]> 2026-07-06T18:10:59+08:00 Skyward/2024/FY/Annual report 0 en-us Annual report Skyward Specialty Insurance Group 2024 Form 10-K Form 10-K English Skyward doc_archive FY FY24 2025-03-03Z 2460737.5 2024 2026-07-06T04:48:48Z 2461227.7005556 2026-07-06T04:50:43Z 2461227.7018866 false Skyward/2024/FY/Annual report 0 Cover 1 table Skyward/2024/FY/Annual report# 17a8ad07ff10e29898ac374189e96437 0 Audit Information 2 Auditor name, auditor location, auditor firm ID table Skyward/2024/FY/Annual report# d7b7dd2f6c72f92907cfaa441356696a 0 Year founded = 2006 Former name(s) = Houston International Insurance Group, Ltd. Primary segments = commercial property and casualty (P&C) Principal lines = general liability, excess liability, professional liability, commercial auto, group accident and health, property, agriculture, credit, surety, and workers’ compensation Who We Are 3 Skyward Specialty, commercial P&C products, non-admitted (E&S) and admitted basis, general liability, excess liability, professional liability, cyber, media liability, commercial auto, group accident and health, property, agriculture, credit, surety, workers’ compensation, specialty reinsurance prose Skyward/2024/FY/Annual report# 3ff37397cf25f3b7fe2dea83e28a69c7 0 Number of segments = one Reportable segments = one Gross written premiums = 44% admitted and 56% non-admitted Our Business and Our Strategy 4 Reportable segment, underwriting divisions, Accident & Health (A&H), Captives, Global Property, Global Agriculture, medical stop loss, group captive solutions, property-only solutions, secondary and reinsurance solutions prose Skyward/2024/FY/Annual report# d90a5f70ca4dcf4d08a9c8e70fa87594 0 Competitive advantages = focus on profitable niches, highly skilled underwriters, superior claims staff and operations, superior business intelligence platform, advanced technology and new risk data, diversified business, attractive and winning culture, high-quality, experienced leadership team Our Competitive Strengths 5 Niche market focus, underwriting approach, underwriting staff, claims team, claims process, SkyBI platform, data repository, business intelligence platform, advanced technology, new risk data prose Skyward/2024/FY/Annual report# 8dbe29c271a58998aa09202fe2b73533 0 Strategic priorities = 'Rule Our Niche' strategy Our Strategy in Action 6 'Rule Our Niche' strategy, underwriting profitability, shareholder value, book value per share, underwriting and claims talent, technology DNA, SkyBI, core operating platforms, existing lines of business, new underwriting divisions, climate change, severe weather events, supply chain uncertainty, financial inflation prose Skyward/2024/FY/Annual report# d935662467720d51cb6081946d3f9257 0 Distribution channels = retail agents, wholesale brokers, select program administrators, and captive managers Marketing and Distribution 7 Marketing and distribution approach, 'Rule Our Niche' strategy, underwriting teams, distribution partners, retail agents, wholesale brokers, program administrators, captive managers prose Skyward/2024/FY/Annual report# 32c80b18518db5f8689cd033d984d2af 0 Underwriting 8 Underwriting approach, 'Rule Our Niche' strategy, underwriting teams, data analytics, SkyBI, risk selection, pricing, policy binding, admitted market, E&S market prose Skyward/2024/FY/Annual report# b6b91b432378e1ccdb45387f116aa764 0 Claims Management 9 Claims department, advanced analytics, technology, customer service, reserve establishment, contribution, subrogation, fraud detection, litigation management, Third Party Administrators (TPAs), independent legal counsel, legal spend management solution, Claims Development Severity Predictor, 'quick strike' program, commercial auto claims prose Skyward/2024/FY/Annual report# aff07ef6ec6ccd31c446929d0cefde1a 0 Technology 10 SkyBI, business intelligence platform, predictive analytics technology, AI, risk selection, pricing, claims handling, core transactional platforms, policy administration, underwriting workbench, billing, claims systems, accident & health, global property, agriculture, surety prose Skyward/2024/FY/Annual report# 5256481b9c4a18c70e5254acd298c955 0 Reinsurance types = quota share, excess of loss, and facultative coverage Property insurance GWP = 29% of gross written premiums Reinsurance 11 Reinsurance, severity events, catastrophes, earnings volatility, quota share, excess of loss, facultative coverage, property insurance, geographic aggregation, hurricanes, convective storms, earthquakes, catastrophe reinsurance, stochastic models, deterministic models prose Skyward/2024/FY/Annual report# db3a843a54e2f0de4574c03f066567a7 0 Maximum company retention by line of business 12 table Skyward/2024/FY/Annual report# 48ef7aa61380295e98cddc71ee4ddd1f 0 Reinsurance by company 13 table Skyward/2024/FY/Annual report# 142cee1af7d92190b248a80da2dffb83 0 Enterprise Risk Management 14 Enterprise risk management (ERM), risk-adjusted return, underwriting, asset portfolio construction, liability duration, market cyclicality, reinsurance, investment strategy, SVP of Finance & ERM, ERM Committee, Economic Capital Model (ECM), risk tolerances, Board's Risk Committee, risk register, operational processes prose Skyward/2024/FY/Annual report# c2b22c1ff8b50f30f3a74fc53600a397 0 Reserves 15 Reserves, incurred and reported claims, IBNR reserves, uncollectible reinsurance, ultimate liability, case reserve, claims management, actuarial reserving techniques, loss reserves prose Skyward/2024/FY/Annual report# f0369ccd0d6fa6662efc91df1a181349 0 Investments 16 Investment portfolio, predictable and stable returns, strategic investments, Enterprise Based Asset Allocation model, Economic Capital Model, investment risk, cash and cash equivalents, investment-grade fixed-maturity securities, Investment Committee of the Board of Directors, third-party investment management firms prose Skyward/2024/FY/Annual report# 97217a25f536a62aca818a74df93dac0 0 Key competitors = Markel Corporation, W.R. Berkley Corporation, American Financial Group Inc., Tokio Marine Holdings, Inc., CNA Financial Corporation, Hiscox, Ltd., RLI Corp., Intact Finance Corporation, Kinsale Capital Group, Inc. Competition 17 Specialty lines property & casualty insurance market, specialty and standard insurers, program administrators, pricing, company reputation, financial strength, broker relationships, product terms and conditions, independent rating agency ratings, claims