Skyward/2024/FY/Annual report

Document info
Document ID	vycbjm4dw4
Organization	Skyward
Year	2024
Period	FY
Period label	FY24
Document category	Annual report
Document type	Form 10-K
Document name	Skyward Specialty Insurance Group 2024 Form 10-K
Publication date	2025-03-03
Language	English
Pages	24
Source	original URL
Transcript	wiki page
Data	data page

This article summarizes Skyward's Annual report published on 2025-03-03 (24 pages).

Cover

[c. 1; p. 1]

Cover

USD ($)	12 Months Ended
	Dec. 31, 2024	Feb. 26, 2025	Jun. 30, 2024
Cover [Abstract]	—	—	—
Document Type	10-K	—	—
Document Annual Report	true	—	—
Document Period End Date	Dec. 31, 2024	—	—
Current Fiscal Year End Date	--12-31	—	—
Document Transition Report	false	—	—
Entity File Number	001-41591	—	—
Entity Registrant Name	SKYWARD SPECIALTY INSURANCE GROUP, INC.	—	—
Entity Incorporation, State or Country Code	DE	—	—
Entity Tax Identification Number	14-1957288	—	—
Entity Address, Address Line One	800 Gessner Road	—	—
Entity Address, Address Line Two	Suite 600	—	—
Entity Address, City or Town	Houston	—	—
Entity Address, State or Province	TX	—	—
Entity Address, Postal Zip Code	77024-4284	—	—
City Area Code	713	—	—
Local Phone Number	935-4800	—	—
Title of 12(b) Security	Common stock, par value $0.01	—	—
Trading Symbol	SKWD	—	—
Security Exchange Name	NASDAQ	—	—
Entity Well-known Seasoned Issuer	No	—	—
Entity Voluntary Filers	No	—	—
Entity Current Reporting Status	No	—	—
Entity Interactive Data Current	Yes	—	—
Entity Filer Category	Large Accelerated Filer	—	—
Entity Small Business	false	—	—
Entity Emerging Growth Company	false	—	—
ICFR Auditor Attestation Flag	true	—	—
Document Financial Statement Error Correction [Flag]	false	—	—
Entity Shell Company	false	—	—
Entity Public Float	—	—	1,333,367,336
Entity Common Stock, Shares Outstanding	—	40,127,908	—
Documents Incorporated by Reference	Portions of the Registrant’s Proxy Statement relating to the 2025 annual meeting of stockholders (the “2025 Proxy Statement”), which will be filed within 120 days of December 31, 2024, are incorporated by reference into Part III of this Form 10-K.	—	—
Entity Central Index Key	0001519449	—	—
Amendment Flag	false	—	—
Document Fiscal Year Focus	2024	—	—
Document Fiscal Period Focus	FY	—	—

Audit Information

[c. 2; p. 2]

Auditor name, location, and firm ID by 12 months ended

	12 Months Ended
	Dec. 31, 2024
Audit Information [Abstract]	—
Auditor Name	Ernst & Young LLP
Auditor Location	Houston, Texas
Auditor Firm ID	42

Business

Who We Are

[c. 3; p. 8] Company formation and business overview

• Skyward Specialty was formed as a Delaware corporation on January 3, 2006, as an insurance holding company.
• The company operated under the name Houston International Insurance Group, Ltd. until rebranding as Skyward Specialty in November 2020.
• Skyward Specialty is a growing specialty insurance company delivering commercial property and casualty (P&C) products and solutions on a non-admitted (E&S) and admitted basis, predominantly in the United States.
• The business focuses on underserved, dislocated, and/or markets where standard insurance coverages are insufficient.
• Customers typically require highly specialized, customized underwriting solutions and claims capabilities.
• The company develops and delivers tailored insurance products and services for niche markets.

[c. 4; p. 8] Diversified portfolio and strategy

• The portfolio of insured risks is highly diversified across industries, distribution channels, and lines of business.
• 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.
• The company insures both short and medium duration liabilities.
• The business mix is principally primary insurance and balanced between E&S and admitted markets.
• A small portion of the business is specialty reinsurance (principally agriculture and credit), focused on attractive specialty classes where approaching through reinsurance is more efficient due to factors like cost of entry and geographic expansion costs.
• This diversification, including businesses not typically aligned with traditional P&C pricing cycles, combined with underwriting and claims expertise, is expected to consistently produce strong growth and profitability across all insurance pricing cycles.

[c. 5; p. 8] Leadership and competitive advantages

• The company is led by an entrepreneurial executive management team with decades of insurance leadership experience in the global P&C industry.
• Leadership is supported by an experienced team with a broad skill set aligned with the company's strategy.
• 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 expected to enable continued profitable business growth.
• The aim is to deliver long-term value for shareholders by generating best-in-class underwriting profitability and book value per share growth across P&C market cycles.

[c. 6; p. 8] Financial strength ratings

• All insurance company subsidiaries are group rated.
• Subsidiaries have financial strength ratings of "A" (Excellent) from A.M. Best Company ("A.M. Best") with a stable outlook.

Our Business and Our Strategy

[c. 7; p. 8] Reportable segment and underwriting divisions overview

• One reportable segment offers a broad array of insurance coverages to various market niches.
• Eight distinct underwriting divisions exist, each with dedicated underwriting leadership and technical staff.
• This structure and expertise aim to serve customer needs, be a value-add partner to distributors, and earn attractive risk-adjusted returns.
• For the year ended December 31, 2024, 44% of gross written premiums were on an admitted basis and 56% were non-admitted.

[c. 8; p. 8] Accident & Health underwriting division

• The Accident & Health (A&H) underwriting division provides medical stop loss to employers who self-insure employee benefits, and covers group and single-employer captives.
• The approach for managing medical costs and claims oversight enables partnerships with select distribution partners.
• It targets small and medium-sized enterprise market segments seeking to control healthcare costs by self-insuring a portion of their healthcare insurance.
• Products are written on an admitted basis and distributed primarily through retail and wholesale broker partners.

[c. 9; p. 8] Captives underwriting division

• The Captives underwriting division provides group captive solutions by leveraging underwriting and claims expertise from other divisions.
• This allows for broadening market reach and writing profitable business with limited additional expense.
• The division writes property, general liability, commercial auto, excess liability, and workers’ compensation lines of business on an E&S and admitted basis.
• Business is often administered through partnerships with third-party captive managers.

[c. 10; p. 8] Global Property and Agriculture underwriting division

• The Global Property underwriting unit provides property-only solutions to large multi-jurisdictional entities with complex property exposures.
• This business is written entirely on an E&S basis and distributed through retail and select wholesale brokers.
• The Global Agriculture underwriting unit provides secondary and reinsurance solutions for crop, livestock, and other renewable resources.

[c. 11; p. 8] Industry Solutions underwriting division

• The Industry Solutions underwriting division includes three units: construction, energy, and inland marine.
• Construction and energy units provide general liability, excess liability, commercial auto, workers’ compensation, and adjacent inland marine solutions.
• These are written principally on an admitted basis for middle market construction and energy production/servicing customers, including alternative/renewable energy.
• The inland marine unit focuses on logistics and other specialty property risk for assets in transit.
• Industry segments often have high severity exposures, addressed with multi-line solutions by skilled underwriters and claims professionals.
• Products are distributed through retail agents and brokers and a select network of wholesalers.

[c. 12; p. 8] Professional Lines underwriting division

• The Professional Lines underwriting division includes three units: management liability, professional liability (including cyber and media liability), and allied health (including life sciences).
• Professional liability and allied health provide primary and excess claims-made liability products.
• These are offered on an E&S and admitted basis, distributed through wholesale and retail brokers depending on the product.

[c. 13; p. 8] Programs underwriting division

• The Programs underwriting division partners with program administrators focused on specific markets aligned with the company's expertise and strategy.
• Partnering with program administrators is considered optimal for profitable participation or market reach, especially when administrators have competitive advantages like scale or proprietary technology.
• The division writes property, general liability, commercial auto liability, excess liability, and workers’ compensation lines of business on an E&S and admitted basis.

[c. 14; p. 8] Surety underwriting division

• The Surety underwriting division provides contract, commercial, and transactional surety solutions for trade and services organizations requiring bonding.
• It primarily focuses on small to medium-sized enterprises with aggregate bond programs up to approximately USD 75.0m for contract and USD 100.0m for commercial and transactional.
• This business is written on an admitted basis and distributed through retail agents and brokers.

[c. 15; p. 8] Transactional E&S underwriting division

• The Transactional E&S underwriting division provides primary and excess non-catastrophe prone property and general liability solutions.
• It emphasizes risks considered hard to place due to complexity, loss history, or limited operating history (e.g., start-ups).
• Success in this market is determined by technical underwriting, thoughtful coverage provisions, pricing, and high-quality broker service.
• The market is accessed exclusively through wholesale brokers.

[c. 16; p. 8] Exited business

• Business units and lines of business previously exited and placed into run-off are referred to as "exited business".

[c. 17; p. 8] Strategy and "Rule Our Niche"

• The company seeks to lead in chosen market niches and establish sustainable competitive positions.
• The strategy, referred to as "Rule Our Niche," is underpinned by five key elements.
• The first element is providing differentiated products, services, and solutions that meet the unique needs of target markets.
• The second element is attracting and retaining exceptional underwriting and claims talent and incentivizing professionals aligned with organizational and corporate goals.
• The third element is amplifying expertise with advanced technology and analytics for superior risk selection, pricing, and claims management.
• The fourth element is empowering underwriting and claims teams with considerable authority for decision-making and expertise application.
• The fifth element is fostering a culture that promotes nimbleness and responsiveness to market opportunities and dislocation.
• This strategy forms the basis for building a strong defensible market position, creating a competitive moat, and winning in chosen markets.
• The principles of this strategy are believed to be key to achieving and sustaining best-in-class underwriting results through P&C insurance pricing cycles.
• The company consistently strives for excellence in risk selection, pricing, and claims outcomes, amplified by advanced technology and analytics.

Our Competitive Strengths

[c. 18; p. 8] Competitive strengths overview

• Competitive strengths include focus on profitable niches, highly skilled underwriters, superior claims staff, superior business intelligence platform, advanced technology, diversified business, attractive culture, and experienced leadership.

[c. 19; p. 8] Profitable niches and underwriting

• Focus on profitable niches of the market that require technical underwriting and claims management as barriers to entry.
• Niche areas of commercial lines P&C markets are an attractive subset of the P&C insurance market, offering opportunities for attractive risk-adjusted returns.
• Actively targets underserved, dislocated, or markets where standard products are insufficient.
• Risks within core markets require efficient, individual underwriting to generate acceptable, sustainable underwriting profit.
• Underwriting divisions are built around deeply experienced underwriters empowered with appropriate authority to make decisions.
• This structure enables offering innovative and unique products and solutions to distribution partners and customers, regardless of risk complexity.
• Underwriters' experience is augmented with data and predictive analytics to differentiate risk selection and pricing decisions while enhancing efficiency.
• Focus on hiring underwriting and technical staff whose expertise and experience differentiate the company.
• Underwriting teams are knowledgeable, experienced, and empowered, which is critical for success in markets with risks difficult to automate.
• Professionals are given freedom to use expertise and judgment in evaluating and pricing risks, rather than strict underwriting rules.

[c. 20; p. 8] Claims staff and operations

• Cultivated a best-in-class and highly specialized team of claims professionals knowledgeable about the niches and lines of business served.
• Claims professionals systematically address first-party claims with fair and equitable solutions and third-party claims with holistic and comprehensive responses.
• Aims to ensure consistent and early loss recognition of indemnity and loss adjustment expenses (LAE).
• Responds quickly to claims with specialized adjusters equipped with expertise, advanced technology, and analytics.
• Technology is deeply embedded in the claims process, leveraging a technology-enabled platform and tools from first notice of loss to investigation to settlement.
• Analytics capabilities provide senior leadership and claims teams with real-time, detailed information on open claims and benchmarks against closed claims.
• Industry expertise, nimble culture, and technology-embedded claims processes enable fair and appropriate claims outcomes for customers.

[c. 21; p. 8] Business intelligence and technology

• SkyBI, the business intelligence platform, provides senior leadership and technical teams with real-time intelligence for superior decision-making.
• SkyBI reflects best practices learned from the management team's experience in P&C insurance and technology sectors.
• SkyBI is a single, comprehensive enterprise-wide data repository for reporting, business intelligence, analytics, and advanced data capabilities.
• Provides information and performance metrics across the company in an easy-to-consume visualized format.
• Data can be filtered by categories including distributor, customer segment, line of business, specific industry, individual underwriter, and specific risk feature.
• SkyBI aids in establishing clear line of sight to objectives and facilitating decision-making processes.
• Every underwriting and claims decision can be augmented with new types of risk data and advanced technology.
• Underwriting decisions are backed by reliable historical data and in-depth risk evaluation from intentional investment in data collection and processing.
• Underwriting and claims prowess is amplified by combining historical data with new forms of risk data and predictive analytics.
• Generative artificial intelligence is utilized in underwriting and claims handling where it enhances effectiveness and efficiency without sacrificing employee expertise.

[c. 22; p. 8] Diversified business

• Built a diversified group of underwriting divisions spanning multiple product lines, industries, geographies, and distribution channels.
• Includes business not typically aligned with traditional P&C cycles.
• Aims to evolve with and adapt to the market by growing certain lines when conditions are favorable and limiting exposure when conditions are less favorable.
• Diversity of the book allows response to and capitalization on market opportunities and dislocations across insurance market and pricing cycles, resulting in a durable insurance franchise.

[c. 23; p. 8] Culture and leadership

• Built a distinctive winning culture, evidenced by internal surveys, public information (Glassdoor, LinkedIn), and selection as a "Best Places to Work in Insurance".
• Key to culture and operating approach is a flat structure of communication and decision-making.
• Staff are trusted to make decisions that produce or exceed desired financial results and are supported by a clear system of performance measurement.
• Adopted a hybrid work schedule providing employees with remote working flexibility.
• Maintains an entrepreneurial environment that encourages and rewards a proactive approach to capitalize on market disruption.
• This environment is consistent with identity as a specialty insurer and a foundation for attracting talent and delivering best-in-class results.
• Led by CEO Andrew Robinson, the executive leadership team is experienced, innovative, and entrepreneurial.
• Leadership team has a track record of success in senior management roles at industry-leading P&C companies and in starting new businesses.
• Entire senior leadership's compensation is directly aligned with shareholders.
• A material portion of each leader's compensation is in long-term and short-term incentives tied to delivering sustainable, best-in-class underwriting returns.
• Executive leadership team has additional long-term incentive targets tied directly to growth in book value per share.

Our Strategy in Action

[c. 24; p. 8] Rule Our Niche strategy tenets

• The "Rule Our Niche" strategy aims to generate best-in-class underwriting profitability for niches and create superior long-term shareholder value through growth in book value per share.
• Core tenets include attracting and retaining blue-chip underwriting and claims talent to expand and enhance market position.
• The company seeks to hire talented technical underwriting professionals with long-standing industry relationships and claims professionals with niche expertise.
• These relationships are crucial for steady access to preferred business.
• The company believes it is a company of choice for top industry talent and will continue to grow its market position by recruiting world-class talent in chosen markets.

[c. 25; p. 8] Technology leverage

• The company leverages its technology DNA to differentiate itself from competitors.
• It has demonstrated a differentiated ability to use new forms of risk data and advanced technology in complex, higher severity risk categories within the specialty P&C insurance market.
• SkyBI enables prompt sensing and quick response to market changes.
• Core operating platforms allow efficient entry into new markets without complex systems.
• This technological advantage positions the company for profitable growth and expansion into additional specialty market niches where it can establish a strong and defensible market position.

[c. 26; p. 8] Business growth and market trends

• The company aims to profitably grow existing lines of business and expand with new underwriting divisions.
• It is positioned to capitalize on trends impacting customers in the United States and globally.
• Trends include increased demand for specialized insurance due to rising and complex risks from climate change/severe weather, supply chain uncertainty, financial inflation, cyber risk, novel health risks, increased litigation, attorney involvement, jury awards, and healthcare delivery/cost.
• Another market trend is the emergence of "micro cycles and micro dislocations" where P&C market segments experience hardening and softening at different times.
• The company has reacted quickly to these trends by launching new underwriting units (many not aligned with P&C cycles), entering underserved markets, partnering with advanced technology providers, and launching new captive solutions.
• Gross written premium growth and profitability indicate momentum and position the company for continued expansion and growth in target markets.

[c. 27; p. 8] Underwriting performance and operational excellence

• The company differentiates on daily excellence to drive best-in-class underwriting performance.
• Achieving long-term goals, including best-in-class underwriting returns and growth in book value per share, depends on day-to-day operational execution across all functional departments (underwriting, product management, claims management).
• SkyBI provides a foundation for senior management to monitor performance, including renewal rates, new business pricing, portfolio performance for individual underwriters, and claims aging/reserving practices/outcomes by claims adjusters.
• Focus on fundamentals driving underwriting excellence is central to the strategy.
• Cross-functional collaboration ensures underwriting, claims, actuarial, and product management teams regularly review performance and trends to implement portfolio, pricing, and coverage changes quickly.

[c. 28; p. 8] Balance sheet strength and reserving practices

• The company uses its balance sheet to capture a larger market share.
• It is committed to establishing and maintaining a strong balance sheet, starting with conservative loss reserves and strong capitalization ratios.
• This is imperative for maintaining confidence of customers, distribution partners, reinsurers, regulators, rating agencies, and shareholders.
• Claims case reserve practices aim to reserve to the expected ultimate loss within 90 days of the first notice of loss.
• The company maintains incurred but not reported reserves ("IBNR") that, combined with case reserves, are above the actuarial central estimate.
• Loss reserves represent the best estimate of ultimate losses.

Marketing and Distribution

[c. 29; p. 8] Marketing and distribution strategy

• The company's marketing and distribution approach mirrors its underwriting strategy and is a key facet of its "Rule Our Niche" strategy.
• Underwriting teams and the company maintain strong relationships and reputations with distribution partners, facilitating new affiliations.
• The company wins with distribution partners due to deep expertise in niche markets, high-caliber underwriters, a culture of innovation, thoughtful product lineup and design, and speed/quality of responsiveness.
• All underwriting divisions invest significant time and effort in sustaining and expanding distribution partner loyalty and long-term relationships.
• The choice of distribution partners is tailored to access specific business, mirroring the tailored underwriting approach for insureds.
• Products are distributed through retail agents, wholesale brokers, select program administrators, and captive managers.
• This distribution approach allows effective and efficient access to targeted business based on market niche needs and dynamics.

Underwriting

[c. 30; p. 8] Underwriting strategy and approach

• Underwriting approach is embedded in the "Rule Our Niche" strategy and is core to market success.
• Underwriting teams are specialized within eight divisions, focusing on specific niches.
• Underwriting approach is underpinned by hiring experienced, best-in-class, and diverse technical underwriters with established track records in specific specialty niche markets.
• Underwriters' skill sets are amplified with advanced technology and data analytics, and they are empowered with appropriate decision-making authority.
• This approach is considered key to superior risk selection and pricing, and producing sustainable best-in-class underwriting results across market cycles.
• Capabilities and experience of underwriting professionals are augmented using new forms of data and analytics for risk selection and pricing.
• Underwriting data is captured in the SkyBI business intelligence platform.
• SkyBI is a comprehensive data repository forming the foundation of reporting, analytics, and other data capabilities, and is a key tool for senior management and business leaders.
• The company is highly selective in policies chosen to bind.
• Underwriters are encouraged to move on quickly if they cannot reasonably expect to bind coverage at a premium and coverage terms that meet company standards.
• When accepting risks, terms and price are established to suit the underlying exposure.
• In the admitted market, the company ensures approved forms and filed rates are appropriate and adequate for accepted risks, while allowing flexibility for specific/unique exposures.
• In the E&S market, freedom of rate and form is used to ensure risk and coverage are appropriate for unique needs and exposures.
• Policies are crafted to offer affordable and appropriate protection for insureds' exposures, while constructing coverage for predictable potential losses and managed claims costs.
• Underwriting teams are supported by active engagement and collaboration with Claims, Actuarial, Product Management, Legal and Compliance, and Finance departments.
• This collaboration ensures trends in business, legal and tort developments, and competitor and regulatory actions are analyzed, shared, and acted upon timely.
• Underwriters are viewed as the center of the company, with all support functions incentivized and measured to support underwriting profitability targets.
• This structure helps surface opportunities and issues early, contributing to nimbleness and ability to leverage market disruptions.
• Underwriting controls and procedures are regularly reviewed to ensure underwriters profitably underwrite each market served.

Claims Management

[c. 31; p. 8] Claims management principles and operations

• Skyward's claims department is guided by six principles: prompt and comprehensive claim investigations using advanced analytics and technology; quality claims handling service with customer engagement; prompt establishment of reserves reflecting ultimate loss estimates; effective pursuit of contribution and subrogation; detection and prevention of fraud; and disciplined litigation management.
• 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.
• The majority of claims are handled in-house.
• Third Party Administrators (TPAs) are utilized for certain claims, including programs, captives, occupational accident, workers compensation, and runoff claims.
• TPAs are actively managed, overseen, and regularly audited to ensure compliance with Skyward's claims handling and reserving guidelines and general best practices.
• Independent legal counsel is retained for liability claims against an insured, selected based on geographical location and expertise.
• Litigation guidelines have been developed for claims professionals and outside counsel to ensure appropriate defense for insureds.
• A legal spend management solution is employed to analyze legal invoices for adherence to case handling and billing practice standards, ensuring reasonable and customary legal costs.

[c. 32; p. 8] Claims technology and efficiency initiatives

• Technology is leveraged to gain efficiencies in the claims-handling process.
• A Claims Development Severity Predictor, a predictive model, has been created and implemented to identify claims likely to lead to large loss development.
• This model allows for early identification, proactive claims management, and summarization of development reasons, and has been integrated into the claims review and management workflow.
• A "quick strike" program has been implemented for commercial auto claims to respond efficiently to claim reports.
• The "quick strike" program involves deploying experienced investigators and vendors to the scene of a reported auto accident, ideally within two hours, regardless of location.
• This quick response aids in evaluating accident facts and circumstances for rapid investigation and, if appropriate, resolving third-party claims quickly.

[c. 33; p. 8] Claims team structure and collaboration

• Claims handlers and managers are organized by line of business to ensure specialized expertise in handling claims.
• Managers and adjusters collaborate closely with underwriting partners to inform them of legal trends and emerging claims issues.
• The goal of this collaboration is to educate underwriters on emerging areas of loss experience to assist in their risk selection processes.

Technology

[c. 34; p. 8] Technology strategy and platforms

• Technology is central to Skyward's operations and decision-making, driving competitive advantages.
• Skyward deploys technology in three primary functional ways: Superior Business Intelligence Platform, Predictive Analytics Technology, and Core Transactional Platforms.
• Superior Business Intelligence Platform:
  • SkyBI provides senior leadership and technical teams with real-time intelligence for decision-making.
  • SkyBI incorporates best practices from management's experience in P&C insurance and technology sectors.
  • SkyBI is a single, comprehensive enterprise-wide data repository for reporting, business intelligence, analytics, and advanced data capabilities.
  • It provides information and performance metrics across the Company in a visualized format.
  • Data can be filtered by categories including distributor, customer segment, line of business, specific industry, individual underwriter, and specific risk feature.
  • SkyBI helps establish clear line of sight to objectives and facilitates decision-making.
• Predictive Analytics Technology:
  • Skyward augments employee capabilities using new risk data and predictive analytics, including AI, for risk selection, pricing, and claims handling.
  • Actions within each underwriting division are intentional to "Rule Our Niche".
  • Skyward aims for constant innovation, with actions specific to each division/market served.
• Core Transactional Platforms:
  • Core operating platforms (policy administration, underwriting workbench, billing, claims systems) are designed for nimble scaling and business expansion.
  • Skyward generally uses customized third-party vendor applications for core operating platforms.
  • The core platform organization is used for all business except accident & health, global property, agriculture, and surety, which require dedicated core processing components due to unique features.
  • Data from all divisions' core operating platforms flows to SkyBI with comparable data quality and granularity.
• The use of advanced technology for underwriting and claims, SkyBI, and core operating platforms creates a flywheel effect.
• This effect allows underwriters to better select risk, claims professionals to better adjudicate claims, unit leaders to better communicate with reinsurance and third-party partners, and senior leadership to better evaluate business trends.
• These tools also improve communication accuracy, effectiveness, and efficiency with distribution partners, reinsurers, and other third-party partners.

[c. 35; p. 8] Cybersecurity and data protection

• Skyward faces external threats to its IT systems, including system failure, customer data theft attempts, and ransomware attacks.
• The technology infrastructure is designed to function through major disruptions.
• Data is replicated in real-time to a third-party cloud disaster recovery site for use during major system failures.
• Data is backed up daily for system restoration.
• Actions to prevent system and data disruptions include:
  • Actively monitoring Cybersecurity and Infrastructure Security Agency’s (“CISA”) cybersecurity directives.
  • Taking immediate action on identified vulnerabilities in directives.
  • Conducting monthly vulnerability scans on all network-attached devices at all locations, with patching applied as needed.
  • Requiring two-factor authentication for system access.
  • Conducting monthly security training for all employees.
  • Implementing endpoint detection agents for threat detection and response.
  • Performing desktop scenarios to practice responses to breaches with cybersecurity insurance partners and retained security consultants.
  • Performing annual penetration testing.
• Skyward constantly reviews its security breach posture and regularly implements updated processes, best practices, and tools.

Reinsurance

[c. 36; p. 8] Reinsurance strategy and types

• Reinsurance is strategically purchased from third parties to protect capital from severity events (large single event losses or catastrophes) and reduce earnings volatility.
• Reinsurance contracts are predominantly one year in length and renew annually, primarily in January and June.
• Factors influencing changes to reinsurance purchases at annual renewal include plans to change underlying insurance coverage, updated loss activity, capital and surplus levels, changes in risk appetite, and the cost and availability of reinsurance treaties.
• Quota share, excess of loss, and facultative reinsurance coverage are purchased to limit exposure from losses on any one occurrence.
• The mix of reinsurance purchased considers efficiency, cost, risk appetite, and specific factors of underlying risks.
• Quota share reinsurance involves the reinsurer assuming a specified percentage of losses from a defined class of business in exchange for a corresponding percentage of premiums, net of a ceding commission.
• Excess of loss reinsurance involves the reinsurer assuming all or a portion of losses for an individual claim or event above a specified amount, in exchange for a negotiated premium, and includes the catastrophe reinsurance program.
• Facultative coverage is a reinsurance contract on individual risks, used to supplement treaty limits or cover risks/perils excluded from treaty reinsurance.

[c. 37; p. 8] Property catastrophe reinsurance program

• As of December 31, 2024, property insurance represented 29% of gross written premiums.
• Aggregation of property writings by geographic area is actively managed and continuously monitored to limit potential loss from severe events like hurricanes, convective storms, and earthquakes.
• Catastrophe reinsurance is purchased to further mitigate aggregation of property losses due to a single event or series of events.
• Third-party stochastic and internal deterministic models are used to analyze the risk of loss aggregation from such events, providing a quantitative view of Probable Maximum Loss (PML) events.
• Based on modeling, an event beyond a 1 in 250-year PML would be required to exhaust the USD 36.0m property catastrophe coverage.
• The company aims to expose no more than 3.0% of stockholders’ equity to a catastrophic loss less than a 1 in 250-year event.
• The current reinsurance program is believed to provide coverage well in excess of theoretical losses from any recorded historical event.

[c. 38; p. 8] Reinsurer credit quality and recoverables

• Reinsurance is sought from reinsurers rated at least "A-" ("Excellent") or better by A.M. Best.
• As of December 31, 2024, 99% of reinsurance recoverables were from reinsurers rated "A-" (Excellent) or better by A.M. Best, or were collateralized by the reinsurer.
• The company retains primary liability to policyholders if reinsurers are unable to pay claims, potentially resulting in losses.
• Allowances are established for uncollectible reinsurance amounts.
• The allowance for uncollectible reinsurance was USD 2.3m at December 31, 2024 and 2023.

[c. 39; p. 8]

Maximum Company Retention by Line of Business

Line of Business	Maximum Company Retention
Accident & Health	$0.90 million per occurrence
Commercial Auto (1)	$1.00 million per occurrence
Excess Casualty (1)(2)	$1.25 million per occurrence
General Liability (1)	$1.50 million per occurrence
Professional Lines (2)	$5.21 million per occurrence
Property (3)	$3.50 million per occurrence
Representation and Warranty	$3.25 million per occurrence
Surety (2)	$4.00 million per occurrence
Workers’ Compensation (2)	$2.33 million per occurrence

(1) Legal defense expenses can force exposure above the maximum company retention for Excess Casualty, Commercial Auto and General Liability.

(2) Reinsurance is subject to a loss ratio cap or aggregate level of loss cover that exceeds a modeled 1:250-year PML event.

(3) Catastrophe loss protection is purchased up to $36.0 million in excess of $12.0 million retention, which provides cover for a 1:250-year PML event.

($ in thousands)
Reinsurer	Reinsurance Recoverables	AM Best Rating
Everest Reinsurance Co.	154,181	A+
eMaxx Captives (1)	144,196	n/r
Partner Reinsurance Co. of the US	52,442	A+
General Reinsurance Corp	48,234	A++
Swiss Reinsurance America Corp	37,789	A+
ACE (Chubb Property & Casualty Ins Company)	36,527	A+
RGA Reinsurance Company	24,945	A+
Randall & Quilter (R&Q Bermuda (SAC) Ltd) (2)	22,663	n/r
Aspen Insurance UK Limited	19,998	A
Insurance Company of the West	18,112	A
Top 10 Total	559,087	—
All Others	298,789	—
Total	857,876	—

(1) This reinsurer facilitates our eMaxx captive. At December 31, 2024, we held collateral in a statutory trust of $188.9 million on our net reinsurance recoverables.

(2) This reinsurer facilitated our LPT reinsurance agreement which was commuted effective January 31, 2025. At December 31, 2024, we held collateral in a statutory trust of $22.7 million on our net reinsurance recoverables.

Enterprise Risk Management

[c. 40; p. 8] Enterprise Risk Management Framework

• The company's Enterprise Risk Management (ERM) is embedded in its operations and guides daily activities.
• The ERM approach aims to achieve an acceptable risk-adjusted return for shareholders while maintaining trust and reliability for those served.
• The company is intentional in its underwriting and asset portfolio construction, balancing liability duration and market cyclicality of the underwriting portfolio.
• Reinsurance is used to manage volatility outside of risk tolerances.
• The investment strategy targets a diversified portfolio that balances portfolio yield, liquidity, volatility, and potential for principal loss.
• The Senior Vice President (SVP) of Finance & ERM oversees critical ERM processes and chairs the cross-functional corporate ERM Committee.
• The company formalizes its view of risk and solvency as potential economic loss using its Economic Capital Model (ECM).
• The ECM output measures potential earnings and capital loss for various scenarios, which are then measured against risk tolerances.
• Risk tolerances are set and updated annually by the ERM Committee and discussed with the Board's Risk Committee.
• The ECM provides a probabilistic modeled view of earnings and capital loss, integrating potential losses from catastrophes, reserving, underwriting, market, credit risk, strategic, and operational risks.
• The SVP of Finance & ERM and the ERM Committee review and maintain a comprehensive risk register with accountabilities for mitigation.
• The top 10 risks are identified, quantified, and reviewed quarterly by the SVP of Finance & ERM and the ERM Committee.
• Reports on these risks are submitted regularly to the Risk Committee by the SVP of Finance & ERM and the ERM Committee.

[c. 41; p. 8] Operational Risk Management Processes

• Operational processes and controls are designed to identify, assess, and manage key risks continuously.
• The Underwriting Committee oversees changes in risk appetite, product line, and division expansion.
• Claims handling practices are monitored against guidelines through regular internal audits, monthly large loss reviews, and a watchlist of potential high-severity claims.
• Actuarial performs quarterly reserve studies, and the Reserve Committee meets quarterly to review and respond to loss emergence trends.
• Key observations from actuarial reviews are discussed with the CEO.
• Underwriting divisions assess rate change and retention on existing business, new business quality, pricing adequacy, and loss emergence compared to expected on a monthly and quarterly basis.
• The SkyBI platform provides real-time portfolio, underwriting, claims, and actuarial analytics to support these processes.

[c. 42; p. 8] ERM Strategic Importance

• ERM is central to the company's decision-making and daily activities.
• ERM is a core component of the strategy to achieve market-leading risk-adjusted returns for shareholders.

Reserves

[c. 43; p. 8] Reserve management and methodology

• Reserves are maintained for specific claims incurred and reported, IBNR reserves, and uncollectible reinsurance.
• Ultimate liability may differ from current reserves.
• The insurance industry carries the risk of inadequate reserves.
• Reserves are continually monitored using new information on reported claims and statistical analyses.
• Anticipated inflation is implicitly reflected in the reserving process through cost trend analysis and historical development review.
• Reserves for losses and LAE are not discounted to reflect estimated present value.
• Case reserves are established when a claim is reported for the estimated ultimate payment, following assessment of coverage, damages, and investigation.
• Estimates for case reserves are based on reserving practices and the claims adjuster's experience and knowledge of the claim type and value.
• Case reserves are periodically revised based on subsequent developments for each claim.
• IBNR reserves are established for estimated future loss payments on incurred but not yet reported claims and potential development on reported claims.
• IBNR reserves are estimated using generally accepted actuarial reserving techniques that consider quantitative loss experience data and qualitative factors.
• Loss reserves are regularly reviewed using various actuarial techniques.
• Reserve estimates are updated as historical loss experience develops, additional claims are reported/settled, and new information becomes available.
• Reserves can be increased or decreased over time as claims move towards settlement, impacting earnings through adverse development or reserve releases.
• Additional information on loss reserves is available in 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.”".

Investments

[c. 44; p. 8] Investment strategy and management

• The company aims to maintain a balanced investment portfolio with predictable and stable returns, augmented by strategic investments for attractive risk-adjusted returns.
• An Enterprise Based Asset Allocation model is used for investment allocation, embedded in the Economic Capital Model, to assess the impact of decisions on capital, liquidity, and risk profile across market scenarios.
• Investment risk is actively managed to balance stable growth and liquidity with compliance to insurance regulatory and rating agency frameworks.
• The portfolio primarily consists of cash and cash equivalents and investment-grade fixed-maturity securities, with additional investments fitting the risk appetite.
• The Board of Directors' Investment Committee reviews and approves the investment policy and strategy.
• The Investment Committee meets quarterly to review investment activities, tactics, and new opportunities.
• The investment portfolio is directed internally and includes both self-managed investments and portfolios managed by select third-party investment management firms.

[c. 45; p. 8] Investment discussion reference

• Additional discussion on investments, including market risks, is available in Item 7 of Form 10-K, "Management’s Discussion and Analysis of Financial Condition and Results of Operations—Investments".

Competition

[c. 46; p. 8] Competition in specialty P&C insurance

• The specialty lines property & casualty insurance market comprises many markets and sub-markets, each with distinct customer needs, products, services, and specific economic and structural features.
• Competition in underwriting divisions comes from other specialty and standard insurers, as well as program administrators.
• 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.
• Due to the diversity of underwriting divisions, competition is broad, with some competitors specific to only a subset of divisions.
• Notable competitors include Markel Corporation, W.R. Berkley Corporation, American Financial Group Inc., Tokio Marine Holdings, Inc., CNA Financial Corporation, Hiscox, Ltd., RLI Corp., Intact Finance Corporation, and Kinsale Capital Group, Inc..

Our Structure

[c. 47; p. 8] Insurance company structure and operations

• 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).
• GMIC, the largest insurance subsidiary, underwrites multiple lines of insurance on an admitted basis in all 50 states and the District of Columbia and is a certified surety bond company listed with the Department of the Treasury.
• 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.
• IIC, a subsidiary of HSIC, underwrites on an admitted basis in all 50 states and the District of Columbia.
• OSIC, a subsidiary of IIC, is an approved surplus lines company in 49 states and the District of Columbia.
• Effective December 31, 2024, the insurance company subsidiaries were restacked into the aforementioned organizational structure to provide the growing surety business with the capital needed to operate more effectively within the surety T-listing market.

