing and severitydistribution of catastrophesinsurance andproducts'' severethrough weatherprogram areadministrators inherentlywho sell to insureds via retail agents and unpredictablebrokers ^{p. 22}.

* Program''Failure administratorsto arerespond providedto withESG specificexpectations'' quotingor andbacklash binding authority, and their failurerelated to complyESG with guidelinestopics could adverselyharm affectbusiness and resultsreputation ^{p. 22}.

* Most''Insurance contractssubsidiaries aremust forcomply awith one-yearStatutory termAccounting andPrinciples (SAP)'', which are renewable;subject someto insuredsconstant arereview repeatby customersthe withNAIC and state newinsurance contractsdepartments ^{p. 22}.

* Financial''Pending forecastingproposals'' includesbefore assumptionsNAIC aboutcommittees renewalcould ratesnegatively andaffect repeatinsurance businessindustry participants if enacted ^{p. 22}.

* Failure,''These orfactors'' perceivedmay failure,prevent tohedging meetstrategies investor/customerfrom ESGeffectively expectationsreducing volatility and could harmmaterially businessadversely andimpact financial reputationresults ^{p. 22}.

* Adverse economic factors likesuch as recession, inflation, high unemployment, or lower economic activity cancould reducelead to fewer policy sales, increaseincreased claim frequency, lead to premium defaults, or cause claim falsification, impacting growth and profitability ^{p. 23}.

* AnNegative economic downturnfactors withmay higheralso unemployment,affect decliningthe spending,ability andto reducedcharge corporateappropriate revenuerates generallyfor negativelyrisk, affectsreduce demandthe fornumber insuranceof productspolicies written, impactingand premiumlimit levelsopportunities andfor profitable profitabilityunderwriting ^{p. 23}.

* NegativeDuring an economic factorsdownturn, cancustomers hindermay thereduce abilityinsurance tocoverage, chargecancel appropriatepolicies, ratesmodify forcoverage, insuredor risksnot and adversely affect the number ofrenew policies written and opportunities for profitable underwriting ^{p. 23}.

* DuringExisting anpolicyholders economicmight downturn,exaggerate customersor mayfalsify reduceclaims insuranceto needs,receive cancelhigher policies,payments modifyduring coverage,an oreconomic not renew policiesdownturn ^{p. 23}.

* The supply of insurance is linked to prevailing prices, insured losses, and industry capital levels, which fluctuate with investment returns in the insurance industry ^{p. 23}.

* The insurance industry is cyclical, characterized by cyclical periods of intense price competition due to excessive underwriting capacity (soft market) and periods of capacity shortages increasingleading to increased premiums (hard market) ^{p. 23}.

* Demand for insurance depends on factors such aslike frequency and severity of catastrophic events, capacity levels, new capital providers, and general economic conditions, all of which fluctuate and can contribute to price declines ^{p. 23}.

* The profitability of most ''P&C insurance companies'' tends to follow this cyclical market patternpatterns, with higher gross written premium growth and improved profitability during hard market cycles ^{p. 23}.

* This cyclical market pattern can be more pronounced in the ''E&S market'' than in the standard insurance market ^{p. 23}.

* When market conditions soften, customers previously in the E&S market may return to the admitted market, exacerbating the effects of rate decreases on financial results ^{p. 23}.

* Quarterly results are expected to continue fluctuating due to general economic conditions, frequency/severity of catastrophe events, fluctuating interest rates, claims exceeding loss reserves, industry competition, deviations from expected premium retention rates, adverse investment performance, and reinsurance coverage costs ^{p. 23}.

* The company aims to hold a diversified investment portfolio managed by professional advisory firms according to its investment policy and reviewed by theits Investment Committee ^{p. 23}.

* A significant portion of the investment portfolio is in ''fixed maturity securities'', or separately managed accounts and limited partnerships primarily invested in fixed maturity securitiesthem ^{p. 23}.

* A low interest rate environment, potentially resulting from federal government actions to slow inflation (e.g., rate cuts, Inflation Reduction Act of 2022), would pressure net investment income, particularlyespecially for fixed maturity securities and short-term investments, adversely affecting operating results ^{p. 23}.

* Recent and future interestincreases ratein increasesinterest rates could cause declines in the valuevalues of fixed income securities portfolios to decline, with the magnitude depending on security duration and the extent of interest rate increases ^{p. 23}.

* MortgageOther fixed income securities, such as mortgage-backed and other asset-backed securities, carry prepayment risk or may not prepay as quickly as expected in a rising interest rate environment ^{p. 23}.

* Credit risk is the risk of investment default or impairment due to deterioration in the financial condition of issuers or insurersguarantors guaranteeingof paymentssecurities held ^{p. 23}.

* The company also invests in ''marketable preferred and common equity securities'' and exchange-traded funds, which are carried at fair market value and are subject to potential losses and market value declines ^{p. 23}.

* The investment portfolio is subject to increased valuation uncertainties when investment markets are illiquid, as is the case with fixed maturity securities held to maturity, separately managed accounts, and limited partnership investments ^{p. 23}.

* Risks for all security types of securities are managed through an investment policy that establishessets parameters, including maximum investment percentages in certain security types and minimum credit quality levels, believed to be within NAIC, Texas Department of Insurance, and Oklahoma Department of Insurance guidelines ^{p. 23}.

* InvestmentAlthough investment strategies aimare notsought tothat correlateare not correlated with insurance and reinsurance exposures, but investment portfolio losses may occur concurrently with underwriting losses, exacerbating their adverse effecteffects ^{p. 23}.

* The companyInvestments may not be able to sell investmentssellable at favorable prices or at all, potentially resulting in significant realized losses depending on general market conditions, interest rates, and credit issues with individual securities ^{p. 23}.

* We are subject to extensive''Extensive regulation, and failure to comply'' may result in penalties like fines and suspensions, adversely affectingaffect financialthe conditionability andto resultsachieve ofbusiness operationsobjectives ^{p. 24}.

* Prior notificationRegulatory requirements may causeimpose business delays''timing and additionalexpense constraints'' affecting business expensesobjectives ^{p. 24}.

* StateCertain transactions between insurance regulatorssubsidiaries haveand broadaffiliates discretionrequire ''prior notice to denythe Texas Department of Insurance'', potentially orcausing revokebusiness licensesdelays forand regulatoryadditional violationsexpenses ^{p. 24}.

* OurLack insuranceof subsidiariesrequisite arelicenses/approvals subjector to risknon-basedcompliance capitalwith regulatory requirements basedcould onlead theto NAIC's'preclusion "riskor basedtemporary capitalsuspension'' model"of andactivities minimumin capital/surplusa restrictionsstate underor Texasother lawpenalties ^{p. 24}.

* FallingInsurance belowsubsidiaries calculatedare subject to ''risk-based capital thresholdsrequirements'' canbased leadon tothe regulatoryNAIC action,model includingand minimum capital/surplus supervision,restrictions rehabilitation,under orTexas liquidationlaw ^{p. 24}.