payment, underwriting and claims teams, Markel Corporation, W.R. Berkley Corporation, American Financial Group Inc., Tokio Marine Holdings, Inc., CNA Financial Corporation, Hiscox, Ltd., RLI Corp., Intact Finance Corporation, Kinsale Capital Group, Inc. prose Skyward/2024/FY/Annual report# 824ddccf845260e15bf3943b54052682 0 Legal name = Skyward Specialty Insurance Group, Inc. Holding-company structure = GMIC, HSIC, IIC, OSIC, Skyward Re, Skyward Underwriters Agency, Inc., Skyward Service Company, Skyward Specialty No. 1 Limited Company State of incorporation = Delaware (for parent) Our Structure 18 Great Midwest Insurance Company (GMIC), Houston Specialty Company (HSIC), Imperium Insurance Company (IIC), Oklahoma Specialty Insurance Company (OSIC), Skyward Re, Skyward Underwriters Agency, Inc., Skyward Service Company, Skyward Specialty No. 1 Limited Company, surety T-listing market, captive reinsurance company, LPT, Lloyd’s corporate member prose Skyward/2024/FY/Annual report# 6cc629929e895aeccc77925a8d543f77 0 Geographic distribution of premiums 19 table Skyward/2024/FY/Annual report# 31aaa8f95ba84978e7035ce6bfd6e718 0 Financial strength rating = A (Excellent) Rating outlook = stable Rating agencies = A.M. Best Ratings 20 Skyward Specialty Insurance Group, Inc., A.M. Best, financial strength rating, profitability, leverage, liquidity, book of business, reinsurance adequacy, quality and estimated market value of assets, adequacy of losses and loss expense reserves, surplus adequacy, capital structure, management experience and competence, market presence prose Skyward/2024/FY/Annual report# 90759ead67dbd9f6d045e1e2d3555580 0 Regulation 21 Insurance regulatory authorities, state insurance laws and regulations, capital and surplus requirements, licensing, product form and rate review, reserve adequacy standards, statutory accounting methods, financial report content, affiliate transactions, investment types and amounts, National Association of Insurance Commissioners (NAIC), federal government, insurance holding company system, Texas, Oklahoma prose Skyward/2024/FY/Annual report# 084b0024c67c7ad101d7c6353799201c 0 Intellectual Property 22 Trademark registrations, intellectual property protection, trademarks, service marks prose Skyward/2024/FY/Annual report# 6e75b66687c66771f55a7d5dfcac14db 0 Employees = approximately 580 as of December 31, 2024 Employees and Human Capital 23 Employees, collective bargaining agreement, culture, diversity of thought, background, perspective, talent, competitive benefits package, medical, dental, vision insurance, 401(k) plan, paid time off, family leave, employee assistance programs, employee stock purchase plan, employee training and development, further education, professional development prose Skyward/2024/FY/Annual report# 49162ffd0d4b691b187a90defcf7bacb 0 Summary of Material Risk Factors 24 Underwriting risk, competition, distribution channels, reinsurance, loss reserves, financial strength rating, coverage interpretation, reinsurer reimbursement, claims payment, economic factors, recession, inflation, unemployment, economic activity, policy sales, claim frequency, premium defaults, falsified claims prose Skyward/2024/FY/Annual report# 9164e62100e4fcc5930d206bb6d6992e 0 Risks Related to Our Business and Industry 25 prose Skyward/2024/FY/Annual report# 6acb9d453bfbe57f0ef394efc7652a83 0 Risks Related to the Market and Economic Conditions 26 prose Skyward/2024/FY/Annual report# 4f28b2b44495002216d2282a1a2e70e8 0 Risks Related to the Regulatory Environment 27 prose Skyward/2024/FY/Annual report# e4e872ad78f483eeb0f8d49e836bab59 0 Risks Related to Our Liquidity and Access to Capital 28 prose Skyward/2024/FY/Annual report# cc01931ee879e3a8ebad018905bda8cc 0 Risks Related to Our Operations 29 prose Skyward/2024/FY/Annual report# df3ddcf8c791bd0d9d376eaa1deb1121 0 Risks Related to Ownership of Our Common Stock 30 prose Skyward/2024/FY/Annual report# 92e9949155a1117b872fb4c15b12d70e 0 Securities Authorized for Issuance Under Equity Compensation Plans 31 prose Skyward/2024/FY/Annual report# b3c1b3859bc0d5b704bf9a25515749ac 0 Recent Sales of Unregistered Equity Securities 32 prose Skyward/2024/FY/Annual report# a87fe0ffaa97326a7fccd62abdc312d0 0 Use of Proceeds from Initial Public Offering 33 prose Skyward/2024/FY/Annual report# 4000b9018fde108b249b01dbf1080b21 0 Issuer Purchases of Equity Securities 34 prose Skyward/2024/FY/Annual report# 865a05df538f3812bbe415f47423545d 0 Dividends 35 prose Skyward/2024/FY/Annual report# 214728a473fc8ee47c4198794d3614ff 0 Performance Graph 36 prose Skyward/2024/FY/Annual report# 2f7a4246ec14a70f1687a9c8be293456 0 Stock performance comparison 37 table Skyward/2024/FY/Annual report# 553153a75a7d62f94763aad099abc943 0 Overview 38 prose Skyward/2024/FY/Annual report# aabf150c8e54b3e54dd6ef2f2fe942e7 0 Results of Operations 39 prose Skyward/2024/FY/Annual report# e233cc85ccf28f40dbdbdfa42a42de34 0 Summary of financial performance 40 table Skyward/2024/FY/Annual report# dc8f89b49db272363d6dd8540db158e0 0 Reconciliation of Non-GAAP Financial Measures 41 prose Skyward/2024/FY/Annual report# ab4e5bd22b4c6127691ec3331176dfe8 0 Return on tangible equity reconciliation 42 table Skyward/2024/FY/Annual report# 3dce963cf580c7d24c6987d32bfc5732 0 Reconciliation of income before income taxes to underwriting income 43 table Skyward/2024/FY/Annual report# f8c8e294b95094c0d56251e981ec18a3 0 Loss and combined ratios 44 table Skyward/2024/FY/Annual report# be2defb99af9cd4244315f3da7939dae 0 Stockholders’ equity and tangible stockholders’ equity 45 table Skyward/2024/FY/Annual report# 2e92a5c53f611beb3dd9cf1135c17352 0 Adjusted return on equity 46 table Skyward/2024/FY/Annual report# ec9984ce774b18b149941ef11f193dac 0 Return on tangible equity 47 table Skyward/2024/FY/Annual report# 51115d76d01c8b6dd67e780aa5fae51c 0 Adjusted return on tangible equity 48 table Skyward/2024/FY/Annual report# 75cbe067dd407c0d50043a5394f31da9 0 Net written premiums = USD 1,123.6m Net earned premiums = USD 1,056.7m Loss ratio increase = 1.3 points Catastrophe losses = Hurricanes Helene, Beryl, Milton Adverse development 2024 = USD 25.7m Adverse development 2023 = USD 10.8m Underwriting Results 49 Net written premiums, net earned premiums, loss ratio, non-cat loss and LAE ratio, cat loss and LAE ratio, prior accident year development, IBNR, LPT prose Skyward/2024/FY/Annual report# ca7b64d242f60cd0c43624eb159c9895 