[c. 48; p. 8] Gross written premiums geographic distribution

• The geographic distribution of gross written premiums for the year ended December 31, 2024, is presented in a table.

[c. 49; p. 8] Other subsidiaries and organizational structure

• Skyward Re, a wholly-owned captive reinsurance company domiciled in the Cayman Islands, was incorporated on January 7, 2020.
• Skyward Re was established to facilitate the LPT, which was commuted effective January 31, 2025.
• Three non-insurance companies are also operated: Skyward Underwriters Agency, Inc., Skyward Service Company, and Skyward Specialty No. 1 Limited Company.
• Skyward Underwriters Agency, Inc. is a licensed agent, managing general agent, and reinsurance broker.
• Skyward Service Company provides various administrative services to the subsidiaries.
• Skyward Specialty No. 1 Limited Company is a UK company and an authorized Lloyd’s corporate member.
• The organizational structure is detailed, with each entity wholly-owned by its immediate parent.

[c. 50; p. 8]

Our Structure

	2024
Texas	11.2%
California	8.8
Florida	8.3
Louisiana	6.8
New York	6.5
Georgia	4.4
Pennsylvania	3.9
New Jersey	3.2
Illinois	2.9
Massachusetts	2.5
All other states	41.5
Total	100.0%

[c. 51; p. 8] Our Structure

Our Structure

Chart / Image:

• SKYWARD SPECIALTY INSURANCE GROUP, INC. is a Delaware corporation.
• SKYWARD SPECIALTY INSURANCE GROUP, INC. has a subsidiary named SKYWARD SERVICE COMPANY.
• SKYWARD SERVICE COMPANY is a Delaware corporation.
• SKYWARD SPECIALTY INSURANCE GROUP, INC. has a subsidiary named GREAT MIDWEST INSURANCE COMPANY.
• GREAT MIDWEST INSURANCE COMPANY is a Texas stock insurance company.
• SKYWARD SPECIALTY INSURANCE GROUP, INC. has a subsidiary named SKYWARD UNDERWRITERS AGENCY, INC.
• SKYWARD UNDERWRITERS AGENCY, INC. is a Texas corporation.
• SKYWARD SPECIALTY INSURANCE GROUP, INC. has a subsidiary named SKYWARD SPECIALTY NO. 1 LIMITED.
• SKYWARD SPECIALTY NO. 1 LIMITED is a United Kingdom company.
• SKYWARD SPECIALTY INSURANCE GROUP, INC. has a subsidiary named SKYWARD RE.
• SKYWARD RE is a Cayman Islands corporation.
• GREAT MIDWEST INSURANCE COMPANY has a subsidiary named HOUSTON SPECIALTY INSURANCE COMPANY.
• HOUSTON SPECIALTY INSURANCE COMPANY is a Texas stock insurance company.
• HOUSTON SPECIALTY INSURANCE COMPANY has a subsidiary named IMPERIUM INSURANCE COMPANY.
• IMPERIUM INSURANCE COMPANY is a Texas stock insurance company.
• IMPERIUM INSURANCE COMPANY has a subsidiary named OKLAHOMA SPECIALTY INSURANCE COMPANY.
• OKLAHOMA SPECIALTY INSURANCE COMPANY is an Oklahoma insurance corporation.

Ratings

[c. 52; p. 8] A.M. Best rating

• Skyward Specialty Insurance Group, Inc. currently holds an "A" (Excellent) rating with a stable outlook from A.M. Best.
• The "A" (Excellent) rating is the third highest among the 13 ratings assigned by A.M. Best, which range from "A++" (Superior) to "D" (Poor).
• A.M. Best evaluates a company's financial and operating performance by reviewing profitability, leverage, liquidity, book of business, reinsurance adequacy, asset quality and market value, adequacy of losses and loss expense reserves, surplus adequacy, capital structure, management experience and competence, and market presence.
• A.M. Best's ratings reflect its opinion on an insurance company’s financial strength, operating performance, and ability to meet policyholder obligations.
• 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.

Regulation

[c. 53; p. 8] Regulation

• The company is regulated by insurance regulatory authorities in the states where it conducts business.
• State insurance laws and regulations primarily protect policyholders, consumers, and claimants, not stockholders or investors.
• State regulation varies by jurisdiction and generally grants broad administrative power to regulators.
• Regulatory powers include setting capital and surplus requirements, licensing insurers and producers, reviewing and approving product forms and rates, establishing reserve adequacy standards, prescribing statutory accounting methods and financial report formats, regulating affiliate transactions, and prescribing investment types and amounts.
• Insurance company regulation is constantly changing due to governmental agencies and legislatures reacting to issues.
• Some state legislatures have considered or enacted laws that alter and increase state authority to regulate insurance companies and holding company systems to prevent federal involvement.
• The National Association of Insurance Commissioners (NAIC) and some state insurance regulators are re-examining existing laws and regulations, focusing on insurer solvency, interpretations of existing laws, and development of new laws.
• Federal initiatives, such as treatment of federal subsidiaries, regulation of quasi-governmental entities, and regulations from federal departments, often affect the insurance industry despite the federal government not directly regulating insurance.
• The company operates as an insurance holding company system.
• The company is subject to insurance holding company laws in Texas, where its primary insurance companies are domiciled, and Oklahoma.
• These statutes require each insurance company in the system to register with its state of domicile's insurance department.
• Information concerning operations within the holding company system that may materially affect the operations, management, or financial condition of domiciled insurers must be furnished.
• All transactions among members of a holding company system must be fair and reasonable.
• Transactions between insurance subsidiaries and their parents and affiliates generally require disclosure to state regulators.
• Notice to or prior approval from the applicable state insurance regulator is generally required for any material or extraordinary transaction.

Intellectual Property

[c. 54; p. 8] Trademark registrations and protection

• The company has applied for various trademark registrations in the United States at both federal and state levels.
• The company will pursue additional trademark registrations and other intellectual property protection if deemed beneficial and cost-effective.
• The company monitors its trademarks and service marks and protects them from unauthorized use as necessary.

Employees and Human Capital

[c. 55; p. 8] Employee overview and culture

• As of December 31, 2024, the company had approximately 580 employees.
• Employees are not subject to any collective bargaining agreement, and no current efforts to implement such an agreement are known.
• The company believes it has good working relations with its employees.
• The company aims to be an employer of choice, fostering a culture committed to diversity of thought, background, and perspective.
• The company strives to cultivate an exceptional workforce to perpetuate its ownership culture and achieve superior business results.
• The goal is to attract, develop, and retain diverse talent, promoting a culture where different viewpoints are valued, and individuals feel respected, treated fairly, and have opportunities to excel.

[c. 56; p. 8] Compensation and benefits

• The company offers a competitive benefits package to support employee well-being.
• Benefits include medical, dental, and vision insurance, a 401(k) plan, paid time off, family leave, and employee assistance programs.
• An employee stock purchase plan is available to all employees.
• The company emphasizes employee training and development, providing opportunities for further education and professional development.

Risk Factors

[c. 57; p. 9] Investment risk disclosure

• Investing in the company's common stock involves a high degree of risk.
• Investors should carefully consider the risks and uncertainties described in the report, including consolidated financial statements and SEC filings, before investing.
• The listed risks are not exhaustive; additional unstated, unknown, or currently immaterial risks may also affect the company.
• If any described risks occur, the company's business, operating results, financial condition, and prospects could be materially harmed.
• Such events could lead to a decline in the common stock price, resulting in a loss of part or all of an investment.

Summary of Material Risk Factors

[c. 58; p. 9] business and operational risks

• Financial condition and results of operations could be materially adversely affected by inaccurate assessment of underwriting risk.
• Competition for business in the industry is intense.
• Reliance on insurance retail agents and brokers, wholesalers, and program administrators exposes the business to certain risks that could adversely affect results.
• Inability to purchase third-party reinsurance in desired amounts on commercially acceptable terms or terms that adequately protect the company may materially adversely affect business, financial condition, and results of operations.
• Losses and loss expense reserves may be inadequate to cover actual losses, which could materially adversely affect financial condition, results of operations, and cash flows.
• A decline in financial strength rating may adversely affect the amount of business written.
• Unexpected changes in the interpretation of coverage or provisions, including loss limitations and exclusions, in policies could materially adversely affect financial condition and results of operations.
• Reinsurers may not reimburse claims on a timely basis, or at all, which may materially adversely affect business, financial condition, and results of operations.
• Failure to accurately and timely pay claims could materially and adversely affect business, financial condition, results of operations, and prospects.
• Adverse economic factors, including recession, inflation, high unemployment, or lower economic activity, could lead to fewer policy sales, increased claim frequency, premium defaults, or falsification of claims, affecting growth and profitability.
• The insurance business is historically cyclical, which may affect financial performance and cause operating results to vary quarter-to-quarter, not indicative of future performance.

[c. 59; p. 9] regulatory and personnel risks

• Extensive regulation may adversely affect the ability to achieve business objectives; non-compliance could lead to penalties, including fines and suspensions, adversely affecting financial condition and results of operations.
• Adverse effects could result from the loss of key personnel or inability to attract and retain qualified personnel.

[c. 60; p. 9] internal control and public company costs

• Ability to maintain effective internal control over financial and management systems and remediate material weaknesses is a risk.
• Costs will increase significantly as a public company, requiring substantial management time for compliance with public company regulations.

Risks Related to Our Business and Industry

[c. 61; p. 9] Underwriting risk and competition

• Financial condition and results of operations could be materially adversely affected by inaccurate assessment of underwriting risk.
• Underwriting success depends on accurately assessing risks and establishing appropriate premium rates.
• Employees, including management and underwriters, make decisions that expose the company to risk.
• Competition in the insurance industry is intense, coming from specialty insurance companies, standard insurance companies, and underwriting agencies.
• Competition factors include price, reputation, financial strength, distribution partner relationships, product terms, rating agency ratings, claims payment speed, and underwriting team experience.
• Increasing consolidation in the insurance industry may further increase competition.
• New industry or legislative developments could increase competition.
• Inability to compete successfully could change supply and demand for insurance, affect pricing ability, and impact retention of existing business or underwriting new business on favorable terms.
• Increased competition limiting business transactions could adversely affect operating results.

[c. 62; p. 9] Distribution channel risks

• Reliance on insurance retail agents, brokers, wholesalers, and program administrators exposes the company to certain risks.
• Most products are distributed through independent retail agents and brokers who own "renewal rights".
• Business model depends on relationships with and success of retail agents and brokers, wholesalers, and program administrators.
• Relationships with distributors can be discontinued or become unprofitable.
• Consolidation of insurance distribution firms may increase their influence on commission rates and concentration of business with particular brokers.
• Premiums collected by brokers and remitted to the company expose the company to credit risk, as payment to the broker may be considered payment to the company in certain jurisdictions.
• Failure of brokers to remit premiums could require the company to provide coverage despite non-payment, potentially declining underwriting profits and adversely affecting financial condition.
• The company reviews financial condition of new brokers and periodically reviews existing distributors for profitability and alignment with business objectives.
• Measures like restricting product access or terminating relationships with distributors may not achieve desired results due to contractual and regulatory requirements.
• Deterioration of distributor relationships or uncompetitive compensation could lead distributors to place more premium with other carriers.
• Distributors exceeding granted authority, failing to transfer collected premiums, or breaching obligations could expose the company to liability.
• Continued consolidation of insurance distribution firms could affect sales channels through loss of market access, market share, talent, or increased commission costs due to greater negotiating leverage.
• Disruption to sales channels could negatively impact results of operations and financial condition.
• Acceleration of digitization subjects the company to risks related to distributors' ability to keep pace, as customers may prefer technology-driven experiences.

[c. 63; p. 9] Reinsurance availability and effectiveness

• Inability to purchase third-party reinsurance on desired or acceptable terms could materially adversely affect business, financial condition, and results of operations.
• Reinsurance is strategically purchased to protect capital from severity events and reduce earnings volatility.
• Failure to renew expiring contracts, enter new arrangements, or expand coverage could increase loss exposure.
• Increased loss exposure could necessitate reducing underwriting commitments, adversely affecting business, financial condition, and results of operations.
• Reinsurers may exclude certain coverages or alter terms in contracts, leading to gaps in reinsurance protection and greater risk/potential losses.

[c. 64; p. 9] Loss and loss expense reserves adequacy

• Inadequate losses and loss expense (LAE) reserves could materially adversely affect financial condition, results of operations, and cash flows.
• Success depends on accurately assessing risks of insured businesses and people.
• Reserves are established as the best estimate for ultimate payment of incurred claims and related adjustment costs.
• Reserves are estimates, and ultimate liability may differ from the estimate.
• Reserving process considers historical data and factors such as claims inflation, claims development patterns, frequency and severity trends, product pricing, legislative activity, social and economic patterns, and litigation/judicial/regulatory trends.
• Variables are affected by internal and external events that could increase loss exposure.
• Loss reserves are continually monitored using new information, statistical techniques, and modeling simulations.
• The process assumes past experience, adjusted for current developments and trends, is appropriate for predicting future events.
• No precise method exists for evaluating the impact of specific factors on reserve adequacy, and actual results may deviate substantially from estimates.
• Uncertainties impacting reserve adequacy include: considerable time to fully appreciate covered loss extent, leading to increased loss estimates over time; new theories of liability enforced retroactively; failure of loss limitations or exclusions; changes in claims or coverage issues.
• Volatility in financial markets, economic events, and other external factors may increase claim numbers and/or severity.
• Elevated inflationary conditions would increase loss costs.
• Adverse economic factors (recession, inflation, high unemployment, lower economic activity) could lead to fewer policy sales or increased claim frequency/severity and premium defaults, affecting growth and profitability.
• Increased costs due to "social inflation" (medical/material costs, technology in vehicles, supply chain disruptions, attorney involvement, litigation financing, lawsuit abuse) could increase claim frequency/severity and affect reserve adequacy.
• Increased claim frequency, even without liability, could escalate evaluation and handling costs beyond established reserves.
• Entering new lines of business or new theories of claims may increase claim frequency and handling costs.
• Inadequate reserves would require increases, reducing net income and stockholders' equity in the period of identification.
• Future loss experience substantially exceeding established reserves could materially adversely affect future earnings, liquidity, and financial rating.

[c. 65; p. 9] Financial strength rating impact

• A decline in financial strength rating may adversely affect the amount of business written.
• Independent rating agencies like A.M. Best assess financial strength and quality of insurers.
• A.M. Best ratings are based on quantitative and qualitative analysis of balance sheet strength, operating performance, and business profile.
• A.M. Best financial strength ratings range from "A++" (Superior) to "F" (liquidation).
• As of the filing date, A.M. Best assigned an "A" (Excellent) financial strength rating with a stable outlook to the company.
• A.M. Best ratings provide an independent opinion of an insurer's ability to meet policyholder obligations and are not an evaluation for investors or a recommendation to buy/sell securities.
• A.M. Best's analysis includes peer comparisons, industry standards, operating plans, philosophy, and management assessments.
• A.M. Best periodically reviews and may revise ratings downward based on analyses of balance sheet strength, operating performance, and business profile.
• Specific building blocks reviewed by A.M. Best include capital adequacy, operating performance, operating profile, and ERM.
• Other factors that could affect A.M. Best's analysis include: changes in business practices from the organizational plan; unfavorable financial, regulatory, or market trends (e.g., excess market capacity); losses exceeding loss reserves; unresolved issues with government regulators; inability to retain senior management or key personnel; significant investment portfolio losses or limited liquidity; or alterations to A.M. Best's capital adequacy assessment methodology.
• A downgrade or withdrawal of the rating could lead to: current and future distribution partners/insureds choosing higher-rated competitors; increased cost or reduced availability of reinsurance; or severe limitation/prevention of writing new and renewal insurance contracts.
• Rating organizations may heighten scrutiny, increase review frequency/scope, request additional information, or increase capital/other requirements due to earnings and capital pressures on financial institutions.
• There is no assurance the rating will remain at its current level, and adverse ratings consequences could materially affect financial condition and results of operations.

[c. 66; p. 9] Policy interpretation changes

• Unexpected changes in interpretation of coverage or provisions, including loss limitations and exclusions, could materially adversely affect financial condition and results of operations.
• No assurance that loss limitations or exclusions will be enforceable as intended.
• Industry practices, legal, judicial, social, and other conditions can lead to unexpected claims and coverage issues.
• Policy limitations on claim periods may be shorter than statutory periods for policyholders.
• Courts or regulatory authorities could nullify/void limitations or exclusions, or legislation could modify/bar their use.
• Governmental actions could result in higher than anticipated losses and LAE.
• Court decisions, such as the 1995 Montrose decision in California, could narrowly read policy exclusions, expanding coverage and requiring new exclusions.
• These issues may adversely affect business by broadening coverage beyond underwriting intent or increasing claim frequency/severity.
• Changes may not become apparent until after affected insurance contracts are issued, meaning full liability may not be known for many years.

[c. 67; p. 9] Reinsurer non-payment risk

• Reinsurers may not reimburse claims timely or at all, materially adversely affecting business, financial condition, and results of operations.
• Reinsurance contracts require premium payments to reinsurers who reimburse for covered policy claims.
• Reinsurers may be called upon to reimburse claims many years after premiums were paid.
• Reinsurance makes the reinsurer liable but does not relieve the ceding insurer of primary liability to policyholders.
• The current reinsurance program aims to limit financial risk.
• Reinsurers may default due to insolvency, lack of liquidity, operational failure, political/regulatory prohibitions, fraud, asserted defenses, or documentation deficiencies.
• Disputes with reinsurers can be time-consuming, costly, and uncertain of success.
• These risks could lead to increased net losses and adversely affect financial condition.
• As of December 31, 2024, reinsurance recoverables totaled USD 857.9m.

[c. 68; p. 9] Claims payment accuracy and timeliness

• Failure to accurately and timely pay claims could materially and adversely affect business, financial condition, results of operations, and prospects.
• Factors affecting claims payment ability include training/experience of claims representatives (including TPAs), management effectiveness, and ability to develop/implement appropriate procedures and systems.
• Inaccurate or untimely claims payment could lead to regulatory/administrative actions, material litigation, reputational damage, and adverse effects on business, financial condition, results of operations, and prospects.
• Ineffective TPA management or inability of internal staff/TPAs to handle claim volume could adversely affect workload capacity.
• This could require slowing growth in affected markets and lead to decreased quality of claims work, adversely affecting operating margins.

[c. 69; p. 9] Catastrophic events and climate change

• Severe weather, climate change effects, catastrophes, pandemics, and man-made events may adversely affect business, results of operations, and financial condition.
• Business is exposed to severe weather, earthquakes, and man-made catastrophes (e.g., explosions, war, terrorist attacks, riots).
• Catastrophes include natural events like severe winter weather, convective storms/tornadoes, windstorms, hailstorms, thunderstorms, and fires.
• Changing weather patterns and climatic conditions (global warming) have increased unpredictability and frequency of natural disasters, including in historically unaffected areas.
• Climate change may increase frequency and severity of extreme weather events, leading to conditions that increase hurricane activity and wildfire risks.
• Catastrophe losses could materially adversely affect business, financial condition, and results of operations, even for events not directly insured (e.g., 2025 California wildfires leading to policy cancellations).
• Increased frequency and severity of weather events (e.g., hurricanes, convective storms) could materially increase losses and affect ability to predict, quantify, reinsure, and manage catastrophe risk.
• Extent of catastrophe losses depends on frequency/severity of insured events and total insured exposure in affected areas.
• Incidence and severity of catastrophes and severe weather are inherently unpredictable.
• Exposure to losses is managed by analyzing probability and severity of loss events and their impact on underwriting and investment portfolios.
• Indirect impact can occur if insured businesses are affected by catastrophes not directly covered, leading to non-payment of premiums on other products.
• Inability to obtain adequate reinsurance coverage at reasonable rates for severe weather and catastrophes could materially adversely affect business and results of operations.
• Business is exposed to risks from pandemics, outbreaks, public health crises, and geopolitical/social events.
• While policy terms are expected to preclude coverage for virus-related claims (e.g., COVID-19), court decisions and governmental actions may challenge exclusions or interpretations.
• Changes to law and regulation related to climate change could directly affect business.
• The current administration's comments and actions (e.g., President Trump signing an executive order to withdraw the U.S. from the Paris Agreement on January 20, 2025) suggest a shift in U.S. climate policy.
• Unclear future actions by the administration or support for legislative changes could have a material adverse effect on business, operational, and financial results.

[c. 70; p. 9] Program administrator compliance

• Failure of program administrators to comply with pre-established guidelines could adversely affect results of operations.
• Certain insurance products are marketed and distributed through program administrators with limited quoting and binding authority.
• Program administrators sell products to insureds via retail agents and brokers and can bind certain risks without initial approval.
• Non-compliance with underwriting guidelines or appointment terms could bind the company to unanticipated risks, adversely affecting results of operations.

[c. 71; p. 9] Renewal and new business expectations

• If actual renewals or new business from repeat insureds do not meet expectations, future written premium and operating results could be materially adversely affected.
• Most contracts are one-year term and renewable.
• Some insurance contracts do not renew, but insureds are repeat customers with regular new contracts.
• Financial forecasting includes assumptions about renewal rates and repeat business.
• Insurance and reinsurance industries are cyclical with intense, often price-based, competition.
• If renewals and repeat business fall short of expectations, or if the company chooses not to write them due to pricing, future written premium and operations would be materially adversely affected.

[c. 72; p. 9] ESG matters and accounting changes

• Increased public attention to environmental, social, and governance (ESG) matters may lead to negative public perception, reputational harm, additional costs, or impact stock price.
• Failure or perceived failure to meet investor/customer ESG expectations could harm business and reputation.
• Backlash from investors or customers regarding ESG topics could also harm business and reputation.
• Damage to reputation from providing policies to certain insureds could decrease demand, materially adversely affect business/operational/financial results, and require resources to rebuild reputation/competitive position/brand strength.
• Changes in accounting practices and future pronouncements may materially affect reported financial results.
• Developments in accounting practices may require considerable additional expenses for compliance, especially for prior period information or retroactive application.
• The impact of accounting changes and future pronouncements cannot be predicted but may affect net income, shareholder's equity, and other financial statement line items.
• Insurance subsidiaries must comply with statutory accounting principles (SAP).
• SAP and its components are subject to constant review by the NAIC, its task forces/committees, and state insurance departments.
• Pending proposals before NAIC committees/task forces, if enacted and adopted at state level, could negatively affect insurance industry participants.
• The NAIC continuously examines existing laws and regulations.
• It is unpredictable whether or in what form reforms will be enacted, or their positive/negative effect on the company.

Risks Related to the Market and Economic Conditions

[c. 73; p. 9] Economic conditions and insurance demand

• Adverse economic factors like recession, inflation, high unemployment, or lower economic activity can reduce policy sales, increase claim frequency, lead to premium defaults, or cause claim falsification, impacting growth and profitability.
• Business revenue, economic conditions, capital market volatility and strength, and inflation affect the business and economic environment, influencing the ability to generate revenue and profits.
• Economic downturns with higher unemployment, declining spending, and reduced corporate revenue generally hurt demand for insurance products, affecting premium levels and profitability.
• Negative economic factors can hinder the ability to charge appropriate rates for risk, reduce the number of policies written, and limit opportunities for profitable underwriting.
• During economic downturns, customers may need less insurance, cancel policies, modify coverage, or not renew policies.
• Existing policyholders may exaggerate or falsify claims for higher payments.
• Significant collapse in economic segments like construction, credit markets, or energy production/servicing could adversely affect results across multiple underwriting divisions.
• These outcomes would reduce underwriting profit if not reflected in charged rates.

[c. 74; p. 9] Insurance market cyclicality

• The insurance business is historically cyclical, which can affect financial performance and cause operating results to vary quarter-to-quarter, not necessarily indicating future performance.
• Insurance carriers have historically experienced significant fluctuations in operating results due to competition, catastrophic events, capacity levels, litigation trends, regulatory constraints, and general economic conditions.
• The supply of insurance relates to prevailing prices, insured losses, and available industry capital, which can fluctuate with changes in investment returns.
• The insurance business is historically cyclical, characterized by periods of intense price competition due to excessive underwriting capacity (soft market) and periods of capacity shortages leading to increased premium levels (hard market).
• Demand for insurance depends on factors like 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&C insurance companies' profitability tends to follow this cyclical market pattern, with higher gross written premium growth and improved profitability during hard market cycles.
• This cyclical pattern is more pronounced in the E&S (Excess and Surplus) market than in the standard insurance market.
• When the standard insurance market hardens, the E&S market typically hardens, with significantly more rapid growth.
• When conditions soften, customers previously in the E&S market may return to the admitted market, exacerbating rate decrease effects on financial results.
• The market can experience "micro cycles" where specific areas harden or soften independently and more drastically than the overall market.
• Operating results are subject to fluctuation and have historically varied quarter-to-quarter.
• Quarterly results are expected to continue fluctuating due to general economic conditions, frequency/severity of catastrophes, fluctuating interest rates, claims exceeding loss reserves, competition, deviations from expected premium retention, adverse investment performance, and reinsurance costs.

[c. 75; p. 9] Investment portfolio performance and risks

• Performance of the investment portfolio is subject to various investment risks that may adversely affect financial results.
• Results of operations depend partly on investment portfolio performance.
• The company aims to hold a diversified investment portfolio managed by professional investment advisory firms according to its investment policy and reviewed by its Investment Committee.
• Investments are subject to general economic conditions, market risks, and risks inherent to specific securities.
• Primary market risk exposures are to changes in interest rates and equity prices.
• A significant portion of the investment portfolio is in fixed maturity securities, or separately managed accounts and limited partnerships primarily invested in fixed maturity securities.
• Interest rates rose materially in 2022 and 2023.
• A low interest rate environment, potentially from federal actions to slow inflation (e.g., recent rate cuts, Inflation Reduction Act of 2022), would pressure net investment income, especially for fixed maturity and short-term investments, adversely affecting operating results.
• Recent and future interest rate increases could cause fixed income securities portfolios to decline in value, with magnitude depending on duration and rate increase.
• Some fixed income securities with call or prepayment options create reinvestment risk in declining rate environments.
• Other fixed income securities, like mortgage-backed and asset-backed securities, carry prepayment risk or may not prepay as quickly as expected in a rising interest rate environment.
• All fixed maturity securities, including those in separately managed accounts and limited partnerships, are subject to credit risk.
• Credit risk is the risk of investment default or impairment due to deterioration in the financial condition of issuers or guarantors.
• Downgrades in credit ratings of fixed maturity securities could significantly negatively affect their market valuation.
• The company also invests in marketable preferred and common equity securities and exchange-traded funds.
• These equity securities are carried at fair market value and are subject to potential losses and market value declines.
• Market and credit risks could reduce net investment income and result in realized investment losses.
• The investment portfolio faces increased valuation uncertainties when investment markets are illiquid, as with fixed maturity securities held to maturity, separately managed accounts, and limited partnership investments.
• Valuation of investments is more subjective in illiquid markets, increasing the risk that estimated fair value does not reflect actual transaction prices.
• Risks for all security types are managed through an investment policy that sets parameters including maximum investment percentages in certain securities and minimum credit quality levels, believed to be within NAIC, Texas Department of Insurance, and Oklahoma Department of Insurance guidelines.
• The Investment Committee periodically reviews Enterprise Based Asset Allocation models for overall risk management.
• While capital preservation is sought, investment objectives may not be achieved, and results can vary substantially over time.
• Investment strategies aim to be uncorrelated with insurance and reinsurance exposures, but investment losses may coincide with underwriting losses, exacerbating adverse effects.

[c. 76; p. 9] Investment liquidity and claims funding

• The company could be forced to sell investments to meet liquidity requirements.
• Premiums received are invested until needed for policyholder claims.
• The duration of the investment portfolio is managed based on the duration of losses and LAE (Loss Adjustment Expense) reserves to ensure sufficient liquidity and avoid liquidating investments to fund claims.
• Risks such as inadequate losses and LAE reserves or unfavorable litigation trends could necessitate selling investments to fund liabilities.
• Investments may not be sold at favorable prices or at all.
• Sales could result in significant realized losses depending on general market conditions, interest rates, and credit issues with individual securities.

Risks Related to the Regulatory Environment

[c. 77; p. 9] Regulatory compliance and penalties

• Extensive regulation may adversely affect the ability to achieve business objectives.
• Failure to comply with regulations may result in penalties, including fines and suspensions, adversely affecting financial condition and results of operations.
• Primary insurance subsidiaries GMIC, HSIC, and IIC are subject to extensive regulation in Texas (state of domicile) and other operating states.
• Insurance regulations primarily protect policyholders, not investors or stockholders.
• Regulations are administered by state departments of insurance and cover capital and surplus, investment and underwriting limitations, affiliate transactions, dividend limitations, changes in control, solvency, and other financial/non-financial aspects.
• Significant changes in laws and regulations could limit discretion or increase business costs.
• State insurance regulators conduct periodic examinations and require annual/other reports on financial condition and holding company issues.
• Regulatory requirements may impose timing and expense constraints, adversely affecting business objectives.
• Insurance subsidiaries are part of an "insurance holding company system" under Texas statutes and regulations.
• Certain transactions between insurance subsidiaries and affiliates require prior notice to the Texas Department of Insurance, potentially causing business delays and additional expenses.
• Failure to file required notifications or comply with other Texas insurance regulations may lead to significant fines and penalties and impair the working relationship with the Texas Department of Insurance.
• State insurance regulators have broad discretion to deny or revoke licenses for reasons including regulation violations.
• Practices based on interpretations of regulations or industry norms may differ from regulatory authorities' interpretations.
• Lack of requisite licenses/approvals or non-compliance could lead to regulators precluding, suspending, or penalizing activities in a state, adversely affecting business operations.
• Changes in insurance industry regulation, laws, or interpretations could interfere with operations and increase compliance costs.

[c. 78; p. 9] Capital requirements and financial stability

• Insurance subsidiaries are subject to risk-based capital requirements based on the NAIC's "risk based capital model" and Texas law's minimum capital and surplus restrictions.
• These requirements establish minimum risk-based capital for overall business operations and identify inadequately capitalized property and casualty insurers by assessing asset/liability risks and net written premium mix.
• Insurers below a calculated threshold may face regulatory actions like supervision, rehabilitation, or liquidation.
• Failure to maintain required risk-based capital levels could adversely affect the insurance subsidiary's ability to maintain regulatory authority and its A.M. Best Rating.

[c. 79; p. 9] Potential for new regulations and legislative changes

• The company may become subject to additional government or market regulation, which could materially adversely impact the business.
• Business could be adversely affected by changes in laws related to asset and reserve valuation, surplus requirements, investment and dividend limitations, enterprise risk, and risk-based capital requirements.
• The U.S. federal government generally does not directly regulate the insurance industry, except for areas like flood, nuclear, and terrorism risks.
• Potential federal legislation could affect the insurance industry in areas such as privatization of government entities (e.g., Freddie Mac, Fannie Mae), reduction in federal subsidies for certain businesses (e.g., agriculture), tort reform, corporate governance, and taxation of reinsurance companies.

[c. 80; p. 9] Tax law changes and NOLs

• Changes to U.S. tax laws and new tax policies could significantly negatively impact the overall economy and the business.
• Legislative or other actions related to taxes could negatively affect the company, its investments, or stockholders.
• U.S. federal income tax rules are constantly under review by legislators, the IRS, and the U.S. Department of the Treasury.
• The company cannot predict the impact of tax law changes on itself, stockholders, or portfolio investments.
• New legislation, U.S. Treasury regulations, administrative interpretations, or court decisions could have adverse consequences.
• Stockholders are advised to consult tax advisors regarding tax legislative, regulatory, or administrative developments and their potential effect on investments.
• The current administration's agenda includes potential U.S. tax law reform, with outlined intentions such as reducing the corporate tax rate, extending certain provisions of the Tax Cuts and Jobs Act of 2017 (TCJA), and imposing new tariffs.
• The combined impact of extending TCJA tax benefits and new tariffs could increase the U.S. deficit, inflation, and interest rates, potentially leading to higher market interest rates, decreased U.S. economic growth, and a possible recession, all negatively impacting the business.
• The ability to utilize net operating loss carryforwards (NOLs) and other tax attributes may be limited.
• As of December 31, 2024, the company had gross federal income tax NOLs of approximately USD 44.7m available to offset future taxable income, prior to Section 382 limitations.
• These NOLs are set to expire beginning in 2032.
• Under Section 382 of the Internal Revenue Code, an "ownership change" (greater than 50% change in equity ownership by certain stockholders over a three-year period) can limit the use of pre-ownership change NOLs to offset post-ownership change income.
• Future ownership changes, some outside of control, may occur.
• Future regulatory changes could also limit the ability to utilize NOLs.
• Inability to offset future taxable income with NOLs could adversely affect net income and cash flows.

[c. 81; p. 9] Holding company liquidity and dividend restrictions

• As a holding company, with operations primarily conducted by insurance subsidiaries, liquidity at the holding company level (including ability to pay dividends and service debt) depends on cash dividends or other permitted payments from insurance subsidiaries.
• Continued operation and growth require substantial capital, so cash dividends on common stock are not intended in the foreseeable future.
• The ability to pay dividends to stockholders and meet debt obligations largely depends on dividends and distributions from primary insurance subsidiaries: GMIC, HSIC, and IIC.
• State insurance laws, including Texas laws, restrict the ability of GMIC, HSIC, and IIC to determine stockholder dividends.
• State insurance regulators require insurance companies to maintain specified levels of statutory capital and surplus.
• Dividend payments are limited to the portion of available policyholder surplus derived from net profits.
• State insurance regulators have broad powers to prevent reduction of statutory surplus to inadequate levels, and there is no assurance that maximum calculated dividends would be permitted.
• State insurance regulators with jurisdiction over dividend payments by insurance subsidiaries may adopt more restrictive statutory provisions in the future.
• Any future dividend determination will be at the discretion of the Board of Directors, based on results of operations, financial condition, contractual debt restrictions, indebtedness, applicable law, and other relevant factors.
• Investors may need to sell common stock for gains, as immediate cash dividends are not expected.

[c. 82; p. 9] Change of control regulations

• Applicable insurance laws may make it difficult to effect a change of control.
• Under Texas insurance laws, acquiring control of a domestic insurer requires written approval from the state insurance commissioner.
• Approval depends on factors including the acquirer's financial strength, plans for the insurer's future operations, and potential anti-competitive results.
• Texas insurance laws apply to direct and indirect acquisition of 10% or more of a Texas-domiciled insurer's voting stock.
• Acquisition of 10% or more of Skyward Specialty's common stock would be considered an indirect change of control, triggering applicable filing requirements under Texas insurance laws, unless a disclaimer of control filing is accepted by the Texas Insurance Department.
• These requirements may discourage acquisition proposals and delay, deter, or prevent a change of control, even if desirable to some stockholders.

Risks Related to Our Liquidity and Access to Capital

[c. 83; p. 9] Future capital requirements and availability

• Additional capital may be required in the future, which may not be available or only available on unfavorable terms.
• Future capital requirements depend on factors including the ability to successfully write new business and establish premium rates and reserves sufficient to cover losses.
• If cash flows from operations are insufficient to fund future operating requirements and cover claim losses, or if the capital position is adversely impacted by a decline in the fair value of the investment portfolio, catastrophe losses, or other events, additional funds may be needed through financings or growth may be curtailed.
• Factors affecting the amount and timing of capital needs include growth rate, profitability, claims experience, reinsurance availability, market disruptions, and other unforeseeable developments.
• If additional capital is needed, equity or debt financing may not be available or may be available only on unfavorable terms.
• Equity financings could result in dilution to stockholders.
• Debt financings may involve covenants restricting business operations.
• Such securities may have rights, preferences, and privileges senior to common stock.
• Inability to obtain adequate capital on favorable terms could materially adversely affect operating plans, business, financial condition, or results of operations.

Risks Related to Our Operations

[c. 84; p. 9] Personnel attraction and retention

• The company could be adversely affected by the loss of key personnel or inability to attract and retain qualified personnel.
• The company depends on attracting and retaining experienced personnel knowledgeable about its business.
• The talent pool for recruitment is limited and can fluctuate based on market dynamics specific to the industry.
• Higher demand for skilled employees could increase compensation expectations, making it difficult to retain and recruit key personnel and maintain desired labor costs.
• Inability to retain and attract talented personnel could prevent the company from maintaining its competitive position in specialized markets, adversely affecting results of operations.