* FailureThese torequirements maintainestablish requiredthe ''minimum risk-based capital'' levelsneeded couldto adverselysupport affectbusiness ouroperations insuranceand subsidiary'sidentify abilityinadequately tocapitalized insurers based maintainon regulatoryasset/liability authorityrisks and ournet A.M.written Bestpremium Ratingmix ^{p. 24}.

* ChangesBusiness tocould U.S.be taxadversely affected by ''changes in laws'' andrelated newto taxasset/reserve policiesvaluation, couldsurplus negativelyrequirements, impactinvestment/dividend thelimitations, overallenterprise economyrisk, and ourrisk-based businesscapital ^{p. 24}.

* Rules''Changes forto U.S. federaltax incomelaws'' taxationand arenew constantlytax underpolicies reviewcould bynegatively legislators,impact the IRS,overall economy and the U.S. Department of the Treasurybusiness ^{p. 24}.

* OnThe July''rules 4, 2025,for HU.RS. 1,federal theincome "Onetaxation'' Bigare Beautifulconstantly Billunder Act"review (OBBBA)by legislators, wasthe signedIRS, intoand lawthe inU.S. theDepartment Unitedof the StatesTreasury ^{p. 24}.

* BasedOn on''July current4, analysis2025'', theseH.R. OBBBA1, provisionsthe are"One notBig expectedBeautiful toBill haveAct" a material(OBBBA), impactwas onsigned ourinto businesslaw orin resultsthe ofUnited operationsStates ^{p. 24}.

* TheseThere NOLsis areno setassurance tothat expirethe beginningbusiness inwill 2032not be ''adversely affected by the OBBBA'' or other tax law changes ^{p. 24}.

* If we cannot offset future taxable income withThese ''NOLs, our net income andare cashset flowsto mayexpire bebeginning adverselyin affected2032'' ^{p. 24}.

* The''Future continuedownership operationchanges'' andor growthregulatory ofchanges ourcould businesslimit willthe requireability substantialto capitalutilize NOLs ^{p. 24}.

* WeIf dounable notto intendoffset tofuture declaretaxable andincome paywith cashNOLs, dividends''net onincome ourand commoncash stockflows'' inmay thebe foreseeableadversely futureaffected ^{p. 24}.

* StateThe insurance''continued laws,operation includingand Texasgrowth'' laws, restrictof the ability of GMIC, HSIC, and IICbusiness towill declarerequire stockholdersubstantial dividendscapital ^{p. 24}.

* StateThere insuranceis regulators''no requireintention insuranceto companiesdeclare toand maintainpay specifiedcash levelsdividends'' ofon statutorycommon capitalstock andin the foreseeable surplusfuture ^{p. 24}.

* ''State insurance regulatorslaws'', haveincluding broadthose powersof toTexas, preventrestrict statutorythe surplusability reductionof to inadequateGMIC, levelsHSIC, and thereIIC isto nodeclare assurance that maximum calculatedstockholder dividends would be permitted ^{p. 24}.

* State insurance regulators mayrequire adoptinsurance morecompanies restrictiveto statutorymaintain provisions''specified regardinglevels dividendof payments by our insurance subsidiariesstatutory incapital theand futuresurplus'' ^{p. 24}.

* InvestorsState mayinsurance needregulators tohave sell''broad commonpowers stockto afterprevent pricereduction appreciation,of whichstatutory may not occur, as the only waysurplus'' to realize futureinadequate gainslevels ^{p. 24}.

* InvestorsThere seekingis immediateno cashassurance that dividends shouldup to the ''maximum notcalculated purchaseamounts'' ourwould commonbe stockpermitted ^{p. 24}.

* ApplicableState insurance lawsregulators may makeadopt a''more changerestrictive ofstatutory controlprovisions'' difficultregarding dividend payments in the future ^{p. 24}.

* TexasInvestors insuranceseeking lawsimmediate applycash todividends direct''should andnot indirectpurchase acquisition of 10% or more of the votingcommon stock of a Texas-domiciled insurer'' ^{p. 24}.

* TheseUnder requirementsTexas mayinsurance discouragelaws, acquisition''written proposalsapproval andfrom delay,the deter,state orinsurance preventcommissioner'' ais changerequired ofbefore acquiring control of Skyward Specialty, even if desirablea todomestic stockholdersinsurer ^{p. 24}.

* ''Future capital requirements'' depend on factors such as the ability to write new business successfully and establish adequate premium rates and reserves sufficient to cover losses ^{p. 25}.

* If ''operational cash flows'' from operations are insufficient, or if the capital position is negativelyadversely impacted by investment portfolio declinesdecline, catastrophe losses, or adverse reserve development, additional funds may be needed through financings or growth curtailment ^{p. 25}.

* ''CapitalThe amount and timing of capital needs'' are affected by growth rate, profitability, claims experience, reinsurance availability, market disruptions, and other unforeseeable developments ^{p. 25}.

* ''EquityIf additional capital is needed, equity or debt financing'' may not be available on favorable terms, or atmay all,be potentiallyon leadingunfavorable to dilution for stockholders or restrictive covenants in debt financingsterms ^{p. 25}.

* InabilityDebt tofinancings obtainmay ''adequateimpose capital''covenants on favorable terms could materially adversely affect operating plans,restricting business, financial condition, or results of operations ^{p. 25}.

* InAccess anto eventcredit ofunder default,the ''assets''Revolving mayCredit beFacility insufficientis subject to repayconditions obligationsthat undermay creditlimit agreementsborrowing ^{p. 25}.

* LossThe ofcompany's key personnel or inabilityability to attract and retain qualifiedexperienced and seasoned personnel couldis adverselycrucial affectfor theits companybusiness ^{p. 26}.

* The talent pool of talent for recruitment is limited and fluctuatessubject based onto market dynamics, potentially leading to increased compensation expectations and difficultydifficulties in retaining/ or recruiting key personnel ^{p. 26}.

* FailureLoss toof retainkey personnel or inability to attract talented personneltalent could preventadversely affect the company from maintaining its's competitive position in specialized markets, impactingand results of operations ^{p. 26}.

* ''SecurityThe breaches,business datais loss,highly cyberattacks,dependent on information technology and ITtelecommunications failures''systems couldfor disruptunderwriting, claims operationsprocessing, damagepolicy reputationpreparation, andpremium adverselyprocessing, affectactuarial businessfunctions, and financial resultsreporting ^{p. 26}.

* TheSome businesssystems ismay highly dependentrely on ''informationthird-party technologyservices andnot telecommunicationsunder systems'the company',s includingdirect underwriting and claims systemscontrol ^{p. 26}.

* Sustained or repeated system failures could limit the company's ability to write/process new business, process renewals, provide customer service, pay claims, or operate normally ^{p. 26}.

* ''Computer viruses, hackers, employee misconduct, and other external hazards'' can expose systems to security breaches orand disruptionscyber-attacks ^{p. 26}.

* A ''data incident'' occurred where attackers acquired certain company data, but an investigation determined it was immaterial, with no evidence of nation-state involvement, global hackers, or misuse of information ^{p. 26}.