0 Gross written premiums by segment 50 Gross written premiums by segment, Industry Solutions, Global Property & Agriculture, Captives, Programs, Accident & Health, Transactional E&S, Professional Lines, Surety table Skyward/2024/FY/Annual report# 04cc9e2c191d33b709138a901a6d591f 0 Losses and LAE 51 Losses and LAE, Non-cat loss and LAE, Cat loss and LAE, Prior accident year development - LPT table Skyward/2024/FY/Annual report# 9059ea02a3320c1ac97d5e0d3f140b3d 0 Loss and LAE reserve development 52 Loss and LAE reserve development, Accident Year, Prior, LPT table Skyward/2024/FY/Annual report# 5440efa04543f7772cd9ddc05ba66cf5 0 Net expenses 53 Net expenses, Net policy acquisition expenses, Other operating and general expenses, Underwriting, acquisition and insurance expenses, commission and fee income table Skyward/2024/FY/Annual report# a4439cc20ff9b09275bf2ce2db581c58 0 Net investment income and gains 54 Net investment income and gains, Short-term investments & cash and cash equivalents, Fixed income, Equities, Alternative and strategic investments, Net unrealized gains on securities still held, Net realized losses table Skyward/2024/FY/Annual report# e0487d97a2a23df57ae405cb427480dc 0 Weighted average credit rating = AA- Average duration fixed income portfolio 2024 = 4.34 years Average duration fixed income portfolio 2023 = 4.24 years Equities portfolio publicly traded = 100.0% Investments 55 Fixed income portfolio, commercial mortgage loans, equities portfolio, alternative investments, strategic investments, market risk, credit risk, interest rate risk prose Skyward/2024/FY/Annual report# a9af9f9e055817690174684a291c3d0b 0 Investment portfolio by asset class 56 Investment portfolio by asset class, Cash and cash equivalents, Short-term investments, Fixed income, Equities, Alternative and strategic investments table Skyward/2024/FY/Annual report# 81f458b28238cebf0b855af070f03b53 0 Fixed income portfolio by security type 57 Fixed income portfolio by security type, U.S. government securities, Corporate securities and miscellaneous, Municipal securities, Residential mortgage-backed securities, Commercial mortgage-backed securities, Other asset-backed securities, Commercial mortgage loans table Skyward/2024/FY/Annual report# f812c20f25720ec1b309b2140f909c59 0 Fixed income portfolio by credit rating 58 Fixed income portfolio by credit rating, AAA, AA, A, BBB, BB and Lower table Skyward/2024/FY/Annual report# b08d91143d780ac1a996d4124aeecb98 0 Equity portfolio by type 59 Equity portfolio by type, Domestic common equities, International common equities, Preferred stock table Skyward/2024/FY/Annual report# 91968f05f050366d98690a0f88d95d69 0 Interest rate sensitivity analysis 60 Interest rate sensitivity analysis, Estimated Fair Value, Estimated Change in Fair Value, Estimated % Increase (Decrease) in Fair Value table Skyward/2024/FY/Annual report# 3c816fa10e7c7d6537aa9aa11b15f771 0 Income tax expense 2024 = USD 33.9m Income tax expense 2023 = USD 24.1m Effective tax rate 2024 = 22.2% Effective tax rate 2023 = 21.9% Other Items 61 Income tax expense, effective tax rate, federal income tax expense, Note 13, Income Taxes prose Skyward/2024/FY/Annual report# 29bef4342e577bb60602fb6998b530d7 0 Insurance subsidiaries = GMIC, HSIC, IIC, OSIC Liquidity and Capital Resources 62 Holding company, insurance subsidiaries, GMIC, HSIC, IIC, OSIC, corporate service fees, consolidated U.S. federal income tax return, corporate tax allocation agreement, state insurance laws, insurance regulators, dividend payments prose Skyward/2024/FY/Annual report# 7ce232b0acfad074ecd89f173a0d60e6 0 Cash Flows 63 Premiums received, claims, cash investment, operating expenses, capital expenditures, reinsurance, timing of cash flows, loss settlements, reinsurance receipts, net reinsurance recoverables, net premiums receivables, investing activities, financing activities prose Skyward/2024/FY/Annual report# ec3e0036629b1c27f0fbbafcc86154e8 0 Cash flows 64 Cash flows, Operating activities, Investing activities, Financing activities, Change in cash and cash equivalents and restricted cash table Skyward/2024/FY/Annual report# 907960ed456d88b55047bc43fabec103 0 FHLB Loan amount = USD 57.0m FHLB Loan interest rate = 4.00% Revolving Credit Facility amount = USD 150.0m Revolving Credit Facility undrawn capacity = USD 107.0m Outstanding under Revolving Credit Facility = USD 43.0m Credit Agreements 65 FHLB Loan, Federal Home Loan Bank of Dallas, Revolving Credit Facility, Debentures, HSIC, SOFR prose Skyward/2024/FY/Annual report# 78d1169fd2b65378919aca0db3360d43 0 Reinsurance balances recoverable 2024 = $857.9m Reinsurance balances recoverable 2023 = $596.3m Contractual Obligations and Commitments 66 Reserves for losses and LAE, reinsurance balances recoverable, policyholders prose Skyward/2024/FY/Annual report# 7842f150d3aced3cf6b9be9dad5d3c1b 0 Contractual obligations 67 Contractual obligations, Reserves for losses and LAE, Long-term debt, Interest on debt obligations, Operating lease obligations table Skyward/2024/FY/Annual report# 6fc2e1f66f57b06064b765309d72de5a 0 Critical Accounting Policies 68 Critical accounting estimates, consolidated financial statements, assets, liabilities, revenues, expenses, contingent assets and liabilities, Note 1, Summary of Significant Accounting Policies, Reserves for unpaid losses and LAE, reported claims, unreported claims, loss severity, loss frequency, inflation prose Skyward/2024/FY/Annual report# 0dbc360f60925f33a9ee44fd15d88ed5 0 Impact of a 5% change in net IBNR on reserves, income, and equity 69 Impact of a 5% change in net IBNR on reserves, income, and equity, Case reserves, IBNR table Skyward/2024/FY/Annual report# 30f1b2105d4f88924f9e221630a341b2 0 ASU 2023-07 effective date = fiscal years beginning after December 15, 2023 ASU 2023-09 effective date = fiscal years beginning after December 15, 2024 ASU 2024-03 issued = November 2024 Recent Accounting Pronouncements 70 ASU 2023-07, Improvements to Reportable Segment Disclosures, FASB, chief operating decision maker, CODM, ASU 2023-09, Improvements to Income Tax Disclosures, public companies, income taxes, ASU 2024-03, income statement expenses prose Skyward/2024/FY/Annual report# d273fe90cc438e46d928498047bd1887 0 Auditor = Independent Registered Public Accounting Firm Audit opinion = unqualified Report date = March 1, 2024 Report of Independent Registered Public Accounting Firm 71 Skyward