[c. 85; p. 9] Information technology and cybersecurity risks

• Security breaches, data loss, cyberattacks, and IT failures could disrupt operations, damage reputation, and adversely affect business, operations, and financial results.
• The business is highly dependent on IT and telecommunications systems, including underwriting and claims systems.
• Systems are used for interacting with brokers and insureds, underwriting, policy preparation, premium processing, actuarial modeling, claims processing and payments, and financial statement preparation.
• Some systems may include or rely on third-party systems not on company premises or under its control.
• Events like natural catastrophes, terrorist attacks, industrial accidents, computer viruses, and cyber-attacks can cause systems to fail or be inaccessible for extended periods.
• Sustained or repeated system failures could severely limit the ability to write and process business, provide customer service, pay claims, or operate normally.
• Computer viruses, hackers, employee misconduct, and external hazards can expose systems to security breaches or disruptions.
• Security measures are in place, but systems and networks may still be subject to breaches or interference, and cybersecurity incidents are likely to continue.
• Such events can result in operational disruptions, unauthorized access, disclosure, or loss of proprietary or customer data.
• Consequences include legal claims, regulatory scrutiny and liability, reputational damage, costs for mitigation, and loss of customers or advisors.
• SEC and state law notification requirements for incidents could exacerbate harm to business, financial condition, and results of operations.
• Publicized attempted security breaches could harm business and reputation even if technology infrastructure and data confidentiality are protected.
• Advances in criminal capabilities, new vulnerabilities, exploitation attempts, data thefts, or physical system break-ins could compromise security measures.
• Third parties to whom functions are outsourced are also subject to these risks.
• While third-party providers' cybersecurity controls are reviewed, success in preventing compromises and disclosures cannot be ensured.
• Increased use of third-party services (e.g., cloud technology, SaaS) can make identifying and responding to cyberattacks more difficult due to dynamic technologies.
• These risks could increase as vendors adopt more cloud-based software services.

[c. 86; p. 9] Growth management and inorganic growth

• The company may not be able to manage its growth effectively.
• Future business growth may require additional capital, systems development, and skilled personnel.
• The company must meet capital needs, expand systems and internal controls, allocate human resources optimally, identify, hire, train, and develop qualified employees, and integrate acquired businesses.
• Failure to manage growth effectively could materially adversely affect business, financial condition, and results of operations.
• Success of inorganic growth through acquisitions depends on identifying appropriate targets, negotiating favorable terms, completing transactions, and successfully integrating targets.
• Anticipated benefits of acquisitions, such as revenue growth, operational efficiencies, or expected synergies, may not be realized.

[c. 87; p. 9] Future growth rates and profitability

• Recent rapid growth rates may not be indicative of future growth.
• Significant revenue growth has been experienced in recent years.
• Future periods may not sustain revenue growth consistent with recent history or at all.
• Revenue growth depends on factors including:
  • Effective product pricing to attract and retain insureds without compromising profitability.
  • Successful deployment and implementation of products, obtaining renewals, and providing excellent support to distribution partners.
  • Attraction and retention of highly qualified underwriters and claims professionals.
  • Enhancement of infrastructure and data reporting systems for effective and efficient product delivery.
  • Successful creation of new distribution channels.
  • Successful introduction of new products and enhancement of existing products.
  • Successful competition against larger companies and new market entrants.
  • Increased brand awareness.
• Failure to accomplish these objectives makes forecasting future results of operations difficult.
• Historical growth rate should not be considered indicative of future performance and may decline.
• Future revenue could grow more slowly or decline for various reasons, including those outlined.
• Operating expenses are expected to increase in future periods.
• If revenue growth does not offset possible expense increases, business, financial position, and results of operations could be harmed, and profitability may not be achieved or maintained.

[c. 88; p. 9] Litigation risks

• The effects of litigation on the business are uncertain and could have an adverse effect.
• The company continually faces risks associated with various types of litigation, including disputes related to insurance claims and general commercial/corporate litigation.
• The company is not currently involved in out-of-the-ordinary litigation with customers.
• Other insurance industry members are targets of class action lawsuits and other litigation, some involving substantial or indeterminate amounts with unpredictable outcomes.
• Social inflation, particularly in third-party claims, can lead to oversized judgments.
• Litigation costs and settlement amounts can be inflated beyond historical reasonable levels, even when cases do not reach judgment.
• Litigation is based on issues including insurance and claim settlement practices.
• The company cannot predict future involvement in such litigation or its impact on the business.

[c. 89; p. 9] Vendor relationships and third-party software

• Loss of key vendor relationships or vendor failure to protect data/information could affect operations.
• The company relies on services and products from many vendors in the U.S. and abroad.
• Vendors include those for computer hardware/software, claim adjustment services, human resource benefits management, and investment management.
• If a vendor experiences bankruptcy, becomes unable to provide services, has systems breached, or fails to protect confidential information, the company may suffer operational impairments and financial losses.
• While vendor risk is generally monitored, including security and stability of critical vendors, proper assessment of risks and costs in third-party relationships may fail, materially and adversely affecting financial condition and results of operations.
• The company anticipates continued reliance on third-party software.
• 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.
• Integration of new third-party software may require significant work and substantial investment of time and resources.
• Use of additional or alternative third-party software would require license agreements, which may not be available on commercially reasonable terms or at all.
• Many risks associated with third-party software use cannot be eliminated and could negatively affect the business.

[c. 90; p. 9] Intellectual property rights

• The company may fail or be unable to protect its intellectual property rights for its proprietary technology platform and brand.
• The company may be sued by third parties for alleged infringement of their proprietary rights.
• Success and ability to compete depend partly on intellectual property, including brand rights and proprietary technology in certain product lines.
• Protection primarily relies on copyright and trade secret laws, and confidentiality agreements with employees, customers, service providers, and partners.
• Steps taken to protect intellectual property may be inadequate.
• Efforts to enforce intellectual property rights may face defenses, counterclaims, and countersuits challenging validity, enforceability, and scope.
• Failure to secure, protect, and enforce intellectual property rights could adversely affect the brand and business.
• Success also depends partly on not infringing on others' intellectual property rights.
• Competitors and other entities/individuals may own or claim intellectual property related to the industry or the company.
• Third parties may claim infringement of their intellectual property rights in the future, and the company may be found to be infringing.
• Claims or litigation could incur significant expenses.
• Successful assertion of claims could require substantial damages or ongoing royalty payments, prevent service offerings, or impose unfavorable terms.
• Even if the company prevails, litigation could be costly, time-consuming, and divert management and key personnel attention from business operations.

Risks Related to Ownership of Our Common Stock

[c. 91; p. 9] Public company operating costs and compliance

• Operating as a public company incurs increased costs and requires substantial management time for compliance initiatives.
• Financial reporting and other requirements may exceed the adequacy of current accounting and management systems and resources.
• Significant legal, accounting, and other expenses are incurred as a public company, especially since no longer an emerging growth company.
• Federal securities laws (Sarbanes-Oxley Act, Dodd-Frank Act) and SEC/Nasdaq rules impose requirements for filing reports and maintaining effective disclosure, financial controls, and corporate governance.
• These regulations increase compliance costs, make activities more time-consuming, and demand significant management and personnel time.
• There is a risk of not producing reliable financial statements or filing them timely with the SEC, or complying with Nasdaq listing requirements.
• Section 404 of the Sarbanes-Oxley Act requires system and process evaluation and testing of internal control over financial reporting, leading to substantial accounting expense and management effort.
• Compliance with Section 404 necessitates maintaining accounting and finance staff/consultants with public company reporting, technical accounting, and internal control knowledge, and providing internal audit services.
• Achieving Section 404 compliance involves a costly and challenging process of documenting and evaluating internal control over financial reporting.
• This process requires dedicating internal resources, engaging outside consultants, adopting a detailed work plan, improving control processes, validating controls through testing, and implementing continuous reporting and improvement.
• There is a risk that neither the company nor its independent registered public accounting firm will conclude that internal control over financial reporting is effective within the prescribed timeframe, potentially leading to adverse financial market reactions and SEC investigations.
• Disclosure controls and procedures are required to ensure information for SEC reports is recorded, processed, summarized, and reported timely.
• Disclosure controls and internal control over financial reporting may not prevent or detect all errors and fraud due to inherent limitations of control systems.
• Control systems provide reasonable, not absolute, assurance, and their design is based on assumptions about future events, which may not hold true.
• Controls may become inadequate over time due to changing conditions or deterioration in compliance, leading to undetected misstatements.
• Failure to achieve and maintain effective internal controls, as required by Section 404 of the Sarbanes-Oxley Act, could harm operating results and financial condition, and negatively affect common stock market price.
• Section 404(b) of the Sarbanes-Oxley Act requires annual management assessments of the effectiveness of internal control over financial reporting.
• Implementing and maintaining substantial internal control systems and procedures is necessary to satisfy Exchange Act reporting requirements.
• Deficiencies identified during assessments may not be remediated timely, and testing/maintaining internal controls may divert management attention.
• Inability to conclude on an ongoing basis that internal control over financial reporting is effective under Section 404(b) could lead to significant remediation costs and scope.
• Material weaknesses or deficiencies in internal control could impede timely and accurate SEC report filings.
• Any of these issues could cause investors to lose confidence, or lead to suspension/termination of Nasdaq listing, negatively affecting stock price.

[c. 92; p. 9] Material weakness in ITGCs

• A material weakness in internal control over information technology general controls (ITGCs) has been identified.
• Failure to remediate this material weakness or maintain effective ITGCs could adversely affect the common stock market price.
• Controls and procedures have inherent limitations, meaning they may not prevent or detect all misstatements.
• Even an effective ITGC system provides only reasonable, not absolute, assurance.
• Management, including the CEO, CFO, and CIO/CTO, evaluated internal control over financial reporting as of December 31, 2024, using COSO criteria.
• A material weakness existed as of December 31, 2024, related to ineffective implementation of ITGCs in user access for systems supporting financial reporting.
• Related process-level IT dependent manual and automated controls relying on affected ITGCs or information from affected IT systems were also deemed ineffective.
• Additional information and management's remediation plan are in "ITEM 9A. CONTROLS & PROCEDURES" of Form 10-K.
• Failure to timely remediate the material weakness or maintain effective ITGCs could lead to significant resource expenditure, fines, penalties, investigations, or judgments, negatively affecting investor confidence and stock price.

[c. 93; p. 9] Stock price volatility and investment risk

• Operating results and stock price may be volatile or decline regardless of operating performance, risking loss of investment.
• The market price of common stock has been and is likely to remain highly volatile, influenced by many factors beyond control.
• Securities markets worldwide have experienced and will likely continue to experience significant price and volume fluctuations.
• Market volatility, general economic, market, or political conditions could cause wide price fluctuations regardless of operating performance.
• Investment in common stock is considered risky, suitable only for those who can withstand significant loss and wide market value fluctuations.
• Factors affecting stock price include: market conditions in the broader stock market; actual or anticipated fluctuations in quarterly financial and operating results; introduction of new products or services by the company or competitors; issuance of new or changed securities analysts’ reports or recommendations; results of operations varying from analyst and investor expectations; short sales, hedging, and other derivative transactions in common stock; company guidance, changes to it, or failure to meet it; strategic actions by the company or competitors; announcements by the company, competitors, or acquisition targets; sales or anticipated sales of large blocks of stock by directors, executive officers, and principal stockholders; additions or departures in the Board, senior management, or other key personnel; regulatory, legal, or political developments; public response to press releases or public announcements; litigation and governmental investigations; changing economic conditions, including social inflation; changes in accounting principles; future indebtedness or securities issuance; default under indebtedness agreements; exposure to capital and credit market risks affecting investment portfolio or capital resources; changes in credit ratings; and other events like natural disasters, war, or terrorism.
• Securities markets have experienced extreme price and volume fluctuations unrelated to company operating performance.
• Investors may not be able to resell shares at or above purchase price due to these factors.
• Broad market fluctuations, general market, economic, and political conditions (e.g., recessions, loss of investor confidence, interest rate changes) may negatively affect common stock market price.
• Stock markets, including Nasdaq, have experienced extreme price and volume fluctuations affecting equity securities.
• Such occurrences could cause stock price to fall and expose the company to costly securities class action litigation, diverting management attention and harming business.

[c. 94; p. 9] Underwriting guidelines and strategy changes

• Management can change underwriting guidelines or strategy without stockholder notice or approval.
• This allows fundamental changes to operations without stockholder approval, potentially resulting in a strategy or underwriting guidelines materially different from those described in the "Business" section or other filings.

[c. 95; p. 9] Anti-takeover provisions

• Anti-takeover provisions in organizational documents could delay management changes and limit share price.
• Provisions in the certificate of incorporation and bylaws could hinder third-party acquisition of control, even if beneficial to common stock value, and prevent stockholder attempts to replace the Board or management.
• These provisions could adversely affect common stock price.
• Charter documents permit the Board to establish director numbers and fill vacancies/new directorships.
• The Board of Directors is classified into three classes with staggered, three-year terms, and directors can only be removed for cause.
• Super-majority voting is required to amend provisions in the certificate of incorporation and bylaws.
• Blank-check preferred stock, with terms set by the Board, could delay or prevent transactions or control changes that might offer a premium price for common stock.
• Stockholders' ability to call special meetings is eliminated.
• Special meetings of stockholders can only be called by the Board, its chairman, or the CEO.
• Stockholder consent action is prohibited unless by unanimous written consent.
• Vacancies on the Board can only be filled by a majority of directors then in office, even if less than a quorum.
• Cumulative voting in director elections is prohibited.
• Advance notice requirements are established for director nominations or proposing matters at annual stockholder meetings.
• As a Delaware corporation, the company is subject to Section 203 of the Delaware General Corporation Law, which may prohibit large stockholders (15% or more of voting stock) from merging or combining for a period.

[c. 96; p. 9] Exclusive forum provisions

• The certificate of incorporation and bylaws designate the Court of Chancery of the State of Delaware as the exclusive forum for substantially all disputes between the company and its stockholders.
• This could limit stockholders' ability to obtain a favorable judicial forum for disputes with the company or its directors, officers, or employees.
• The Court of Chancery of the State of Delaware is the exclusive forum for: derivative actions on the company's behalf; actions asserting breach of fiduciary duty by directors, officers, employees, or stockholders; actions arising under DGCL or the certificate of incorporation/bylaws where DGCL confers jurisdiction; actions to interpret, apply, enforce, or determine validity of the certificate of incorporation or bylaws; and actions asserting a claim governed by the internal affairs doctrine.
• The certificate of incorporation and bylaws also state that federal district courts of the United States are the sole and exclusive forum for causes of action arising under the Securities Act, unless the company consents otherwise.
• Section 22 of the Securities Act creates concurrent jurisdiction for federal and state courts over suits to enforce duties/liabilities created by the Securities Act.
• There is uncertainty whether a court would enforce the federal exclusive forum provision, and stockholders are not deemed to have waived compliance with federal securities laws.
• This exclusive forum provision would not apply to suits under the Exchange Act or other claims where federal courts have exclusive jurisdiction.
• If enforced, this choice of forum provision may limit a stockholder's ability to bring a claim in a preferred judicial forum, potentially discouraging lawsuits.
• If a court finds the choice of forum provision inapplicable or unenforceable, the company may incur additional costs resolving actions in other jurisdictions, which could materially adversely affect business, financial condition, or results of operations.

Cybersecurity

[c. 97; p. 10] Cybersecurity risk management and strategy

• IT Systems are central to nearly all business operations, including internal/external communications, document management, and shared work environments.
• Responding to cybersecurity incidents and threats is a key component of the overall ERM strategy.
• A Crisis Response Plan (CRP) has been implemented to respond to cybersecurity incidents and threats.
• Management and IT personnel have implemented processes for assessing, identifying, managing, and escalating material cybersecurity risks, integrated into overall risk management.
• Cybersecurity risks are included in the annual risk universe evaluated by the enterprise risk management committee.
• Risk owners are assigned to develop and track mitigation plans for heightened cybersecurity risks identified by the ERM process.
• Security events and data incidents are evaluated, ranked by severity, prioritized for response/remediation, and reviewed for materiality, operational/business impact, and privacy impact.
• The cybersecurity risk management program uses the National Institute of Standards and Technology framework, categorizing risks into identify, protect, detect, respond, recover, and govern.
• Company-wide policies and procedures cover cybersecurity matters, including encryption standards, antivirus protection, remote access, multifactor authentication, confidential information, and internet/social media/email use.
• A detailed crisis response playbook is followed in the event of an incident.
• Investments in IT security have expanded, including additional end-user training, layered defenses, critical asset identification/protection, strengthened monitoring/alerting, and expert engagement.
• Defenses are regularly tested through technical simulations and drills (including penetration tests) and operational policy/procedure reviews with third-party experts.
• The IT security team monitors alerts, discusses threat levels/trends/remediation, prepares a quarterly cyber scorecard, collects cybersecurity data, and conducts an annual risk assessment.
• Periodic external penetration tests, red team testing, and maturity testing are conducted to assess processes, procedures, and the threat landscape.
• In an incident, outside cybersecurity legal counsel consults with other third parties, including communication/notification as required.
• Cybersecurity vendors perform investigation services and assist with recovery/restoration of impacted IT System services.
• Cybersecurity experts assist with incident validation and ransomware demands.
• Cybersecurity insurance providers are involved in incident response.
• Processes are in place to oversee and identify cybersecurity risks from key third-party service providers.
• Third-party service providers are required to provide SOC-1 or SOC-2 reports and their cybersecurity/disaster recovery plans.

[c. 98; p. 10] Cybersecurity governance and oversight

• Cybersecurity risk management and strategy processes are overseen by leaders from the Information Security Team, with assistance from Compliance and Legal teams.
• These individuals have decades of experience in IT roles, including security, auditing, compliance, systems, and programming.
• They monitor prevention, mitigation, detection, and remediation of cybersecurity incidents through their management and participation in risk management processes and the crisis response plan.
• They report appropriate items to the Risk Committee.
• The Risk Committee of the Board of Directors oversees cybersecurity strategy, reviews cybersecurity and other IT risks/controls/procedures, and receives periodic updates from management on cybersecurity measures.
• The review includes a thorough discussion of cybersecurity threat risks and their potential operational impact.
• A separate process exists for communicating with the Risk Committee during a specific cybersecurity incident.
• Members of the Crisis Management Team provide initial awareness communication to the CEO/Chair of the Board, who then informs the Chair of the Risk Committee.
• Following an initial assessment by senior management and IT Systems personnel, a follow-up communication is provided to the CEO and Risk Committee Chair to determine if escalation to the full Board is warranted.

[c. 99; p. 10] Cybersecurity risk impact

• Cybersecurity threats have not materially affected business strategy, results of operations, or financial condition.
• A cybersecurity incident resulting in a serious compromise of IT Systems or a demand for payment to restore IT Systems could have a material adverse effect.
• Such an incident could negatively impact the ability to operate the business effectively and divert management/financial resources.

Properties

[c. 100; p. 11] Office facilities

• The company leases its primary executive offices and insurance operations in Houston, Texas.
• These offices occupy approximately 20,400 square feet of space.
• The lease for the Houston office space expires in 2029.
• Additional office space is leased where appropriate.
• Management considers the office facilities suitable and adequate for current operations.

Legal Proceedings

[c. 101; p. 12] Legal proceedings

• The company is party to legal proceedings arising in the ordinary course of business.
• The company believes the outcome of these matters, individually and in aggregate, will not have a material adverse effect on its consolidated financial position.

Market for Registrant's Common Equity, Related Stockholder Matters and Issuer Purchases of Equity Securities

[c. 102; p. 13] Common stock trading and holders

• Common shares began trading on the NASDAQ Global Select Market under the symbol "SKWD" on January 13, 2023.
• Prior to January 13, 2023, there was no public market for the company's common shares.
• As of February 26, 2025, there were approximately 5 holders of record of the common stock.
• The number of record holders does not represent the total number of stockholders due to shares being held by brokers and institutions on behalf of stockholders.

Securities Authorized for Issuance Under Equity Compensation Plans

[c. 103; p. 13] Equity compensation plan information

• Information regarding equity compensation plans will be included in the definitive proxy statement filed with the SEC for the 2025 Annual Meeting of Stockholders and is incorporated by reference.

Recent Sales of Unregistered Equity Securities

[c. 104; p. 13] Securities issuance details

• Information regarding securities issued or granted during the period covered by this Annual Report on Form 10-K that were not registered under the Securities Act is set forth below.
• The information in Item 5 reflects a 4-for-1 reverse stock split, effective January 3, 2023.
• Immediately before the IPO, all preferred stock converted into 16,305,113 shares of common stock.
• The issuance of these common shares was exempt from Securities Act registration requirements under Section 3(a)(9) of the Securities Act.
• This exemption applies to an exchange of securities by the issuer with existing security holders exclusively, where no commission or other remuneration was paid directly or indirectly for soliciting the exchange.
• No underwriters were involved in this share issuance.

Use of Proceeds from Initial Public Offering

[c. 105; p. 13] IPO Details and Proceeds

• The IPO closed on January 18, 2023.
• The company issued and sold 4,750,000 shares of common stock.
• Selling stockholders sold 4,202,383 shares.
• Underwriters fully exercised their option to purchase 1,342,857 additional shares of common stock from selling stockholders.
• The offer and sale of shares in the IPO were registered under the Securities Act via a Form S-1 registration statement (File No. 333-265326).
• The registration statement was declared effective by the SEC on January 12, 2023.
• Barclays Capital Inc. and Keefe, Bruyette & Woods, Inc. were representatives of the underwriters.
• The public offering price was USD 15.00 per share.
• Net proceeds to the Company were approximately USD 62.3m, after deducting underwriting discounts and specific incremental IPO expenses.
• All proceeds from the IPO were distributed to the Company’s insurance company subsidiaries.

Issuer Purchases of Equity Securities

[c. 106; p. 13] Equity securities purchases

• The company did not purchase any of its equity securities during the period covered by this Annual Report on Form 10-K.

Dividends

[c. 107; p. 13] Dividend policy

• The company does not currently intend to pay cash dividends on its common stock in the foreseeable future.
• Any future dividend payments will be at the discretion of the Board of Directors.
• Future dividend determinations will depend on results of operations, financial condition, applicable legal restrictions, and other factors deemed relevant by the Board of Directors.
• Investors may need to sell common stock holdings to realize future gains, as price appreciation may not occur.
• Investors seeking immediate cash dividends should not purchase the company's common stock.

Performance Graph

[c. 108; p. 13] Shareholder return performance graph

• The performance graph compares the cumulative total shareholder return of an investment in the company's common stock, the Nasdaq Composite Index, and the Nasdaq Insurance Index.
• The comparison period is from January 13, 2023 (the date the common stock began trading on Nasdaq) through December 31, 2024.
• The graph assumes an initial investment of USD 100.
• Historical results are not indicative of future performance.
• The graph is not considered "soliciting material" or "filed" for purposes of Section 18 of the Exchange Act.
• The graph is not subject to liabilities under Section 18 of the Exchange Act.
• The graph is not incorporated by reference into any filings under the Securities Act.

[c. 109; p. 13]

Performance Graph

	January 13, 2023	December 31, 2023	December 31, 2024
Skyward Specialty Insurance Group, Inc.	100.00	177.38	264.61
Nasdaq Composite Index	100.00	135.49	174.30
Nasdaq Insurance Index	100.00	103.37	128.30

[c. 110; p. 13] Performance Graph

Performance Graph

Chart / Image:

• Y-axis represents values from $100.00 to $300.00.
• X-axis represents dates: January 13, 2023, December 31, 2023, and December 31, 2024.
• The blue line with circular markers represents "Skyward Specialty Insurance Group, Inc.".
• The magenta line with circular markers represents "Nasdaq Composite Index".
• The cyan line with circular markers represents "Nasdaq Insurance Index".
• On January 13, 2023, Skyward Specialty Insurance Group, Inc. value is approximately $100.00.
• On January 13, 2023, Nasdaq Composite Index value is approximately $100.00.
• On January 13, 2023, Nasdaq Insurance Index value is approximately $100.00.
• On December 31, 2023, Skyward Specialty Insurance Group, Inc. value is approximately $175.00.
• On December 31, 2023, Nasdaq Composite Index value is approximately $135.00.
• On December 31, 2023, Nasdaq Insurance Index value is approximately $105.00.
• On December 31, 2024, Skyward Specialty Insurance Group, Inc. value is approximately $265.00.
• On December 31, 2024, Nasdaq Composite Index value is approximately $170.00.
• On December 31, 2024, Nasdaq Insurance Index value is approximately $128.00.

Management’s Discussion and Analysis of Financial Condition and Results of Operations

Overview

[c. 111; p. 14] Business overview and strategy

• The company is a specialty insurance provider of commercial P&C products and solutions, primarily in the United States.
• Products are offered on both a non-admitted (E&S) and admitted basis.
• The company focuses on underserved, dislocated, or inadequately covered markets, requiring highly specialized and customized underwriting and claims solutions.
• The portfolio of insured risks is highly diversified across industries, distribution channels, and lines of business.
• Lines of business include general liability, excess liability, professional liability (cyber and media liability), commercial auto, group accident and health, property, agriculture, credit, surety, and workers’ compensation.
• The business mix includes both short and medium duration liabilities, is principally primary insurance, and is balanced between E&S and admitted markets.
• A small portion of the business is specialty reinsurance, primarily in agriculture and credit, focused on attractive specialty classes where reinsurance is more efficient due to factors like cost of entry and geographic expansion.
• This diversification, including businesses not typically aligned with traditional P&C pricing cycles, combined with underwriting and claims expertise, aims to produce consistent growth and profitability across all insurance pricing cycles.
• The company's strategy, "Rule Our Niche," focuses on leading in chosen market niches and establishing sustainable competitive positions.
• This strategy aims to build a strong defensible market position, create a competitive moat, and achieve best-in-class underwriting results through P&C insurance pricing cycles.
• The company strives for excellence in risk selection, pricing, and claims outcomes, amplified by advanced technology and analytics.

Results of Operations

[c. 112; p. 14] Financial results summary

• The table summarizes results for the years ended December 31, 2024 and 2023.

[c. 113; p. 14]

Net written premiums, net earned premiums, & underwriting income by years ended December 31

	Years Ended December 31,
($ in thousands)	2024	2023
Gross written premiums	1,743,232	1,459,829
Ceded written premiums	(619,654)	(549,138)
Net written premiums	1,123,578	910,691
Net earned premiums	1,056,722	829,143
Commission and fee income	6,703	6,064
Losses and LAE	669,809	515,237
Underwriting, acquisition and insurance expenses	311,757	243,444
Underwriting income (1)	81,859	76,526
Net investment income	80,686	40,322
Net investment gains (losses)	6,256	11,072
Income before income taxes	152,739	110,102
Net income	118,828	85,984
Adjusted operating income (1)	126,650	80,847
Loss and LAE ratio	63.4%	62.1%
Expense ratio	28.9%	28.6%
Combined ratio	92.3%	90.7%
Adjusted loss and LAE ratio (1)	62.3%	62.3%
Expense ratio	28.9%	28.6%
Adjusted combined ratio (1)	91.2%	90.9%
Return on equity	16.3%	15.9%
Return on tangible equity (1)	18.6%	19.0%
Adjusted return on equity (1)	17.4%	14.9%
Adjusted return on tangible equity (1)	19.8%	17.9%

(1) See “Reconciliation of Non-GAAP Financial Measures” in this Item 2.

Reconciliation of Non-GAAP Financial Measures

[c. 114; p. 14] Adjusted operating income reconciliation

• The table provides a reconciliation of adjusted operating income to net income for the years ended December 31, 2024 and 2023.

[c. 115; p. 14] Underwriting income reconciliation

• The table provides a reconciliation of underwriting income to income before federal income tax expense for the years ended December 31, 2024 and 2023.

[c. 116; p. 14] Adjusted loss ratio and adjusted combined ratio reconciliation

• The table provides a reconciliation of the adjusted loss and LAE ratio and adjusted combined ratio to the loss and LAE ratio and combined ratio for the years ended December 31, 2024 and 2023.

[c. 117; p. 14] Tangible stockholders’ equity reconciliation

• The table provides a reconciliation of tangible stockholders’ equity to stockholders’ equity for the years ended December 31, 2024 and 2023.

[c. 118; p. 14] Adjusted return on equity reconciliation

• The table provides a reconciliation of adjusted return on equity to return on equity for the years ended December 31, 2024 and 2023.

[c. 119; p. 14] Return on tangible equity reconciliation

• Return on tangible equity for the years ended December 31, 2024 and 2023 reconciles to return on equity.

[c. 120; p. 14] Adjusted return on tangible equity reconciliation

• Adjusted return on tangible equity for the years ended December 31, 2024 and 2023 reconciles to return on equity.

[c. 121; p. 14]

Adjusted operating income by pre-tax and after-tax

	2024		2023
($ in thousands)	Pre-tax	After-tax	Pre-tax	After-tax
Income as reported	152,739	118,828	110,102	85,984
Less (add):	—	—	—	—
Net investment gains (losses)	6,256	4,942	11,072	8,747
Net impact of LPT	(11,598)	(9,162)	1,427	1,127
Other (loss) income	(167)	(132)	(632)	(499)
Other expenses	(4,392)	(3,470)	(5,364)	(4,238)
Adjusted operating income	162,640	126,650	103,599	80,847

($ in thousands)	2024	2023
Income before income taxes	152,739	110,102
Add:	—	—
Interest expense	9,496	10,024
Amortization expense	2,007	1,798
Other expenses	4,392	5,364
Less (add):	—	—
Net investment income	80,686	40,322
Net investment gains	6,256	11,072
Other loss	(167)	(632)
Underwriting income	81,859	76,526

($ in thousands)	2024	2023
Net earned premiums	1,056,722	829,143
Losses and LAE	669,809	515,237
Pre-tax net impact of loss portfolio transfer	(11,598)	1,427
Adjusted losses and LAE	658,211	516,664
Loss ratio	63.4%	62.1%
Less: Net impact of LPT	1.1%	(0.2)%
Adjusted loss ratio	62.3%	62.3%
Combined ratio	92.3%	90.7%
Less: Net impact of LPT	1.1%	(0.2)%
Adjusted combined ratio	91.2%	90.9%

($ in thousands)	2024	2023
Stockholders’ equity	793,999	661,031
Less: Goodwill and intangible assets	87,348	88,435
Tangible stockholders’ equity	706,651	572,596

($ in thousands)	2024	2023
Numerator: adjusted operating income	126,650	80,847
Denominator: average stockholders’ equity	727,515	541,347
Adjusted return on equity	17.4%	14.9%

($ in thousands)	2024	2023
Numerator: net income	118,828	85,984
Denominator: average tangible stockholders’ equity	639,624	452,194
Return on tangible equity	18.6%	19.0%

($ in thousands)	2024	2023
Numerator: adjusted operating income	126,650	80,847
Denominator: average tangible stockholders’ equity	639,624	452,194
Adjusted return on tangible equity	19.8%	17.9%

Underwriting Results

[c. 122; p. 14] Premiums

• Net written premiums were USD 1,123.6m compared to USD 910.7m in 2023, an increase of USD 212.9m or 23.4%.
• The increase in net written premiums was primarily driven by the same reasons as gross written premiums.
• Net earned premiums for 2024 were USD 1,056.7m compared to USD 829.1m for 2023, an increase of USD 227.6m, or 27.4%.
• The increase in net earned premiums was primarily driven by the same reasons as gross written premiums.
• Gross written premiums increased YoY due to double-digit premium growth from captives, surety, transactional E&S, programs, and global property & agriculture underwriting divisions.
• The company broadened and diversified its product portfolio in 2024, growing in areas less exposed to P&C cycles.
• Gross written premium increases were primarily driven by: new captive members and growth in existing captives; new product offerings, including participation in the Small Business Administration ("SBA") Bond Guarantee Program, and regional expansion in surety; new business and rate in transactional E&S; the addition of four new programs, including Aviation; and new business in global agriculture.
• Gross written premium increases were slightly offset by downward pricing pressure in the global property market and intentional actions to address profitability in commercial auto.

[c. 123; p. 14] Losses and LAE

• The 2024 loss ratio increased 1.3 points compared to 2023, primarily due to the net impact of prior accident year development related to the LPT, which added 1.1 points to the loss ratio.
• The non-cat loss and LAE ratio for 2024 improved 0.3 points compared to 2023, primarily driven by a shift in the mix of business.
• The 2024 cat loss and LAE ratio increased 0.3 points compared to 2023, primarily due to catastrophe losses from Hurricanes Helene and Beryl in Q3 2024 and Hurricane Milton in Q4 2024.
• In 2024, the Company transitioned from evaluating reserves on a policy year basis to an accident year basis, resulting in earlier recognition of underlying claim trends, better alignment of exposure to risks, and adherence to industry best practices.
• In prior years, the Company's methodology allocated IBNR from its policy year analysis to accident year.
• As a result of transitioning to accident year, IBNR within short-tail/monoline specialty lines, multi-line solutions, and exited lines was reallocated for the years ended December 31, 2023, 2022, 2021, and 2020, and certain amounts have been conformed to the current year presentation.
• For the year ended December 31, 2024, the Company recognized adverse development related to prior years’ loss and loss expense reserves of USD 25.7m.
• Of the USD 25.7m adverse development, USD 10.1m and USD 15.2m in multi-line solutions and exited lines, respectively, were related to losses previously subject to the LPT from accident years 2018 and prior.
• During the year ended December 31, 2023, the Company recognized adverse development related to prior years’ loss and loss expense reserves of USD 10.8m.
• Adverse development of USD 11.7m in multi-line solutions in 2023 was driven by greater than expected severity in auto, general, and excess liability lines of business primarily from accident years 2020 to 2022.
• The 2023 adverse development was partially offset by favorable development in short-tail/monoline specialty lines, specifically in the property line of business primarily from accident years 2021 and 2022.

[c. 124; p. 14] Expense Ratio

• The expense ratio for 2024 increased 0.3 points compared to 2023, primarily driven by business mix shift partially offset by earnings leverage.
• The expense ratios presented exclude the impact of IPO related stock compensation and secondary offering expenses, which are reported in other expenses in the consolidated statements of operations and comprehensive income.

[c. 125; p. 14] Investment Results

• Beginning January 1, 2024, the company simplified investment portfolio classifications to align with strategy and underlying risk characteristics.
• The prior period has been reclassified to conform to the current period presentation.
• Net investment income for the year ended 2024 increased USD 40.4m compared to 2023.
• The increase in income from the fixed income portfolio for 2024 compared to 2023 was due to a larger asset base from increased allocation and a higher book yield of 5.2% at December 31, 2024 (prior: 4.5% at December 31, 2023).
• The increase in income from short-term investments & cash and cash equivalents for 2024 compared to 2023 was due to higher investment yields and a larger asset base.
• The fair value of the alternative and strategic investments portfolio for 2024 increased compared to 2023 due to an increase in the fair value of limited partnership investments.

[c. 126; p. 14]

Total gross written premiums by line of business

	Years Ended December 31,
($ in thousands)	2024	2023	Change	% Change
Industry Solutions	317,198	305,476	11,722	3.8%
Global Property & Agriculture	311,402	273,191	38,211	14.0%
Captives	241,902	167,624	74,278	44.3%
Programs	218,407	178,726	39,681	22.2%
Accident & Health	173,073	151,701	21,372	14.1%
Transactional E&S	169,053	122,508	46,545	38.0%
Professional Lines	159,785	154,565	5,220	3.4%
Surety	152,429	106,056	46,373	43.7%
Total gross written premiums (1)	1,743,249	1,459,847	283,402	19.4%

(1) Excludes exited business.

	Twelve months ended December 31,
	2024		2023
($ in thousands)	Losses and LAE	% of Net Earned Premiums	Losses and LAE	% of Net Earned Premiums
Losses and LAE:
Non-cat loss and LAE	640,257	60.6%	504,664	60.9%
Cat loss and LAE (1)	17,954	1.7%	12,000	1.4%
Prior accident year development - LPT	11,598	1.1%	(1,427)	(0.2)%
Total losses and LAE	669,809	63.4%	515,237	62.1%
Adjusted losses and LAE (2) :	—	—	—	—
Non-cat loss and LAE	640,257	60.6%	504,664	60.9%
Cat loss and LAE (1)	17,954	1.7%	12,000	1.4%
Total adjusted losses and LAE (2)	658,211	62.3%	516,664	62.3%

(1) Current accident year.