* Future cybersecurity events could lead to operational disruptions, unauthorized access, todisclosure or loss of proprietary or customer data, legal claims, regulatory scrutiny, reputational damage, and increased costs ^{p. 26}.

* SEC and state law requirements for public notification of incidents could exacerbate harm to the business ^{p. 26}.

* ''Third parties'' to whom functions are outsourced are also subject to these risks, and while their cybersecurity controls are reviewed, successful prevention of compromises or disclosures cannot be ensured ^{p. 26}.

* TheIncreased companyuse reviews and assessesof third-party providers'services cybersecurity(e.g., controlscloud buttechnology, cannotsoftware ensureas completea protectionservice) againstcan complicate identification and compromisesresponse orto disclosurescyberattacks ^{p. 26}.

* IncreasedThe userapid growth of ''third-partyartificial services''intelligence (e.g.,AI) cloudand technology,machine SaaS)learning canmay complicate identification andalter responsethe tocompetitive cyberattackslandscape ^{p. 26}.

* ''ArtificialThe intelligencecompany uses (AI) andfor machinerisk learning''selection, arepricing, evolvingand technologiesclaims thathandling mayand impactcontinues theto businessresearch and operationsimplement AI-based solutions ^{p. 26}.

* EmployeesThe usecompany's AIcompetitive forposition riskcould selection,be pricing,harmed andif claimscompetitors handlingleverage AI tosolutions improvemore effectivenessquickly andor efficiencyeffectively ^{p. 26}.

* Failure to manage growth effectively, couldincluding materiallymeeting adverselycapital affectneeds, businessexpanding systems, financialoptimizing conditionhuman resources, and resultsintegrating ofacquisitions, operationscould materially adversely affect the business ^{p. 26}.

* ''InorganicSuccess of inorganic growth through acquisitions'' depends on identifying appropriate targets, negotiating favorable terms, completing transactions, and successful integration ^{p. 26}.

* SustainingFuture revenue growth may not be sustainable at rates consistent with recent history is not guaranteed ^{p. 26}.

* Revenue growth depends on factors including effective product pricing, successful product deployment and renewals, attracting/retaining qualified personnelunderwriters and claims professionals, enhancing infrastructure/ and data reporting systems, creating new distribution channels, introducing new products, competing effectively, and increasing brand awareness ^{p. 26}.

* Failure to accomplish these objectives makes forecasting future results of operations difficult ^{p. 26}.

* Historical growth raterates should not be considered indicative of future performance and may decline ^{p. 26}.

* RevenueFuture revenue could grow more slowly or decline, and operating expenses could increase, potentially harming the business inand futurepreventing periodsprofitability ^{p. 26}.

* The ''Apollo acquisition andis integrationexpected ofto Apollo''provide maystrategic adverselybenefits, affectexpand business,specialty financialinsurance conditioncapabilities, and resultsenhance presence in the ofLloyd’s operationsmarket ^{p. 26}.

* The acquisitionThere is expectedno toassurance providethat strategicanticipated benefits from the acquisition, expandsuch specialtyas insurancegrowth capabilitiesopportunities, andwill enhancebe presencerealized inwithin the Lloyd’sexpected timeframe or at marketall ^{p. 26}.

* ''IntegrationThe risks''success includeof challengesthe inacquisition integratingdepends Apollo’son operations,retaining systems,key technologyApollo platformsemployees, partners, and personnelcustomers, with loss potentially divertingnegatively managementimpacting attention,the disruptingacquired business, and incurringoverall unexpected costs or delaysoperations ^{p. 26}.

* ThereCultural isand nooperational assurancedifferences thatbetween growththe opportunitiescompany orand otherApollo, benefitsparticularly fromregarding the acquisitionLloyd’s willmarket, bemay realizedcreate within thechallenges expectedin timeframeharmonizing orpolicies atand allprocedures ^{p. 26}.

* LossAdditional ofindebtedness keyincurred personnelfor orthe business relationshipsacquisition could negativelylimit impactfinancial theflexibility valueor ofincrease the acquiredcost business and overallof operationscapital ^{p. 26}.

* ''RegulatoryThe andcompany compliancecontinually faces risks'' increaseassociated duewith tovarious expansiontypes intoof newlitigation, jurisdictionsincluding insurance claims and markets,general includingcommercial theand Lloyd’scorporate marketlitigation ^{p. 26}.

* Failure to properly assess and understandvendor risks, andincluding costssecurity in third-partyand relationshipsstability, could materially and adversely affect financial condition and results of operations ^{p. 26}.

* The company anticipates continued reliance on ''third-party software'' ^{p. 26}.

* While commercially reasonable alternatives to current licensed third-party software are believed to exist, this may not always be the case, or replacement could be difficult or costly ^{p. 26}.

* Integration of new third-party software may require significant work, and investment of time, and resources ^{p. 26}.

* Obtaining license agreements for additional or alternative third-party software may not be possible on commercially reasonable terms or available at all ^{p. 26}.

* Many risksRisks associated with third-party software use cannot be eliminated and could negatively affect the business ^{p. 26}.

* The company may fail or be unable to protect its ''intellectual property rights'' for its proprietary technology platform and brand, or may face infringement lawsuits ^{p. 26}.

* TheSuccess companyand mayability beto suedcompete bydepend thirdpartly partieson forintellectual allegedproperty, infringementincluding ofbrand theirrights and proprietary rightstechnology in certain product lines ^{p. 26}.

* SuccessThe andcompany abilityprimarily torelies competeon dependcopyright partlyand ontrade intellectualsecret propertylaws, including brand rights and proprietaryconfidentiality technologyagreements usedto inprotect certainintellectual productproperty linesrights ^{p. 26}.

* Efforts to enforce intellectual property rights may face defenses, counterclaims, and countersuits challenging validity, enforceability, and scope ^{p. 26}.

* Success also depends partly on not infringing on the intellectual property rights of others ^{p. 26}.

* CompetitorsThird and other entitiesparties may ownclaim orinfringement claimof their intellectual property relatedrights, potentially leading to thesignificant industryexpenses, substantial damages, ongoing royalty payments, prevention from offering services, or companyother unfavorable terms ^{p. 26}.

* The company expects to incur increased costs asand amanagement publictime companydue andto itsoperating managementas devotesa substantialpublic time to compliance initiativescompany ^{p. 27}.

* As a public company, particularly aand large accelerated filer, the company incurs significant legal, accounting, and other expenses not present as a private company ^{p. 27}.

* Federal securities laws, including the Sarbanes-Oxley Act and Dodd-Frank Act, and rules by the SEC/Nasdaq and Nasdaq,rules impose requirements on public companies, forincreasing filingcompliance reports and maintaining effective disclosure, financial controls,costs and corporatemanagement governancetime ^{p. 27}.

* Pursuant to Section 404 of the Sarbanes-Oxley Act, the company must perform system and process evaluation and testing of its internal control over financial reporting ^{p. 27}.

* Compliance with Section 404 requires substantial accounting expense and significant management effortseffort, including maintaining staff and consultants with public company reporting, technical accounting, and internal control knowledge ^{p. 27}.