Specialty Insurance Group, Inc., consolidated financial statements, consolidated balance sheets, consolidated statements of operations, comprehensive income (loss), changes in stockholders’ equity, cash flows, accounting principles generally accepted in the United States of America, Public Company Accounting Oversight Board, PCAOB, internal control over financial reporting, Internal Control—Integrated Framework (2013), Committee of Sponsoring Organizations of the Treadway Commission, COSO prose Skyward/2024/FY/Annual report# 246db0c837c459f60d9bbed7c2f68f86 0 Audit opinion = unqualified Report date = March 3, 2025 Opinion on Internal Control Over Financial Reporting 72 Internal control over financial reporting, Internal Control—Integrated Framework, Committee of Sponsoring Organizations of the Treadway Commission, COSO criteria, Skyward Specialty Insurance Group, Inc., material weakness, information technology general controls, ITGCs, user access, financial reporting processes, process-level IT dependent manual and automated controls, consolidated financial statements, PCAOB standards prose Skyward/2024/FY/Annual report# 254ea7857f27998b1ac7ee344b69882d 0 Basis for Opinion 73 Management's responsibility, auditor's responsibility, PCAOB standards, audit procedures prose Skyward/2024/FY/Annual report# b0a5802278a0c97d1036e0b03d3c0495 0 Auditor = Ernst & Young LLP Auditor since = 2021 Headquarters = Houston, Texas Report date = March 3, 2025 Definition and Limitations of Internal Control Over Financial Reporting 74 Definition and limitations of internal control over financial reporting, policies and procedures, prevention and detection of misstatements prose Skyward/2024/FY/Annual report# ac7e2873bfe0d58022c43d5853b308c5 0 Auditor = Skyward Specialty Insurance Group, Inc. Consolidated financial statements as of = December 31, 2023 and 2022 Internal control over financial reporting as of = December 31, 2023 Report dated = February 29, 2024 Other auditors report dated = March 10, 2023 Report of Independent Registered Public Accounting Firm 75 Audit of consolidated financial statements, opinion on financial position and cash flows, audit of internal control over financial reporting prose Skyward/2024/FY/Annual report# 736c4cbc8b053f70e2edee7a6849ca72 0 Opinion on the Financial Statements 76 Audited consolidated financial statements, consolidated balance sheets, consolidated statements of operations and comprehensive income, stockholders' equity, cash flows prose Skyward/2024/FY/Annual report# 47bb911674b3269fb8631a8981148eb0 0 Basis for Opinion 77 Management's responsibility for financial statements, auditors' responsibility, PCAOB standards, audit procedures prose Skyward/2024/FY/Annual report# 49f3adf5f2c3b39ad090486703e2dd53 0 Critical Audit Matter 78 Critical audit matter, audit committee communication, material accounts or disclosures, auditors' judgments prose Skyward/2024/FY/Annual report# 9741026a0ba84da5c7b71728e2e78c5f 0 Reserves for unpaid losses and LAE = USD 1.8bn at December 31, 2024 Valuation of Reserves for Unpaid Losses and Loss Adjustment Expenses 79 Reserves for unpaid losses and LAE, incurred but not reported reserves (IBNR), estimation methods, actuarial procedures, audit procedures prose Skyward/2024/FY/Annual report# 71a17e853facff2152aa29f1a89243bb 0 Consolidated balance sheets 80 Consolidated balance sheets, accompanying notes prose Skyward/2024/FY/Annual report# 532e878faa8a77485d81013b21db9f27 0 Consolidated balance sheets 81 table Skyward/2024/FY/Annual report# 8ce6156e9432616d6686c566c8db6f92 0 Consolidated statements of operations and comprehensive income 82 Consolidated statements of operations and comprehensive income, accompanying notes prose Skyward/2024/FY/Annual report# 139b06f024ad284ce3e2d090e6abb935 0 Consolidated statements of operations 83 table Skyward/2024/FY/Annual report# 0eb3c2bb7e91ea2d41f5491a12704bc7 0 Consolidated statements of stockholders’ equity 84 Consolidated statements of stockholders’ equity, accompanying notes prose Skyward/2024/FY/Annual report# 896df4ab6c3f32575418afc9b8975f2f 0 Consolidated statements of changes in stockholders’ equity 85 table Skyward/2024/FY/Annual report# 8db58c19b49e5eea17af1ae55a20735c 0 Consolidated statements of cash flows 86 Consolidated statements of cash flows, accompanying notes prose Skyward/2024/FY/Annual report# c1982747fd37e1afd523d7adbf5e2171 0 Consolidated statements of cash flows 87 table Skyward/2024/FY/Annual report# 2a3e5d4addd6ee8f054f62475f74db06 0 Legal name = Skyward Specialty Insurance Group, Inc. State of incorporation = Delaware Year founded = 2006 Number of insurance subsidiaries = Four Number of non-risk bearing subsidiaries = Three A. Description of Business 88 Insurance holding company, specialty insurance, commercial property and casualty insurance, underwriting divisions, wholly owned insurance subsidiaries, captive reinsurance company, non-risk bearing subsidiaries prose Skyward/2024/FY/Annual report# 39741fc4163d83c42cbaa825590059e1 0 B. Basis of Presentation 89 Consolidated financial statements, Generally Accepted Accounting Principles (GAAP), estimates and assumptions, intercompany transactions prose Skyward/2024/FY/Annual report# 5cd7848f84e0fb03685f1fab4a13cbb8 0 C. Cash and Cash Equivalents 90 Cash and cash equivalents, fixed maturity securities, carrying value, fair value prose Skyward/2024/FY/Annual report# 8978e823905a0ced99f1cbc5ea840825 0 D. Restricted Cash 91 Restricted cash, legal restriction, unremitted insurance premiums, fiduciary capacity, assets on deposit, collateral for reinsurance balances prose Skyward/2024/FY/Annual report# 562168b934bdd12008c2af1ae03209d7 0 E. Investments 92 Available for Sale fixed maturities, unrealized loss position, credit-related factors, allowance for credit losses, Held-to-maturity fixed maturity securities, historical loss rate prose Skyward/2024/FY/Annual report# c228bf0e8473cd6029670d914084d83c 0 F. Reinsurance 93 Prospective reinsurance, proportional reinsurance, excess of loss reinsurance, facultative reinsurance, ceded unearned premium, reinsurance balances recoverable, retroactive reinsurance, loss portfolio transfers, adverse development covers prose Skyward/2024/FY/Annual report# 40707f65b48eb2725eb1c0b30f67dd94 0 G. Concentration of Credit Risk 94 Concentrations of credit risk, financial instruments, cash and cash equivalents, restricted cash, investments, premiums