(2) See "Reconciliation of Non-GAAP Financial Measures" included in this Item 2.

($ in thousands)	Development
	(Favorable) Adverse
Accident Year	2024	2023
Prior	25,535	4,333
2020	(606)	4,341
2021	978	289
2022	(1,479)	1,807
2023	1,300	—
Total	25,728	10,770
Reserve development on losses subject to LPT	25,300	—
Reserve development on losses excluding losses subject to LPT	428	10,770

	Twelve months ended December 31,
	2024		2023
($ in thousands)	Expenses	% of Net Earned Premiums	Expenses	% of Net Earned Premiums
Net policy acquisition expenses	149,975	14.2%	108,514	13.0%
Other operating and general expenses	161,782	15.3%	134,930	16.3%
Underwriting, acquisition and insurance expenses	311,757	29.5%	243,444	29.3%
Less: commission and fee income	(6,703)	(0.6%)	(6,064)	(0.7%)
Total net expenses	305,054	28.9%	237,380	28.6%

	Twelve months ended December 31,
$ in thousands	2024	2023
Short-term investments & cash and cash equivalents	17,643	11,677
Fixed income	57,631	36,547
Equities	2,745	2,212
Alternative and strategic investments	2,667	(10,114)
Net investment income	80,686	40,322
Net unrealized gains on securities still held	7,921	11,130
Net realized losses	(1,665)	(58)
Net investment gains	6,256	11,072

Investments

[c. 127; p. 14] Investment portfolio composition

• The investment portfolio primarily consists of investment grade fixed income securities, which are predominantly highly-rated and liquid bonds, and commercial mortgage loans.

[c. 128; p. 14] Fixed income portfolio credit quality and duration

• The weighted average credit rating of the available-for-sale fixed income portfolio was "AA-" by Standard & Poor’s Financial Services, LLC ("Standard & Poor’s") at December 31, 2024 and 2023.
• Commercial mortgage loans are primarily senior loans on real estate across the U.S..
• The average duration of the fixed income portfolio was approximately 4.34 years at December 31, 2024, and 4.24 years at December 31, 2023.

[c. 129; p. 14] Equities portfolio composition

• The equities portfolio primarily consists of domestic preferred stocks, common equities, exchange traded funds, limited partnerships, limited liability corporations, and other types of equity interests.
• 100.0% of the equities portfolio is publicly traded.

[c. 130; p. 14] Alternative and strategic investments

• Alternative investments consist of promissory notes, limited partnerships, joint ventures, and equity interests.
• Underlying alternative investments are primarily floating rate senior secured loans, comprised of short duration, collateralized, asset-oriented credit investments.
• Limited partnerships and joint ventures are subject to future increases or decreases in asset value as assets are monetized and income is distributed.
• Strategic investments consist of equity interests in private entities within the insurance industry.

[c. 131; p. 14] Market risk overview

• Market risk is the risk of economic losses due to adverse changes in the estimated fair value of a financial instrument resulting from changes in interest rates, equity prices, foreign currency exchange rates, and commodity prices.
• The primary components of market risk affecting the company are credit risk and interest rate risk.
• The company does not have significant exposure to foreign currency exchange rate risk or commodity risk.

[c. 132; p. 14] Credit risk management

• Credit risk is the potential loss from adverse changes in an issuer’s ability to repay debt obligations.
• Exposure to credit risk exists as a holder of debt instruments in core fixed income and opportunistic fixed income portfolios.
• The risk management strategy and investment policy is to invest primarily in debt instruments of high credit quality issuers and to limit credit exposure by ratings categories and per issuer.
• At December 31, 2024, the core fixed income portfolio had an average rating of "AA-".
• Approximately 81.5% of securities in the core fixed income portfolio were rated "A" or better by at least one nationally recognized rating organization at December 31, 2024.
• The policy is to invest in investment grade fixed income securities for stable income, supplemented by opportunistic fixed income and equity securities for diversification and risk-adjusted returns.
• Approximately 1.7% of the core fixed income portfolio was unrated or rated below investment-grade at December 31, 2024.
• The company monitors the financial condition of all issuers in its portfolio through investment managers.
• Credit risk also exists with third-party reinsurers; the company is ultimately liable to policyholders for ceded risks.
• Reinsurance contracts do not limit ultimate obligations to pay claims, and amounts recoverable from reinsurers might not be collected.
• To address this, reinsurance is purchased from reinsurers rated at least "A-" (Excellent) or better by A.M. Best.
• Periodic credit reviews of reinsurers are performed with the reinsurance broker.
• At December 31, 2024, 99% of reinsurance recoverables were from reinsurers rated "A-" (Excellent) or better by A.M. Best, or were collateralized through funds held, trusts, and letters of credit by the reinsurer.
• If a reinsurer suffers a credit downgrade, options like commutation, novation, and letters of credit may be considered to lessen asset impairment risk.

[c. 133; p. 14] Interest rate risk management

• Interest rate risk is the risk of economic losses due to adverse changes in interest rates.
• The primary market risk to the investment portfolio is interest rate risk associated with fixed income securities.
• Fluctuations in interest rates directly affect the market valuation of these securities; rising rates decrease fair value, falling rates increase fair value.
• Interest rate risk is managed by investing in securities with varied maturity dates and by managing the duration of the investment portfolio in relation to the duration of reserves.
• Duration is the weighted average payment period of cash flows, weighted by the present value of cash flows.
• Duration targets for the core fixed income investment portfolio are set after considering the estimated duration of liabilities and other factors.
• Fixed maturity securities had a weighted average effective duration of 4.34 years as of December 31, 2024.
• Fixed income securities subject to interest rate risk had a fair value of USD 1,292.2m at December 31, 2024.
• Opportunistic fixed income securities are excluded from interest rate sensitivity analysis as they are primarily floating rate and treated as held-to-maturity.
• Changes in interest rates immediately affect comprehensive income and stockholders’ equity but not ordinarily net income.
• Actual results may differ from hypothetical changes in market rates assumed in sensitivity analysis.
• Sensitivity analysis does not reflect actions taken to mitigate hypothetical fair value losses.

[c. 134; p. 14] Equity price risk management

• Equity price risk represents potential economic losses due to adverse changes in equity security prices.
• At December 31, 2024, approximately 6.7% of the fair value of the investment portfolio (excluding cash and cash equivalents and short-term investments) was invested in equity securities.
• Equity price risk is managed through portfolio diversification.
• A tail-risk management strategy is maintained to provide protection for the equity portfolio if there is a significant decline in the S&P 500 within a 30-day period.

[c. 135; p. 14]

Investments

	2024		2023
($ in thousands)	Carrying Value	% of Total	Carrying Value	% of Total
Cash and cash equivalents	121,603	6.1%	65,891	3.9%
Short-term investments	274,929	13.8%	270,259	16.1%
Fixed income	1,318,708	66.2%	1,067,721	63.6%
Equities	106,254	5.3%	118,249	7.0%
Alternative and strategic investments	170,929	8.6%	157,458	9.4%
Total portfolio	1,992,423	100.0%	1,679,578	100.0%

	2024		2023
($ in thousands)	Carrying Value	% of Total	Carrying Value	% of Total
U.S. government securities	26,486	2.0%	44,166	4.1%
Corporate securities and miscellaneous	425,628	32.3%	383,420	35.9%
Municipal securities	84,716	6.4%	92,778	8.7%
Residential mortgage-backed securities	393,833	29.9%	281,626	26.4%
Commercial mortgage-backed securities	69,364	5.2%	29,934	2.8%
Other asset-backed securities	292,191	22.2%	185,727	17.4%
Total fixed income portfolio, available-for-sale	1,292,218	98.0%	1,017,651	95.3%
Commercial mortgage loans	26,490	2.0%	50,070	4.7%
Total fixed income portfolio	1,318,708	100.0%	1,067,721	100.0%

	2024		2023
($ in thousands)	Fair Value	% of Total	Fair Value	% of Total
AAA	483,099	37.3%	493,252	48.6%
AA	141,177	10.9%	105,906	10.4%
A	429,703	33.3%	233,487	22.9%
BBB	216,602	16.8%	154,096	15.1%
BB and Lower	21,637	1.7%	30,910	3.0%
Total fixed income portfolio, available-for-sale	1,292,218	100.0%	1,017,651	100.0%

	2024		2023
($ in thousands)	Fair Value	% of Total Fair Value	Fair Value	% of Total Fair Value
Domestic common equities	70,665	66.5%	71,502	60.5%
International common equities	34,425	32.4%	39,389	33.3%
Preferred stock	1,164	1.1%	7,358	6.2%
Equities	106,254	100.0%	118,249	100.0%

($ in thousands)	Estimated Fair Value	Estimated Change in Fair Value	Estimated % Increase (Decrease) in Fair Value
300 basis point increase	1,118,982	(173,236)	(13.4)%
200 basis point increase	1,177,074	(115,144)	(8.9)%
100 basis point increase	1,234,820	(57,398)	(4.4)%
No change	1,292,218	—	0.0%
100 basis point decrease	1,349,269	57,051	4.4%
200 basis point decrease	1,405,973	113,755	8.8%
300 basis point decrease	1,462,329	170,111	13.2%

Other Items

[c. 136; p. 14] Income taxes

• Income tax expense for the year ended December 31, 2024 was USD 33.9m, compared to USD 24.1m for the year ended December 31, 2023.
• The effective tax rate for the year ended December 31, 2024 was 22.2%, compared to 21.9% for the year ended December 31, 2023.
• For a reconciliation between actual federal income tax expense and the amount computed at the indicated statutory rate for the years ended December 31, 2024 and 2023, refer to Note 13, "Income Taxes" in the consolidated financial statements included in Item 8 of this Form 10-K.

Liquidity and Capital Resources

[c. 137; p. 14] Holding Company Structure and Funding

• The company is organized as a holding company, with operations primarily conducted by wholly-owned insurance subsidiaries: GMIC, HSIC (Texas-domiciled), and IIC (Texas-domiciled), and OSIC (Oklahoma-domiciled).
• The holding company receives cash through corporate service fees from operating subsidiaries, payments from consolidated tax allocation agreements, dividends from subsidiaries (subject to limitations), bank loans, draws on revolving loan agreements, and issuance of equity and debt securities.
• Proceeds from these sources are used to contribute funds to insurance subsidiaries for premium growth, pay dividends and taxes, and for other business purposes.

[c. 138; p. 14] Intercompany Reimbursements and Tax Allocation

• Skyward Service Company receives corporate service fees from operating subsidiaries to reimburse most incurred operating expenses.
• Expense reimbursement via corporate service fees is based on actual expected costs with no mark-up.
• The company files a consolidated U.S. federal income tax return with its subsidiaries.
• Under the corporate tax allocation agreement, each participant is charged or refunded taxes based on what they would have paid or received if filing on a separate return basis with the IRS.

[c. 139; p. 14] Insurance Subsidiary Dividend Restrictions

• Applicable state insurance laws restrict insurance subsidiaries from declaring stockholder dividends without prior regulatory approval.
• State insurance regulators require insurance companies to maintain specified levels of statutory capital and surplus.
• Dividend payments are limited to the portion of available policyholder surplus derived from net profits on an insurer’s business.
• Insurance regulators have broad powers to prevent reduction of statutory surplus to inadequate levels, and there is no assurance that maximum calculated dividends would be permitted.
• State insurance regulatory authorities may adopt more restrictive statutory provisions regarding dividend payments in the future.
• Insurance subsidiaries did not pay dividends to the holding company for the years ended December 31, 2024, and 2023.
• Additional information regarding insurance companies is available in Note 23, “Statutory Accounting Principles and Regulatory Matters” to the consolidated financial statements in Item 8 of Form 10-K.

[c. 140; p. 14] Holding Company Liquidity and Outlook

• The holding company had USD 2.9m in cash and investments at December 31, 2024, compared to USD 3.0m at December 31, 2023.
• The company believes it has sufficient liquidity to meet operating cash needs, obligations, and committed capital expenditures for the next 12 months.

Cash Flows

[c. 141; p. 14] Cash flow sources and uses

• The most significant source of cash is premiums received from insureds, typically at the beginning of the coverage period, net of related commission.
• The most significant cash outflow is for claims incurred by policyholders, which occur after premium receipt, often years later.
• Cash is invested in various investment securities to earn interest and dividends.
• Cash is also used for operating expenses (salaries, rent, taxes) and capital expenditures (technology systems).
• Reinsurance is used to manage policy risk, involving ceding part of premiums to reinsurers and collecting cash back when covered losses are paid.
• The timing of cash flows from operating activities can vary due to the timing of payments and receipts.
• Significant payments and receipts, including loss settlements and subsequent reinsurance receipts, can influence operating cash flows in a given period.
• Management believes cash receipts from premiums and investment income proceeds are sufficient to cover cash outflows in the foreseeable future.

[c. 142; p. 14] Cash flow summary

• The document provides a table detailing cash flows for the years ended December 31, 2024 and 2023.

[c. 143; p. 14] Operating cash flow drivers

• The decrease in cash provided by operating activities in 2024 compared to 2023 was primarily due to an increase in cash outflows from net reinsurance recoverables and net premiums receivables.
• Cash from operations can vary period-to-period due to the timing of premium receipts, claim payments, and reinsurance activity.
• Cash flows from operations in both 2023 and 2024 were primarily used to fund investing activities.

[c. 144; p. 14] Investing cash flow drivers

• Net cash used in investing activities in 2024 was primarily driven by purchases of fixed maturity securities, partially offset by sales and maturities of investment securities and sales of short-term investments.
• Net cash used in investing activities in 2023 was primarily driven by purchases of fixed maturity securities.

[c. 145; p. 14] Financing cash flow drivers

• Net cash used in financing activities in 2024 was driven by net payments on debt.

[c. 146; p. 14]

Change in cash and cash equivalents and restricted cash by activities

($ in thousands)	2024	2023
Cash and cash equivalents provided by (used in):
Operating activities	305,115	338,187
Investing activities	(243,694)	(493,809)
Financing activities	(4,232)	130,947
Change in cash and cash equivalents and restricted cash	57,189	(24,675)

Credit Agreements

[c. 147; p. 14] FHLB Loan

• On August 30, 2024, the company entered into the FHLB Loan with the Federal Home Loan Bank of Dallas (FHLB) under its Advances and Security Agreement.
• The FHLB Loan is a 4.5-year term loan for a principal amount of USD 57.0m.
• The FHLB Loan requires interest-only payments during its term, with principal due in full at maturity.
• The interest rate for the FHLB Loan is fixed at 4.00% over its term.
• The FHLB Loan is fully secured by a pledge of specific investment securities of HSIC.
• Proceeds from the FHLB Loan were used to fund the redemption of the March 15, 2024 draw on the Revolving Credit Facility and to redeem USD 7.0m of the March 29, 2023 draw on the Revolving Credit Facility.

[c. 148; p. 14] Revolving Credit Facility

• On March 29, 2023, the company entered into an unsecured Revolving Credit Facility with a syndicate of participating banks.
• The Revolving Credit Facility provides up to a USD 150.0m revolving credit facility and a letter of credit sub-facility of up to USD 30.0m.
• On March 14, 2024, the company drew USD 50.0m on the Revolving Credit Facility to fund the redemption of the Debentures using these proceeds and existing cash.
• On August 30, 2024, the company fully redeemed the March 15, 2024 draw on the Revolving Credit Facility and redeemed USD 7.0m of the March 29, 2023 draw on the Revolving Credit Facility.
• As of December 31, 2024, USD 43.0m was outstanding under the Revolving Credit Facility, with USD 107.0m of undrawn capacity.
• Interest on the Revolving Credit Facility is payable quarterly.
• The interest rate on the Revolving Credit Facility is SOFR plus a margin of 150 to 190 basis points, based on the debt to total capital ratio, and a credit spread adjustment of 10 basis points.
• At December 31, 2024, the six-month SOFR on the Revolving Credit Facility was 4.25%, plus a margin of 1.60%.
• The company is subject to covenants on the Revolving Credit Facility, including minimum net worth, maximum debt to capital ratio, minimum A.M. Best Rating, and minimum liquidity.
• As of December 31, 2024, the company was in compliance with all Revolving Credit Facility covenants.

[c. 149; p. 14] Debentures

• In August 2006, the company received USD 58.0m in proceeds from a debenture offering through Delos Capital Trust (the Trust).
• The Trust's sole asset is Fixed/Floating Rate Junior Subordinated Deferrable Interest Debentures (Trust Preferred) with a principal amount of USD 59.8m, issued by the company.
• The Trust also holds USD 1.8m in cash from the issuance of Trust common shares purchased by the company, equal to 3% of the Trust capitalization.
• On March 15, 2024, the company redeemed the Debentures and paid USD 1.4m of accrued interest.

[c. 150; p. 14] Subordinated Debt

• In May 2019, the company issued unsecured subordinated notes (the Notes) with an aggregate principal amount of USD 20.0m.
• Interest on the subordinated notes is fixed at 7.25% for the first eight years and 8.25% fixed thereafter.
• Early retirement of the debt before the eight-year commitment requires all interest payments to be paid in full, along with the return of all capital.
• Principal payment for the Notes is due at maturity on May 24, 2039, and interest is payable quarterly.

[c. 151; p. 14] Debt to Capitalization Ratio

• At December 31, 2024, the ratio of total debt outstanding (including the FHLB Loan, Revolving Credit Facility, and Notes) to total capitalization (total debt plus stockholders’ equity) was 13.1%.
• At December 31, 2023, the ratio of total debt outstanding (including the Term Loan, Revolver, Trust Preferred, and Notes) to total capitalization was 16.3%.

[c. 152; p. 14] Share Repurchase Program

• In October 2024, the Board of Directors approved a share repurchase program authorizing the repurchase of up to USD 50.0m of common stock.
• Shares may be repurchased via open market purchases, privately-negotiated transactions, block purchases, accelerated share repurchase agreements, or a combination of methods, including Rule 10b5-1 trading plans.
• The timing, manner, price, and amount of repurchases are at the company's discretion.
• The share repurchase program does not require the repurchase of any specific number of shares and can be modified, suspended, or terminated at any time.
• As of December 31, 2024, no shares had been repurchased under this plan.

Contractual Obligations and Commitments

[c. 153; p. 14] Contractual obligations and commitments

• Contractual obligations and commercial commitments are presented by due date as of December 31, 2024.
• Reserves for losses and LAE represent the best estimate of the ultimate cost of settling reported and unreported claims and related expenses.
• Estimating reserves for losses and LAE involves complex and subjective judgments.
• Actual losses and settlement expenses paid may deviate substantially from the reserve estimates in financial statements.
• The timing for payment of estimated losses is not fixed or determinable on an individual or aggregate basis.
• Assumptions for estimating payments due by period are based on the company's own, industry, and peer group claims payment experience.
• There is a risk that amounts paid in any period will differ significantly from disclosed amounts due to uncertainty in estimating payment timing.
• Disclosed amounts are gross of anticipated amounts recoverable from reinsurers.
• Reinsurance balances recoverable on reserves for losses and LAE are reported separately as assets, not netted with liabilities, because reinsurance does not discharge liability to policyholders.
• Reinsurance balances recoverable on reserves for paid and unpaid losses and LAE totaled USD 857.9m at December 31, 2024.
• Reinsurance balances recoverable on reserves for paid and unpaid losses and LAE totaled USD 596.3m at December 31, 2023.

[c. 154; p. 14]

Contractual obligations by payments due by period

	Payments due by period
($ in thousands)	Total	Less Than One Year	One Year or More
Reserves for losses and LAE	1,782,383	433,204	1,349,179
Long-term debt	120,000	—	120,000
Interest on debt obligations	41,443	6,246	35,197
Operating lease obligations	3,632	968	2,664
Total	1,947,458	440,418	1,507,040

Critical Accounting Policies

[c. 155; p. 14] Critical accounting estimates overview

• Critical accounting estimates are important to financial condition and results of operations and require significant judgment.
• Significant judgment is used concerning future results and developments in applying these estimates and preparing consolidated financial statements.
• Judgments and estimates affect reported amounts of assets, liabilities, revenues, expenses, and disclosure of material contingent assets and liabilities.
• Actual results may differ materially from estimates and assumptions.
• Estimates are evaluated regularly using relevant information.
• Detailed discussion of accounting policies is in Note 1, "Summary of Significant Accounting Policies" to consolidated financial statements in Item 8 of Form 10-K.

[c. 156; p. 14] Reserves for unpaid losses and LAE

• Reserves for unpaid losses and LAE are the largest and most complex estimate in the consolidated balance sheet.
• These reserves represent the estimated ultimate cost of all unreported and reported but unpaid insured claims and the cost to adjust these losses as of or before the balance sheet date.
• Reserves for losses and LAE are not discounted to reflect estimated present value.
• Estimates are made using individual case-basis valuations of reported claims, statistical analyses, and various actuarial procedures.
• Estimates are based on historical information, industry and peer group information, and estimates of future trends in variable factors like loss severity, loss frequency, and inflation.
• Estimates are regularly reviewed and adjusted as experience develops or new information becomes known.
• During the loss settlement period, estimates of liability on a claim are often refined and adjusted upward or downward.
• Ultimate liability may exceed or be less than revised estimates, and ultimate settlement may vary significantly from the estimate in financial statements.
• Reserves for unpaid losses and LAE are categorized into case reserves and IBNR.
• A table sets forth gross and net reserves for unpaid losses and LAE at December 31, 2024 and 2023.

[c. 157; p. 14] Case reserves and IBNR

• Case reserves are established for individual claims reported to the company.
• Notification of losses comes from insureds, their agents, or brokers.
• Case reserves estimate ultimate losses from a claim, including defense costs, based on provided information.
• Claims department personnel use knowledge of specific claims and advice from internal and external experts (underwriters, legal counsel) to estimate expected ultimate losses.
• Third-Party Administrators (TPAs) are used in limited circumstances to assist in claim adjustment.
• Internal claims managers oversee TPA activities and monitor their claim handling to prescribed standards.
• The incurred but not reported (IBNR) reserve is derived by estimating the ultimate unpaid reserve liability and subtracting case reserves.
• Management's best estimate of the ultimate unpaid liability is set by the Reserve Committee.
• The Reserve Committee considers actuarial indications and other factors such as underwriting, claims handling, economic, legal, and environmental changes.
• The Reserve Committee includes the Chief Actuary, Chief Financial Officer, and Chief Claims Officer.
• The Reserve Committee meets quarterly to review actuarial reserving recommendations from the Chief Actuary and determines the best estimate for the reserve for losses and LAE.
• The actuary estimates an initial expected ultimate loss ratio for each underwriting division when establishing quarterly actuarial recommendations.
• Input from underwriting and claims departments, including premium pricing assumptions and historical experience, is considered in setting reserves.

[c. 158; p. 14] Reserve drivers and actuarial methods

• Reserves are driven by factors including litigation and regulatory trends, legislative activity, climate change, social and economic patterns, and claims inflation assumptions.
• Reserve estimates reflect current inflation in legal claims' settlements.
• Reserve estimates assume no losses from significant new legal liability theories.
• Reserve estimates assume no significant changes in the regulatory and legislative environment.
• The impact of potential changes in the regulatory or legislative environment is difficult to quantify without specific new regulation or legislation.
• The company will attempt to quantify the impact of significant new regulation or legislation, but accuracy or success is not assured.
• The actuarial review considers multiple actuarial methods to estimate the reserve for losses and LAE.
• These methods utilize the initial expected loss ratio, statistical analysis of past claims reporting and payment patterns, claims frequency and severity, paid loss experience, industry loss experience, and changes in market conditions, policy forms, exclusions, and exposures.
• Actuarial methods used include: Reported and/or Paid Loss Development Methods, Reported Bornhuetter-Ferguson Methods, and Paid Bornhuetter-Ferguson Method.
• For less mature policy years, the Bornhuetter-Ferguson Method is the primary method for ultimate loss indications.
• For more mature policy years, the company transitions to Reported and/or Paid Loss Development Methods.
• Reported methods are primarily relied upon when case reserving is consistently applied across policy years.
• When there is a change in reserving philosophy, both reported and paid methods are blended in the evaluation of ultimate loss indications.

[c. 159; p. 14] Reserve variability and development

• Actual loss experience may not conform to assumptions, even though reserve estimates are believed to be reasonable.
• Actual ultimate loss ratio could differ from the initial expected loss ratio.
• Actual reporting and payment patterns could differ from expected patterns, which are based on company and industry data.
• Ultimate settlement of losses and related LAE may vary significantly from estimates in financial statements.
• Estimates are regularly reviewed and adjusted as experience develops or new information becomes known.
• Such adjustments are included in the results of current operations.
• "Development" is the amount by which estimated losses differ from those originally reported for a period.
• Development is unfavorable when losses settle for more than reserved or subsequent estimates indicate reserve increases on unresolved claims.
• Development is favorable when losses settle for less than reserved or subsequent estimates indicate reserve reductions on unresolved claims.
• Favorable or unfavorable development of loss reserves is reflected in the results of operations in the period estimates are changed.
• A 5% change in net IBNR would result in a USD 38.4m change in reserves for losses and LAE.
• A 5% change in net IBNR would result in a USD 30.4m change in net income and stockholders’ equity.

[c. 160; p. 14]

Gross and net by case reserves and IBNR

	2024				2023
($ in thousands)	Gross	% of Total	Net	% of Total	Gross	% of Total	Net	% of Total
Case reserves	567,192	31.8%	342,612	30.8%	561,474	42.7%	318,863	37.1%
IBNR	1,215,191	68.2%	768,925	69.2%	753,027	57.3%	540,154	62.9%
Total	1,782,383	100.0%	1,111,537	100.0%	1,314,501	100.0%	859,017	100.0%

Recent Accounting Pronouncements

[c. 161; p. 14] Recent Accounting Pronouncements - Segment Disclosures

• In November 2023, the FASB issued ASU 2023-07, "Improvements to Reportable Segment Disclosures (Topic 280)".
• ASU 2023-07 requires segment disclosures for: (i) significant segment expenses regularly provided to the chief operating decision maker ("CODM"), (ii) how the CODM uses reported measures of segment profitability for performance assessment and resource allocation, and (iii) the title and position of the CODM.
• Entities with a single reportable segment must provide full segment disclosures.
• The guidance is effective for fiscal years beginning after December 15, 2023, and interim periods within fiscal years beginning after December 15, 2024.
• This update is applied retrospectively to all prior periods presented.
• Additional segment disclosures have been added as required by ASU 2023-07.
• There was no impact to the consolidated financial statements from ASU 2023-07.

[c. 162; p. 14] Recent Accounting Pronouncements - Income Tax Disclosures

• In December 2023, the FASB issued ASU 2023-09, "Improvements to Income Tax Disclosures (Topic 740)".
• ASU 2023-09 requires public companies to provide enhanced annual rate reconciliation disclosures, including specific categories and additional information meeting a quantitative threshold.
• This update also requires public companies to disaggregate income taxes paid by federal, state, and foreign taxes.
• The guidance is effective for fiscal years beginning after December 15, 2024.
• The amendments are not expected to have a material impact on the consolidated financial statements.

[c. 163; p. 14] Recent Accounting Pronouncements - Income Statement Expense Disclosures

• In November 2024, the FASB issued ASU 2024-03, requiring disaggregated disclosure of income statement expenses for public business entities ("PBEs").
• ASU 2024-03 does not change expense captions on the income statement but requires disaggregation of certain expense captions into specified categories in footnotes.
• A footnote disclosure is required for specific expenses, presented in a tabular format, for relevant income statement expense captions that include any of the following natural expenses: (1) purchases of inventory, (2) employee compensation, (3) depreciation, (4) intangible asset amortization, and (5) depreciation, depletion, and amortization recognized as part of oil- and gas-producing activities or other types of depletion expenses.
• The tabular disclosure will also include certain other expenses, when applicable.
• In January 2025, the FASB issued ASU 2025-01 to clarify the effective date of ASU 2024-03 as the first annual reporting period beginning after December 15, 2026, and interim reporting periods within annual reporting periods beginning after December 15, 2027.
• The effect of the amendments on the consolidated financial statements is currently being evaluated.

Quantitative and Qualitative Disclosures About Market Risk

[c. 164; p. 15] Market risk disclosures

• Qualitative and Quantitative Disclosures about Market Risk are included in Item 7 of this Form 10-K under “Investments—Market Risk”.

Financial Statements

Report of Independent Registered Public Accounting Firm

[c. 165; p. 16] Independent auditor's report

• The report is addressed to the Stockholders and the Board of Directors of Skyward Specialty Insurance Group, Inc.

Opinion on Internal Control Over Financial Reporting

[c. 166; p. 16] Internal control over financial reporting

• Skyward Specialty Insurance Group, Inc.'s internal control over financial reporting as of December 31, 2024, was audited based on criteria established in the Internal Control—Integrated Framework issued by the Committee of Sponsoring Organizations of the Treadway Commission (2013 framework) (the COSO criteria).
• The Company has not maintained effective internal control over financial reporting as of December 31, 2024, based on the COSO criteria, due to a material weakness.
• A material weakness is a deficiency, or combination of deficiencies, in internal control over financial reporting, such that there is a reasonable possibility that a material misstatement of the company’s annual or interim financial statements will not be prevented or detected on a timely basis.
• A material weakness existed as of December 31, 2024, related to the ineffective implementation of information technology general controls ("ITGCs") in the area of user access for systems supporting the Company’s financial reporting processes.
• Related process-level IT dependent manual and automated controls that rely upon the affected ITGCs, or information from IT systems with affected ITGCs, were also deemed ineffective.
• The consolidated balance sheets as of December 31, 2024 and 2023, and related consolidated statements of operations and comprehensive income (loss), stockholders’ equity and cash flows for each of the three years ended December 31, 2024, were audited in accordance with PCAOB standards.
• This material weakness was considered in determining the nature, timing, and extent of audit tests for the 2024 consolidated financial statements.
• The report on internal control does not affect the report dated March 3, 2025, which expressed an unqualified opinion on the consolidated financial statements.

Basis for Opinion

[c. 167; p. 16] Auditor's responsibility and audit scope

• The Company's management is responsible for maintaining effective internal control over financial reporting and for its assessment included in the Management’s Report on Internal Control over Financial Reporting.
• The auditor's responsibility is to express an opinion on the Company’s internal control over financial reporting based on their audit.
• The auditor is a public accounting firm registered with the PCAOB and is required to be independent in accordance with U.S. federal securities laws and applicable rules and regulations of the SEC and the PCAOB.
• The audit was conducted in accordance with PCAOB standards.
• PCAOB standards require planning and performing the audit to obtain reasonable assurance that effective internal control over financial reporting was maintained in all material respects.
• The audit included understanding internal control over financial reporting, assessing the risk of a material weakness, testing and evaluating the design and operating effectiveness of internal control, and performing other necessary procedures.
• The auditor believes their audit provides a reasonable basis for their opinion.

Definition and Limitations of Internal Control Over Financial Reporting

[c. 168; p. 16] Internal Control Over Financial Reporting Definition

• Internal control over financial reporting is a process designed to provide reasonable assurance regarding the reliability of financial reporting and the preparation of financial statements for external purposes in accordance with generally accepted accounting principles.
• Internal control over financial reporting includes policies and procedures that:
  • Pertain to the maintenance of records that accurately and fairly reflect the company's transactions and asset dispositions.
  • Provide reasonable assurance that transactions are recorded for financial statement preparation in accordance with GAAP, and that receipts and expenditures are authorized by management and directors.
  • Provide reasonable assurance regarding prevention or timely detection of unauthorized acquisition, use, or disposition of company assets that could materially affect financial statements.
• Due to inherent limitations, internal control over financial reporting may not prevent or detect misstatements.
• Projections of effectiveness evaluations to future periods risk controls becoming inadequate due to changing conditions or deterioration in compliance with policies or procedures.

[c. 169; p. 16]

Definition and Limitations of Internal Control Over Financial Reporting

/s/ Ernst & Young LLP
We have served as the Company’s auditor since 2021.
Houston, Texas
March 3, 2025

Report of Independent Registered Public Accounting Firm

[c. 170; p. 16] Independent auditor's report

• The report is addressed to the Stockholders and the Board of Directors of Skyward Specialty Insurance Group, Inc.

Opinion on the Financial Statements

[c. 171; p. 16] Audit Opinion

• The consolidated financial statements of Skyward Specialty Insurance Group, Inc. and subsidiaries (the Company) as of December 31, 2024 and 2023, and for each of the three years ended December 31, 2024, have been audited.
• The audit included the consolidated balance sheets, statements of operations and comprehensive income, stockholders' equity, cash flows, related notes, and financial statement schedules listed in Item 15.
• The auditors' opinion is that the consolidated financial statements fairly present, in all material respects, the financial position of the Company at December 31, 2024 and 2023, and the results of its operations and cash flows for each of the three years ended December 31, 2024.
• The financial statements conform with U.S. generally accepted accounting principles.

Basis for Opinion

[c. 172; p. 16] Auditor responsibilities and standards

• The Company's management is responsible for the financial statements.
• The auditor's responsibility is to express an opinion on the Company’s financial statements based on their audits.
• The auditor is a public accounting firm registered with the PCAOB and is required to be independent in accordance with U.S. federal securities laws and applicable rules and regulations of the Securities and Exchange Commission and the PCAOB.
• Audits were conducted in accordance with PCAOB standards.
• PCAOB standards require planning and performing the audit to obtain reasonable assurance that financial statements are free of material misstatement, whether due to error or fraud.
• Audits included procedures to assess and respond to risks of material misstatement, whether due to error or fraud.
• Procedures included examining, on a test basis, evidence regarding amounts and disclosures in the financial statements.
• Audits also included evaluating accounting principles used, significant estimates made by management, and the overall presentation of the financial statements.
• The audits provide a reasonable basis for the auditor's opinion.

Critical Audit Matter

[c. 173; p. 16] Critical audit matter definition

• The critical audit matter communicated relates to accounts or disclosures material to the financial statements and involved especially challenging, subjective, or complex judgments.
• Communication of the critical audit matter does not alter the opinion on the consolidated financial statements as a whole.
• The communication does not provide a separate opinion on the critical audit matter or the related account or disclosure.

Valuation of Reserves for Unpaid Losses and Loss Adjustment Expenses

[c. 174; p. 16] Valuation of Reserves for Unpaid Losses and Loss Adjustment Expenses

• The Company's reserves for unpaid losses and loss adjustment expenses (LAE) were USD 1.8bn at December 31, 2024, with a significant portion representing incurred but not reported reserves (IBNR).
• Reserves for unpaid losses and LAE represent the estimated ultimate cost of all unreported and reported but unpaid insured claims and the cost to adjust losses incurred as of the balance sheet date.
• The Company estimates these reserves using individual case-basis valuations of reported claims, statistical analyses, and various actuarial procedures.
• Estimates are based on historical information, industry and peer group information, and trends in factors like loss severity, loss frequency, and inflation.
• Auditing management's estimate of reserves for unpaid losses and LAE, including IBNR, was complex and involved actuarial specialists due to significant estimation uncertainty.
• Estimation uncertainty is associated with evaluating management's methods and assumptions, including loss development factors, expected loss ratios, and trends applied to historical experience.
• These assumptions significantly affect the valuation of IBNR reserves.
• Audit procedures for the Company's reserves for unpaid losses and LAE included evaluating the selection of actuarial methods used by management, comparing them to prior periods and industry practices, with assistance from actuarial specialists.
• The audit also evaluated assumptions used in actuarial methods by comparing significant assumptions (loss development factors, expected loss ratios, trends) to the Company’s historical experience and current industry benchmarks and trends.
• An independent range of reserve estimates was developed and compared to management’s best estimate for unpaid losses and LAE.
• A review of the development of prior year reserve estimates was also performed.

[c. 175; p. 16]

Valuation of Reserves for Unpaid Losses and Loss Adjustment Expenses

/s/ Ernst & Young LLP
We have served as the Company’s auditor since 2021.
Houston, Texas
March 3, 2025

Consolidated balance sheets

[c. 176; p. 16] Consolidated financial statements notes

• The accompanying notes are an integral part of the consolidated financial statements.