* The company mustengages maintainin accountinga and finance staffcostly and consultantschallenging withprocess publicto companydocument reporting,and technical accounting, andevaluate internal control knowledgeover financial reporting to satisfycomply with Section 404 requirements and provide internal audit services ^{p. 27}.

* TheThere processis toa documentrisk andthat evaluateneither the company nor its independent registered public accounting firm will conclude that internal control over financial reporting is costlyeffective andwithin challenging,the requiringprescribed dedicatedtimeframe, internalpotentially resources,leading outsideto consultants,adverse andfinancial amarket reactions detailedor workSEC planinvestigations ^{p. 27}.

* The company's doesdisclosure notcontrols expectand its disclosure controlsprocedures or internal control over financial reporting tomay not prevent or detect all errors and fraud, as control systems provide only reasonable, not absolute, assurance ^{p. 27}.

* InherentDue limitationsto ininherent control systems meanlimitations, misstatements due to error or fraud may occur and not be detected ^{p. 27}.

* FailureIf the company is unable to achieve and maintain effective internal controls, asits requiredoperating byresults Sectionand 404financial ofcondition thecould Sarbanes-Oxleybe Actharmed, could harm operating results and financialthe condition,market andprice negativelyof affect theits common stock pricenegatively affected ^{p. 27}.

* The company is required tomust document and test internal control procedures to satisfy Section 404(b) of the Sarbanes-Oxley Act, which mandatesrequiring annual management assessments of internal control effectiveness ^{p. 27}.

* AssessmentsDuring assessments, the company may identify deficiencies that cannot be remediated timely, and testing/maintaining internal controls may divert management's attention ^{p. 27}.

* InabilityIf tothe concludecompany onconcludes an ongoing basis thatits internal control over financial reporting is not effective could lead to significant, remediation costs and scope,operational andeffects impedecould timelybe and accurate SEC filingssignificant ^{p. 27}.

* Any materialMaterial weaknesses or deficiencies couldin causeinternal investorscontrol tocould loseimpede confidencetimely orand leadaccurate toSEC Nasdaqreporting, listingpotentially suspension/termination,causing negativelyloss affectingof theinvestor commonconfidence stockor tradingNasdaq pricelisting suspension/termination ^{p. 27}.

* AThe company identified a material weakness in its internal control over information technology general controls ("ITGCs") was identified as of December 31, 2024, andwhich was remediated as ofby December 31, 2025 ^{p. 27}.

* Failure to maintain an effective system of internal controls could adversely affect the market price of the common stock ^{p. 27}.

* The effectiveness of controls is subject to inherent limitations, and eventhere anis effectiveno ITGCassurance systemcontrols provideswill onlyprevent reasonableor assurancedetect all misstatements ^{p. 27}.

* MaterialIf additional material weaknesses or significant deficiencies couldare adverselyidentified, affectthe reputationcompany ormay investorbe perceptions,unable negativelyto impactingprovide thetimely tradingand pricereliable offinancial commoninformation shares,or andmay incur additionalincorrectly remediationreport costsit ^{p. 27}.

* The company's operatingcannot resultsassure andthat stockadditional pricematerial mayweaknesses beor volatilerestatements orwill not declinearise regardlessin ofthe operatingfuture performance,due riskingto lossinadequate ofinternal investmentcontrols ^{p. 27}.

* Investment in the common stock is considered risky, suitablerequiring onlytolerance for those who can withstand significant loss and wide market value fluctuations ^{p. 27}.

* FundamentalThis allows fundamental changes to operations may occur without stockholder approval, potentially resulting in a strategy or underwriting guidelines materially different from those described in the "Business" section or other filings ^{p. 27}.

* Anti-takeover provisions in organizational documents, Delaware law, and federal/state regulations maycould discourage, delay,prevent or preventdelay a beneficial change of control and limit share price ^{p. 27}.

* TheCharter documents permit the ''Board of Directors'' willto beestablish classifiedthe intonumber threeof classes with staggered, three-year terms,directors and directors may only be removedfill forvacancies/new causedirectorships ^{p. 27}.

* SpecialThe meetings''ability of stockholders canto onlycall bespecial called by the Board of Directors, the chairman of the Board, or the chiefmeetings'' executiveis officereliminated ^{p. 27}.

* Cumulative''Vacancies voting inon the electionBoard of Directors'' may be filled only by a majority of directors isthen in office, even if less than a prohibitedquorum ^{p. 27}.

* TheAs certificatea ofDelaware incorporationcorporation, andthe bylawscompany designateis thesubject Courtto of''Section Chancery203 of the StateDelaware ofGeneral DelawareCorporation asLaw'', thewhich exclusivemay forumprohibit forlarge substantiallystockholders all(owning disputes15% betweenor more) from merging or combining with the company andfor itsa stockholdersperiod ^{p. 27}.

** ThisAny exclusiveaction forumto provision would notinterpret, apply, toenforce, suitsor enforcingdetermine duties/liabilitiesthe createdvalidity byof the Exchangecertificate Actof incorporation or other claims where federal courts have exclusive jurisdictionbylaws ^{p. 27}.

* ''Crisis Response Plan (CRP)'' is implemented to efficiently and effectively respond to cybersecurity incidents and threats, forming an importanta component of the overall ERM strategy ^{p. 28}.

* ''ManagementCybersecurity andrisk IT personnelmanagement'' haveprocesses implementedare processesintegrated forinto assessing,overall identifying,risk managingmanagement, andincluding escalatingannual materialevaluation cybersecurityby risks,the integrated into overallenterprise risk management committee ^{p. 28}.

* ''Investments in IT security'' have expanded, including additional end-user training, layered defenses, critical asset identification/protection, strengthened monitoring/alerting, and expert engagement ^{p. 28}.

* ''Defenses are regularly tested'' through simulations, andtechnical drills at a technical level (including penetration tests), and byreviews reviewingof operational policies/procedures with third-party experts ^{p. 28}.

* ''IT security team'' monitors alerts, discusses threat levels, /trends, and /remediation, prepares a quarterly cyber scorecard, collects data on cybersecurity threats/risk areas, and conducts an annual risk assessmentassessments ^{p. 28}.

* ''OutsideExternal cybersecurity legal counsel'' would consult and coordinate with other third parties, (including communication/notification), cybersecurityand vendors (investigationnotification, recovery, restoration), cybersecurity experts (incident validation, ransomware assistance), and cybersecurity insurance providers in the event of an incident ^{p. 28}.

* ''IndividualsInformation overseeingSecurity cybersecurityTeam leaders'' have decades of experience in IT roles, including security, auditing, compliance, systems, and programming ^{p. 28}.

* ''These individuals'' monitor prevention, mitigation, detection, and remediation of cybersecurity incidents through their management and participation in risk management processes, includingand the crisis response plan operation, and report to the Risk Committee ^{p. 28}.