receivable, U.S. government securities, money market funds, diversification, credit exposure prose Skyward/2024/FY/Annual report# 85b91dd2bf3d07d5f4ebfc6c5fbd62e2 0 H. Deferred Policy Acquisition Costs 95 Policy acquisition costs, deferred policy acquisition costs, ceding commissions, premium deficiency, unamortized acquisition costs, anticipated investment income prose Skyward/2024/FY/Annual report# dcbd70900c7e1d5e72d2b6e66c0238d3 0 I. Goodwill and Intangible Assets 96 Goodwill and intangible assets, business combination, purchase price allocation, identifiable intangible assets, indefinite-lived intangible assets, recoverability review, goodwill impairment prose Skyward/2024/FY/Annual report# 611694308b6486c89b32e1a258f4857e 0 J. Property and Equipment 97 Property and equipment, depreciation expense, depreciation periods prose Skyward/2024/FY/Annual report# 287323ef4e9ddb7773407dbd2cd8086c 0 K. Leases 98 Right-of-use assets, lease liabilities, operating leases, sublease income prose Skyward/2024/FY/Annual report# 6d9ed238eeb1c9e7587189748ae22039 0 L. Reserves for Losses and Loss Adjustment Expenses 99 Reserves for unpaid losses and loss adjustment expenses, actuarial procedures, loss severity, loss frequency, inflation prose Skyward/2024/FY/Annual report# 3848f15217766c3613480be9c598bbe2 0 M. Premiums 100 Property and casualty premiums, surety premiums, accident and health premiums, gross premiums written, ceded premiums, premiums receivable, allowance for credit losses, unearned premiums, ceded unearned premiums prose Skyward/2024/FY/Annual report# 6da27bd5444981b8f53de6440a7a0bb4 0 N. Commission and Fee Income 101 SUA commission revenue, SUA fee income, transaction price, performance obligation prose Skyward/2024/FY/Annual report# 77edf4afb87c1cca13a3be3a15fe5e05 0 O. Income Taxes 102 Income tax expense, provision for income taxes, deferred tax assets and liabilities, valuation allowance, uncertain tax positions, consolidated federal income tax return, premium taxes prose Skyward/2024/FY/Annual report# 7ca0ca239dc47f4c1dc99bb4ef547503 0 P. Fair Value of Financial Instruments 103 Fair value, financial instruments, fair value hierarchy, Level 1 measurements, Level 3 measurements prose Skyward/2024/FY/Annual report# 0cf1c3049cc4afbbb3cac4ef68737b95 0 Q. Stock-Based Compensation 104 Employee stock options, equity instrument awards, share-based payments, Employee Stock Purchase Plan (ESPP) prose Skyward/2024/FY/Annual report# d446231bf956f33862c1ba3973de46a0 0 R. Earnings Per Share 105 Basic earnings per share, undistributed earnings, participating securities, common shares, preferred shares, stock notes, contingently issuable instruments, share-based awards prose Skyward/2024/FY/Annual report# e588dabee18349e650054d6f214e2388 0 S. Recent Accounting Pronouncements 106 ASU 2023-07, ASU 2023-09, ASU 2024-03, reportable segment disclosures, income tax disclosures, income statement expenses prose Skyward/2024/FY/Annual report# ea7e522dee99f98b642edf3ae034e1e3 0 2. Goodwill and Intangible Assets 107 Indefinite-lived intangible assets, finite-lived intangible assets, insurance licenses, trademarks, policy renewals, agency relationships, non-compete/exclusivity agreements, amortization expense prose Skyward/2024/FY/Annual report# 077b17e252ba8a0162a1040398de0365 0 Goodwill by segment at December 31, 2024 108 Goodwill by segment, Accident and Health, Surety, Industry Solutions, Other table Skyward/2024/FY/Annual report# 6fa2668350a26bb3da88370b042bfa03 0 Goodwill by segment at December 31, 2023 109 Goodwill by segment, Accident and Health, Surety, Industry Solutions, Other table Skyward/2024/FY/Annual report# 9465e81ad9f9491d94996a080d2b3b43 0 Other intangible assets at December 31, 2024 110 Other intangible assets, Agent Relationships, Non-competes, Trademarks, Licenses table Skyward/2024/FY/Annual report# f6dc056e3ebd55c0c4db92dd5b08416d 0 Other intangible assets at December 31, 2023 111 Other intangible assets, Agent Relationships, Non-competes, Trademarks, Licenses table Skyward/2024/FY/Annual report# 9a32b7d3aa704892ebd8303f74f4c3c0 0 Future amortization expense 112 Future amortization expense table Skyward/2024/FY/Annual report# c458784484ca5bf0febb61f2f9f12080 0 3. Investments 113 Fixed maturity securities, asset-backed securities, U.S. government agencies mortgage-backed fixed maturity securities, FHLB Loan, Advances and Security Agreement, pledged assets, residential mortgage-backed securities, short-term investments, cash and cash equivalents, available-for-sale fixed maturity securities, unrealized loss position, credit impairment prose Skyward/2024/FY/Annual report# 651f18806411530e79cef05b4b04cef2 0 Fixed maturity securities at December 31, 2024 114 Fixed maturity securities, U.S. government securities, corporate securities, municipal securities, residential mortgage-backed securities, commercial mortgage-backed securities table Skyward/2024/FY/Annual report# 2d7577aace75ef7454aa8105b6679bf5 0 Fixed maturity securities at December 31, 2023 115 Fixed maturity securities, U.S. government securities, corporate securities, municipal securities, residential mortgage-backed securities, commercial mortgage-backed securities table Skyward/2024/FY/Annual report# 2fb20467adefbb8fa7eea1da81256a93 0 Maturity distribution of fixed maturity securities 116 Maturity distribution of fixed maturity securities, mortgage-backed securities, other asset-backed securities table Skyward/2024/FY/Annual report# 6f2860f00b1428a12f56f834c23a8a17 0 Fixed maturity securities by contractual maturity at December 31, 2024 117 Fixed maturity securities by contractual maturity, U.S. government securities, corporate securities, municipal securities table Skyward/2024/FY/Annual report# 37f299dea650c9783cec8bea2156721c 0 Fixed maturity securities by contractual maturity at December 31, 2023 118 Fixed maturity securities by contractual maturity, U.S. government securities, corporate securities, municipal securities table Skyward/2024/FY/Annual report# c26b365c26b1310ba8444cb968b95830 0 Net realized investment gains and losses 119 Net realized investment gains and losses, fixed maturity securities, equity securities, mortgage loans table Skyward/2024/FY/Annual report# 561467761cd00e83420bb079a9085af8 0 Net unrealized investment gains and losses 120 Net unrealized investment gains and losses, fixed maturity securities, equity securities table Skyward/2024/FY/Annual