[c. 177; p. 16]

Assets, liabilities, and stockholders’ equity by December 31

	December 31,
	2024	2023
($ in thousands, except share and per share amounts)
Assets
Investments:
Fixed maturity securities, available-for-sale, at fair value (amortized cost of $ 1,320,266 and $ 1,047,713 , respectively)	1,292,218	1,017,651
Fixed maturity securities, held-to-maturity, at amortized cost (net of allowance for credit losses of $ 243 and $ 329 , respectively)	39,153	42,986
Equity securities, at fair value	106,254	118,249
Mortgage loans, at fair value	26,490	50,070
Equity method investments	98,594	110,653
Other long-term investments	33,182	3,852
Short-term investments, at fair value	274,929	270,226
Total investments	1,870,820	1,613,687
Cash and cash equivalents	121,603	65,891
Restricted cash	35,922	34,445
Premiums receivable, net	321,641	179,235
Reinsurance recoverables, net	857,876	596,334
Ceded unearned premium	203,901	186,121
Deferred policy acquisition costs	113,183	91,955
Deferred income taxes	30,486	21,991
Goodwill and intangible assets, net	87,348	88,435
Other assets	86,698	75,341
Total assets	3,729,478	2,953,435
Liabilities and stockholders’ equity	—	—
Liabilities:	—	—
Reserves for losses and loss adjustment expenses	1,782,383	1,314,501
Unearned premiums	637,185	552,532
Deferred ceding commission	40,434	37,057
Reinsurance and premium payables	177,070	150,156
Funds held for others	102,665	58,588
Accounts payable and accrued liabilities	76,206	50,880
Notes payable	100,000	50,000
Subordinated debt, net of debt issuance costs	19,536	78,690
Total liabilities	2,935,479	2,292,404
Stockholders’ equity	—	—
Common stock, $ 0.01 par value, 500,000,000 shares authorized, 40,127,908 and 39,863,756 shares issued and outstanding, respectively	401	399
Additional paid-in capital	718,598	710,855
Stock notes receivable	—	( 5,562 )
Accumulated other comprehensive loss	( 22,120 )	( 22,953 )
Retained earnings (accumulated deficit)	97,120	( 21,708 )
Total stockholders’ equity	793,999	661,031
Total liabilities and stockholders’ equity	3,729,478	2,953,435

Consolidated statements of operations and comprehensive income

[c. 178; p. 16] consolidated financial statements

• The accompanying notes are an integral part of the consolidated financial statements.

[c. 179; p. 16]

Revenues, expenses, income, and comprehensive income by years ended December 31

	Years Ended December 31,
($ in thousands, except share and per share amounts)	2024	2023	2022
Revenues:
Net earned premiums	1,056,722	829,143	615,994
Commission and fee income	6,703	6,064	5,199
Net investment income	80,686	40,322	36,931
Net investment gains (losses)	6,256	11,072	( 15,705 )
Other (loss) income	( 167 )	( 632 )	1
Total revenues	1,150,200	885,969	642,420
Expenses:	—	—	—
Losses and loss adjustment expenses	669,809	515,237	402,512
Underwriting, acquisition and insurance expenses	311,757	243,444	182,171
Interest expense	9,496	10,024	6,407
Amortization expense	2,007	1,798	1,547
Other expenses	4,392	5,364	—
Total expenses	997,461	775,867	592,637
Income before income taxes	152,739	110,102	49,783
Income tax expense	33,911	24,118	10,387
Net income	118,828	85,984	39,396
Net income attributable to participating securities	—	1,677	18,879
Net income attributable to common stockholders	118,828	84,307	20,517
Comprehensive income	—	—	—
Net income	118,828	85,984	39,396
Other comprehensive income (loss):	—	—	—
Unrealized gains and losses on investments:	—	—	—
Net change in unrealized gains (losses) on investments, net of tax	9,792	25,516	( 48,545 )
Reclassification adjustment for (losses) gains on securities no longer held, net of tax	( 8,959 )	( 4,984 )	420
Total other comprehensive income (loss)	833	20,532	( 48,125 )
Comprehensive income (loss)	119,661	106,516	( 8,729 )
Per share data:	—	—	—
Basic earnings per share	2.97	2.34	1.24
Diluted earnings per share	2.87	2.24	1.21
Weighted-average common shares outstanding	—	—	—
Basic	40,056,475	36,031,907	16,568,393
Diluted	41,377,460	38,317,534	32,653,194

Consolidated statements of stockholders’ equity

[c. 180; p. 16] Consolidated financial statements notes

• The accompanying notes are an integral part of the consolidated financial statements.

[c. 181; p. 16]

Consolidated statements of stockholders’ equity

	Years Ended December 31,
($ in thousands, except share amounts)	2024	2023	2022
Preferred shares:
Balance at beginning of year	—	1,969,660	1,969,660
Preferred stock conversion to common shares	—	( 1,969,660 )	—
Balance at December 31	—	—	1,969,660
Common shares:	—	—	—
Balance at beginning of year	39,863,756	16,599,666	16,533,620
Issuance of shares	264,152	6,958,977	66,046
Preferred stock conversion to common shares	—	16,305,113	—
Balance at December 31	40,127,908	39,863,756	16,599,666
Preferred stock:	—	—	—
Balance at beginning of year	—	20	20
Preferred stock conversion to common shares	—	( 20 )	—
Balance at December 31	—	—	20
Common stock:	—	—	—
Balance at beginning of year	399	168	168
Issuance of common stock	2	22	—
Preferred stock conversion to common shares	—	161	—
Proceeds from equity offerings, net	—	48	—
Balance at December 31	401	399	168
Treasury stock:	—	—	—
Balance at beginning of year	—	( 2 )	( 2 )
Preferred stock conversion to common shares	—	2	—
Balance at December 31	—	—	( 2 )
Additional paid-in capital:	—	—	—
Balance at beginning of year	710,855	577,289	575,159
Issuance of common stock	7,743	9,213	2,130
Preferred stock conversion to common shares	—	( 143 )	—
Proceeds from equity offerings, net	—	124,496	—
Balance at December 31	718,598	710,855	577,289
Stock notes receivable:	—	—	—
Balance at beginning of year	( 5,562 )	( 6,911 )	( 9,092 )
Employee equity transactions	5,562	1,349	2,181
Balance at December 31	—	( 5,562 )	( 6,911 )
Accumulated other comprehensive loss:	—	—	—
Balance at beginning of year	( 22,953 )	( 43,485 )	4,640
Other comprehensive income (loss), net of tax	833	20,532	( 48,125 )
Balance at December 31	( 22,120 )	( 22,953 )	( 43,485 )
Retained earnings (accumulated deficit):	—	—	—
Balance at beginning of year	( 21,708 )	( 105,417 )	( 144,813 )
Cumulative effect on adoption of ASU No. 2016-13	—	( 2,275 )	—
Net income	118,828	85,984	39,396
Balance at December 31	97,120	( 21,708 )	( 105,417 )
Total stockholders’ equity	793,999	661,031	421,662

Consolidated statements of cash flows

[c. 182; p. 16] Consolidated financial statements notes

• The accompanying notes are an integral part of the consolidated financial statements.

[c. 183; p. 16]

Cash flows from operating, investing, and financing activities by years ended December 31

	Years Ended December 31,
($ in thousands)	2024	2023	2022
Cash flows from operating activities
Net income	118,828	85,984	39,396
Adjustments to reconcile net income to net cash provided by (used in) operating activities:	—	—	—
Net investment (gains) losses	( 6,256 )	( 11,072 )	15,705
Depreciation and amortization expense	3,358	3,891	4,097
Stock-based compensation expense	9,395	8,525	2,287
Undistributed loss (earnings) from long-term investments	( 6,338 )	6,730	( 16,032 )
Deferred income tax, net	( 8,708 )	9,383	10,267
Changes in operating assets and liabilities:	—	—	—
Premiums receivable, net	( 142,406 )	( 40,020 )	( 27,057 )
Reinsurance recoverables, net	( 261,542 )	( 17,270 )	( 45,032 )
Ceded unearned premium	( 17,780 )	( 28,476 )	( 19,672 )
Deferred policy acquisition costs	( 21,228 )	( 23,017 )	( 9,482 )
Federal income taxes	4,500	( 1,892 )	—
Losses and loss adjustment expenses	467,882	172,744	162,208
Unearned premiums	84,653	110,023	79,221
Deferred ceding commission	3,377	7,208	( 651 )
Reinsurance and premium payables	26,914	36,460	( 6,223 )
Funds held for others	44,077	21,730	7,271
Accounts payable and accrued liabilities	19,177	2,285	7,583
Other, net	( 12,788 )	( 5,029 )	5,052
Net cash provided by operating activities	305,115	338,187	208,938
Cash flows from investing activities:	—	—	—
Purchase of fixed maturity securities, available-for-sale	( 617,606 )	( 459,672 )	( 268,781 )
Purchase of illiquid investments	( 75 )	( 1,675 )	( 4,873 )
Purchase of equity securities	( 14,077 )	( 26,009 )	( 53,548 )
Purchase of equity method investments	( 32,173 )	—	—
Purchase of intangible assets	—	( 50 )	—
Investment in direct and indirect loans	27,480	2,984	( 9,767 )
Purchase of property and equipment	( 4,224 )	( 3,108 )	( 2,325 )
Proceeds from the sales of fixed maturity securities, available-for-sale	217,468	26,626	13,964
Maturities, calls, transfers and paydowns of fixed maturity securities, available-for-sale	122,694	48,957	44,500
Maturities, calls and paydowns of fixed maturity securities held-to-maturity	6,015	11,444	—
Proceeds from the sales of equity securities	37,534	40,201	37,177
Sales of and distributions from equity method and other long-term investments	14,073	3,572	3,421
Change in short-term investments	( 4,799 )	( 149,068 )	43,120
Change in receivable/payable for securities	34	76	529
Cash provided by deposit accounting	3,962	11,913	3,202
Net cash used in investment activities	( 243,694 )	( 493,809 )	( 193,381 )
Cash flows from financing activities:	—	—	—
Employee share purchases	—	1,350	2,180
Repayment of stock notes receivable	5,562	—	—
Proceeds from long term borrowings	107,000	50,000	—
Payments on long term borrowings and trust preferred	( 116,794 )	( 50,000 )	—
Proceeds from initial public offering	—	129,597	—
Net cash (used in) provided by financing activities	( 4,232 )	130,947	2,180
Net increase (decrease) in cash and cash equivalents and restricted cash	57,189	( 24,675 )	17,737
Cash and cash equivalents and restricted cash at beginning of period (1)	100,336	125,011	107,274
Cash and cash equivalents and restricted cash at end of period (1)	157,525	100,336	125,011
Supplemental disclosure of cash flow information:	—	—	—
Cash paid for interest	8,573	10,667	5,761
Cash paid for federal income taxes	36,980	15,800	—

(1) The sum of cash and cash equivalents and restricted cash from the consolidated balance sheets.

A. Description of Business

[c. 184; p. 16] Company overview and structure

• Skyward Specialty Insurance Group, Inc. (the "Company") is a Delaware corporation organized in 2006, operating as an insurance holding company.
• The Company is a specialty insurance company operating in one segment, delivering commercial property and casualty products insurance coverages through its underwriting divisions.
• The Company has four wholly owned insurance company subsidiaries based in the United States.
• Great Midwest Insurance Company ("GMIC") underwrites insurance on an admitted basis and is a certified surety bond company listed with the U.S. Department of the Treasury.
• Houston Specialty Insurance Company ("HSIC"), a subsidiary of GMIC, underwrites insurance on a non-admitted basis.
• Imperium Insurance Company ("IIC"), a subsidiary of HSIC, underwrites insurance on an admitted basis.
• Oklahoma Specialty Insurance Company ("OSIC"), a subsidiary of IIC, underwrites insurance on a non-admitted basis.
• The Company has a wholly owned captive reinsurance company subsidiary, Skyward Re, domiciled in the Cayman Islands.
• Skyward Re assumed net reserves for certain divisions, related to a retroactive reinsurance contract, from the Company’s insurance companies and retroceded these net reserves to a third-party reinsurer.
• The Company has three non-risk bearing wholly owned subsidiaries.
• Skyward Underwriters Agency, Inc. ("SUA") is a managing general insurance agent and reinsurance broker for property and casualty risks in specialty niche markets.
• Skyward Service Company provides various administrative services to the Company’s subsidiaries.
• Skyward Specialty No. 1 Limited is a Lloyd’s corporate member authorized to invest in Lloyd’s syndicates.

B. Basis of Presentation

[c. 185; p. 16] Basis of presentation

• The Company’s consolidated financial statements are prepared in accordance with generally accepted accounting principles in the United States of America ("GAAP").
• GAAP differs in some respects from the principles followed in reports to insurance regulatory authorities.
• The consolidated financial statements include the accounts of the holding company and its subsidiaries.
• All intercompany transactions and balances have been eliminated in consolidation.
• Preparation of consolidated financial statements in conformity with GAAP requires the Company to make estimates and assumptions that affect reported amounts and accompanying notes.
• Actual results could differ from these estimates.

C. Cash and Cash Equivalents

[c. 186; p. 16] Cash and cash equivalents definition

• Cash and cash equivalents include cash on hand and fixed maturity securities with original maturities of three months or less.
• The carrying value of the Company’s cash and cash equivalents approximates fair value.

D. Restricted Cash

[c. 187; p. 16] Restricted cash definition and sources

• Cash with a legal restriction on withdrawal or use by the consolidated group is recorded as restricted cash.
• The carrying value of the Company’s restricted cash approximates fair value.
• SUA holds unremitted insurance premiums in a fiduciary capacity to third-party insurance companies as restricted cash.
• The Company is required by state regulations to maintain assets on deposit with certain states and hold cash as collateral for certain reinsurance balances.
• Cash held in a depository account for others, or restricted by a state, is recorded as restricted cash.

E. Investments

[c. 188; p. 16] Available-for-sale investments accounting

• Investments in fixed maturities classified as available-for-sale are carried at fair value.
• For available-for-sale fixed maturities in an unrealized loss position, the Company first determines intent to sell or likelihood of being required to sell before maturity or recovery of cost basis.
• If intent to sell or likelihood of required sale exists, amortized cost is written down to fair value, with losses recognized in net investment gains on consolidated statements of operations.
• If neither criterion is met, the Company determines if unrealized losses are due to credit-related factors.
• If unrealized losses are credit-related, an allowance for credit losses is determined using present value of cash flows compared to amortized cost.
• The allowance for credit losses is limited to the amount by which fair value is below amortized cost.
• Changes in the allowance for credit losses are recognized in net investment income on the consolidated statements of operations.
• Credit losses limited by fair value are recognized in stockholders’ equity, net of taxes, as a component of accumulated other comprehensive loss.
• Unrealized losses not credit-related continue to be recognized in stockholders’ equity, net of taxes, as a component of accumulated other comprehensive loss.

[c. 189; p. 16] Held-to-maturity investments accounting

• Investments in fixed maturity securities held-to-maturity are carried at amortized cost net of an allowance for credit losses.
• The allowance for credit losses represents the current estimate of expected credit losses.
• The Company develops a historical loss rate from Moody’s multi-year cumulative loss rates for asset-backed securities.
• The historical loss rate is adjusted for current conditions and reasonable and supportable forecasts.
• Changes in the allowance for credit losses are recognized in net investment income on the consolidated statements of operations.

[c. 190; p. 16] Equity securities accounting

• Equity securities include common stock, preferred stock, and mutual funds (even those primarily investing in debt securities).
• Investments in equity securities with a readily determinable fair value are carried on the balance sheet at fair value using quoted market prices.
• Changes in the carrying value of equity securities are included in net investment (losses) gains within the consolidated statements of operations.

[c. 191; p. 16] Mortgage loans accounting

• Investments in mortgage loans are classified as held for investment and carried at cost adjusted for unamortized premiums, discounts, and loan fees.
• Uncollectible amounts are written off in the period they are determined to be uncollectible.
• Interest on loans is recognized as interest receivable and included in other assets on the consolidated balance sheet.
• The Company elected the fair value option for mortgage loans effective January 1, 2023, as transition relief from ASU 2016-13 adoption.
• Under the fair value option, mortgage loans are measured at fair value, and changes in unrealized gains and losses are reported in net investment (losses) gains on the consolidated statements of operations.
• Interest income and amortization continue to be recognized in net investment income on the consolidated statements of operations.

[c. 192; p. 16] Equity method investments accounting

• Equity method investments include equity and equity securities of non-public entities and indirect investments in loans and loan collateral.
• The Company has equity investments in certain limited partnerships and corporations where it has significant influence but not control.
• The Company is not the primary beneficiary of variable interest entities and does not consolidate them.
• The equity method is used for investments in unconsolidated subsidiaries.
• Under the equity method, initial investment is recorded at cost and adjusted based on proportionate share of distributions and net income or loss of the investee.
• The difference between investment cost and proportionate share of underlying equity in net assets is a component of investment income.
• The Company amortizes this difference as an adjustment to its pro-rata share of equity method income over the useful life of the underlying asset.
• For equity securities of non-public entities where the Company lacks significant influence and a readily determinable fair value, investments are carried at cost, minus impairment, and adjusted for observable price changes in orderly transactions for identical or similar investments.
• Investments in indirect collateralized loans and loan collateral are held through and accounted for as an ownership interest in an unconsolidated subsidiary.
• Ownership interests in unconsolidated subsidiaries include investments in partnerships, joint ventures, and special purpose investment vehicles.
• The Company uses the equity method for these investments where it has significant influence but not control.

[c. 193; p. 16] Other long-term investments

• Other long-term investments consist of an investment in a limited partnership held at net asset value (NAV) and other long-term investment securities.

[c. 194; p. 16] Short-term investments

• Short-term investments primarily consist of money market funds.
• Short-term investments are carried at cost, which approximates fair value.

[c. 195; p. 16] Net investment income and realized gains/losses

• Net investment income consists of interest, dividends, and equity in earnings (losses) of unconsolidated subsidiaries, net of investment expenses.
• Interest income is recognized on an accrual basis.
• Dividends are recognized as earned at the ex-dividend date.
• Interest income on mortgage-backed and other asset-backed securities is recognized using the effective-yield method based on estimated principal repayments.
• Amortization of premium and accretion of discounts on debt securities are included in interest income.
• Net realized gains and losses on investments are recognized in net income using the specific identification method.

F. Reinsurance

[c. 196; p. 16] Reinsurance accounting principles

• The Company purchases prospective reinsurance for certain lines of business on a proportional, excess of loss, and facultative basis.
• Proportional reinsurance requires sharing losses and expenses with the reinsurer in exchange for a share of premiums.
• Excess of loss reinsurance shares losses, either proportionally or entirely, above a certain dollar threshold, for a negotiated cost.
• Facultative reinsurance covers specific risks and/or policies on either a proportional or excess of loss basis.
• Ceded unearned premium and reinsurance balances recoverable on paid and unpaid losses and settlement expenses are reported separately as assets.
• Reinsurance does not relieve the Company of its legal liability to policyholders.
• Reinsurance on unpaid losses and settlement expenses represents estimates of the portion of liabilities recoverable from reinsurers.
• On the Consolidated Statements of Operations, net earned premiums, losses and loss adjustment expenses, net, and underwriting, acquisition, and insurance expenses are presented net of reinsurance ceded.
• The Company purchases retroactive reinsurance for certain lines of business through loss portfolio transfers (LPT) and adverse development covers.
• Retroactive reinsurance contracts provide indemnification for losses related to past loss events, with the reinsurer sharing losses based on dollar thresholds.
• Income from retroactive reinsurance contracts is deferred and amortized into net income over the settlement period.
• Losses from retroactive reinsurance contracts are charged to net income immediately.
• Subsequent changes in the measurement of retroactive reinsurance contracts are accounted for using a full retrospective method.

[c. 197; p. 16] Deposit accounting for reinsurance

• Certain ceded reinsurance contracts that management determines do not transfer significant insurance risk are accounted for using the deposit method.
• The evaluation of significant insurance risk transfer assesses both timing risk and underwriting risk.
• A reinsurance contract may not transfer significant insurance risk if either underwriting risk, timing risk, or both are not deemed transferred.
• For contracts transferring only significant timing risk but not sufficient underwriting risk, a deposit asset is recorded equal to the initial cash outflow, offset by cash inflows from reinsurers.
• If cash outflows are expected to differ from cash inflows, an accretion rate is established at inception based on actuarial estimates.
• The deposit accounting asset is increased/decreased to the estimated receivable amount over the contract term.
• Deposit accretion is based on the expected rate of return implied from estimated cash inflows and outflows.
• The Company periodically reassesses the estimated ultimate receivable and the related expected rate of return on the deposit asset.
• Accretion of the deposit asset, including changes from estimated cash flow changes, is reflected as part of investment income.
• Several reinsurance contracts require deposit accounting due to insufficient underwriting risk transfer.
• No reinsurance contracts required deposit accounting due to insufficient timing risk transfer.

[c. 198; p. 16] Reinsurance recoverables and credit risk

• Reinsurance recoverables are carried net of an allowance for credit losses.
• The allowance for credit losses represents the current estimate of expected credit losses.
• The Company develops a historical loss rate using the A.M. Best impairment rate and rating transition study, which provides historical loss data for similarly rated reinsurance companies based on expected receivable duration.
• The historical loss rate is adjusted for current conditions, reasonable and supportable forecasts, and current economic conditions.
• Changes in the allowance for credit losses are recognized in underwriting, acquisition, and insurance expenses on the consolidated statements of operations.
• Reinsurance does not relieve the Company of its legal liability to policyholders.
• The Company continuously monitors the financial condition of its reinsurers, including reviewing annual financial statements and insurance industry developments.
• The Company analyzes credit risk of reinsurance recoverables by monitoring reinsurers' financial strength ratings from A.M. Best.
• The Company assesses the adequacy of collateral obtained where applicable.
• If reinsurers fail to fulfill obligations, the Company has access to collateral.
• Reinsurance collateral from reinsurers was USD 337.0m as of December 31, 2024, and USD 257.5m as of December 31, 2023.
• Reinsurance recoverables present potential exposures to individual reinsurers.
• Everest Reinsurance Co. represented 18.0% of reinsurance recoverable balances at December 31, 2024, and 20.4% at December 31, 2023.
• eMaxx Captives represented 16.8% of reinsurance recoverable balances at December 31, 2024, and 20.4% at December 31, 2023.
• Everest Reinsurance Co. and eMaxx Captives were the only reinsurers representing 10% or more of the Company’s reinsurance recoverable balances.
• Everest Reinsurance Co.'s financial strength rating from A.M. Best was A+ at December 31, 2024, and 2023.
• eMaxx Captives was not rated by A.M. Best at December 31, 2024, and 2023.

G. Concentration of Credit Risk

[c. 199; p. 16] Credit risk concentration

• Financial instruments that could lead to credit risk concentrations include cash and cash equivalents, restricted cash, investments, and premiums receivable, in addition to reinsurance recoverables.
• Cash equivalents and short-term investments consist of U.S. government securities and money market funds.
• Investments are diversified across various industries and geographic regions.
• The Company limits credit exposure to any single financial institution or issuer.
• The Company believes there is no significant concentration of credit risk related to cash and investments.
• As of December 31, 2024 and 2023, outstanding premiums receivable are diversified due to the large number of customer entities and their spread across different lines of business and geographic regions.
• Failure by distribution sources to remit premiums could lead to premium write-offs and a corresponding loss of income.

H. Deferred Policy Acquisition Costs

[c. 200; p. 16] Policy acquisition costs and premium deficiency

• Policy acquisition costs include commissions and premium taxes that vary with and are directly related to the production of new or renewal business.
• The Company defers policy acquisition costs and related ceding commissions, charging or crediting them to earnings proportionally with premium earned over the policy's life.
• A premium deficiency is recognized if expected losses, loss adjustment expenses, and unamortized acquisition costs exceed related unearned premiums.
• To recognize a premium deficiency, the Company first charges unamortized acquisition costs to expense to eliminate the deficiency.
• If the premium deficiency exceeds unamortized acquisition costs, a liability is accrued for the excess deficiency.
• Anticipated investment income is considered when determining premium deficiencies.
• Management determined no premium deficiency existed as of December 31, 2024 and 2023.

I. Goodwill and Intangible Assets

[c. 201; p. 16] Goodwill and intangible assets accounting policy

• Goodwill and intangible assets are recorded following a business combination.
• Goodwill is the excess of the purchase price over the fair value of acquired assets and assumed liabilities.
• The Company reviews purchase price allocation for up to one year post-acquisition and may make adjustments within this period.
• Identifiable intangible assets with a finite useful life are amortized over the period they are expected to contribute to future cash flows.
• Indefinite-lived intangible assets are not amortized.
• Goodwill and identifiable intangible assets are reviewed for recoverability annually in the fourth quarter, or on an interim basis if circumstances indicate a carrying amount may not be recoverable.
• No goodwill impairment was recorded for the years ended December 31, 2024 and 2023.

J. Property and Equipment

[c. 202; p. 16] Property and equipment accounting

• Property and equipment, included in other assets on the consolidated balance sheets, is recorded at cost less accumulated depreciation.
• Depreciation expense is recognized on a straight-line basis for financial statement purposes over periods ranging from three to seven years.

K. Leases

[c. 203; p. 16] Lease accounting policies

• Right-of-use (ROU) assets are included in other assets on the consolidated balance sheets.
• Lease liabilities are included in accounts payable and accrued liabilities on the consolidated balance sheets.
• For operating leases, the Company determines if a contract contains a lease at inception.
• The Company recognizes operating lease ROU assets and lease liabilities based on the present value of future minimum lease payments at the commencement date.
• The Company uses its incremental borrowing rate, based on information available at the commencement date, to determine the present value of future payments, as it does not have the interest rate implicit in its leases.
• Lease agreements may include options to extend or terminate.
• Options are exercised at the Company's discretion and are included in operating lease liabilities if it is reasonably certain the option will be exercised.
• Lease agreements have lease and non-lease components, which are accounted for as a single lease component.
• Operating lease cost for future minimum lease payments is recognized on a straight-line basis over the lease term.
• Sublease income is recognized on a straight-line basis over the sublease term.

L. Reserves for Losses and Loss Adjustment Expenses

[c. 204; p. 16] Reserves for losses and loss adjustment expenses

• Reserves for unpaid losses and loss adjustment expenses (LAE) represent the estimated ultimate cost of all unreported and reported but unpaid insured claims and the cost to adjust losses incurred as of the balance sheet date.
• Estimates for reserves are made using individual case-basis valuations of reported claims, statistical analyses, and various actuarial procedures.
• Estimates are based on historical information, industry and peer group information, and estimates of future trends in variable factors such as loss severity, loss frequency, and inflation.
• Estimates are regularly reviewed and adjusted as experience develops or new information becomes known.
• During the loss settlement period, estimates of liability on a claim may be refined and adjusted upward or downward.
• The ultimate liability may exceed or be less than the revised estimates, and the ultimate settlement of losses and related LAE may vary significantly from the estimate in financial statements.
• If actual liabilities exceed recorded amounts, there will be an adverse effect.
• If recorded reserves are determined to be more than adequate, it would lead to a reduction in reserves.

M. Premiums

[c. 205; p. 16] Premium recognition and receivables

• The Company earns and recognizes property and casualty and surety premiums on a pro-rata basis over the policy terms.
• Accident and health premiums are earned as billed, based on census data.
• Gross premiums written are reduced by ceded premiums from proportional, facultative, and excess of loss reinsurance costs for prospective reinsurance.
• Premiums receivable include deferred premiums, which are installment payments due from insureds under their policy payment terms.
• Premiums receivable are carried net of an allowance for credit losses, which represents the current estimate of expected credit losses.
• The Company develops a historical loss rate for credit losses using historical write-offs and aging of receivables.
• This historical loss rate is adjusted for current conditions, reasonable and supportable forecasts, and the ability to cancel coverage after a premium is past due.
• Changes in the allowance for credit losses are recognized in underwriting, acquisition, and insurance expenses on the consolidated statements of operations.

[c. 206; p. 16] Unearned premiums

• Unearned premiums represent the portion of gross premiums written applicable to the unexpired terms of insurance policies or reinsurance contracts in force.
• Ceded unearned premiums represent the portion of ceded premiums written applicable to the unexpired terms of insurance policies or reinsurance contracts in force.
• These unearned premiums are calculated on a pro-rata basis over the terms of the policies for both direct and ceded amounts.

N. Commission and Fee Income

[c. 207; p. 16] SUA commission revenue

• SUA commission revenue is generated from placing insurance policies on reinsurance programs via a reinsurance broker.
• The Company's single performance obligation for SUA commission revenue is the placement of insurance policies.
• The transaction price for SUA commission revenue is fixed at contract inception and based on a percentage of premiums placed.
• The Company recognizes 100% of the transaction price as revenue when the performance obligation is satisfied at the point a policy is placed, as there are no constraints on revenue.

[c. 208; p. 16] SUA fee income

• SUA fee income is generated from placing insurance policies with a third-party insurance company.
• The Company's single performance obligation for SUA fee income is the placement of the policy.
• The transaction price for SUA fee income is variable at contract inception and based on a percentage of premium, which is determined by risk factors that vary monthly (e.g., employee census data, worker roles).
• The Company estimates its transaction price over the life of the policy using the expected value method.
• Revenue from SUA fee income is recognized at the point the policy is placed.
• Changes in the estimate of variable consideration for SUA fee income are recognized in the month they occur.

O. Income Taxes

[c. 209; p. 16] Income tax accounting principles

• Income tax expense is accrued for tax effects of transactions reported on consolidated financial statements.
• Provision for income taxes includes currently due taxes plus deferred taxes from temporary differences between financial statement and income tax purposes.
• A valuation allowance is established for any deferred tax asset not expected to be realized.
• Deferred tax assets and liabilities are measured using enacted tax rates expected to apply to taxable income in the years temporary differences are expected to be recovered or settled.
• The effect on deferred tax assets and liabilities from a change in tax rates is recognized in income in the period that includes the enactment date.
• A liability for uncertain tax positions is recorded if it is more likely-than-not that the tax position will not be sustained upon examination by the appropriate tax authority.
• Changes in the liability for uncertain tax positions are reflected in income tax expense in the period when a new uncertain tax position arises, judgment changes about the likelihood of an uncertainty, the tax issue is settled, or the statute of limitation expires.
• Any potential net interest income or expense and penalties related to uncertain tax positions are recorded on the Consolidated Statements of Operations.

[c. 210; p. 16] Tax filings and premium taxes

• The Company files a consolidated federal income tax return in the United States and certain other state tax returns.
• Admitted insurance subsidiaries pay premium taxes on gross written premiums in lieu of most state income or franchise taxes.
• Premium tax expense is recognized within underwriting, acquisition and insurance expense on the Consolidated Statements of Operations.

P. Fair Value of Financial Instruments

[c. 211; p. 16] Fair Value Measurement Framework

• Fair value for each class of financial instrument is estimated based on the framework in fair value accounting guidance.
• The guidance prioritizes observable inputs and minimizes unobservable inputs for fair value measurement.
• Fair value hierarchy disclosures are based on the quality of inputs used.
• The hierarchy gives highest priority to unadjusted quoted prices in active markets for identical assets or liabilities (Level 1 measurements).
• The hierarchy gives lowest priority to unobservable inputs (Level 3 measurements).
• The Company uses widely recognized, third-party pricing sources to determine fair values of financial instruments.
• The Company understands the valuation methodologies and inputs of these third-party pricing sources.
• Further details regarding fair value disclosures are in Note 4.

Q. Stock-Based Compensation

[c. 212; p. 16] Stock-based compensation accounting

• Estimated fair value of employee stock options and similar awards are expensed.
• Compensation cost for equity instrument awards to employees is measured based on grant-date fair value.
• Compensation expense is recognized over the service period during which awards are expected to vest.
• Tax effects related to share-based payments are made through net earnings.
• Further discussion and disclosures regarding stock-based compensation are in note 18.

[c. 213; p. 16] Employee Stock Purchase Plan (ESPP)

• The Company's employee stock purchase plan ("ESPP") allows all employees to purchase common stock at a discount.
• Compensation cost for the ESPP is recognized on a straight-line basis over the offering period.

R. Earnings Per Share

[c. 214; p. 16] Basic EPS calculation methodology

• Basic earnings per share (EPS) is calculated using the two-class method.
• Undistributed earnings are allocated to participating securities based on their potential share in earnings, assuming all earnings for the period have been distributed.
• Basic EPS is calculated by dividing net income attributable to common stockholders by the weighted-average number of common shares outstanding for the period.
• Common shares with unsatisfied contingencies, such as vesting requirements, are excluded from basic EPS.
• The Company's preferred shares participate in dividends and distributions with common stock on an as-converted basis and are considered a participating security.
• Instruments awarded to employees that grant the right to purchase common stock at a fixed price were included as potential common shares, weighted for the portion of the period they were granted, if dilutive.
• Common and preferred shares financed by stock notes are contingently issuable instruments, requiring the holder to return shares if stock notes are not paid off.
• These contingently issuable instruments are excluded from basic and diluted EPS if specified conditions are not met, presuming the end of the period is the end of the contingency period.
• The impact of contingently issuable instruments on diluted EPS was calculated using the treasury stock method and included in the reconciliation of the denominator for basic and diluted EPS computations for the year ended December 31, 2023.
• All outstanding stock notes were settled during 2024, resulting in no impact on the Company's basic and diluted EPS computations for the year ended December 31, 2024.

[c. 215; p. 16] Diluted EPS calculation methodology

• Instruments convertible into common shares are included in diluted weighted-average common shares outstanding on an if-converted basis, using the legal conversion rate for the respective period, if dilutive.
• Share-based awards to employees with only service conditions are included as potential common shares, weighted for the unvested portion of the period, if dilutive.
• Share-based awards to employees with performance and service or market conditions are included as potential common shares, presuming the end of the period is the end of the contingency period, if dilutive.
• If common share adjustments increase EPS or reduce loss per share, the effect is anti-dilutive, and diluted net earnings or net loss per share is computed excluding these common share equivalents.

S. Recent Accounting Pronouncements

[c. 216; p. 16] Recent accounting standards adopted

• In November 2023, the FASB issued ASU 2023-07, Improvements to Reportable Segment Disclosures (Topic 280).
• ASU 2023-07 requires segment disclosures for:
  • significant segment expenses regularly provided to the chief operating decision maker (“CODM”).
  • how the CODM uses reported measure(s) of segment profitability in assessing segment performance and resource allocation.
  • the title and position of the CODM.
• Entities with a single reportable segment must provide full segment disclosures.
• The guidance became effective for fiscal years beginning after December 15, 2023, and interim periods within fiscal years beginning after December 15, 2024.
• This update is applied retrospectively to all prior periods presented.
• The Company has added additional segment disclosures as required by ASU 2023-07, detailed in Note 12.

[c. 217; p. 16] Recent accounting standards not yet adopted

• In December 2023, the FASB issued ASU 2023-09, Improvements to Income Tax Disclosures (Topic 740).
• ASU 2023-09 requires public companies to provide enhanced rate reconciliation disclosures annually, including specific categories and additional information meeting a quantitative threshold.
• This update also requires public companies to disaggregate income taxes paid by federal, state, and foreign taxes.
• The guidance is effective for fiscal years beginning after December 15, 2024.
• The Company is evaluating the effect of ASU 2023-09 and currently does not expect a material impact on its consolidated financial statements.
• In November 2024, the FASB issued ASU 2024-03, requiring disaggregated disclosure of income statement expenses for public business entities (“PBEs”).
• ASU 2024-03 does not change expense captions on the income statement but requires disaggregation of certain expense captions into specified categories in footnotes.
• ASU 2024-03 requires a footnote disclosure about specific expenses by requiring PBEs to disaggregate, in a tabular presentation, each relevant income statement expense caption that includes any of the following natural expenses:
  • purchases of inventory.
  • employee compensation.
  • depreciation.
  • intangible asset amortization.
  • depreciation, depletion, and amortization recognized as part of oil- and gas-producing activities or other types of depletion expenses.
• The tabular disclosure will also include certain other expenses, when applicable.
• In January 2025, the FASB issued ASU 2025-01 to clarify the effective date of ASU 2024-03 as the first annual reporting period beginning after December 15, 2026, and interim reporting periods within annual reporting periods beginning after December 15, 2027.
• The Company is evaluating the effect of the amendments on its consolidated financial statements.