* ''The Risk Committee of the Board of Directors'' oversees cybersecurity strategy, reviews cybersecurity and other IT risks, controls, and procedures, and receives periodic updatesreports from managementthese individuals on cybersecurity measureappropriate adequacy/effectivenessitems ^{p. 28}.

* ''ReviewRisk byCommittee of the RiskBoard Committeeof Directors'' includesoversees thoroughcybersecurity discussionstrategy, ofreviews cybersecurity threatand other IT risks/controls/procedures, and theirreceives potentialperiodic operationalupdates from management on cybersecurity impactmeasures ^{p. 28}.

* The company leases its primary''Primary executive offices'' and insurance operations are leased in Houston, Texas ^{p. 29}.

* The leasedHouston office space in Houston isoccupies approximately ''20,400 square feet'' ^{p. 29}.

* The lease for the Houston office space expires in ''2029'' ^{p. 29}.

* TheAdditional companyoffice leasesspace additionalis office spaceleased as neededappropriate ^{p. 29}.

* Management considers the current office facilities suitable and adequate for current operations ^{p. 29}.

* The company believes that the outcome of these legal matters, both individually and in aggregate, will not materially adversely affect its consolidated financial position ^{p. 30}.

* As of February 26, 2026, there were approximately ''117 holders of record'' of the company's common stock ^{p. 31}.

* TheThis number of holders of record does not represent the total number of stockholders duebecause tomany shares beingare held by brokers and other institutions on behalf of stockholders ^{p. 31}.

{{Indexing|====== Securities Authorized for Issuance Under Equity Compensation Plans|Equity compensation plans, definitive proxy statement, SEC, 2026 Annual Meeting of Stockholders, 2026 Proxy Statement, Part III|ch7st6ifed|kind=prose|order=32}}====

* Information regarding equity compensation plans will be included in the definitive proxy statement filed with the SEC for the 2026 Annual Meeting of Stockholders ("2026 Proxy Statement") and is incorporated by reference ^{p. 32}.

* ThisRefer informationto isPart incorporatedIII byfor referencedetails intoon thesecurities currentauthorized documentfor issuance under equity compensation plans ^{p. 32}.

* ''UnregisteredInformation is provided regarding securities'' informationissued isor providedgranted by the company that were not registered under the Securities Act forduring the period covered by this Annual Report on Form 10-K ^{p. 33}.

* On ''January 1, 2026'', the company paid approximately ''$555.0 million'' for the Apollo acquisition, as per the Apollo SPAs ^{p. 33}.

* The payment for the Apollo acquisition included ''$371.0 million'' in cash'' ^{p. 33}.

* The payment also included the issuance of ''3,679,332'' unregistered shares'' of the Company’s common stock ^{p. 33}.

* The performance graph compares the cumulative total shareholder return of an investment in theSkyward company'sSpecialty Insurance Group, Inc. common stock, the Nasdaq Composite Index, and the Nasdaq Insurance Index ^{p. 34}.

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

* AnThe graph assumes an initial investment of $100 is assumed for the graph ^{p. 34}.

* The returnsReturns are based on historical results and are not indicative of future performance ^{p. 34}.

* The graph is not considered "soliciting material" or "filed" for purposes of Section 18 of the Exchange Act, nor is it subject to liabilities under that Section ^{p. 34}.

* The graph is not subjectdeemed to liabilitiesbe underincorporated Sectionby 18reference ofinto any filings under the ExchangeSecurities Act ^{p. 34}.

** December 31, 2023: Approximately $175177.00 ^{p. 34}

* ''Nasdaq Composite Index cumulative(Magenta totalLine) returnperformance'':

** December 31, 2024: Approximately $173174.00 ^{p. 34}

* ''Nasdaq Insurance Index cumulative(Cyan totalLine) returnperformance'':

** December 31, 2025: Approximately $129128.00 ^{p. 34}

{{Indexing|Stock performance of====== Skyward Specialty Insurance Group, Inc.stock andprice versus indices|Stock performance, Skyward Specialty Insurance Group, Inc., Nasdaq Composite Index, Nasdaq Insurance Index|ch7st6ifed|kind=table|order=35}}====

* TheSkyward companySpecialty Insurance Group is a growing specialty insurance providercompany ofproviding commercial P&C products and solutions, primarily in the United States, on both non-admitted (E&S) and admitted bases, primarily in the United States ^{p. 35}.

* The company focuses on underserved, dislocated, markets or marketsthose where standard insurance coverages are insufficient for businesses ^{p. 35}.

* The company's portfoliodevelops ofand insureddelivers riskstailored isinsurance highlyproducts diversifiedand across industries, distribution channels, andservices linesfor ofniche businessmarkets ^{p. 35}.

* A portion of the business is ''specialty reinsurance'', primarily in agriculture and credit, focused on attractive specialty classes where reinsurance offersis more efficient marketdue to factors like cost of entry and geographic expansion ^{p. 35}.

* This diversification, including businesses not typically aligned with traditional P&C pricing cycles, combined with underwriting and claims expertise, aims forto produce consistent strong growth and profitability across all insurance pricing cycles ^{p. 35}.

* The company's strategy, "Rule Our Niche," focusesaims onto leadinglead in chosen market niches and establishingestablish sustainable competitive positions ^{p. 35}.

* This strategy aimsforms tothe buildbasis for building a strong defensible market position, createcreating a competitive moat, and achieve best-in-class underwriting results through P&C insurancewinning pricingchosen cyclesmarkets ^{p. 35}.

* In the ''first quarter of 2025'', theunderwriting companydivisions were updated its underwriting divisions to align with management oversight, resource allocation, and operating performance evaluation ^{p. 35}.

* A ''ninth division'', ''Agriculture and Credit (Re)insurance'', was added, incorporatingincluding the Global Agriculture unit (previously with Global Property) and the Mortgage and Credit units ^{p. 35}.

* TheThis ''Industry Solutionsnew division'' wasfocuses on specialty classes where reinsurance offers renameda Constructionmore &attractive Energymarket Solutionsentry ^{p. 35}.

* The ''InlandIndustry Marine unitSolutions'' isdivision nowwas partrenamed of the''Construction Transactional E&S divisionEnergy Solutions'' ^{p. 35}.

* The ''ProgramsInland Marine'' unit is now Specialtypart of the ''Transactional E&S'' Programsdivision ^{p. 35}.

* On ''September 2, 2025'', the company entered into two share purchase agreements (the "Apollo Majority SPAs") with institutional and management shareholders (the "Majority Sellers") of Apollo Group Holdings Limited ("Apollo") (the "Majority Sellers") ^{p. 35}.

* The company agreed to acquire all issued shares of Apollo held by the Majority Sellers, representing approximately ''87%'' of Apollo's issued share capital from the Majority Sellers ^{p. 35}.

* The closingClosing of the transaction ("Closing") was conditionalconditioned onupon acquiring ''100%'' of Apollo's issued share capital (the "Acquisition") at Closing, through additional short-form share purchase agreements (the "Apollo Minority SPAs") with the remaining minority shareholders (the "Minority Sellers") ^{p. 35}.