report# db4095a93ce0098ecf387afa1c47cf74 0 Net investment income 121 Fixed maturity securities, equity securities, mortgage loans, short-term investments, cash, investment expenses table Skyward/2024/FY/Annual report# 1e1bd78380a1591fb60e36240b3d2d53 0 Deferred income taxes 122 Fixed maturity securities, deferred income taxes table Skyward/2024/FY/Annual report# 8da44381ea5db006e71af12547f81853 0 4. Fair Value Measurements 123 Fair value measurements, market approach, third-party investment managers, pricing vendors, three-level hierarchy, Level 1 inputs, Level 2 inputs, Level 3 inputs, U.S. government securities, mutual funds, common stock, preferred stocks, municipal securities, corporate securities, commercial mortgage-backed securities, residential mortgage-backed securities, other asset-backed securities prose Skyward/2024/FY/Annual report# ebf6a20b8362c1eb5fdad9676f5f8bf5 0 Fair value of subordinated debt at December 31, 2024 124 Fair value of subordinated debt table Skyward/2024/FY/Annual report# 72b91e9c5837a5d1defbde13129e5957 0 Fair value of financial instruments 125 Fair value of financial instruments table Skyward/2024/FY/Annual report# f5bb7e5293100ec2c96496d0ada386a8 0 Fair value hierarchy of financial instruments at December 31, 2024 126 Fair value hierarchy, fixed maturity securities, U.S. government securities, corporate securities, municipal securities, residential mortgage-backed securities, commercial mortgage-backed securities, other asset-backed securities table Skyward/2024/FY/Annual report# 57337e179169edfc503bd4adc5846ea6 0 Fixed maturity securities by type 127 Fixed maturity securities by type, U.S. government securities, corporate securities, municipal securities, residential mortgage-backed securities, commercial mortgage-backed securities, other asset-backed securities table Skyward/2024/FY/Annual report# 87a24465bf7f5e05eeb6f8faac733ba0 0 Fixed maturity securities and mortgage loans activity 128 Fixed maturity securities, mortgage loans, net investment gains (losses), accumulated comprehensive income (loss) table Skyward/2024/FY/Annual report# aebde98be8c7dc2f800b8fc2487ba38a 0 Mortgage loans activity 129 Mortgage loans, net investment gains (losses) table Skyward/2024/FY/Annual report# fda7d9fe861d4178a8f032187068c6a6 0 Notes payable and subordinated debt 130 Notes payable, subordinated debt, FHLB Loan, revolving credit facility, junior subordinated interest debentures, unsecured subordinated notes table Skyward/2024/FY/Annual report# eb76c4322e1e401a33b1ebd61048dc3c 0 5. Mortgage Loans 131 Separately Managed Accounts (SMA1, SMA2), direct investments in mortgage loans, mortgage loan portfolios, real estate, uncollectible amounts on loans, foreclosure, non-producing income prose Skyward/2024/FY/Annual report# 1574611f3986a568554e67675feb08cf 0 Mortgage loans by property type 132 Mortgage loans by property type, commercial, retail, hospitality, industrial table Skyward/2024/FY/Annual report# ddc0a9413d45bbfcfdbb5b9505369133 0 Mortgage loans by property type 133 Mortgage loans by property type, commercial, retail, hospitality, office, multi-family, industrial table Skyward/2024/FY/Annual report# 349f723e072055fbb3cf4d6c5f029381 0 6. Equity Method Investments and Other 134 Equity method investments, RISCOM, agent relationships, collateralized loans, loan collateral, SMA1, SMA2 prose Skyward/2024/FY/Annual report# 627e459961c6220bf404162903773393 0 Indirect investments in collateralized loans and loan collateral 135 Indirect investments, collateralized loans, loan collateral, Arena Special Opportunities Fund, JVM Funds LLC, RISCOM, Hudson Ventures Fund 2 LP, Arena SOP LP, Brewer Lane Ventures Fund II LP, Dowling Capital Partners LP table Skyward/2024/FY/Annual report# 9819421befa9e954a6c1f22341cd4f0e 0 Indirect investments in collateralized loans and loan collateral 136 Indirect investments, collateralized loans, loan collateral, Arena Special Opportunities Fund, RISCOM, Dowling Capital Partners LP, Universa Black Swan LP, Brewer Lane Ventures Fund II LP, Hudson Ventures Fund II LP, Arena SOP LP, JVM Funds LLC table Skyward/2024/FY/Annual report# 866e756bee0066d2d3cdef1a835cdafe 0 Indirect investments in collateralized loans and loan collateral 137 Indirect investments, collateralized loans, loan collateral, Brewer Lane Ventures Fund II LP, Hudson Ventures Fund 2 LP, Dowling Capital Partners LP table Skyward/2024/FY/Annual report# 68bec56357278e41114f55274689a1b3 0 Investment in RISCOM 138 Investment in RISCOM, underlying equity, recorded investment balance table Skyward/2024/FY/Annual report# 85554431a7ce17ef3ff5f6a866e88ea8 0 Investment in JVM Funds LLC 139 Investment in JVM Funds LLC, underlying equity, recorded investment balance table Skyward/2024/FY/Annual report# 167a487ab6def95cc4d33009c56dbd48 0 Investment in indirect loans and loan collateral 140 Investment in indirect loans, loan collateral, SMA1, SMA2 table Skyward/2024/FY/Annual report# de0bbd9e0567b02d1a56d00bf2d7ebc7 0 Rating agency = A.M. Best Commuted LPT = January 31, 2025 LPT counterparty = R&Q Re (Bermuda) Ltd. Uncollectible reinsurance recoverable balance = $13.6 million 7. Allowance for Credit Losses 141 Reinsurance recoverables, credit risk, financial strength rating, A.M. Best, reinsurance payables, letters of credit, funds held, reinsurance balances, LPT, R&Q Re (Bermuda) Ltd. prose Skyward/2024/FY/Annual report# 99837d3294d62b54c4aa0b7f5cc0ed7f 0 Premiums receivable and allowance for uncollectible premiums 142 Premiums receivable, allowance for uncollectible premiums table Skyward/2024/FY/Annual report# 70072cf03f4ccef0786e797381506977 0 Premiums receivable and allowance for uncollectible premiums 143 Premiums receivable, allowance for uncollectible premiums, ASU 2016-13 table Skyward/2024/FY/Annual report# a5ce00e1936be39f60fa7be4636bfda8 0 Reinsurance recoverables by A.M. best rating 144 Reinsurance recoverables, A.M. Best Rating, A-, B++ to B+, Not rated table Skyward/2024/FY/Annual report# 7e4e11bb74deb57e704c3af67d37928c 0 Reinsurance recoverables and allowance for uncollectible reinsurance 145 Reinsurance recoverables, allowance for uncollectible reinsurance table Skyward/2024/FY/Annual report# 161ea418d06004793dfb92e9586fe726 0 Reinsurance recoverables and allowance for uncollectible reinsurance 146 Reinsurance recoverables, allowance for uncollectible reinsurance table Skyward/2024/FY/Annual report# b57d5fb667c1f154cea342f544e401f2 0 