2. Goodwill and Intangible Assets

[c. 218; p. 16] Goodwill and intangible assets overview

• The tables present the carrying amount and changes in the balance of goodwill by reporting unit at December 31, 2024 and 2023.
• The tables present the carrying amount and changes in the balance of other intangible assets at December 31, 2024 and 2023.
• The Company's indefinite-lived intangible assets include insurance licenses and trademarks.
• The Company's finite-lived intangible assets, including policy renewals, agency relationships (within agent relationships), and non-compete/exclusivity agreements (within non-competes), had a weighted average useful life of approximately 15 years as of December 31, 2024.

[c. 219; p. 16] Intangible assets amortization expense

• The Company recognized approximately USD 1.1m in amortization expense for the year ended December 31, 2024.
• The Company recognized approximately USD 1.5m in amortization expense for the years ended December 31, 2023 and 2022.
• A table sets forth the estimated future net amortization expense of intangible assets.

[c. 220; p. 16]

Goodwill net balance by segment

($ in thousands)	Accident and Health	Surety	Industry Solutions	Other	Total
Goodwill
Gross balance at December 31, 2023	91,577	6,781	10,204	3,879	112,441
Accumulated impairment at December 31, 2023	( 44,821 )	—	—	( 1,886 )	( 46,707 )
Net balance at December 31, 2024	46,756	6,781	10,204	1,993	65,734

($ in thousands)	Accident and Health	Surety	Industry Solutions	Other	Total
Goodwill
Gross balance at December 31, 2022	91,577	6,781	10,204	3,879	112,441
Accumulated impairment at December 31, 2022	( 44,821 )	—	—	( 1,886 )	( 46,707 )
Net balance at December 31, 2023	46,756	6,781	10,204	1,993	65,734

($ in thousands)	Agent Relationships	Non-competes	Trademarks	Licenses	Total
Other Intangible Assets
Gross balance at December 31, 2023	24,491	1,117	999	14,019	40,626
Accumulated amortization at December 31, 2023	( 16,808 )	( 1,117 )	—	—	( 17,925 )
Amortization	( 1,087 )	—	—	—	( 1,087 )
Net balance at December 31, 2024	6,596	—	999	14,019	21,614

($ in thousands)	Agent Relationships	Non-competes	Trademarks	Licenses	Total
Other Intangible Assets
Gross balance at December 31, 2022	24,441	1,117	999	14,019	40,576
Accumulated amortization at December 31, 2022	( 15,547 )	( 893 )	—	—	( 16,440 )
Additions	50	—	—	—	50
Amortization	( 1,261 )	( 224 )	—	—	( 1,485 )
Net balance at December 31, 2023	7,683	—	999	14,019	22,701

($ in thousands)
Years Ending December 31,	Amount
2025	1,016
2026	553
2027	553
2028	553
2029	553

3. Investments

[c. 221; p. 16] Investment portfolio fair value and amortized cost

• Tables set forth amortized cost and fair value by investment category at December 31, 2024 and December 31, 2023.
• Amortized cost and estimated fair value of fixed maturity securities, available for sale, at December 31, 2024 are shown by contractual maturity.
• Expected maturities may differ from contractual maturities due to borrower call/prepayment rights or portfolio sales prior to maturity driven by interest rates, tax considerations, or other factors.
• Fixed maturity securities, held-to-maturity, at December 31, 2024 consisted entirely of asset-backed securities not due at a single maturity date.

[c. 222; p. 16] Pledged assets

• At December 31, 2024, the Company had U.S. government agencies mortgage-backed fixed maturity securities with a carrying value of approximately USD 66.2m pledged as collateral for a loan (the "FHLB Loan") from the Federal Home Loan Bank of Dallas ("FHLB").
• The Company retains all rights regarding these pledged securities under the Advances and Security Agreement.
• At December 31, 2024, the Company had assets with fair values of approximately USD 28.0m pledged as collateral for performance obligations under reinsurance agreements.
• The Company retains all rights regarding these pledged securities under the trust agreements.
• Pledged assets for reinsurance agreements included USD 24.3m in residential mortgage-backed securities, USD 2.2m in short-term investments, and USD 1.5m in cash and cash equivalents and other assets.

[c. 223; p. 16] Unrealized losses and impairment assessment

• Tables set forth gross unrealized losses and corresponding fair values of investments, aggregated by length of time in a continuous unrealized loss position as of December 31, 2024 and 2023.
• The Company monitors available-for-sale fixed maturity securities with fair values less than cost or amortized cost for impairment, requiring significant management judgment.
• Judgments could change, potentially impacting reported amounts negatively.
• Factors considered for fixed maturity securities include issuer financial condition (receipt of scheduled principal and interest), and intent to sell (likelihood of being required to sell before recovery).
• As of December 31, 2024, the Company had 778 lots of fixed maturity securities in an unrealized loss position.
• The Company does not intend to sell these securities and is not likely to be required to sell them before maturity or recovery of cost basis.
• The Company reviewed investments at December 31, 2024, and determined no credit impairment existed in gross unrealized holding losses.
• For U.S. government and municipal securities, the decline in fair values was due to interest rate changes, not credit quality.
• The Company does not intend to sell these U.S. government and municipal securities and expects recovery, thus not considering them impaired.
• For corporate securities and miscellaneous, the decline in fair values was due to interest rate changes, not credit quality.
• The Company reviewed issuers for significant adverse changes in financial condition, credit enhancement quality, ratings decreases, negative outlooks, or payment failures.
• After review, the decline in fair values for corporate securities was attributed to interest rates, not credit quality.
• The Company does not intend to sell these corporate securities and expects recovery, thus not considering them impaired.
• For residential mortgage-backed, commercial mortgage-backed, and other asset-backed securities, the decline in fair values was due to interest rate changes, not credit quality.
• The Company does not intend to sell these mortgage-backed and asset-backed securities and expects recovery, thus not considering them impaired.

[c. 224; p. 16] Net investment gains (losses)

• A table sets forth the components of net investment gains (losses) for the years ended December 31, 2024, 2023, and 2022.

[c. 225; p. 16] Proceeds from sales of securities

• A table sets forth the proceeds from sales of available-for-sale fixed maturity securities and equity securities for the years ended December 31, 2024, 2023, and 2022.

[c. 226; p. 16] Net investment income

• A table sets forth the components of net investment income for the years ended December 31, 2024, 2023, and 2022.

[c. 227; p. 16] Net unrealized gains (losses)

• A table sets forth the change in net unrealized gains (losses) on the Company’s investment portfolio, net of deferred income taxes, included in other comprehensive loss for the years ended December 31, 2024, 2023, and 2022.

[c. 228; p. 16] Regulatory deposits

• Various state regulations require the Company to maintain cash, investment securities, or letters of credit on deposit with states in a depository account.
• At December 31, 2024, cash and investment securities on deposit had carrying values of approximately USD 66.8m.
• At December 31, 2023, cash and investment securities on deposit had carrying values of approximately USD 65.3m.

[c. 229; p. 16]

3. Investments

($ in thousands)	Amortized Cost	Gross Unrealized Gains	Gross Unrealized Losses	Allowance for Credit Losses	Fair Value
December 31, 2024
Fixed maturity securities, available-for-sale:
U.S. government securities	26,577	35	( 126 )	—	26,486
Corporate securities and miscellaneous	433,298	5,618	( 13,288 )	—	425,628
Municipal securities	89,966	116	( 5,366 )	—	84,716
Residential mortgage-backed securities	408,585	1,875	( 16,627 )	—	393,833
Commercial mortgage-backed securities	70,262	545	( 1,443 )	—	69,364
Other asset-backed securities	291,578	2,447	( 1,834 )	—	292,191
Total fixed maturity securities, available-for-sale	1,320,266	10,636	( 38,684 )	—	1,292,218
Fixed maturity securities, held-to-maturity:	—	—	—	—	—
Other asset-backed securities	39,396	—	( 436 )	( 243 )	38,717
Total fixed maturity securities, held-to-maturity	39,396	—	( 436 )	( 243 )	38,717

($ in thousands)	Amortized Cost	Gross Unrealized Gains	Gross Unrealized Loss	Allowance for Credit Losses	Fair Value
December 31, 2023
Fixed maturity securities, available-for-sale:
U.S. government securities	44,685	202	( 721 )	—	44,166
Corporate securities and miscellaneous	392,773	6,408	( 15,761 )	—	383,420
Municipal securities	98,266	655	( 6,143 )	—	92,778
Residential mortgage-backed securities	292,568	3,556	( 14,498 )	—	281,626
Commercial mortgage-backed securities	31,411	449	( 1,926 )	—	29,934
Other asset-backed securities	188,010	1,221	( 3,504 )	—	185,727
Total fixed maturity securities, available-for-sale	1,047,713	12,491	( 42,553 )	—	1,017,651
Fixed maturity securities, held-to-maturity:	—	—	—	—	—
Other asset-backed securities	43,315	—	( 1,969 )	( 329 )	41,017
Total fixed maturity securities, held-to-maturity	43,315	—	( 1,969 )	( 329 )	41,017

($ in thousands)	Amortized Cost	Fair Value
Due in less than one year	23,332	23,292
Due after one year through five years	279,144	273,755
Due after five years through ten years	197,373	192,929
Due after ten years	49,992	46,854
Mortgage-backed securities	478,847	463,197
Other asset-backed securities	291,578	292,191
Total	1,320,266	1,292,218

	Less than 12 Months		12 Months or More		Total
($ in thousands)	Fair Value	Gross Unrealized Losses	Fair Value	Gross Unrealized Losses	Fair Value	Gross Unrealized Losses
December 31, 2024
Fixed maturity securities, available-for-sale:
U.S. government securities	15,938	( 34 )	2,297	( 92 )	18,235	( 126 )
Corporate securities and miscellaneous	136,888	( 2,060 )	81,232	( 11,228 )	218,120	( 13,288 )
Municipal securities	41,930	( 1,046 )	27,687	( 4,320 )	69,617	( 5,366 )
Residential mortgage-backed securities	201,407	( 3,366 )	82,496	( 13,261 )	283,903	( 16,627 )
Commercial mortgage-backed securities	9,411	( 126 )	13,178	( 1,317 )	22,589	( 1,443 )
Other asset-backed securities	75,119	( 721 )	29,851	( 1,113 )	104,970	( 1,834 )
Total fixed maturity securities, available-for-sale	480,693	( 7,353 )	236,741	( 31,331 )	717,434	( 38,684 )
Fixed maturity securities, held-to-maturity:	—	—	—	—	—	—
Other asset-backed securities	2,144	( 2 )	36,573	( 434 )	38,717	( 436 )
Total fixed maturity securities, held-to-maturity:	2,144	( 2 )	36,573	( 434 )	38,717	( 436 )
Total	482,837	( 7,355 )	273,314	( 31,765 )	756,151	( 39,120 )

	Less than 12 Months		12 Months or More		Total
($ in thousands)	Fair Value	Gross Unrealized Losses	Fair Value	Gross Unrealized Losses	Fair Value	Gross Unrealized Losses
December 31, 2023
Fixed maturity securities, available-for-sale:
U.S. government securities	7,342	( 25 )	25,604	( 696 )	32,946	( 721 )
Corporate securities and miscellaneous	26,742	( 570 )	174,947	( 15,191 )	201,689	( 15,761 )
Municipal securities	16,815	( 290 )	47,269	( 5,853 )	64,084	( 6,143 )
Residential mortgage-backed securities	37,634	( 602 )	103,495	( 13,896 )	141,129	( 14,498 )
Commercial mortgage-backed securities	4,942	( 74 )	15,290	( 1,852 )	20,232	( 1,926 )
Other asset-backed securities	27,887	( 106 )	75,253	( 3,398 )	103,140	( 3,504 )
Total fixed maturity securities, available-for-sale	121,362	( 1,667 )	441,858	( 40,886 )	563,220	( 42,553 )
Fixed maturity securities, held-to-maturity:	—	—	—	—	—	—
Other asset-backed securities	—	—	41,017	( 1,969 )	41,017	( 1,969 )
Total fixed maturity securities, held-to-maturity:	—	—	41,017	( 1,969 )	41,017	( 1,969 )
Total	121,362	( 1,667 )	482,875	( 42,855 )	604,237	( 44,522 )

($ in thousands)	2024	2023	2022
Gross realized gains
Fixed maturity securities, available-for sale	2,662	1,042	313
Equity securities	8,062	6,035	3,865
Other	127	2	36
Total	10,851	7,079	4,214
Gross realized losses	—	—	—
Fixed maturity securities, available-for sale	( 8,161 )	( 1,879 )	( 958 )
Equity securities	( 4,132 )	( 5,256 )	( 3,827 )
Other	( 223 )	( 2 )	( 76 )
Total	( 12,516 )	( 7,137 )	( 4,861 )
Net unrealized gains (losses) on investments	—	—	—
Equity securities	7,500	11,516	( 15,058 )
Mortgage loans	421	( 386 )	—
Net investment gains (losses)	6,256	11,072	( 15,705 )

($ in thousands)	2024	2023	2022
Fixed maturity securities, available-for sale	217,468	26,626	13,964
Equity securities	37,534	40,201	37,177

($ in thousands)	2024	2023	2022
Income:
Fixed maturity securities, available-for sale	57,574	34,703	18,481
Fixed maturity securities, held-to-maturity	4,177	4,163	5,375
Equity securities	2,720	3,418	3,579
Equity method investments	2,524	( 9,434 )	6,015
Mortgage loans	5,153	5,474	4,767
Indirect loans	( 2,400 )	( 4,155 )	4,846
Short-term investments and cash	14,851	11,392	1,498
Other	3,000	318	( 77 )
Total investment income	87,599	45,879	44,484
Investment expenses	( 6,913 )	( 5,557 )	( 7,553 )
Net investment income	80,686	40,322	36,931

($ in thousands)	2024	2023	2022
Fixed maturity securities	1,046	25,952	( 60,918 )
Deferred income taxes	( 213 )	( 5,420 )	12,793
Total	833	20,532	( 48,125 )

4. Fair Value Measurements

[c. 230; p. 16] Fair value measurement principles

• The Company's financial instruments include assets and liabilities carried at fair value, and those carried at cost or amortized cost but disclosed at fair value.
• The market approach is generally applied to determine fair value, using prices and data from market transactions involving identical or comparable assets and liabilities.
• Fair value of investments is determined using data primarily from third-party investment managers or pricing vendors.
• Periodic analyses are performed on third-party prices to ensure they are reasonable estimates of fair value, including reviewing month-to-month fluctuations and comparing valuations from different pricing services for identical securities.

[c. 231; p. 16] Fair value hierarchy levels

• The Company classifies financial instruments into a three-level hierarchy.
• Level 1: Inputs are unadjusted, quoted prices for identical assets or liabilities in active markets at the measurement date.
• Level 2: Inputs are other than quoted prices included in Level 1 that are observable for the asset or liability through corroboration with market data at the measurement date.
• Level 3: Unobservable inputs that reflect management’s best estimate of what market participants would use in pricing the asset or liability at the measurement date.

[c. 232; p. 16] Fair value estimation methods by instrument type

• U.S. government securities, mutual funds, and common stock: Fair value is measured using unadjusted quoted prices for identical instruments in an active exchange, representing Level 1 inputs.
• Preferred stocks, municipal securities, corporate securities, and miscellaneous: A pricing model is used that utilizes market-based inputs such as trades in illiquid markets for specific securities or active markets for similar securities.
  • The model considers benchmark yields, issuer spreads, security terms and conditions, and other market data, representing Level 2 fair value inputs.
• Commercial mortgage-backed securities, residential mortgage-backed securities, and other asset-backed securities: A pricing model is used that utilizes market-based inputs including dealer quotes, market spreads, and yield curves.
  • Individual tranches may be evaluated by determining cash flows using security terms, collateral performance, credit information, benchmark yields, and estimated prepayments, representing Level 2 fair value inputs.
• Fixed maturity securities (available for sale) and equity securities classified as Level 3: These include corporate securities and other asset-backed securities managed by an independent asset manager and priced by an independent pricing provider.
  • The provider estimates value using the discounted net present value of cash flows method with an unobservable discount rate.
  • The discount rate spread represents the risk associated with future cash flows, including inflation, opportunity cost, and time value of money, representing Level 3 fair value inputs.

[c. 233; p. 16] Discount rate range for Level 3 fixed maturity and equity securities

• The range of the discount rate for Level 3 fixed maturity and equity securities is set forth as of December 31, 2024.

[c. 234; p. 16] Mortgage loans fair value estimation

• Mortgage loans have variable interest rates and are collateralized by real property.
• Fair value of mortgage loans is determined using the income approach with observable and unobservable (Level 3) inputs.
• The unobservable input is the spread applied to a prime rate for discounting cash flows.
• This spread represents the incremental cost of capital based on the borrower’s ability to make future payments and the collateral value relative to the loan balance, subject to judgment and uncertainty.
• The range and weighted average of the spread, weighted by relative fair value, are set forth as of December 31, 2024, and December 31, 2023.

[c. 235; p. 16] Investment in RedBird Capital Partners

• The Company holds an investment in a limited partnership with RedBird Capital Partners, which invests in Bishop Street Underwriters, LLC (MGA), included in other long-term investments.
• The investment had a fair value of USD 28.2m at December 31, 2024, determined using the net asset value.
• Procedures to assess reasonableness of fair value include obtaining and reviewing audited financial statements.
• The unfunded commitment related to this investment was USD 24.4m at December 31, 2024.
• The Company may sell its interest with appropriate prior written notice and general partner approval.
• This investment is measured at fair value using the net asset value per share practical expedient under Accounting Standard Codification 820-10 and is not classified in the fair value hierarchy.

[c. 236; p. 16] Fair value hierarchy tables

• Tables setting forth the Company’s investments within the fair value hierarchy are provided for December 31, 2024, and December 31, 2023.
• Tables setting forth changes in fair value of instruments carried at fair value with a Level 3 measurement are provided for the years ended December 31, 2024, and 2023.

[c. 237; p. 16] Nonrecurring fair value measurements and disclosures

• Certain assets, including investments in indirect loans and loan collateral, equity method investments, and other invested assets, are measured at fair value on a nonrecurring basis only when impaired.
• The Company is required to disclose fair values of other financial instruments where practicable to estimate fair value, in addition to those recorded at fair value in the consolidated balance sheets.
• Estimated fair value amounts, defined as the quoted market price, are determined using available market information and other valuation methodologies.
• Considerable judgment is required for fair value estimates when quoted market prices are unavailable, meaning estimates are not necessarily indicative of amounts realizable in a current market exchange.
• Different market assumptions or estimation methodologies may affect estimated fair value amounts.
• Methods and assumptions used for estimating fair value disclosures of other financial instruments are provided.

[c. 238; p. 16] Fair value estimation for other financial instruments

• Fixed maturity securities, held-to-maturity: Consist of senior and junior notes with target rates of return.
  • As of December 31, 2024, fair value was determined using the income approach with unobservable (Level 3) inputs.
• Notes payable: Carrying value approximates estimated fair value because notes accrue interest at current market rates plus a spread.
  • Fair value is determined using the income approach with observable (Level 2) inputs.
• Subordinated debt: Consists of Unsecured Subordinated Notes due May 24, 2039, with a fixed interest rate.
  • Fair value is determined using the income approach with observable (Level 2) inputs.

[c. 239; p. 16] Carrying and fair values of debt

• A table sets forth the Company’s carrying and fair values of notes payable and subordinated debt as of December 31, 2024, and December 31, 2023.
• Other financial instruments qualify as insurance-related products and are specifically exempted from fair value disclosure requirements.

[c. 240; p. 16]

4. Fair Value Measurements

	December 31, 2024
High	8.00%
Low	5.70%
Weighted average	6.60%

	December 31, 2024	December 31, 2023
High	10.00%	9.50%
Low	7.00%	3.25%
Weighted average	7.93%	7.05%

December 31, 2024
($ in thousands)	Level 1	Level 2	Level 3	Total
Fixed maturity securities, available-for-sale:
U.S. government securities	26,486	—	—	26,486
Corporate securities and miscellaneous	—	354,815	70,813	425,628
Municipal securities	—	84,716	—	84,716
Residential mortgage-backed securities	—	393,833	—	393,833
Commercial mortgage-backed securities	—	69,364	—	69,364
Other asset-backed securities	—	285,084	7,107	292,191
Total fixed maturity securities, available-for-sale	26,486	1,187,812	77,920	1,292,218
Fixed maturity securities, held-to-maturity:	—	—	—	—
Other asset-backed securities	—	—	38,717	38,717
Total fixed maturity securities, held-to-maturity	—	—	38,717	38,717
Equity securities:	—	—	—	—
Common stocks	64,251	—	—	64,251
Preferred stocks	—	1,164	—	1,164
Mutual funds	40,839	—	—	40,839
Total equity securities	105,090	1,164	—	106,254
Mortgage loans	—	—	26,490	26,490
Short-term investments	274,929	—	—	274,929
Total	406,505	1,188,976	143,127	1,738,608

December 31, 2023
($ in thousands)	Level 1	Level 2	Level 3	Total
Fixed maturity securities, available-for-sale:
U.S. government securities	44,166	—	—	44,166
Corporate securities and miscellaneous	—	383,420	—	383,420
Municipal securities	—	92,778	—	92,778
Residential mortgage-backed securities	—	281,626	—	281,626
Commercial mortgage-backed securities	—	29,934	—	29,934
Other asset-backed securities	—	185,727	—	185,727
Total fixed maturity securities, available-for-sale	44,166	973,485	—	1,017,651
Fixed maturity securities, held-to-maturity:	—	—	—	—
Other asset-backed securities	—	—	41,017	41,017
Total fixed maturity securities, held-to-maturity:	—	—	41,017	41,017
Equity securities:	—	—	—	—
Common stocks	67,425	—	—	67,425
Preferred stocks	—	7,358	—	7,358
Mutual funds	43,466	—	—	43,466
Total equity securities	110,891	7,358	—	118,249
Mortgage loans	—	—	50,070	50,070
Short-term investments	270,226	—	—	270,226
Total	425,283	980,843	91,087	1,497,213

($ in thousands)	Fixed Maturity Securities, Available-For-Sale	Mortgage Loans
Balance at December 31, 2023	—	50,070
Total gains (losses) for the period recognized in net investment gains (losses)	( 195 )	420
Issuances	—	649
Settlements	—	( 24,649 )
Purchases	77,979	—
Sales/Disposals	( 374 )	—
Total unrealized gains for the period recognized in accumulated comprehensive income (loss)	510	—
Balance at December 31, 2024	77,920	26,490
Total gains for the period recognized in net investment gains (losses) attributable to the change in unrealized gains or losses relating to assets held as of period end	—	411

($ in thousands)	Mortgage Loans
Balance at December 31, 2022	52,842
Total losses for the period recognized in net investment gains (losses)	( 385 )
Issuances	27,642
Settlements	( 30,029 )
Balance at December 31, 2023	50,070
Total losses for the period recognized in net investment gains (losses) attributable to the change in unrealized gains or losses relating to assets held as of period end	( 426 )

	December 31, 2024		December 31, 2023
($ in thousands)	Carrying Value	Fair Value	Carrying Value	Fair Value
Notes payable
FHLB Loan	57,000	56,200	—	—
Revolving credit facility	43,000	43,000	50,000	50,000
Notes payable	100,000	99,200	50,000	50,000
Subordinated debt	—	—	—	—
Junior subordinated interest debentures	—	—	59,186	59,794
Unsecured subordinated notes	19,536	20,541	19,504	21,378
Subordinated debt, net of debt issuance costs	19,536	20,541	78,690	81,172

5. Mortgage Loans

[c. 241; p. 16] Mortgage loan portfolio overview

• The Company has invested in Separately Managed Accounts ("SMA1" and "SMA2").
• As of December 31, 2024 and December 31, 2023, the Company held direct investments in mortgage loans from various creditors through SMA1 and SMA2.
• The Company’s mortgage loan portfolios are primarily senior loans on real estate across the U.S..
• Loans earn interest at a fixed spread above a prime rate.
• Loans mature in approximately 2 to 3 years from loan origination.
• Principal amounts of loans range between 64% to 80% of the property’s appraised value at the time the loans were made.

[c. 242; p. 16] Mortgage loan financial data

• The carrying value of the Company’s mortgage loans as of December 31, 2024 and December 31, 2023 is set forth in a table.
• The Company’s gross investment income for mortgage loans for the years ended December 31, 2024, 2023 and 2022 is set forth in a table.

[c. 243; p. 16] Mortgage loan collectibility and status

• Uncollectible amounts on loans are determined on an individual loan basis based on consultations with the Company’s specialized investment manager, consideration of adverse situations affecting borrower repayment ability, estimated value of underlying collateral, and other relevant factors.
• The Company writes off uncollectible amounts in the period they are determined to be uncollectible.
• There was no write-off for uncollectible amounts during the years ended December 31, 2024, 2023 and 2022.
• As of December 31, 2024, no mortgage loans were in the process of foreclosure.
• As of December 31, 2024, no mortgage loans were not producing income for the previous 12 months.
• As of December 31, 2023, approximately USD 7.1m of mortgage loans were in the process of foreclosure.
• As of December 31, 2023, USD 6.8m of mortgage loans were not producing income for the previous 12 months.

[c. 244; p. 16]

5. Mortgage Loans

($ in thousands)	December 31, 2024	December 31, 2023
Commercial	8,474	14,469
Retail	10,032	16,072
Hospitality	7,984	12,744
Industrial	—	6,785
—	26,490	50,070

($ in thousands)	2024	2023	2022
Commercial	2,025	2,340	1,242
Retail	1,853	1,853	1,255
Hospitality	1,277	1,034	411
Office	—	203	385
Multi-family	—	44	909
Industrial	—	—	565
—	5,155	5,474	4,767

6. Equity Method Investments and Other

[c. 245; p. 16] Equity method investments overview

• Table presents carrying value and ownership percentage of the Company’s equity method investments as of December 31, 2024 and 2023.
• Table presents components of net investment income (loss) from equity method investments for the years ended December 31, 2024, 2023, and 2022.
• Table presents unfunded commitment of equity method investments as of December 31, 2024 and 2023.

[c. 246; p. 16] Equity method investment accounting

• Difference between investment cost and proportionate share of underlying equity in net assets is allocated to the equity method investment's assets and liabilities.
• Company amortizes the difference in net assets over the useful life of a similar asset as the underlying equity method investment.
• For investment in RISCOM, a similar asset is agent relationships, and the Company amortizes this difference over a 15-year useful life.
• Table presents the Company’s recorded investment in RISCOM compared to its share of underlying equity as of December 31, 2024 and 2023.
• Table presents the Company’s recorded investment in JVM Funds LLC compared to its share of underlying equity as of December 31, 2024 and 2023.

[c. 247; p. 16] Indirect loans and loan collateral

• As of December 31, 2024 and 2023, the Company held indirect investments in collateralized loans and loan collateral through SMA1 and SMA2.
• Table presents the carrying value of SMA1 and SMA2 as of December 31, 2024 and 2023.

[c. 248; p. 16]

Carrying value & ownership % by equity method investments

($ in thousands)	December 31, 2024		December 31, 2023
	Carrying Value	Ownership %	Carrying Value	Ownership %
Arena Special Opportunities Fund, LP units	34,936	15.3%	41,046	16.2%
JVM Funds LLC units	17,229	10.1%	20,061	10.1%
RISCOM	5,013	20.0%	4,121	20.0%
Hudson Ventures Fund 2 LP units	4,967	2.5%	4,669	2.5%
Arena SOP LP units	1,474	10.9%	2,463	12.3%
Brewer Lane Ventures Fund II LP units	1,040	2.4%	560	2.5%
Dowling Capital Partners LP units	666	5.0%	1,708	6.2%
—	65,325	—	74,628	—

($ in thousands)	2024	2023	2022
Arena Special Opportunities Fund, LP units	2,375	( 2,880 )	3,719
RISCOM	1,492	884	1,471
Dowling Capital Partners LP units	1,463	927	502
Universa Black Swan LP units	—	( 988 )	( 3,028 )
Brewer Lane Ventures Fund II LP	( 110 )	( 78 )	—
Hudson Ventures Fund II LP units	( 153 )	170	379
Arena SOP LP units	( 989 )	( 6,271 )	3,042
JVM Funds LLC	( 1,554 )	( 1,198 )	( 70 )
—	2,524	( 9,434 )	6,015

($ in thousands)	December 31, 2024	December 31, 2023
Brewer Lane Ventures Fund II LP units	4,077	4,610
Hudson Ventures Fund 2 LP units	397	848
Dowling Capital Partners LP units	386	386
—	4,860	5,844

($ in thousands)	December 31, 2024	December 31, 2023
Investment in RISCOM:
Underlying equity	3,756	2,620
Difference	1,258	1,501
Recorded investment balance	5,013	4,121

($ in thousands)	December 31, 2024	December 31, 2023
Investment in JVM Funds LLC:
Underlying equity	16,624	19,304
Difference	605	757
Recorded investment balance	17,229	20,061

($ in thousands)	December 31, 2024	December 31, 2023
SMA1	20,296	30,816
SMA2	12,973	5,209
Investment in indirect loans and loan collateral	33,269	36,025

7. Allowance for Credit Losses

[c. 249; p. 16] Premiums receivable allowance for credit losses

• Tables set forth changes in the allowance for expected credit losses on premiums receivable for the years ended December 31, 2024 and 2023.

[c. 250; p. 16] Reinsurance recoverables credit risk and allowance

• The Company analyzes credit risk of reinsurance recoverables by monitoring financial strength ratings from A.M. Best.
• Financial strength ratings are assessed annually and throughout the year as A.M. Best provides updates.
• Adequacy of credit enhancements (reinsurance payables, letters of credit, funds held) is assessed.
• A table sets forth the Company’s reinsurance recoverables net of credit enhancements by A.M. Best as of December 31, 2024.
• Reinsurance balances are considered past due when they are 90 days past due.
• Tables set forth changes in the allowance for estimated uncollectible reinsurance for the years ended December 31, 2024 and 2023.
• On January 31, 2025, the Company commuted the LPT with R&Q Re (Bermuda) Ltd. ("R&Q") related to accident years 2018 and prior.
• The uncollectible reinsurance recoverable balance related to the LPT was recognized as a net increase of USD 13.6m to the allowance for estimated uncollectible reinsurance.
• This amount was subsequently written-off during the year ended December 31, 2024.

[c. 251; p. 16]

7. Allowance for Credit Losses

($ in thousands)	Premiums Receivable, Net	Allowance for Estimated Uncollectible Premiums
Balance at December 31, 2023	179,235	964
Current period change for estimated uncollectible premiums	—	3,235
Write-offs of uncollectible premiums receivable	—	( 1,895 )
Recoveries of amounts previously written off	—	128
Balance at December 31, 2024	321,641	2,432

($ in thousands)	Premiums Receivable, Net	Allowance for Estimated Uncollectible Premiums
Balance at December 31, 2022	139,215	629
Cumulative effect of adoption of ASU 2016-13 at January 1, 2023	—	—
Current period change for estimated uncollectible premiums	—	748
Write-offs of uncollectible premiums receivable	—	( 513 )
Recoveries of amounts previously written off	—	100
Balance at December 31, 2023	179,235	964

	December 31, 2024
A.M. Best Rating	Reinsurance Recoverables, Gross, Amortized Cost	Percent of Total
A- and above	837,807	97.4%
B++ to B+	6,021	0.7
Not rated	16,343	1.9

($ in thousands)	Reinsurance Recoverables, Net	Allowance for Estimated Uncollectible Reinsurance
Balance at December 31, 2023	596,334	2,295
Current period change for estimated uncollectible reinsurance	—	13,585
Write-offs of uncollectible reinsurance recoverables	—	( 13,585 )
Balance at December 31, 2024	857,876	2,295
Balance at	—	—

($ in thousands)	Reinsurance Recoverables, Net	Allowance for Estimated Uncollectible Reinsurance
Balance at December 31, 2022	581,359	—
Cumulative effect of adoption of ASU 2016-13 at January 1, 2023	—	2,295
Current period change for estimated uncollectible reinsurance	—	—
Write-offs of uncollectible reinsurance recoverables	—	—
Balance at December 31, 2023	596,334	2,295

8. Property and Equipment

[c. 252; p. 16] Property and equipment components and depreciation

• Property and equipment components are included within other assets on the consolidated balance sheets as of December 31, 2024 and 2023.
• Depreciation expense related to property and equipment was USD 2.9m for the year ended December 31, 2024.
• Depreciation expense related to property and equipment was USD 3.2m for the year ended December 31, 2023.
• Depreciation expense related to property and equipment was USD 3.6m for the year ended December 31, 2022.

[c. 253; p. 16]

8. Property and Equipment

(in thousands)	2024	2023
Leasehold improvements	3,056	1,892
Equipment	4,506	5,033
Software	33,972	29,189
—	41,534	36,114
Accumulated depreciation	( 29,355 )	( 27,044 )
Total	12,179	9,070

9. Leases

[c. 254; p. 16] Lease accounting and expenses

• The Company determines if a contract contains a lease at inception and recognizes a right-of-use asset (within other assets) and lease liability (within accounts payable and accrued liabilities) based on the present value of future lease payments.
• If leases do not provide an implicit interest rate, the Company uses its incremental borrowing rate based on the inception date information to determine the lease liability.
• The Company's leases are primarily for office facilities, classified as operating leases.
• Lease terms range from less than 1 year to 6 years, with some including extension options.
• Lease expense for the years ended December 31, 2024, 2023, and 2022 was USD 2.1m, USD 2.8m, and USD 2.6m, respectively.

[c. 255; p. 16] Lease information tables

• A table provides information regarding the Company’s leases as of December 31, 2024 and 2023.
• A table presents the Company’s lease expenses for the years ended December 31, 2024, 2023 and 2022.
• A table sets forth the future minimum lease payment obligations of the Company’s operating leases at December 31, 2024.

[c. 256; p. 16]

9. Leases

(in thousands)	2024	2023
Operating lease right-of-use assets	3,135	4,905
Operating lease liabilities	3,213	5,228
Operating lease weighted-average remaining lease term	4.39 years	4.55 years
Operating lease weighted-average discount rate	5.01%	3.95%

(in thousands)	2024	2023	2022
Operating lease expense	1,714	2,583	2,414
Short-term lease expense	421	184	220
Total lease expense	2,135	2,767	2,634
Operating cash outflows from operating leases	2,082	2,636	2,382

(in thousands)	2024
2025	968
2026	779
2027	686
2028	651
2029	415
Thereafter	133
Total future minimum operating lease payments	3,632
Less imputed interest	( 419 )
Total operating lease liability	3,213

10. Notes Payable & Subordinated Debt

[c. 257; p. 16] FHLB Loan

• On August 30, 2024, the Company entered into the FHLB Loan pursuant to the Advances and Security Agreement.
• The FHLB Loan is a 4.5-year term loan with a principal amount of USD 57.0m.
• The FHLB Loan requires interest-only payments during its term, with principal due in full at maturity.
• The interest rate for the FHLB Loan is fixed at 4.00% over the term.
• The FHLB Loan is fully secured by a pledge of specific investment securities of HSIC.
• Proceeds from the FHLB Loan were used to fund redemptions of draws on the Revolving Credit Facility.

[c. 258; p. 16] Revolving Credit Facility

• The Company entered into an agreement for a new unsecured revolving credit facility (the “Revolving Credit Facility”) with a syndicate of participating banks during Q1 2023.
• The Revolving Credit Facility provided up to a USD 150.0m revolving credit facility and a letter of credit sub-facility of up to USD 30.0m.
• As of December 31, 2023, the Company had drawn USD 50.0m on the Revolving Credit Facility.
• During Q1 2024, the Company drew an additional USD 50.0m on the Revolving Credit Facility to pay off the principal on its existing Debentures.
• On September 6, 2024, the Company redeemed USD 57.0m of the draws on the Revolving Credit Facility.
• Interest on the Revolving Credit Facility is payable quarterly.
• The interest rate on the Revolving Credit Facility is SOFR plus a margin of 150 to 190 bps, based on the debt to total capital ratio, and a credit spread adjustment of 10 bps.
• At December 31, 2024, the six-month SOFR on the Revolving Credit Facility was 4.25%, plus a margin of 1.60%.
• The Company is subject to covenants on the Revolving Credit Facility, including minimum net worth, maximum debt to capital ratio, minimum A.M. Best Rating, and minimum liquidity.
• As of December 31, 2024, the Company was in compliance with all covenants.