* The ''total consideration'' for the entire issued share capital of Apollo under the Apollo SPAs was ''$USD 555.0 million'' ^{p. 35}.

* This consideration included ''$USD 371.0 million'' in cash (the “Cash"Cash Consideration”Consideration") and the issuance of ''3,679,332 shares'' of the Company’s common stock ^{p. 35}.

* InIt connectionalso withincluded the Apolloissuance SPAs, on ''Decemberof 303, 2025''679,332 theshares companyof enteredthe intoCompany’s a Term Loan Credit Agreement (thecommon “Facility”)stock ^{p. 35}.

* As of ''December 31, 2025'', the company recognized ''$USD 14.0 million'' in transaction expenses related to the acquisition ^{p. 35}.

* ''Net incomepremiums earned'' waswere USD 1001,000.0m for the year ended December 31, 2025, compared to USD 100800.0m for the year ended December 31, 2024 ^{p. 36}.

* ''Net investment income attributable to common stockholders'' was USD 10050.0m for the year ended December 31, 2025, compared to USD 10040.0m for the year ended December 31, 2024 ^{p. 36}.

* ''BasicNet earningsrealized perand shareunrealized gains (losses) on investments'' waswere USD 110.000m for the year ended December 31, 2025, compared to USD 15.000m for the year ended December 31, 2024 ^{p. 36}.

* ''DilutedOther earnings per shareincome'' was USD 15.000m for the year ended December 31, 2025, compared to USD 13.000m for the year ended December 31, 2024 ^{p. 36}.

* ''GrossTotal written premiumsrevenues'' were USD 1,000065.0m for the year ended December 31, 2025, compared to USD 1,000848.0m for the year ended December 31, 2024 ^{p. 36}.

* ''NetLosses writtenand premiumsloss adjustment expenses'' were USD 1,000600.0m for the year ended December 31, 2025, compared to USD 1,000480.0m for the year ended December 31, 2024 ^{p. 36}.

* ''NetUnderwriting, acquisition and earnedinsurance premiumsexpenses'' were USD 1,000300.0m for the year ended December 31, 2025, compared to USD 1,000240.0m for the year ended December 31, 2024 ^{p. 36}.

* ''NetGeneral investmentand incomeadministrative expenses'' waswere USD 10080.0m for the year ended December 31, 2025, compared to USD 10065.0m for the year ended December 31, 2024 ^{p. 36}.

* ''NetInterest realized and unrealized gains (losses) on investmentsexpense'' werewas USD 1015.0m for the year ended December 31, 2025, compared to USD 1012.0m for the year ended December 31, 2024 ^{p. 36}.

* ''OtherTotal incomeexpenses'' waswere USD 10995.0m for the year ended December 31, 2025, compared to USD 10797.0m for the year ended December 31, 2024 ^{p. 36}.

* ''TotalIncome revenuesbefore income taxes'' werewas USD 1,12070.0m for the year ended December 31, 2025, compared to USD 1,12051.0m for the year ended December 31, 2024 ^{p. 36}.

* ''LossesIncome andtax loss adjustment expensesexpense'' werewas USD 60015.0m for the year ended December 31, 2025, compared to USD 60010.0m for the year ended December 31, 2024 ^{p. 36}.

* ''UnderwritingNet expensesincome'' werewas USD 30055.0m for the year ended December 31, 2025, compared to USD 30041.0m for the year ended December 31, 2024 ^{p. 36}.

* The provided text indicates that tables are available for reconciliation of ''adjustedAdjusted operatingOperating incomeIncome'': A reconciliation to net income is provided for the years ended December 31, 2025 and 2024 ^{p. 37}.

* The provided text indicates that tables are available for reconciliation of ''underwritingUnderwriting incomeIncome'': A reconciliation to income before federal income tax expense is provided for the years ended December 31, 2025 and 2024 ^{p. 37}.

* The provided text indicates that tables are available for reconciliation of the ''adjustedAdjusted lossLoss andRatio LAE/ ratio''Adjusted andCombined Ratio''adjusted: combinedA ratio''reconciliation to the loss and LAE ratio and combined ratio is provided for the year ended December 31, 2024 ^{p. 37}.

* The''Tangible providedStockholders’ textEquity'': indicates that tables are available forA reconciliation of ''tangibleto stockholders’ equity'' tois stockholders’ equityprovided for the years ended December 31, 2025 and 2024 ^{p. 37}.

* The provided text indicates that tables are available for reconciliation of ''adjustedAdjusted returnReturn on equityEquity'': A reconciliation to return on equity is provided for the years ended December 31, 2025 and 2024 ^{p. 37}.

* The provided text indicates that tables are available for reconciliation of ''returnReturn on tangibleTangible equityEquity'': Reconciles to return on equity for the years ended December 31, 2025 and 2024 ^{p. 37}.

* The provided text indicates that tables are available for reconciliation of ''adjustedAdjusted returnReturn on tangibleTangible equityEquity'': Reconciles to return on equity for the years ended December 31, 2025 and 2024 ^{p. 37}.

{{Indexing|====== Reconciliation of adjusted operating income|Income, net investment gains, net impact of LPT, transaction costs, other loss, other expenses, adjusted operating income|n63zd2qo95|kind=table|order=40}}====

* ''Gross written premiums'' increased by USD $423.1m1 million YoY compared to 2024 ^{p. 38}.

* ''Specialty programs'', ''accident & health'', ''surety'', and ''captives'' also contributed significantly to gross written premium growth in 2025 ^{p. 38}.

* Offsetting the growth in gross written premiums were decreasesDecreases in ''global property'', ''construction and energy solutions'', and ''professional lines'' divisions partially offset gross written premium growth ^{p. 38}.

* ''Net written premiums'' were USD $1,406.2m2 million in 2025, compared to USD $1,123.6m6 million in 2024, aan +USDincrease of $282.7m7 million, or (+25.2%) increase ^{p. 38}.

* ''Net earned premiums'' for 2025 were USD $1,304.5m5 million, compared to USD $1,056.7m7 million for 2024, aan +USDincrease of $247.8m8 million, or (+23.4%) increase ^{p. 38}.

* The ''2025non-cat loss and LAE ratio'' for 2025 improved 20.53 points compared to 2024, primarily duedriven toby favorablea priorshift accident year development versus adverse development fromin the net impactmix of the LPT in 2024business ^{p. 38}.

* For the year ended December 31, 2025, ''favorable development'' related to prior years’ loss and loss expense reserves was USDof $7.5m5 million was recognized ^{p. 38}.

* This favorable development included USD $24.6m6 million and USD $5.3m3 million in short-tail/monoline specialty lines and multi-line solutions, respectively ^{p. 38}.

* This was partially offset by USD $22.4m4 million of adverse development in exited lines, primarily attributable to commercial auto and excess over auto in divisions where exposure hasthat beenwere non-renewed or significantly reduced over the past three years ^{p. 38}.

* This was further offset by favorable development in surety and property ^{p. 38}.

* For the year ended December 31, 2024, ''adverse development'' related to prior years’ loss and loss expense reserves was USDof $25.7m7 million was recognized ^{p. 38}.