Depreciation expense = FY24: USD 2.9m 8. Property and Equipment 147 Depreciation expense prose Skyward/2024/FY/Annual report# d556e01bbbb8ae6cb1f68c679e5e3af8 0 Property and equipment, net 148 Property and equipment, leasehold improvements, equipment, software, accumulated depreciation table Skyward/2024/FY/Annual report# 3a1e575407f46d1ace60c30bb80c3017 0 Lease expense = FY24: $2.1 million Lease terms = less than 1 year to 6 years 9. Leases 149 Lease contracts, right-of-use assets, lease liabilities, lease payments, office facilities, operating leases prose Skyward/2024/FY/Annual report# 97ad2b0eaabe2b942969febe536545c3 0 Operating lease information 150 Operating lease right-of-use assets, operating lease liabilities, weighted-average remaining lease term, weighted-average discount rate table Skyward/2024/FY/Annual report# d1575de5b7145af07a728b72bd51b8de 0 Lease expense and cash outflows 151 Operating lease expense, short-term lease expense, total lease expense, operating cash outflows from operating leases table Skyward/2024/FY/Annual report# 85d3b31c2afff415a856ac253fb99852 0 Future minimum operating lease payments 152 Future minimum operating lease payments, imputed interest, total operating lease liability table Skyward/2024/FY/Annual report# fff14f93f1ed5f2859b27b9705d19bad 0 FHLB Loan principal = USD 57.0m FHLB Loan term = 4.5-year FHLB Loan interest rate = 4.00% Revolving Credit Facility amount = USD 150.0m Revolving Credit Facility letter of credit sub-facility = USD 30.0m Revolving Credit Facility interest rate = SOFR plus 150 to 190 bps Revolving Credit Facility SOFR = Dec 31, 2024: 4.25% 10. Notes Payable & Subordinated Debt 153 FHLB Loan, Revolving Credit Facility, Debentures, investment securities, covenants prose Skyward/2024/FY/Annual report# a893a0ad33a681edca52d83daec1ae10 0 Reverse stock split = 4-for-1 IPO shares offered = 4,750,000 IPO price per share = $15.00 IPO net proceeds = $62.0 million Authorized common stock shares = 500,000,000 Authorized preferred stock shares = 10,000,000 Preferred Shares converted = 1,969,660 Common stock from conversion = 16,305,113 Follow-on shares sold = 2,150,000 11. Stockholders Equity 154 Reverse stock split, Initial Public Offering (IPO), authorized shares, Preferred Shares Conversion, Follow-On Offering prose Skyward/2024/FY/Annual report# 1cee996d3f435950ca89356d8a0c4116 0 Number of segments = one Reportable segments = commercial property and casualty Geographic regions = United States Segment basis = internal financial information reviewed by CODM Segment profit measure = gross written premiums, underwriting income, income before income taxes 12. Segment 155 Reportable segment, commercial property and casualty products, underwriting divisions, Chief Operating Decision Maker (CODM), accounting policies, segment performance, resource allocation, competitive analysis, management compensation prose Skyward/2024/FY/Annual report# 580e0eba3da136ba896eab36aebcb760 0 Segment information 156 Industry Solutions, Global Property & Agriculture, Captives, Programs, Accident & Health, Transactional E&S, Professional Lines, Surety, continuing business, exited business table Skyward/2024/FY/Annual report# 1b786048d363f7a4682b6d19765af54d 0 Underwriting income and expenses 157 Underwriting income, net earned premiums, commission and fee income, total underwriting revenues, losses and LAE, amortization of policy acquisition costs, other operating and general expenses, total underwriting expenses, net underwriting income table Skyward/2024/FY/Annual report# eab06f68384e70c6cae9b08e62113b0f 0 Return on equity and book value per share 158 Return on equity, book value per share table Skyward/2024/FY/Annual report# ffacfc467739c594dad0ccc91b866bac 0 Federal statutory income tax rate = 21% Federal income taxes paid = FY24: USD 37.0 million Federal net operating loss carryforwards = USD 44.7 million Net operating losses expiration = beginning in 2032 Sec 382 limitation = USD 2.8 million Capital loss carryforward deferred tax asset = Dec 31, 2024: USD 1.7 million 13. Income Taxes 159 Provision for income taxes, effective tax rate, federal statutory income tax rate, federal income taxes, federal income tax returns, uncertain tax positions, interest and penalties, federal net operating loss carryforwards, Internal Revenue Code Section 382, valuation allowance, capital loss carryforward, deferred tax asset prose Skyward/2024/FY/Annual report# 891dfc7d96d6d714c35f213fea122165 0 Income tax expense 160 Current income tax expense, deferred tax (benefit) expense, total income tax expense table Skyward/2024/FY/Annual report# 974dc65a343dd2e26cb37a374cc42e18 0 Reconciliation of income tax expense 161 Income tax expense at federal statutory rate, tax advantaged investments, other, total income tax expense table Skyward/2024/FY/Annual report# d445a8709833af5392032630adc834c5 0 Deferred tax assets 162 Deferred tax assets, unearned premiums, losses and loss adjustment expenses, net operating losses, unrealized losses on fixed maturity securities, stock options/awards, other, total deferred tax assets, valuation allowance, deferred policy acquisition costs, unrealized gains on equity securities, other long-term investments, depreciation table Skyward/2024/FY/Annual report# f88be6ee7eb9c48876ceb0dac500f146 0 14. Reserves for Losses and Loss Adjustment Expenses 163 Losses and LAE reserves, multi-line solutions, short-tail/monoline specialty lines, exited lines, underwriting divisions, policy year basis, accident year basis prose Skyward/2024/FY/Annual report# 6995d3d3d271b3b693604bef1b5f6f6b 0 Loss and LAE reserve development 164 Reserves for losses and LAE, reinsurance recoverable on unpaid claims, incurred net of reinsurance, paid net of reinsurance table Skyward/2024/FY/Annual report# d867079df7b819ade9dcfb2aec982720 0 Short Duration Contract Disclosures 165 Losses and LAE reserves, estimated reserves for losses and LAE, cumulative reported claims, claim counts prose Skyward/2024/FY/Annual report# fd061bfbfc30deed7787ac42b15f82a9 0 Incurred losses and ALAE, net of reinsurance 166 Incurred Losses and Allocated Loss Adjustment Expense (ALAE), IBNR, Reported Claims by Accident Year table Skyward/2024/FY/Annual report# 1c1c731351d400e2d59014aac04ebc52 0 Cumulative paid losses and ALAE, net of reinsurance 167 Cumulative Paid Losses and ALAE by Accident Year table Skyward/2024/FY/Annual report# c47c12326cf35049bba08e5db9a7abc5 