[c. 259; p. 16] Debentures

• In May 2019, the Company agreed to issue unsecured subordinated notes (the “Notes”) with an aggregate principal amount of USD 20.0m.
• Interest on the Notes is fixed at 7.25% for the first 8 years and 8.25% thereafter.
• Early retirement of the Notes before the 8-year commitment requires all interest payments to be paid in full, plus the return of outstanding principal.
• Principal on the Notes is due at maturity on May 24, 2039, and interest is payable quarterly.
• The Notes have junior priority to all previously issued debt.
• The Company reports debt related to the Notes in its December 31, 2024 and 2023 consolidated balance sheets, net of debt issuance costs of approximately USD 0.5m.
• These deferred financing costs are presented as a direct deduction from the carrying amount of the subordinated debt.
• In August 2006, the Company received USD 58.0m of proceeds from a debenture offering through Delos Capital Trust (the “Trust”).
• The sole asset of the Trust consists of Fixed/Floating Rate Junior Subordinated Deferrable Interest Debentures (the “Debentures”) with a principal amount of USD 59.8m issued by the Company.
• The Trust also held cash of USD 1.8m from the issuance of Trust common shares purchased by the Company, equal to 3% of the Trust capitalization.
• On March 15, 2024, the Company redeemed the Debentures and paid USD 1.4m of accrued interest.

11. Stockholders Equity

[c. 260; p. 16] Reverse stock split

• The Board of Directors approved a 4-for-1 reverse stock split of the Company’s common stock on September 23, 2022.
• The reverse stock split became effective January 3, 2023.
• All share and per share information in the consolidated financial statements and notes have been retroactively adjusted to reflect the reverse stock split for all periods presented.

[c. 261; p. 16] Initial public offering

• The Company completed its initial public offering (IPO) on January 18, 2023.
• 4,750,000 shares were offered by the Company at a price of USD 15.00 per share.
• Net proceeds from the IPO were approximately USD 62.0m, after deducting underwriting discounts and specific incremental expenses.
• Upon closing of the IPO, the Company filed an amended and restated certificate of incorporation.
• The amended certificate increased the number of authorized shares to 500,000,000 shares of common stock (par value USD 0.01 per share) and 10,000,000 shares of preferred stock (par value USD 0.01 per share).

[c. 262; p. 16] Preferred shares conversion

• Preferred Shares had liquidation preference over common stock for the face value of USD 50.00 per share and any declared but unpaid dividends to related common shares at the applicable conversion rate.
• Preferred Shares provided the holder the option to convert them into common stock at any time based on the Option Conversion Rate.
• Preferred Shares were subject to mandatory conversion upon the closing of an IPO at the Mandatory Conversion Rate.
• As of December 31, 2022, the Mandatory Conversion Rate allowed conversion into common stock based on a conversion price of USD 6.04 per common share.
• On January 18, 2023, 1,969,660 Preferred Shares converted to 16,305,113 shares of common stock upon the closing of the Company’s IPO.

[c. 263; p. 16] Follow-on offering

• The Company completed its follow-on offering on November 20, 2023.
• 2,150,000 shares were sold by the Company at a price of USD 30.50 per share.
• Net proceeds were approximately USD 62.5m, after deducting underwriting discounts and specific incremental expenses directly attributable to the offering.

12. Segment

[c. 264; p. 16] Reportable segment overview

• The Company has one reportable segment offering commercial property and casualty products and solutions, predominantly in the United States, on a non-admitted (E&S) and admitted basis.
• The segment consists of eight distinct underwriting divisions, referred to as "continuing business," with dedicated underwriting leadership and technical staff.
• The segment definition is based on how internally reported financial information is reviewed by the Chief Operating Decision Maker (CODM) to analyze performance, make decisions, and allocate resources.
• The Company's CODM is the chief executive officer.
• Accounting policies for the segment are consistent with Note 1 "Summary of Significant Accounting Policies" of Form 10-K.
• The CODM assesses segment performance and allocates resources based on gross written premiums by net underwriting division, underwriting income, and income before income taxes (reported on consolidated statements of operations).
• Segment assets are reported on the balance sheet as total consolidated assets.
• Gross written premiums by underwriting division, net underwriting income, and consolidated net income are used to monitor budget versus actual results.
• The CODM uses net underwriting income, return on equity, and growth in book value per share for competitive analysis by benchmarking against competitors.
• Competitive analysis and monitoring of budgeted versus actual results are used to assess segment performance and establish management's compensation.

[c. 265; p. 16] Financial data tables

• A table presents gross written premiums by underwriting division for the years ended December 31, 2024, 2023, and 2022.
• A table presents reported segment net underwriting income, significant segment expenses, and a reconciliation of net underwriting income to net income for the years ended December 31, 2024, 2023, and 2022.
• A table presents return on equity and book value per share for the years ended December 31, 2024, 2023, and 2022.

[c. 266; p. 16]

Gross written premiums by segment

	Years Ended December 31,
($ in thousands)	2024	2023	2022
Industry Solutions	317,198	305,476	267,628
Global Property & Agriculture	311,402	273,191	205,081
Captives	241,902	167,624	124,286
Programs	218,407	178,726	163,653
Accident & Health	173,073	151,701	130,808
Transactional E&S	169,053	122,508	75,098
Professional Lines	159,785	154,565	93,011
Surety	152,429	106,056	79,062
Total continuing business	1,743,249	1,459,847	1,138,627
Exited business	( 17 )	( 18 )	5,325
Total gross written premiums	1,743,232	1,459,829	1,143,952

($ in thousands)	2024	2023	2022
Underwriting income
Revenues:
Net earned premiums	1,056,722	829,143	615,994
Commission and fee income	6,703	6,064	5,199
Total underwriting revenues	1,063,425	835,207	621,193
Expenses:	—	—	—
Losses and LAE	669,809	515,237	402,512
Amortization of policy acquisition costs	149,975	108,514	65,695
Other operating and general expenses	161,782	134,930	116,476
Total underwriting expenses	981,566	758,681	584,683
Net underwriting income	81,859	76,526	36,510
Reconciliation of net underwriting income to net income:	—	—	—
Net underwriting income	81,859	76,526	36,510
Add:	—	—	—
Net investment income	80,686	40,322	36,931
Net investment gains (losses)	6,256	11,072	( 15,705 )
Other (loss) income	( 167 )	( 632 )	1
Less:	—	—	—
Interest expense	9,496	10,024	6,407
Amortization expense	2,007	1,798	1,547
Other expenses	4,392	5,364	—
Income before income taxes	152,739	110,102	49,783
Income tax expense	33,911	24,118	10,387
Net income	118,828	85,984	39,396

	2024	2023	2022
Return on equity	16.3%	15.9%	9.3%
Book value per share	19.79	16.72	25.82

13. Income Taxes

[c. 267; p. 16] income tax expense and effective tax rate

• The Company's income tax expense components are presented for the years ended December 31, 2024, 2023, and 2022.
• The provision for income taxes generally does not deviate substantially from the statutory tax rate.
• The effective tax rate may vary slightly from the statutory rate due to tax adjustments for tax-exempt income, dividends-received deduction, and non-deductible expenses.
• Differences between income taxes expected at the federal statutory income tax rate of 21% and the reported income tax expense are presented for the years ended December 31, 2024, 2023, and 2022.

[c. 268; p. 16] deferred tax assets and liabilities

• The tax effects of temporary differences giving rise to significant portions of deferred tax assets and deferred tax liabilities are presented as of December 31, 2024, and 2023.

[c. 269; p. 16] federal income taxes and examinations

• The Company paid USD 37.0m in federal income taxes during the year ended December 31, 2024.
• The Company's federal income tax returns for tax years 2021 to 2023 are subject to examination by the Internal Revenue Service.
• The Company has no current U.S. federal or state and local income tax examinations ongoing.

[c. 270; p. 16] uncertain tax positions and accruals

• As of December 31, 2024, the Company carried no balance for uncertain tax positions.
• The Company had no accrual for the payment of interest and penalties at December 31, 2024, or 2023.

[c. 271; p. 16] net operating loss carryforwards

• The Company has federal net operating loss carryforwards of approximately USD 44.7m.
• These net operating losses are set to expire beginning in 2032.
• The Company is limited on the utilization of USD 44.7m of net operating losses under Internal Revenue Code Section 382 ("Sec 382") due to an "ownership change" in 2014.
• The Sec 382 limitation is expected to result in an expiration of USD 2.8m (USD 0.6m tax effected) of net operating losses [p.16, p.16].
• A valuation allowance was established against the balance of net operating losses expected to expire without utilization.

[c. 272; p. 16] capital loss carryforward

• The Company generated a capital loss carryforward in 2022, resulting in a deferred tax asset of USD 1.7m as of December 31, 2024.
• No valuation allowance is recorded against this deferred tax asset as the Company expects to utilize this carryforward before it expires in 2027.

[c. 273; p. 16] deferred tax valuation allowance

• The Company provides a valuation allowance against deferred tax assets when it is more likely-than-not that some portion, or all, of deferred tax assets will not be realized.
• The deferred tax valuation allowance at December 31, 2024, and 2023 was USD 0.6m.

[c. 274; p. 16]

13. Income Taxes

($ in thousands)	2024	2023	2022
Current income tax expense	42,626	14,736	120
Deferred tax (benefit) expense related to temporary differences	( 8,715 )	9,382	10,267
Total income tax expense	33,911	24,118	10,387

	2024		2023		2022
($ in thousands)	Amount	Percentage	Amount	Percentage	Amount	Percentage
Income tax expense at federal statutory rate	32,075	21.0%	23,121	21.0%	10,454	21.0%
Tax advantaged investments	( 239 )	( 0.2 )	( 295 )	( 0.3 )	( 324 )	( 0.7 )
Other	2,075	1.4	1,292	1.2	257	0.6
Total income tax expense	33,911	22.2%	24,118	21.9%	10,387	20.9%

($ in thousands)	2024	2023
Deferred tax assets:
Unearned premiums	18,178	15,365
Losses and loss adjustment expenses	16,967	11,581
Net operating losses	9,389	10,655
Unrealized losses on fixed maturity securities, available-for-sale	5,893	6,113
Stock options/awards	2,453	1,714
Other	6,067	4,237
Total deferred tax assets	58,947	49,665
Less valuation allowance	( 586 )	( 586 )
Total deferred tax assets after valuation allowance	58,361	49,079
Deferred tax liabilities:	—	—
Deferred policy acquisition costs	15,277	11,528
Unrealized gains on equity securities	4,818	3,243
Other long-term investments	2,625	6,460
Depreciation	1,426	1,260
Section 481(a) adjustment	1,391	3,477
Other	2,338	1,120
Total deferred tax liabilities	27,875	27,088
Deferred income taxes	30,486	21,991

14. Reserves for Losses and Loss Adjustment Expenses

[c. 275; p. 16] Loss development evaluation categories

• The Company presents loss development on a consolidated basis.
• Net ultimate loss and LAE are evaluated under three sub-categories: multi-line solutions, short-tail/monoline specialty lines, and exited lines.
• These disaggregated groupings have more homogeneous risk characteristics with similar development patterns and are generally subject to similar trends.
• Short-tail/Monoline Specialty Lines include global property & agriculture, accident & health, surety, and professional lines underwriting divisions.
  • These are market niches served with monoline solutions, generally having shorter durations for losses to fully develop.
  • Losses are generally reported within a short period from the date of loss, and claims are often settled and paid within a relatively short timeframe.
  • Can be impacted by larger, more complex losses due to factors like difficulty determining actual damages, and legal/regulatory impediments extending settlement times.
• Multi-line Solutions include industry solutions, programs, captives, and transactional E&S underwriting divisions.
  • These are market niches where the Company provides multiple products, most frequently as an integrated solution.
  • Predominantly made up of occurrence liability, including general liability, excess liability, and commercial auto.
  • Have a longer duration for losses to fully develop compared to short-tail/monoline specialty lines.
  • Longer-tail nature and unique claim characteristics introduce more uncertainty, as claims can be impacted by changes in regulation, inflation, and other unforeseen factors over time.
• Exited lines include all underwriting units placed in run-off and are presented separately from ongoing lines of business.

[c. 276; p. 16] Reserve evaluation methodology change

• In 2024, the Company transitioned from evaluating reserves on a policy year basis to an accident year basis.
• This transition results in earlier recognition of underlying claim trends, better alignment of exposure to risks, and adherence to commonly used industry best practices.
• In prior years, the Company's methodology allocated IBNR from its policy year analysis to accident year.
• As a result of transitioning to accident year, IBNR within short-tail/monoline specialty lines, multi-line solutions, and exited lines was reallocated for the years ended December 31, 2023, 2022, 2021, and 2020.
• Certain amounts have been conformed to the current year presentation.
• A table sets forth the reconciliation of unpaid losses and loss adjustment expenses ("LAE") as reported in the consolidated balance sheets as of and for the years ended December 31, 2024, 2023, and 2022.

[c. 277; p. 16] Prior year loss and LAE reserve development

• For the year ended December 31, 2024, the Company recognized adverse development related to prior years’ loss and loss expense reserves of USD 25.7m.
  • This was primarily related to losses previously subject to the LPT from accident years 2018 and prior.
  • Multi-line solutions accounted for USD 10.1m of this adverse development.
  • Exited lines accounted for USD 15.2m of this adverse development.
• For the year ended December 31, 2023, the Company recognized adverse development related to prior years’ loss and loss expense reserves of USD 10.8m.
  • Adverse development of USD 11.7m in multi-line solutions was driven by greater than expected severity in auto, general, and excess liability lines of business, primarily from accident years 2020 to 2022.
  • This adverse development was partially offset by favorable development in short-tail/monoline specialty lines.
  • The favorable development was in the property line of business, primarily from accident years 2021 and 2022.
• During the year ended December 31, 2022, the Company’s net incurred losses for accident years 2021 and prior developed adversely by USD 33.8m.
  • Adverse development of USD 20.2m in exited lines was due to:
    • Losses previously subject to the LPT from accident years 2018 and prior.
    • Increased frequency and severity in general and professional liability lines from accident years 2019 through 2021.
  • Adverse development of USD 13.0m in multi-line solutions was driven by an increase in the frequency and severity of claims in commercial auto and general liability from accident years 2018 through 2021.

[c. 278; p. 16]

14. Reserves for Losses and Loss Adjustment Expenses

($ in thousands)	2024	2023	2022
Reserves for losses and LAE, beginning of period	1,314,501	1,141,757	979,549
Less: reinsurance recoverable on unpaid claims, beginning of period	( 455,484 )	( 435,986 )	( 381,338 )
Reserves for losses and LAE, beginning of period, net of reinsurance	859,017	705,771	598,211
Incurred, net of reinsurance, related to:	—	—	—
Current period	657,783	505,894	374,475
Prior years	25,728	10,770	33,849
Total incurred, net of reinsurance	683,511	516,664	408,324
Paid, net of reinsurance, related to:	—	—	—
Current period	136,731	109,937	105,928
Prior years	294,260	253,481	194,836
Total paid	430,991	363,418	300,764
Net reserves for losses and LAE, end of period	1,111,537	859,017	705,771
Plus: reinsurance recoverable on unpaid claims, end of period	670,846	455,484	435,986
Reserves for losses and LAE, end of period	1,782,383	1,314,501	1,141,757

Short Duration Contract Disclosures

[c. 279; p. 16] Losses and LAE reserves estimation

• Losses and LAE reserves represent the Company’s best estimate of the ultimate net cost of all reported and unreported losses that are unpaid as of the balance sheet dates.
• Estimated reserves for losses and LAE include accumulated estimates for claims reported and unpaid prior to the balance sheet dates.
• Estimated reserves for losses and LAE include estimates (based on projections of relevant historical data) of increases in claims costs for claims already reported.
• Estimated reserves for losses and LAE include estimates of claims incurred but not reported.
• Estimated reserves for losses and LAE include estimates of expenses for investigating and adjusting all incurred and unpaid claims.
• The Company measures claim counts by incident when determining the cumulative number of reported claims.
• Claim counts include all reported claims, even if the Company does not establish a liability for the claim (i.e., reserve for loss and loss adjustment expenses).

Short-tail/Monoline Specialty Lines

[c. 280; p. 16]

Incurred losses and ALAE, net of reinsurance by accident year

($ in thousands except number of claims)
Incurred Losses and Allocated Loss Adjustment Expense (“ALAE”), Net of Reinsurance						As of December 31, 2024
	Years Ended December 31,						Reported Claims
Accident Year	2020*	2021*	2022*	2023*	2024	IBNR	Reported Claims
2020	56,141	55,324	55,420	55,305	55,305	1,147	1,311
2021	—	92,780	93,429	92,143	92,134	6,536	1,627
2022	—	—	108,299	105,394	104,095	15,316	2,383
2023	—	—	—	190,565	191,865	68,001	4,880
2024	—	—	—	—	280,147	161,230	4,502
Total	—	—	—	—	723,546	—	—
Cumulative net paid loss and ALAE from the table below	Cumulative net paid loss and ALAE from the table below	Cumulative net paid loss and ALAE from the table below	Cumulative net paid loss and ALAE from the table below	Cumulative net paid loss and ALAE from the table below	( 359,673 )	—	—
Net reserves for loss and ALAE before 2020	Net reserves for loss and ALAE before 2020	Net reserves for loss and ALAE before 2020	Net reserves for loss and ALAE before 2020	Net reserves for loss and ALAE before 2020	3,353	—	—
Total net reserves for loss and ALAE	Total net reserves for loss and ALAE	Total net reserves for loss and ALAE	Total net reserves for loss and ALAE	Total net reserves for loss and ALAE	367,226	—	—
*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited

($ in thousands)
Cumulative Paid Losses and ALAE, Net of Reinsurance ($ in thousands)
	Years Ended December 31,
Accident Year	2020*	2021*	2022*	2023*	2024
2020	14,002	35,479	40,000	43,737	49,688
2021	—	18,447	56,803	67,912	78,439
2022	—	—	27,773	64,594	77,150
2023	—	—	—	33,795	100,705
2024	—	—	—	—	53,691
Total	—	—	—	—	359,673
*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited

Multi-line Solutions

[c. 281; p. 16]

Incurred losses and ALAE, net of reinsurance by accident year

($ in thousands except number of claims)
Incurred Losses and ALAE, Net of Reinsurance ($ in thousands)											As of December 31, 2024
Accident Year	Years Ended December 31,											Reported Claims
Accident Year	2015*	2016*	2017*	2018*	2019*	2020*	2021*	2022*	2023*	2024	IBNR	Reported Claims
2015	103,191	114,266	117,024	117,024	119,216	114,863	115,863	116,413	116,413	117,955	( 834 )	5,386
2016	—	63,223	62,843	62,843	62,643	84,579	84,579	84,829	84,829	85,434	1,276	4,739
2017	—	—	65,332	65,332	64,260	78,166	78,166	78,766	78,766	80,493	2,105	5,588
2018	—	—	—	74,476	74,476	69,319	71,719	73,019	73,019	75,686	4,856	5,104
2019	—	—	—	—	107,432	109,226	112,378	115,530	116,230	116,206	3,918	6,119
2020	—	—	—	—	—	113,030	124,076	128,111	132,495	132,125	4,716	5,539
2021	—	—	—	—	—	—	156,067	158,891	160,331	160,546	16,119	6,702
2022	—	—	—	—	—	—	—	236,909	242,097	242,358	33,477	8,562
2023	—	—	—	—	—	—	—	—	306,511	306,511	132,772	8,180
2024	—	—	—	—	—	—	—	—	—	353,933	246,281	6,557
Total	—	—	—	—	—	—	—	—	—	1,671,247	—	—
Cumulative net paid loss and ALAE from the table below	Cumulative net paid loss and ALAE from the table below	Cumulative net paid loss and ALAE from the table below	Cumulative net paid loss and ALAE from the table below	Cumulative net paid loss and ALAE from the table below	Cumulative net paid loss and ALAE from the table below	Cumulative net paid loss and ALAE from the table below	Cumulative net paid loss and ALAE from the table below	Cumulative net paid loss and ALAE from the table below	Cumulative net paid loss and ALAE from the table below	( 1,038,650 )	—	—
Net reserves for loss and ALAE before 2015	Net reserves for loss and ALAE before 2015	Net reserves for loss and ALAE before 2015	Net reserves for loss and ALAE before 2015	Net reserves for loss and ALAE before 2015	Net reserves for loss and ALAE before 2015	Net reserves for loss and ALAE before 2015	Net reserves for loss and ALAE before 2015	Net reserves for loss and ALAE before 2015	Net reserves for loss and ALAE before 2015	( 1,532 )	—	—
Total net reserves for loss and ALAE	Total net reserves for loss and ALAE	Total net reserves for loss and ALAE	Total net reserves for loss and ALAE	Total net reserves for loss and ALAE	Total net reserves for loss and ALAE	Total net reserves for loss and ALAE	Total net reserves for loss and ALAE	Total net reserves for loss and ALAE	Total net reserves for loss and ALAE	631,065	—	—
*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited

($ in thousands)
Cumulative Paid Losses and ALAE, Net of Reinsurance ($ in thousands)
	Years Ended December 31,
Accident Year	2015*	2016*	2017*	2018*	2019*	2020*	2021*	2022*	2023*	2024
2015	44,152	72,137	88,833	99,401	108,291	107,214	109,622	109,706	113,703	115,116
2016	—	23,239	42,528	53,352	58,895	69,691	72,544	75,855	77,160	77,760
2017	—	—	23,770	41,945	53,093	61,354	67,926	71,109	73,770	75,714
2018	—	—	—	26,201	42,568	47,226	58,655	65,635	69,893	70,128
2019	—	—	—	—	33,019	50,933	71,053	87,816	99,451	106,765
2020	—	—	—	—	—	29,499	60,680	82,236	105,283	121,097
2021	—	—	—	—	—	—	37,118	73,293	102,772	125,749
2022	—	—	—	—	—	—	—	50,148	114,794	165,854
2023	—	—	—	—	—	—	—	—	63,079	122,186
2024	—	—	—	—	—	—	—	—	—	58,281
Total	—	—	—	—	—	—	—	—	—	1,038,650
*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited

Exited Lines — all lines in runoff

[c. 282; p. 16] reconciliation of loss development tables

• The table presents the reconciliation of net incurred and paid loss development tables to balance sheet reserves for losses and loss adjustment expenses at December 31, 2024 and 2023.
• The following table sets forth the historical average annual payout of incurred losses and allocated loss adjustment expenses (claims duration) for short-duration contracts, based on disaggregated information in the paid loss development tables, net of reinsurance.

[c. 283; p. 16]

Incurred losses and ALAE, net of reinsurance by accident year

($ in thousands except number of claims)
Incurred Losses and ALAE, Net of Reinsurance ($ in thousands)											As of December 31, 2024
	Years Ended December 31,											Reported Claims
Accident Year	2015*	2016*	2017*	2018*	2019*	2020*	2021*	2022*	2023*	2024	IBNR	Reported Claims
2015	61,810	65,063	68,008	70,803	75,187	79,853	79,853	80,603	80,603	82,092	1,145	4,581
2016	—	93,019	92,996	91,372	93,577	97,301	98,301	100,651	100,651	102,801	959	4,893
2017	—	—	75,159	79,581	81,785	65,735	68,346	68,646	68,646	70,885	1,598	4,339
2018	—	—	—	74,357	68,990	76,506	79,006	84,165	84,165	92,082	5,586	4,910
2019	—	—	—	—	87,115	73,635	77,770	79,414	79,572	79,823	5,786	5,632
2020	—	—	—	—	—	132,248	136,469	137,835	137,907	137,671	11,424	4,828
2021	—	—	—	—	—	—	83,322	91,188	91,323	92,095	10,923	2,398
2022	—	—	—	—	—	—	—	12,717	12,240	11,800	902	234
2023	—	—	—	—	—	—	—	—	—	—	—	1
2024	—	—	—	—	—	—	—	—	—	—	—	—
Total	—	—	—	—	—	—	—	—	—	669,249	—	—
Cumulative net paid loss and ALAE from the table below	Cumulative net paid loss and ALAE from the table below	Cumulative net paid loss and ALAE from the table below	Cumulative net paid loss and ALAE from the table below	Cumulative net paid loss and ALAE from the table below	Cumulative net paid loss and ALAE from the table below	Cumulative net paid loss and ALAE from the table below	Cumulative net paid loss and ALAE from the table below	Cumulative net paid loss and ALAE from the table below	Cumulative net paid loss and ALAE from the table below	( 597,904 )	—	—
Net reserves for loss and ALAE before 2015	Net reserves for loss and ALAE before 2015	Net reserves for loss and ALAE before 2015	Net reserves for loss and ALAE before 2015	Net reserves for loss and ALAE before 2015	Net reserves for loss and ALAE before 2015	Net reserves for loss and ALAE before 2015	Net reserves for loss and ALAE before 2015	Net reserves for loss and ALAE before 2015	Net reserves for loss and ALAE before 2015	15,344	—	—
Total net reserves for loss and ALAE	Total net reserves for loss and ALAE	Total net reserves for loss and ALAE	Total net reserves for loss and ALAE	Total net reserves for loss and ALAE	Total net reserves for loss and ALAE	Total net reserves for loss and ALAE	Total net reserves for loss and ALAE	Total net reserves for loss and ALAE	Total net reserves for loss and ALAE	86,689	—	—
*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited

($ in thousands)
Cumulative Paid Losses and ALAE, Net of Reinsurance ($ in thousands)
	Years Ended December 31,
Accident Year	2015*	2016*	2017*	2018*	2019*	2020*	2021*	2022*	2023*	2024
2015	9,026	41,653	55,610	65,269	73,100	78,249	80,077	80,923	82,188	83,290
2016	—	36,592	57,638	70,253	78,070	81,181	87,482	91,556	95,114	97,462
2017	—	—	34,176	52,103	51,985	50,545	57,457	62,924	66,498	68,480
2018	—	—	—	25,553	60,149	39,870	54,339	67,001	74,604	79,860
2019	—	—	—	—	28,636	28,954	30,948	45,696	57,341	65,847
2020	—	—	—	—	—	102,725	98,202	102,132	114,543	120,831
2021	—	—	—	—	—	—	41,540	57,820	66,012	72,923
2022	—	—	—	—	—	—	—	2,155	4,077	9,211
2023	—	—	—	—	—	—	—	—	—	—
2024	—	—	—	—	—	—	—	—	—	—
Total	—	—	—	—	—	—	—	—	—	597,904
*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited

($ in thousands)	2024	2023
Net reserves for losses and ALAE:
Short-tail/Monoline Specialty Lines	367,226	235,191
Multi-line Solutions	631,065	485,099
Exited Lines	86,689	112,607
Reserves for losses and ALAE, net of reinsurance	1,084,980	832,897
Reinsurance recoverable on unpaid claims:	—	—
Short-tail/Monoline Specialty Lines	275,204	199,044
Multi-line Solutions	380,344	252,146
Exited Lines	15,298	4,294
Total reinsurance recoverable on unpaid claims	670,846	455,484
Unallocated LAE	26,557	26,120
Reserves for losses and LAE at end of year	1,782,383	1,314,501

Average Annual Percentage Payout of Incurred Claims by Age, Net of Reinsurance
	Years
	1*	2*	3*	4*	5*	6*	7*	8*	9*	10*
Short-Tail/Monoline Specialty Lines	21.8%	37.7%	10.8%	9.1%	10.8%	N/A	N/A	N/A	N/A	N/A
Multi-line Solutions	26.0%	22.0%	15.0%	12.4%	9.9%	3.7%	2.4%	1.3%	2.0%	1.2%
Exited Lines	29.6%	17.1%	8.1%	9.7%	9.2%	7.8%	4.2%	2.4%	1.9%	1.3%
*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	*Supplementary information and unaudited	—	—	—	—	—	—

15. Commission and Fee Income

[c. 284; p. 16] Skyward Underwriters Agency, Inc. overview

• Skyward Underwriters Agency, Inc. (SUA) is a subsidiary of the Company.
• SUA functions as a managing general insurance agent and reinsurance broker.
• SUA specializes in property and casualty and accident and health risks within specialty niche markets.
• Commission and fee income is primarily generated from SUA for placing insurance policies with third-party insurance or reinsurance companies.

[c. 285; p. 16] Commission and fee income tables

• A table sets forth the Company’s disaggregated revenues from contracts with customers for the years ended December 31, 2024, 2023, and 2022.
• A table sets forth the Company’s opening and closing balances of contract assets from commission and fee income for the years ended December 31, 2024, 2023, and 2022.

[c. 286; p. 16]

15. Commission and Fee Income

($ in thousands)	2024	2023	2022
SUA commission revenue	3,595	2,864	3,224
SUA fee income	2,928	2,732	1,597
Other	180	468	378
Total commission and fee income	6,703	6,064	5,199

($ in thousands)	Contract Assets
Balance at December 31, 2022	1,292
Balance at December 31, 2023	976
Balance at December 31, 2024	1,416

16. Underwriting, Acquisition and Insurance Expenses

[c. 287; p. 16] Underwriting, acquisition, and insurance expenses components

• The table sets forth the components of underwriting, acquisition, and insurance expenses for the years ended December 31, 2024, 2023, and 2022.

[c. 288; p. 16]

16. Underwriting, Acquisition and Insurance Expenses

($ in thousands)	2024	2023	2022
Amortization of policy acquisition costs	149,975	108,514	65,695
Other operating and general expenses	161,782	134,930	116,476
Total underwriting, acquisition and insurance expenses	311,757	243,444	182,171

17. Reinsurance

[c. 289; p. 16] Reinsurance agreements and recoverables

• The Company uses reinsurance agreements to increase capacity for larger risks and manage exposure within its capital resources.
• The Company remains obligated for ceded amounts if reinsurers fail to meet their obligations.
• Tables detail the effects of reinsurance on written and earned premiums and losses and loss adjustment expenses for 2024, 2023, and 2022.
• A table outlines components of reinsurance recoverables and ceded unearned premium as of December 31, 2024, and December 31, 2023.

[c. 290; p. 16] Reinsurer trust accounts

• The Company has agreements with several reinsurers for funded trust accounts, with the Company as the sole beneficiary.
• These trust accounts provide additional security for collecting claim recoverables under reinsurance contracts.
• The Company does not carry these trust accounts on its balance sheet, as custody is only assumed if the reinsurer fails to pay amounts due.
• As of December 31, 2024, the market value of these accounts was approximately USD 196.9m.
• The trust amount is periodically adjusted by mutual agreement based on claim payments and loss reserve recoverables.

[c. 291; p. 16] LPT retroactive reinsurance agreement

• In Q1 2020, the Company entered into an LPT retroactive reinsurance agreement with R&Q.
• Reinsurance recoverable from R&Q was USD 22.7m at December 31, 2024, and USD 20.9m at December 31, 2023.
• The LPT was commuted effective January 31, 2025, and the Company received the full reinsurance recoverable balance.

[c. 292; p. 16] Deposit method accounting for ceded reinsurance

• Certain ceded reinsurance contracts that transfer only significant timing risk and insufficient underwriting risk are accounted for using the deposit method.
• The Company's deposit asset was USD 25.9m at December 31, 2024, and USD 29.9m at December 31, 2023.
• This deposit asset was included in other assets on the consolidated balance sheets.

[c. 293; p. 16]

Net premiums & ceded losses and LAE incurred by Written & Earned

	2024		2023		2022
($ in thousands)	Written	Earned	Written	Earned	Written	Earned
Direct premiums	1,458,637	1,375,917	1,241,180	1,155,835	1,012,239	951,121
Assumed premiums	284,595	282,662	218,649	193,971	131,713	113,610
Ceded premiums	( 619,654 )	( 601,857 )	( 549,138 )	( 520,663 )	( 468,409 )	( 448,737 )
Net premiums	1,123,578	1,056,722	910,691	829,143	675,543	615,994
Ceded losses and LAE incurred	—	534,295	—	337,011	—	311,257

($ in thousands)	2024	2023
Ceded unpaid losses and LAE	670,846	455,484
Ceded paid losses and LAE	166,663	122,287
Loss portfolio transfer	22,662	20,858
Allowance for credit losses	( 2,295 )	( 2,295 )
Reinsurance recoverables	857,876	596,334
Ceded unearned premium	203,901	186,121

18. Stock Based Compensation

[c. 294; p. 16] 2022 Long-Term Incentive Plan

• The Company's 2022 Long-Term Incentive Plan (the "2022 Plan") was approved by the Compensation Committee on September 23, 2022, and became effective on January 12, 2023.
• The 2022 Plan replaced the Company’s prior Long Term Incentive Plan (the "2020 Plan").
• The 2022 Plan allows for granting restricted stock, restricted stock units, performance stock units, stock options, and cash-based performance awards to select employees and non-employee directors.
• 3,200,656 shares of common stock were available for issuance under the 2022 Plan.
• In November 2024, the Compensation Committee approved a program allowing Board of Directors members to defer annual restricted stock unit awards to the fifth anniversary of the grant date, the tenth anniversary of the grant date, or the date of separation from the Company.
• This deferral program will be available for Directors who opt in for their 2025 grant.

[c. 295; p. 16] Stock options

• The grant date fair value of options under the 2022 Plan was determined using the Black-Scholes model, with a contractual term of 10 years less the weighted average service period.
• Volatility for the Black-Scholes model was based on historical volatility of comparable publicly traded insurance companies.
• Stock options granted to employees during the year ended December 31, 2023, were valued at approximately USD 4.4m based on grant date fair value.
• The aggregate intrinsic value of options outstanding was USD 27.0m at December 31, 2024, and USD 14.3m at December 31, 2023.
• The weighted-average remaining contractual life of options outstanding at December 31, 2024, was 8.0 years.

[c. 296; p. 16] Restricted stock awards and units

• The fair value of restricted stock and restricted stock units under the 2022 Plan for awards granted at the time of the Company’s IPO was the IPO price of USD 15.00 per share.
• The fair value of subsequent grants was equal to the closing stock price on the grant date.
• Expense for these equity-based incentives is based on fair value at grant date and amortized over their vesting period.
• Restricted stock and restricted stock units granted to employees and the Board of Directors were valued at approximately USD 8.5m in 2024, USD 17.7m in 2023, and USD 2.6m in 2022, based on grant date fair value.
• Board of Directors members were granted 19,453 shares in 2024, 23,482 shares in 2023, and 15,196 shares in 2022, with a service period of one year.
• The total fair value of shares vested for employees and Board of Directors members was USD 3.8m in 2024, USD 0.5m in 2023, and USD 2.2m in 2022.

[c. 297; p. 16] Unrecognized compensation cost and expense

• As of December 31, 2024, total unrecognized compensation cost related to non-vested, stock-based compensation awards was USD 13.9m.
• The weighted average period over which this cost is expected to be recognized is 1.4 years.
• The Company recognized stock-based compensation expense of USD 9.4m in 2024, USD 8.5m in 2023, and USD 2.3m in 2022.

[c. 298; p. 16] Employee Stock Purchase Plan (ESPP)

• The Company’s 2022 Employee Stock Purchase Plan (the "ESPP") was approved by the Compensation Committee on September 23, 2022, and became effective on May 15, 2023.
• Under the ESPP, employees can choose to have a percentage of their annual base earnings withheld to purchase common stock at two specified intervals each year.
• The purchase price is 85% of the lower of the beginning-of-interval or end-of-interval market price.
• 376,548 common shares have been reserved under the ESPP.
• The grant date fair value of options under the ESPP was determined using the Black-Scholes model, with a term of 6 months (length of time between grant date and exercisable date).
• Volatility for the ESPP Black-Scholes model was based on historical volatility of comparable publicly traded insurance companies.
• As of December 31, 2024, 95,266 shares had been purchased under the ESPP.
• The Company recognized ESPP expense of USD 0.5m in 2024 and USD 0.2m in 2023.
• As of December 31, 2024, the fair value of unrecognized ESPP expense was USD 0.3m.