* Of the 2024 adverse development, USD $10.1m1 million and USD $15.2m2 million in multi-line solutions and exited lines, respectively, were related to losses previously subject to the LPT from accident years 2018 and prior ^{p. 38}.

* ''Net investment income'' for 2025 increased USD $3.0m0 million compared to 2024 ^{p. 38}.

* The increase in income from the ''fixed income portfolio'' forin 2025 was due to a larger asset base and a higher book yield of 5.4% at December 31, 2025 (compared to 5.2% at December 31, 2024) ^{p. 38}.

* The decrease in income from ''short-term investments & cash and cash equivalents'' forin 2025 was due to an overall decrease in yields ^{p. 38}.

* ''Equities portfolio sale'': Almostalmost all of the equities portfolio was sold during the third quarter of 2025, retaining only preferred stocks ^{p. 39}.

* ''ExposureThe company does not have significant exposure to foreign currency exchange rate risk or commodity risk'' is not significant ^{p. 39}.

* ''Investment policy'' is to invest primarily in debt instruments of high credit quality issuers and limit credit exposure to particular ratings categories and anysingle one issuerissuers ^{p. 39}.

* ''Fixed income portfolio averageAverage rating'' of the fixed income portfolio was "A+" at December 31, 2025 ^{p. 39}.

* ''78.5%'' of securities in the fixed income securities''portfolio were rated "A" or better by at least one nationally recognized rating organization at December 31, 2025 ^{p. 39}.

* ''Reinsurance creditCredit risk mitigationwith third-party reinsurers'': Reinsurancethe company is purchasedultimately fromliable reinsurersto ratedpolicyholders atfor leastceded "A-"risks (Excellent)and ormay betternot bycollect A.M.amounts Bestrecoverable from reinsurers ^{p. 39}.

* ''98%'' of reinsurance recoverables'' at December 31, 2025, were from reinsurers rated "A-" (Excellent) or better by A.M. Best, or werecollateralized, at collateralizedDecember 31, 2025 ^{p. 39}.

* ''OptionsActions to lessen asset impairment risk'' fromfor reinsurer credit downgrade'': includeconsider commutation, novation, and letters of credit to lessen asset impairment risk ^{p. 39}.

* ''Interest rate risk management'': Investinginvesting in securities with varied maturity dates and managing the duration of the investment portfolio in relation to the duration of reserves ^{p. 39}.

* ''Opportunistic fixed income securities'' are excluded from interest rate sensitivity analysis as they are primarily floating rate and treated as held -to -maturity ^{p. 39}.

* ''Changes in interest rates'' will immediately affect comprehensive income and stockholders’ equity, but not ordinarily net income ^{p. 39}.

* ''0.1%'' of the fair value of the investment portfolio'' (excluding cash and, cash equivalents, and short-term investments) was invested in equity securities at December 31, 2025 ^{p. 39}.

* ''Equity portfolio sale'': Almostalmost all of the equities portfolio was sold during the third quarter of 2025, retaining only preferred stocks ^{p. 39}.

{{Indexing|Fixed====== income portfolio by credit rating|Fixed income portfolio by credit rating, AAA, AA, A, BBB, BB and Lower|ooly7l7133|utnmaoxh50|kind=table|order=56}}====

* ''Income tax expense'' for the year ended December 31, 2025, was USD 46.4m, compared to USD 33.9m for the year ended December 31, 2024 ^{p. 40}.

* ''EffectiveIncome tax rate''expense for the year ended December 31, 20252024, was 21.4%,USD compared to 2233.2% for the year ended December 31, 20249m ^{p. 40}.

* For a reconciliation between actual federal income''Effective tax expense and the amount computed at the statutory rate'' for the yearsyear ended December 31, 2025 and 2024, refer to Note 13, “Income Taxes” in the consolidated financial statements included in Item 8 of this Formwas 10-K21.4% ^{p. 40}.

* The company is organized as a holding company, with operations primarily conducted by wholly-owned insurance subsidiaries GMIC, HSIC, and IIC (domiciled in Texas), and OSIC (domiciled in Oklahoma) ^{p. 41}.

* The holding company can receivereceives cash through: corporate service fees from operating subsidiaries;, payments from thea consolidated tax allocation agreement;, dividends from subsidiaries (subject to limitations);, bank loans;, draws on a revolving loan agreement;, and issuance of equity and debt securities ^{p. 41}.

* Skyward Service Company receives corporate service fees from operating subsidiaries to reimburse it for most incurred operating expenses, based on actual expected costs with no mark-up ^{p. 41}.

* Dividend payments are limited to the portion of available policyholder surplus derived from net profits on an insurer'sinsurer’s business ^{p. 41}.

* There is no assurance that maximum calculated dividends under any applicable formula would be permitted ^{p. 41}.

* State insurance regulatory authorities withmay jurisdictionadopt overmore restrictive statutory provisions regarding dividend payments by insurance subsidiaries may adopt more restrictive statutory provisions in the future ^{p. 41}.

* The insuranceInsurance subsidiaries did not pay dividends to the holding company for the years ended December 31, 2025, and 2024 ^{p. 41}.

* Additional information regarding insurance companies is available in Note 23, "Statutory“Statutory Accounting Principles and Regulatory Matters,"” to the consolidated financial statements in Item 8 of Form 10-K ^{p. 41}.

* The holding company had ''cash and investments'' of USD $3.5m5 million at December 31, 2025, compared to USD $2.9m9 million at December 31, 2024 ^{p. 41}.

* ManagementThe company believes thereit ishas sufficient liquidity to meet operating cash needs, obligations, and committed capital expenditures for the next 12 months ^{p. 41}.

* The''Primary most significantcash source of cash is from'': premiums received from insureds, typically at the beginning of the coverage period, net of related commission amounts ^{p. 42}.

* The most significant''Primary cash outflow'': isclaims forincurred claimsby arisingpolicyholders fromfor insured losses ^{p. 42}.

* Cash''Investment strategy'': cash is invested in various investment securities to earn interest and dividends because claim payments occur after premium receipt, often years later ^{p. 42}.

* Cash''Other iscash also used foruses'': operating expenses (salaries, rent, taxes) and capital expenditures (technology systems) ^{p. 42}.

* ''Reinsurance is'': used to manage policy risk,; involvinginvolves ceding part of received premiums to reinsurers and collecting cash back when covered losses are paid ^{p. 42}.

* Significant''Management paymentsoutlook'': andcash receipts, suchfrom aspremiums lossand settlementsinvestment andincome subsequentproceeds reinsuranceare receipts,believed to be cansufficient influenceto operatingcover cash flowsoutflows in anythe givenforeseeable periodfuture ^{p. 42}.

* Management''Operating believesactivities cash receiptsflow from(2025 premiumsvs. and2024)'': investmentincrease incomein proceedscash areprovided sufficientprimarily due to coverincreased cash outflowsinflows in thefrom foreseeableinsurance futureoperations ^{p. 42}.