[c. 299; p. 16]

18. Stock Based Compensation

	Award Payout Range	Requisite Service Period	Target Stock and Stock Units
Year ended December 31, 2024
Market condition awards	0 %– 150 %	3 years	32,058
Performance condition awards	0 %– 150 %	3 years	76,881
Service condition awards	N/A	1 – 4 years	124,025
—	—	—	232,964
Year ended December 31, 2023	—	—	—
Market condition awards	0 %– 150 %	3 years	37,622
Performance condition awards	0 %– 150 %	3 years	95,456
Service condition awards	N/A	1 – 4 years	968,778
Stock options	N/A	3 – 4 years	759,990
—	—	—	1,861,846
Year ended December 31, 2022	—	—	—
Market condition awards	0 %– 150 %	3 years	28,495
Performance condition awards	0 %– 150 %	3 years	26,210
Service condition awards	N/A	1 – 3 years	144,137
—	—	—	198,842

	Stock
Outstanding at January 1, 2024	759,990
Outstanding at December 31, 2024	759,990

	Weighted-Average Exercise Price	Stock
Outstanding at January 1, 2023		—
Granted	15.00	759,990
Outstanding at December 31, 2023	—	759,990

	Weighted-Average Grant-Date Fair Value	Stock and Stock Units
Non-vested at January 1, 2024	15.13	1,445,449
Granted (1)	31.72	268,631
Vested	13.16	( 285,957 )
Forfeited (2)	18.27	( 102,640 )
Non-vested at December 31, 2024	19.06	1,325,483
Non-vested at January 1, 2023	12.55	419,896
Granted (1)	16.07	1,101,856
Vested	13.39	( 40,645 )
Forfeited (2)	15.29	( 35,658 )
Non-vested at December 31, 2023	15.13	1,445,449
Non-vested at January 1, 2022	13.23	375,643
Granted (1)	14.17	198,842
Vested	15.16	( 144,042 )
Forfeited (2)	12.51	( 10,547 )
Non-vested at December 31, 2022	12.55	419,896

(1) Increases above the 100% target level are reflected as granted in the period after which performance-based stock unit goals are achieved.

(2) Decreases below the 100% target level are reflected as forfeited.

19. Earnings Per Share

[c. 300; p. 16] Earnings per share calculation basis

• The table presents the compilation of basic and diluted net earnings per share for the years ended December 31, 2024, 2023, and 2022.
• The Company's preferred shares are participating securities, sharing in dividends and distributions with common stock on an as-converted basis.
• Instruments granted to employees that allow the purchase of common stock at a fixed price were included as potential common shares, weighted for the portion of the period they were granted, if dilutive.
• The table presents anti-dilutive instruments excluded from the calculation of diluted weighted-average common share equivalents for the years ended December 31, 2024, 2023, and 2022.
• The table presents common share equivalents of contingently issuable instruments excluded from basic earnings per share for the years ended December 31, 2024, 2023, and 2022.

[c. 301; p. 16]

19. Earnings Per Share

($ in thousands, except for share and per share amounts)	2024	2023	2022
Numerator
Net income	118,828	85,984	39,396
Less: Undistributed income allocated to participating securities	—	( 1,677 )	( 18,879 )
Net income attributable to common stockholders (numerator for basic earnings per share)	118,828	84,307	20,517
Add back: Undistributed income allocated to participating securities	—	1,677	18,879
Net income (numerator for diluted earnings per share under the two-class method)	118,828	85,984	39,396
Denominator	—	—	—
Basic weighted-average common shares	40,056,475	36,031,907	16,568,393
Dilutive effect of preferred shares	—	716,708	15,245,533
Dilutive effect of stock notes	—	696,110	519,080
Dilutive effect of stock units	917,510	736,837	320,188
Dilutive effect of options	403,475	135,972	—
Diluted weighted-average common share equivalents	41,377,460	38,317,534	32,653,194
Basic earnings per share	2.97	2.34	1.24
Diluted earnings per share	2.87	2.24	1.21

	2024	2023	2022
Stock Notes	—	—	60,576
Stock units	20,346	3,931	—
Options	859	914	—

	2024	2023	2022
Common shares	—	920,864	22,919
Preferred shares, if converted	—	—	1,059,602
Total	—	920,864	1,082,521

20. Employee Benefit Plan

[c. 302; p. 16] 401(k) plan contributions

• The Company sponsors the 401(k) Plan (the "Plan"), available to substantially all employees.
• The Plan is subject to the Employee Retirement Income Security Act of 1974.
• The Company makes discretionary matching contributions to the Plan.
• Company matching contributions to the Plan were USD 3.2m in 2024, USD 2.9m in 2023, and USD 2.4m in 2022.

RISCOM

[c. 303; p. 16] RISCOM relationship and transactions

• RISCOM provides wholesale brokerage services to the Company.
• RISCOM and the Company have a managing general agency agreement.
• The Company holds a 20% ownership interest in RISCOM.
• Net earned premium and gross commission expense related to these agreements for the years ended December 31, 2024, 2023, and 2022 were as follows.
• Premiums receivable as of December 31, 2024, were USD 12.6m.
• Premiums receivable as of December 31, 2023, were USD 10.6m.

[c. 304; p. 16]

RISCOM

($ in thousands)	2024	2023	2022
Net earned premium	108,130	99,736	91,051
Commissions	25,372	24,177	23,472

Other

[c. 305; p. 16] Advisory and professional services fees

• Advisory and professional services fees and expense reimbursements paid to affiliated stockholders and directors were USD 0.6m in 2024, USD 3.6m in 2023, and USD 3.4m in 2022.

[c. 306; p. 16] Related party transactions references

• Notes 5, 6, and 10 provide information on investments involving affiliated companies and additional related party transactions.
• Note 11 details related party transactions concerning the Company’s common and preferred shares.

Litigation

[c. 307; p. 16] legal actions and reserves

• The Company is a defendant in various legal actions arising from claims under insurance policies and contracts.
• These actions are considered when estimating losses and loss adjustment expense reserves.
• The Company is also a defendant in legal actions related to bad faith claims, disputes with third parties, or alleged errors and omissions.
• Accruals for these items are recorded when losses are probable and reasonably estimable.
• Based on present information, available insurance coverage, and advice from outside legal counsel, the Company believes the resolution of these matters will not, individually or in aggregate, materially adversely affect its consolidated financial position, results of operations, or cash flows.

Indemnification

[c. 308; p. 16] Indemnification for asset sales

• The Company has provided indemnifications to certain buyers in conjunction with the sale of business assets and subsidiaries.
• Certain indemnifications cover typical representations and warranties related to responsibilities under sales contracts.
• The potential exposure from these indemnifications is difficult to determine due to the variety of matters, operations, and scenarios covered.
• Some indemnifications have no time limit.
• The Company currently believes no significant claims exist related to these indemnifications.

23. Statutory Accounting Principles and Regulatory Matters

[c. 309; p. 16] Statutory financial performance

• Statutory net income: USD 108.2m for 2024; USD 73.1m for 2023; USD 50.5m for 2022.
• Statutory capital and surplus: USD 710.6m as of December 31, 2024; USD 602.9m as of December 31, 2023.

[c. 310; p. 16] Insurance subsidiary restructuring

• Effective December 31, 2024, the Company restacked its insurance company subsidiaries, making GMIC the lead insurance company.
• HSIC became a wholly owned subsidiary of GMIC.
• IIC became a wholly owned subsidiary of HSIC.
• OSIC became a wholly owned subsidiary of IIC.

[c. 311; p. 16] Dividend restrictions and payments

• Dividend payments to the Company from GMIC are restricted by Texas state law regarding amounts payable without regulatory approval.
• Maximum dividend amount payable by GMIC without prior approval is subject to restrictions related to policyholder surplus, net income, and dividends declared/distributed in the preceding 12 months.
• As of December 31, 2024, GMIC is not restricted from paying ordinary dividends.
• GMIC did not declare or pay any dividend during the year ended December 31, 2024.
• HSIC did not declare or pay any dividends during the year ended December 31, 2023.

[c. 312; p. 16] Risk Based Capital requirements

• Property and casualty insurance companies are subject to Risk Based Capital (RBC) requirements specified by the National Association of Insurance Commissioners (NAIC).
• RBC requirements determine the amount of capital and surplus based on various risk factors.
• As of December 31, 2024, GMIC’s statutory capital and surplus substantially exceeded regulatory requirements.
• As of December 31, 2023, HSIC’s statutory capital and surplus substantially exceeded regulatory requirements.

24. Subsequent Events

[c. 313; p. 16] Skyward Re commutation with R&Q

• On January 31, 2025, Skyward Re commuted its existing Loss Portfolio Transfer and Adverse Development and Retrocession Agreement, dated April 1, 2020, with R&Q via a Commutation Agreement.
• Skyward Re received USD 11.7m in cash from the commutation.
• At December 31, 2024, the Company strengthened LPT loss reserves and increased the paid loss reinsurance recoverable by USD 25.3m.
• At December 31, 2024, the Company increased the allowance for estimated uncollectible reinsurance by USD 13.6m, which was subsequently written-off during the year ended December 31, 2024.
• At December 31, 2024, the Company recognized a deferred gain of USD 2.0m.

Controls and Procedures

Evaluation of Disclosure Controls and Procedures

[c. 314; p. 17] Disclosure controls and procedures evaluation

• Management, including the principal executive officer and principal financial officer, evaluated the effectiveness of disclosure controls and procedures as of the end of the period covered by the Annual Report on Form 10-K.
• As of December 31, 2024, the disclosure controls and procedures were concluded to be not effective due to a material weakness in internal control over financial reporting.
• Despite the identified material weakness, management does not believe it adversely affected reported operating results or financial condition.
• Management determined that the financial statements and other information in the report and other periodic filings fairly present the financial condition, results of operations, and cash flows for the periods presented in accordance with U.S. GAAP.

Management’s Report on Internal Control over Financial Reporting

[c. 315; p. 17] Internal Control over Financial Reporting

• Management is responsible for establishing and maintaining adequate internal control over financial reporting as defined in Rules 13a-15(f) and 15d-15(f) under the Securities Exchange Act of 1934.
• Internal control over financial reporting is designed to provide reasonable assurance regarding the reliability of financial reporting and the preparation of financial statements for external purposes in accordance with generally accepted accounting principles in the United States of America.
• Internal control over financial reporting includes policies and procedures that pertain to the maintenance of records that accurately and fairly reflect transactions and dispositions of assets.
• Internal control over financial reporting includes policies and procedures that provide reasonable assurance that transactions are recorded as necessary for financial statement preparation in accordance with GAAP, and that receipts and expenditures are made only with management and director authorizations.
• Internal control over financial reporting includes policies and procedures that provide reasonable assurance regarding prevention or timely detection of unauthorized acquisition, use, or disposition of assets that could materially affect financial statements.

[c. 316; p. 17] Material Weakness in Internal Control

• Management assessed the effectiveness of internal control over financial reporting as of December 31, 2024, using criteria from the COSO Internal Control—Integrated Framework (2013).
• As of December 31, 2024, management concluded that internal control over financial reporting was not effective due to a material weakness.
• A material weakness is a deficiency, or combination of deficiencies, in internal control over financial reporting that creates a reasonable possibility of a material misstatement in annual or interim financial statements not being prevented or detected timely.
• The material weakness as of December 31, 2024, related to the ineffective implementation of information technology general controls (ITGCs) in user access for systems supporting the Company’s financial reporting processes.
• Related process-level IT dependent manual and automated controls relying on affected ITGCs, or information from IT systems with affected ITGCs, were also deemed ineffective.
• This material weakness did not result in any material misstatements to the financial statements in this Form 10-K.
• No changes were identified as required for previously issued financial statements.
• Substantive procedures for the year ended December 31, 2024, have been completed.
• Management believes consolidated financial statements in this Form 10-K have been prepared in accordance with U.S. GAAP.
• The CEO and CFO certified that, to their knowledge, the financial statements and other financial information in this Form 10-K fairly present in all material respects the financial condition, results of operations, and cash flows for the periods presented.
• Ernst & Young LLP issued an unqualified opinion on the financial statements, included in Item 8 of this Form 10-K.
• Ernst & Young LLP also issued a report on internal control over financial reporting as of December 31, 2024, which appears in Item 8.

Planned Material Weakness Remediation Activities

[c. 317; p. 17] Material weakness remediation activities

• Management is implementing measures to remediate control deficiencies contributing to the material weakness related to the design of ITGCs in user access over certain information technology.
• Remediation actions include enhancing the IT compliance oversight function and expanding the team with experience in designing and implementing ITGCs.
• A training program addressing ITGCs and policies is being developed and implemented, including educating control owners on control principles and requirements.
• Documentation underlying ITGCs is being developed and maintained to promote knowledge transfer during IT personnel and function changes.
• An IT management review and testing plan is being implemented to monitor ITGCs.
• Enhanced quarterly reporting on remediation measures is provided to the Audit Committee of the board of directors.

Changes in Internal Control over Financial Reporting

[c. 318; p. 17] Internal control over financial reporting

• No changes in internal control over financial reporting occurred during the year ended December 31, 2024, except for those related to the identified material weakness.
• These changes have not materially affected, nor are they reasonably likely to materially affect, the company's internal control over financial reporting.

Limitations on Effectiveness of Controls and Procedures

[c. 319; p. 17] Limitations of disclosure controls

• Management acknowledges that disclosure controls and procedures, regardless of design and operation, can only offer reasonable assurance of achieving control objectives.
• The design of disclosure controls and procedures must consider resource constraints and require management to exercise judgment in weighing the benefits against the costs of potential controls.

Other Information

[c. 320; p. 18] Director and officer trading arrangements

• During the quarter ended December 31, 2024, none of the directors or officers (as defined in Rule 16a-1(f) of the Securities Exchange Act of 1934) adopted, terminated, or modified a Rule 10b5-1 trading arrangement or non-Rule 10b5-1 trading arrangement (as defined in Item 408 of Regulation S-K).

Directors, Executive Officers and Corporate Governance

[c. 321; p. 19] Information incorporation by reference

• Information required by Item 10 of Form 10-K will be included in the 2025 Proxy Statement and is incorporated by reference.

Executive Compensation

[c. 322; p. 20] Executive compensation disclosure

• Information required by Item 11 of Form 10-K will be included in the 2025 Proxy Statement and is incorporated by reference.

Security Ownership of Certain Beneficial Owner and Management and Related Stockholder Matters

[c. 323; p. 21] Information incorporation by reference

• The information required by Item 12 of Form 10-K will be included in the 2025 Proxy Statement and is incorporated by reference.

Certain Relationships and Related Transactions, and Director Independence

[c. 324; p. 22] Information incorporation by reference

• The information required by Item 13 of Form 10-K will be included in the 2025 Proxy Statement and is incorporated herein by reference.

Principal Accounting Fees and Services

[c. 325; p. 23] independent registered public accounting firm

• Our independent registered public accounting firm is Ernst & Young LLP, Houston, Texas.
• Auditor Firm ID: 42.
• The information required by Item 14 of Form 10-K will be included in our 2025 Proxy Statement and is incorporated herein by reference.

Exhibits, Financial Statement Schedules.

[c. 326; p. 24] Financial Statements Listing

• The consolidated financial statements of the Company are filed as part of Form 10-K and included in Item 8.
• Reports of Independent Registered Public Accounting Firm are included.
• Consolidated Balance Sheets as of December 31, 2024 and 2023 are included.
• Consolidated Statements of Operations and Comprehensive Income (loss) for the three years ended December 31, 2024, 2023, and 2022 are included.
• Consolidated Statements of Stockholders’ Equity for the three years ended December 31, 2024, 2023, and 2022 are included.
• Consolidated Statements of Cash Flows for the three years ended December 31, 2024, 2023, and 2022 are included.

[c. 327; p. 24] Exhibits Listing

• A listing of exhibits is provided.
• Exhibits marked with an asterisk are filed herewith.
• Management contracts or compensatory plans or arrangements are included.

[c. 328; p. 24]

Schedule number by schedule description

Schedule Number	Schedule Description	Page
I.	Summary of Investments — Other Than in Related Parties at December 31, 2024	103
II.	Financial Information of Registrant (Parent Company) for the years ended December 31, 2024, 2023 and 2022	104
IV.	Supplementary Reinsurance Information for the years ended December 31, 2024, 2023, and 2022	108
V.	Valuation and Qualifying Accounts for the years ended December 31, 2024, 2023, and 2022	109
VI.	Supplementary Information Concerning Property — Casualty Insurance Operations for the years ended December 31, 2024, 2023, and 2022	110

Exhibit Number	Exhibit Description
3.1	Amended and Restated Certificate of Incorporation (incorporated by reference to Exhibit 3.1 to the Company's Current Report on Form 8-K filed with the Commission on January 18, 2023).
3.2	Amended and Restated Bylaws (incorporated by reference to Exhibit 3.2 to the Company's Current Report on Form 8-K filed with the Commission on January 18, 2023).
4.1	Amended and Restated Stockholders’ Agreement, dated March 12, 2014, by and among the Company and the stockholders listed therein (incorporated by reference to Exhibit 4.1 to the Company's Registration Statement on Form S-1, filed with the SEC on November 14, 2022).
4.2	Description of Capital Stock (incorporated by reference to Exhibit 4.2 to the Company’s Annual Report on Form 10-K, filed with the SEC on March 28, 2023).
10.1+	Share Purchase and Award Agreement and form of agreements thereunder in use before 2016 (incorporated by reference to Exhibit 10.1 to the Company's Registration Statement on Form S-1, filed with the SEC on November 14, 2022).
10.2+	2016 Equity Incentive Program and form of award agreements thereunder (incorporated by reference to Exhibit 10.2 to the Company's Registration Statement on Form S-1, filed with the SEC on November 14, 2022).
10.3+	2020 Long Term Incentive Plan and form of award agreements thereunder (incorporated by reference to Exhibit 10.3 to the Company's Registration Statement on Form S-1, filed with the SEC on November 14, 2022).
10.4+	Skyward Specialty Insurance Group, Inc. 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 10.4 to the Company's Registration Statement on Form S-1, filed with the SEC on November 14, 2022).
10.5+	Skyward Specialty Insurance Group, Inc. 2022 Employee Stock Purchase Plan (incorporated by reference to Exhibit 10.5 to the Company's Registration Statement on Form S-1, filed with the SEC on November 14, 2022).
10.6+	Form of Restricted Stock Units Agreement and form of notice under the Company's 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 99.6 to the Company's Registration Statement on Form S-8, filed with the SEC on January 12, 2023).

Exhibit Number	Exhibit Description
10.7+	Form of Restricted Stock Agreement under the Company’s 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 99.7 to the Company's Registration Statement on Form S-8, filed with the SEC on January 12, 2023).
10.8+	Form of Nonstatutory Stock Option Agreement and form of notice under the Company's 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 99.8 to the Company's Registration Statement on Form S-8, filed with the SEC on January 12, 2023).
10.9+	Form of Incentive Stock Option Agreement and form of notice under the Company's 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 99.9 to the Company's Registration Statement on Form S-8, filed with the SEC on January 12, 2023).
10.10+	Form of Performance-Based Restricted Stock Units Agreement under the Company’s 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 10.10 to the Company’s Annual Report on Form 10-K, filed with the SEC on March 28, 2023).
10.11+	Performance-Based Restricted Stock Units Agreement under the Company’s 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 10.11 to the Company’s Annual Report on Form 10-K, filed with the SEC on March 28, 2023).
10.12+	Performance Unit Agreement under the Company’s 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 10.12 to the Company’s Annual Report on Form 10-K, filed with the SEC on March 28, 2023).
10.13+	Amended Form of Performance Share (GBVPS) Agreement under the Company’s 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 10.13 to the Company’s Annual Report on Form 10-K, filed with the SEC on April 1, 2024).
10.14+	Amended Form of Performance Share (Executives) Agreement under the Company’s 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 10.14 to the Company’s Annual Report on Form 10-K, filed with the SEC on April 1, 2024).
10.15+	Amended Form of Performance Share (Others) Agreement under the Company’s 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 10.15 to the Company’s Annual Report on Form 10-K, filed with the SEC on April 1, 2024).
10.16+	Amended Form of Performance Cash Units Agreement under the Company’s Long-Term Incentive Plan. (incorporated by reference to Exhibit 10.16 to the Company’s Annual Report on Form 10-K, filed with the SEC on April 1, 2024).
10.17+	Amended Form of the Restricted Stock Unit (Executives) Agreement under the Company’s 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 10.17 to the Company’s Annual Report on Form 10-K, filed with the SEC on April 1, 2024).
10.18+	Amended Form of Restricted Stock Unit (Others) Agreement under the Company’s 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 10.18 to the Company’s Annual Report on Form 10-K, filed with the SEC on April 1, 2024).
10.19+	Amended Form of Long-Term Performance Cash Plan and Award Letter under the Company’s 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 10.19 to the Company’s Annual Report on Form 10-K, filed with the SEC on April 1, 2024).
10.20+	Form of Indemnification Agreement (incorporated by reference to Exhibit 10.6 to the Company's Registration Statement on Form S-1, filed with the SEC on November 14, 2022).
10.21+	Employment Agreement, dated May 22, 2020, by and between the Registrant and Andrew Robinson, with Amendment No. 1 dated January 1, 2022 (incorporated by reference to Exhibit 10.7 to the Company's Registration Statement on Form S-1, filed with the SEC on November 14, 2022).
10.22+*	Form of Non-Employee Director Deferred Restricted Stock Unit Agreement and Form of Notice Under the Company’s 2022 Long-Term Incentive Plan.
10.23	Commutation and Release Agreement by and among R&Q Re (Bermuda) Ltd., Skyward Re, Houston Specialty Insurance Company, Imperium Insurance Company, and Great Midwest Insurance Company, dated January 31, 2025 (incorporated by reference to Exhibit 10.1 to the Company's Current Report on Form 8-K filed with the Commission on February 5, 2025).
10.24	Investment Management Agreement by and among Arena Investors, LP, Houston Specialty Insurance Company, Imperium Insurance Company, and Great Midwest Insurance Company, dated November 6, 2015, with a Supplemental Acknowledgement dated January 13, 2016, a Supplemental Acknowledgement dated May 17, 2021, Supplemental Acknowledgement B dated May 17, 2021, an Amendment Agreement effective March 15, 2022, and a Supplemental Acknowledgement dated March 23, 2022 (incorporated by reference to Exhibit 10.15 to the Company's Registration Statement on Form S-1, filed with the SEC on November 14, 2022).

Exhibit Number	Exhibit Description
10.25	Second Amendment Agreement effective as of December 8, 2023, to that certain Investment Management Agreement dated November 6, 2015, by and among Arena Investors, LP, Houston Specialty Insurance Company, Imperium Insurance Company, and Great Midwest Insurance Company (incorporated by reference to Exhibit 10.26 to the Company’s Annual Report on Form 10-K, filed with the SEC on April 1, 2024).
10.26	Credit Agreement, dated March 29, 2023, by and among Skyward Specialty Insurance Group, Inc., the lenders from time to time party thereto and Truist Bank, as administrative agent (incorporated by reference to Exhibit 10.1 to the Company's Current Report on Form 8-K filed with the Commission on April 3, 2023).
10.27	First Amendment dated as of February 26, 2024, to that certain Credit Agreement, dated March 29, 2023, by and among Skyward Specialty Inc., the lenders from time to time party thereto and Truist Bank, as administrative agent (incorporated by reference to Exhibit 10.28 to the Company’s Annual Report on Form 10-K, filed with the SEC on April 1, 2024).
10.28	Guaranty Agreement, dated March 29, 2023, by and among Skyward Service Company, Skyward Underwriters Agency, Inc., the loan parties identified on the signature pages thereto and Truist Bank. (incorporated by reference to Exhibit 10.2 to the Company's Current Report on Form 8-K filed with the Commission on April 3, 2023).
10.29	Advances and Security Agreement, dated August 1, 2024, by and between Houston Specialty Insurance Company, a wholly owned insurance company subsidiary of the Company and the Federal Home Loan Bank of Dallas (incorporated by reference to Exhibit 10.1 to the Company’s Current Report on Form 8-K filed with the Commission on September 6, 2024).
10.30+*	Form of Severance Agreement between the Company and executive officers (other than the CEO)
10.31+*	Amendment No. 2 to Employment Agreement between the Registrant and Andrew Robinson dated March 1, 2025 .
19*	Skyward Specialty Insurance Securities Trading Policy
21.1*	List of Subsidiaries of the Company
23.1	Consent of Ernst & Young LLP, Independent Registered Public Accounting Firm.
31.1	Certification of Principal Executive Officer pursuant to Rule 13a-14(a) or Rule 15d-14(a) of the Securities Exchange Act of 1934, as adopted pursuant to Section 302 of the Sarbanes-Oxley Act of 2002.
31.2	Certification of Principal Financial and Accounting Officer pursuant to Rule 13a 14(a) or Rule 15d 14(a) of the Securities Exchange Act of 1934, as adopted pursuant to Section 302 of the Sarbanes-Oxley Act of 2002.
32.1	Certification of Principal Executive Officer pursuant to 18 U.S.C. Section 1350, as adopted pursuant to Section 906 of the Sarbanes-Oxley Act of 2002.
97	Policy for Recovery of Erroneously Awarded Incentive Compensation (“Clawback Policy”) (incorporated by reference to Exhibit 97 to the Company’s Annual Report on Form 10-K, filed with the SEC on April 1, 2024).
101.INS	Inline XBRL Instance Document – the instance document does not appear in the Interactive Data File because XBRL tags are embedded within the Inline XBRL document.
101.SCH	Inline XBRL Taxonomy Extension Schema With Embedded Linkbase Documents
104	Cover Page Interactive Date File (embedded within the Inline XBRL document)

Schedule I — summary of investments — other than in related parties

[c. 329; p. 24]

Schedule I — summary of investments — other than in related parties

($ in thousands)	Cost	Fair Value (if applicable)	Amount on Balance Sheet
December 31, 2024
Fixed maturity securities, available for sale:
U.S. government securities	26,577	26,486	26,486
Corporate securities and miscellaneous	433,298	425,628	425,628
Municipal securities	89,966	84,716	84,716
Residential mortgage-backed securities	408,585	393,833	393,833
Commercial mortgage-backed securities	70,262	69,364	69,364
Other asset-backed securities	291,578	292,191	292,191
Total fixed maturity securities, available for sale	1,320,266	1,292,218	1,292,218
Fixed maturity securities, held to maturity:	—	—	—
Other asset-backed securities	39,396	38,717	39,153
Total fixed maturity securities, held to maturity	39,396	38,717	39,153
Equity securities:	—	—	—
Common stocks	48,530	64,251	64,251
Preferred stocks	1,138	1,164	1,164
Mutual funds	33,643	40,839	40,839
Total equity securities	83,311	106,254	106,254
Mortgage loans	26,485	26,490	26,490
Other long-term investments	33,231	33,182	33,182
Short-term investments	274,926	274,929	274,929
Total	1,777,615	1,771,790	1,772,226

Balance sheets (parent company)

[c. 330; p. 24] Financial statement notes

• See accompanying notes to financial statements.

[c. 331; p. 24]

Balance sheets (parent company)

	December 31,
($ in thousands)	2024	2023
Assets
Investments:
Investment in subsidiaries	853,670	743,025
Short-term investments, at fair value	14,000	10,593
Total investments	867,670	753,618
Cash and cash equivalents	2,943	3,024
Deferred income taxes	30,486	5,899
Goodwill and intangible assets, net	12,641	12,641
Other assets	2,905	15,908
Total assets	916,645	791,090
Liabilities and Stockholders’ Equity	—	—
Liabilities:	—	—
Accounts payable and accrued liabilities	3,110	1,369
Notes payable	100,000	50,000
Subordinated debt, net of debt issuance costs	19,536	78,690
Total liabilities	122,646	130,059
Stockholders’ Equity:	—	—
Stockholders’ equity	793,999	661,031
Total liabilities and stockholders’ equity	916,645	791,090

(parent company)

[c. 332; p. 24] Financial statement notes

• See accompanying notes to financial statements.

[c. 333; p. 24]

Revenues, expenses, and net income by years ended December 31

	Years Ended December 31,
($ in thousands)	2024	2023	2022
Revenues:
Net investment income	3,212	3,822	2,567
Net investment (losses) gains	963	( 963 )	( 6 )
Other loss	( 2 )	( 27 )	—
Total revenues	4,173	2,832	2,561
Expenses	—	—	—
Operating expenses	10,632	—	—
Interest expense	8,140	9,815	6,407
Amortization expense	920	313	81
Other expenses	9,646	451	—
Total expenses	29,338	10,579	6,488
Loss before income tax expense	( 25,165 )	( 7,747 )	( 3,927 )
Income tax expense	33,578	6,808	( 1,209 )
Loss before equity in earnings of subsidiaries	( 58,743 )	( 14,555 )	( 2,718 )
Equity in undistributed earnings of subsidiaries	177,571	100,539	42,114
Net income	118,828	85,984	39,396

Schedule ii — statements of cash flows (parent company)

[c. 334; p. 24] Financial statement notes

• See accompanying notes to financial statements.

[c. 335; p. 24]

Net cash provided by operating activities by years ended December 31

	Years Ended December 31,
($ in thousands)	2024	2023	2022
Cash flows from operating activities:
Net income	118,828	85,984	39,396
Adjustments to reconcile net income to net cash used in operating activities	( 121,563 )	( 95,947 )	( 42,672 )
Net cash provided by operating activities	( 2,735 )	( 9,963 )	( 3,276 )
Cash flows from investing activities:	—	—	—
Capital contributions to subsidiaries	—	( 122,800 )	—
Distributions from investment in subsidiaries	8,500	6,500	4,000
Change in short-term investments	( 3,407 )	( 10,569 )	—
Net cash (used in) provided by investing activities	5,093	( 126,869 )	4,000
Cash flows from financing activities:	—	—	—
Repayment of stock notes receivable	5,561	1,350	2,180
Proceeds from long term borrowings	107,000	50,000	—
Payments on long term borrowings and trust preferred	( 115,000 )	( 50,000 )	—
Proceeds from equity offerings	—	128,887	—
Proceeds from employee stock purchase plan	—	710	—
Net cash provided by financing activities	( 2,439 )	130,947	2,180
Net increase (decrease) in cash and cash equivalents and restricted cash	( 81 )	( 5,885 )	2,904
Cash and cash equivalents and restricted cash at beginning of year	3,024	8,909	6,005
Cash and cash equivalents and restricted cash at end of year	2,943	3,024	8,909
Supplemental disclosure of cash flow information:	—	—	—
Cash paid for interest	8,573	10,667	5,761
Cash paid for federal income taxes	36,980	15,800	—

Notes to Financial Statements

[c. 336; p. 24] Intercompany loan

• Skyward Specialty entered into an Intercompany Loan Promissory Note with Houston Specialty Insurance Company (HSIC) on September 30, 2024.
• Skyward Specialty borrowed USD 57.0m from HSIC under the Promissory Note.
• Interest on the Promissory Note is payable monthly at a fixed annual rate of 4.00%.
• The principal of the Promissory Note is due at maturity.
• There are no prepayment penalties and no collateral was given for the Promissory Note.

[c. 337; p. 24] Subsidiary funding

• During the year ended December 31, 2024, Skyward Specialty provided funds for a new subsidiary, Skyward Specialty No. 1 Limited Company.
• Skyward Specialty No. 1 Limited Company is a UK company authorized as a Lloyd’s corporate member to invest in Lloyd’s syndicates.

Financial Instruments Disclosed, But Not Carried, At Fair Value

[c. 338; p. 24] Promissory Note Fair Value

• The Promissory Note between Skyward Specialty and HSIC is included in notes payable.
• Skyward Specialty determined the fair value of the Promissory Note using the income approach with observable inputs.
• The Promissory Note is classified as Level 2 in the fair value hierarchy.
• As of December 31, 2024, the carrying value of the Promissory Note was USD 57.0m, and its fair value was USD 56.3m.

Schedule iv — reinsurance

[c. 339; p. 24]

Gross amount, Ceded to other companies, Assumed from other companies by Accident & Health, Property & Casualty

	Years Ended December 31,
	2024		2023		2022
($ in thousands)	Accident & Health	Property & Casualty	Accident & Health	Property & Casualty	Accident & Health	Property & Casualty
Gross amount	173,073	1,285,564	151,702	1,089,478	130,377	881,862
Ceded to other companies	( 86,503 )	( 533,151 )	( 79,091 )	( 470,047 )	( 70,291 )	( 398,118 )
Assumed from other companies	—	284,595	—	218,649	431	131,282
Net amount	86,570	1,037,008	72,611	838,080	60,517	615,026
Percentage of amount assumed to net	—%	27.4%	—%	26.1%	0.7%	21.3%

Schedule V — valuation and qualifying accounts

[c. 340; p. 24]

Schedule V — valuation and qualifying accounts

($ in thousands)	Valuation Allowance For Deferred Tax Assets	Allowance for Uncollectible Reinsurance Recoverable	Allowance for Uncollectible Premiums Receivable
Balance at January 1, 2022	586	—	261
Charged to costs and expenses	—		584
Amounts written off	—		( 216 )
Balance at December 31, 2022	586	—	629
Cumulative effect of adoption of ASU 2016-13 at January 1, 2023	—	2,295	—
Charged to costs and expenses	—	—	748
Amounts written off	—	—	( 513 )
Recoveries of amounts previously written off	—	—	100
Balance at December 31, 2023	586	2,295	964
Charged to costs and expenses	—	13,585	3,235
Amounts written off	—	( 13,585 )	( 1,895 )
Recoveries of amounts previously written off	—	—	128
Balance at December 31, 2024	586	2,295	2,432

Insurance operations

[c. 341; p. 24]

Insurance operations

	As of and Years Ended December 31,
($ in thousands)	2024	2023	2022
Deferred policy acquisition costs	113,183	91,955	68,938
Reserve for losses and loss adjustment expenses	1,782,383	1,314,501	1,141,757
Unearned premiums	637,185	552,532	442,509
Net earned premium (1)	1,056,722	829,143	615,994
Net investment income	80,686	40,322	36,931
Losses and loss adjustment expenses (current year) (1)	657,783	516,664	393,939
Losses and loss adjustment expenses (prior years) (1)(2)	25,728	—	14,385
Amortization of policy acquisition costs (1)	149,975	108,514	65,695
Paid claims and claim adjustment expenses (1)	430,991	363,418	300,764
Net premiums written (1)	1,123,578	910,691	675,543
Ceded unearned premium	203,901	186,121	157,645
Deferred ceding commission	40,434	37,057	29,849

(1) Amount is presented net of reinsurance.

(2) Amount does not include gain on retroactive reinsurance which is included in losses and loss adjustment expenses presented on the Consolidated Statements of Operations.

SIGNATURES

[c. 342; p. 24] Report signing authorization

• The report was signed on behalf of the registrant by the undersigned, duly authorized, pursuant to the requirements of Section 13 or 15(d) of the Securities Exchange Act of 1934.
• The report was signed by the indicated persons on behalf of the Registrant, in their capacities and on the dates indicated, pursuant to the requirements of the Securities Exchange Act of 1934.

[c. 343; p. 24]

Signatures by Skyward Specialty Insurance Group, Inc.

	Skyward Specialty Insurance Group, Inc.
Dated: March 3, 2025	/s/ Andrew Robinson
—	Andrew Robinson Chairman and Chief Executive Officer

Signature	Title	Date
/s/ Andrew Robinson	Chairman and Chief Executive Officer	March 3, 2025
Andrew Robinson	(Principal Executive Officer)	March 3, 2025
/s/ Mark Haushill	Chief Financial Officer	March 3, 2025
Mark Haushill	(Principal Financial and Accounting Officer)	March 3, 2025
/s/ Gena Ashe	Director	March 3, 2025
Gena Ashe	Director	March 3, 2025
/s/ Robert Creager	Director	March 3, 2025
Robert Creager	Director	March 3, 2025
/s/ Marcia Dall	Director	March 3, 2025
Marcia Dall	Director	March 3, 2025
/s/ James Hays	Director	March 3, 2025
James Hays	Director	March 3, 2025
/s/ Anthony J. Kuczinski	Director	March 3, 2025
Anthony J. Kuczinski	Director	March 3, 2025
/s/ Michael Morrissey	Director	March 3, 2025
Michael Morrissey	Director	March 3, 2025
/s/ Katharine Terry	Director	March 3, 2025
Katharine Terry	Director	March 3, 2025