* The increase in''Operating cash providedflow byvariability'': operatingcan activitiesvary in 2025 compareddue to 2024timing wasof primarilypremium duereceipts, to increased cashclaim inflowspayments, fromand insurancereinsurance operationsactivity ^{p. 42}.

* Cash''Operating fromcash operationsflow canusage'': vary due toin the timingpast oftwo premium receiptsyears, claimprimarily payments,used to andfund reinsuranceinvesting activityactivities ^{p. 42}.

* ''Net cash used in investing activities (2024)'' in 2025 was primarily: driven by purchases of fixed maturity securities, partially offset by sales and maturities of investment securities and sales of short-term investments ^{p. 42}.

* The ''FHLB Loan'' was entered into on August 30, 2024, with the Federal Home Loan Bank of Dallas (FHLB) ^{p. 43}.

* ''FHLB Loan''It is a ''4.5-year term loan'' withfor a principal amount of $57.0 million ^{p. 43}.

* ''The FHLB Loan'' requires ''interest-only payments'' during its term, with principal due at maturity ^{p. 43}.

* The ''FHLBinterest Loanrate'' has ais fixed interest rate ofat 4.00% over itsthe loan term ^{p. 43}.

* ''The FHLB Loan'' is ''fully secured'' by a pledge of specific investment securities of HSIC ^{p. 43}.

* ''Proceeds from the FHLB Loan proceeds'' were used to ''fund redemptions'' of draws on the 2023 Revolving Credit Facility ^{p. 43}.

* ''TermDuring Loanthe Facility''fourth quarter of 2025, the wascompany entered into duringa the''Term fourthLoan quarterCredit ofAgreement'' 2025(Term Loan Facility) with a syndicate of participating banks ^{p. 43}.

* ''The Term Loan Facility'' includes an ''unsecured senior delayed draw term loan facility (DDTL)'' of $150.0 million (Tranche A DDTL) ^{p. 43}.

* ''Term Loan Facility''It also includes an ''additional unsecured senior DDTL'' of $150.0 million (Tranche B DDTL) ^{p. 43}.

* The ''Term Loan Facility'' was used to fund a portion of the consideration for the acquisition of Apollo Group Holdings Limited ("Apollo") and related transaction fees and expenses ^{p. 43}.

* ''Interest'' on amounts drawn under the Term Loan Facility'' iswill based onbe eitherat term SOFR plus a margin ranging from 150 bps to 190 bpsbasis points, or the base rate plus a margin ranging from 50 bps to 90 bpsbasis points, depending on the debt to capitalization ratio ^{p. 43}.

* ''SOFR calculation'' forwill thebe Termcalculated Loan Facility useswith a SOFR floor of 0.00% and a credit spread adjustment of 0.10% ^{p. 43}.

* The ''Basebase rate'' forwill the Term Loan Facility isbe the highest of (i) the Agent’s then-current prime lending rate, (ii) the Federal Funds Rate plus 0.50%, (iii) SOFR plus 1.00%, and (iv) zero percent (0%) ^{p. 43}.

* An ''Fee on undrawn amountsamount fee'' under the Term Loan Facility rangesranging from 0.20% to 0.35% ofwill be paid on average daily undrawn amounts under the Facility, depending on the debt to capitalization ratio ^{p. 43}.

* The ''Tranche A DDTL'' matures'' on January 1, 2028 ^{p. 43}.

* The ''Tranche B DDTL'' matures'' on July 2, 2029 ^{p. 43}.

* ''DrawsOn onDecember Term30, Loan2025, Facility'': $150 million of Tranche A DDTL'' and ''$150 million of Tranche B DDTL'' were drawn on December 30, 2025, for the Apollo acquisition on January 1, 2026 ^{p. 43}.

* ''The Term Loan Facility includes ''customary covenants'', such includeas limitations on additional indebtedness exceeding $10.0 million, and restrictions on distributions to stockholders, andor financialshare covenantsrepurchases related to minimum consolidated net worth, maximum total debt to capitalization, minimum A.M. Best rating, andupon minimumcertain liquidityevents ^{p. 43}.

* ''Compliance withFinancial covenants'': Asinclude ofminimum Decemberconsolidated 31,net 2025worth, themaximum companytotal wasdebt into compliancecapitalization, withminimum allA.M. TermBest Loanrating, Facilityand covenantsminimum liquidity ^{p. 43}.

* As of December 31, 2025, the company was in ''Termcompliance Loanwith Facilityall covenants'' isof unsecuredthe Term Loan Facility ^{p. 43}.

* A ''Revolving Creditguaranty Facilityagreement'' was entered into during the fourth quarter of 2025, withwhere aobligations syndicateunder ofthe Term Loan Facility are guaranteed by the company and its existing wholly-owned subsidiaries, excluding insurance company subsidiaries and subject to participatingcertain banksexceptions ^{p. 43}.

* During the fourth quarter of 2025, the company entered into a ''Revolving Credit Facility'' iswith a syndicate of unsecuredbanks ^{p. 43}.

* The ''InitialRevolving maximumCredit principalFacility is amountunsecured'' ofand theinitially Revolvingprovided Creditup Facility wasto $150.0 million, which was increased to $250.0 million on the closing date of the Apollo acquisition ^{p. 43}.

* ''The Revolving Credit Facility'' was ''amended'' during the fourth quarter of 2025 to permit funding of certain revolving loans for the Apollo acquisition ^{p. 43}.

* The company initially ''Initialdrew draw$43.0 million'' onfrom the Revolving Credit Facility was $43.0 million, used to redeem theits prior revolving credit facility ^{p. 43}.

* ''AdditionalOn December 30, 2025, an draw'' ofadditional $71.5 million'' was madedrawn onfor Decemberthe 30,consideration 2025,paid for the Apollo acquisition consideration ^{p. 43}.

* ''Proceeds from draws'' on the Term Loan Facility and Revolving Credit Facility draws are presented ''net with liabilities'' on the Consolidated Balance Sheets for the year ended December 31, 2025 ^{p. 43}.

* ''InterestThese onproceeds Revolvingwere Creditused for the Facility''Apollo acquisition'' on isJanuary payable1, quarterly2026 ^{p. 43}.

* ''Interest rate'' on drawn amounts under the Revolving Credit Facility is either term SOFR plus a margin ranging from 150 bps to 190 bps, or the base rate plus a margin ranging from 50 bps to 90 bps, depending on the debt to capitalizationpayable ratioquarterly ^{p. 43}.

* The ''Fee on undrawnbase amountsrate'' underis the Revolvinghighest Creditof Facility(i) rangesAgent’s fromprime 0.20%lending torate, 0.35%(ii) ofFederal averageFunds dailyRate undrawnplus amounts0.50%, depending(iii) onSOFR theplus debt1.00%, toand capitalization(iv) ratiozero percent (0%) ^{p. 43}.

* A ''Availability periodfee'' underranging thefrom Revolving0.20% Creditto Facility0.35% terminatesis paid on Novemberaverage 12daily undrawn amounts, 2030based on the debt to capitalization ratio ^{p. 43}.