0 Incurred losses and ALAE, net of reinsurance 168 Incurred Losses and ALAE, IBNR, Reported Claims by Accident Year table Skyward/2024/FY/Annual report# 955b998ed2d94b0c5f342032e1d7b7a3 0 Cumulative paid losses and ALAE, net of reinsurance 169 Cumulative paid losses and ALAE, net of reinsurance table Skyward/2024/FY/Annual report# a9325bec453420b3e627c6d7b5714662 0 Balance sheet reserves for losses and loss adjustment expenses = December 31, 2024 and 2023 Exited Lines — all lines in runoff 170 Reconciliation of net incurred and paid loss development tables to balance sheet reserves, historical average annual payout of incurred losses and allocated loss adjustment expenses, short-duration contracts prose Skyward/2024/FY/Annual report# ff5d5e9e6eea9c362aaa5eeec6be1930 0 Historical average annual payout of incurred losses and ALAE 171 Incurred losses and ALAE, net of reinsurance table Skyward/2024/FY/Annual report# f162d7a7c93caa2853bfdd0a18b13ed5 0 Cumulative paid losses and ALAE, net of reinsurance 172 Cumulative paid losses and ALAE, net of reinsurance table Skyward/2024/FY/Annual report# f2d1e8fabe3fe70ce3ef79fb5d74a078 0 Net reserves for losses and ALAE 173 Net reserves for losses and ALAE, reinsurance recoverable on unpaid claims, unallocated LAE table Skyward/2024/FY/Annual report# 9452254b6bffb455b8a960bfed63f727 0 Average annual percentage payout of incurred claims by age 174 Average annual percentage payout of incurred claims by age, net of reinsurance table Skyward/2024/FY/Annual report# d19cd5f36b856f15e6bcbbd243200864 0 Subsidiary = Skyward Underwriters Agency, Inc. (SUA) 15. Commission and Fee Income 175 Skyward Underwriters Agency, Inc. (SUA), managing general insurance agent, reinsurance broker, property and casualty, accident and health risks, specialty niche markets, commission and fee income prose Skyward/2024/FY/Annual report# 452b780c605ff260201dc75150b20131 0 Commission and fee income 176 SUA commission revenue, SUA fee income, other commission and fee income table Skyward/2024/FY/Annual report# cdd69568b6120a8bece366d4ec0933d3 0 Contract assets 177 Contract assets table Skyward/2024/FY/Annual report# d31cab6ae39d32294f9f5243d08acf2c 0 16. Underwriting, Acquisition and Insurance Expenses 178 Underwriting, acquisition and insurance expenses components prose Skyward/2024/FY/Annual report# 7b5e8d52929a9037995f1d762ba82081 0 Underwriting, acquisition and insurance expenses 179 Amortization of policy acquisition costs, other operating and general expenses, total underwriting, acquisition and insurance expenses table Skyward/2024/FY/Annual report# 418d1e1b9b996a38aacac538c88558e5 0 Market value of funded trust accounts = USD 196.9 million at December 31, 2024 LPT retroactive reinsurance agreement = R&Q during the first quarter of 2020 Reinsurance recoverable from R&Q = USD 22.7 million at December 31, 2024 LPT commuted = January 31, 2025 Deposit asset for certain ceded reinsurance contracts = USD 25.9 million at December 31, 2024 17. Reinsurance 180 Reinsurance agreements, loss exposure, funded trust accounts, LPT retroactive reinsurance agreement, R&Q, reinsurance recoverable, deposit asset prose Skyward/2024/FY/Annual report# 7b127307b8b753445202b7c8b43afb4f 0 Premiums and ceded losses and LAE incurred 181 Direct premiums, assumed premiums, ceded premiums, net premiums, ceded losses and LAE incurred table Skyward/2024/FY/Annual report# 8bba57e4601aa64cecf8f4af00dc9866 0 Ceded unpaid losses and LAE 182 Ceded unpaid losses and LAE, ceded paid losses and LAE, loss portfolio transfer, allowance for credit losses, reinsurance recoverables, ceded unearned premium table Skyward/2024/FY/Annual report# 4d8fc4f9bc9c0aceb41a4f511c3d38b9 0 Plan = 2022 Long-Term Incentive Plan Shares available for issuance = 3,200,656 Deferral program approval = November 2024 Grant date fair value of options = Black-Scholes model Stock options granted to employees = USD 4.4 million Aggregate intrinsic value of options outstanding = USD 27.0 million at December 31, 2024 Weighted-average remaining contractual life of options outstanding = 8.0 years at December 31, 2024 18. Stock Based Compensation 183 2022 Long-Term Incentive Plan, 2020 Plan, restricted stock, restricted stock units, performance stock units, stock options, cash-based performance awards, deferral program, Black-Scholes model, volatility prose Skyward/2024/FY/Annual report# 599adf5058ff5f6a4d134b90fffb395a 0 ESPP expense 184 Market condition awards, performance condition awards, service condition awards, stock options table Skyward/2024/FY/Annual report# e77e5439a6a9ed4ca32fd3b447a69d7b 0 Stock outstanding 185 Stock outstanding table Skyward/2024/FY/Annual report# c325f69dbc9cee29d28a466e2bd0aa21 0 Stock options 186 Stock options table Skyward/2024/FY/Annual report# 677b874a589bcc86c49e4bd7413bcdbd 0 Non-vested stock and stock units 187 Non-vested stock and stock units table Skyward/2024/FY/Annual report# 618b38279d6cefef0ebdde1361c17b29 0 19. Earnings Per Share 188 Preferred shares, participating securities, dividends, distributions, common stock, employee stock options, diluted EPS calculations prose Skyward/2024/FY/Annual report# 3f1714dde425912bdb24222742e21523 0 Earnings per share 189 Net income, undistributed income, net income attributable to common stockholders, basic weighted-average common shares, dilutive effect of preferred shares, dilutive effect of stock notes table Skyward/2024/FY/Annual report# 35e0e8364db4424d794294b942a15064 0 Stock notes, stock units, and options 190 Stock notes, stock units, options table Skyward/2024/FY/Annual report# 02770e5db468e58a65f77c558def78fa 0 Common and preferred shares 191 Common shares, preferred shares table Skyward/2024/FY/Annual report# 38eff6d860aeb06f6495cfa3c2902926 0 Matching contributions = USD 3.2m for the year ended December 31, 2024 20. Employee Benefit Plan 192 401(k) Plan, Employee Retirement Income Security Act of 1974, employee contributions, matching contributions prose Skyward/2024/FY/Annual report# 562d305dca8ca125a495512c225fd9e7 0 Ownership interest in RISCOM = 20% Premiums receivable = December 31, 2024: $12.6 million Riscom 193 RISCOM, wholesale brokerage services, managing general agency agreement, premiums receivable prose Skyward/2024/FY/Annual report# 9f69a73a26f29de64389550940bde877 0 Premiums receivable and commissions for 2022-2024 194 Net earned premium, commissions table Skyward/2024/FY/Annual report# 8ee6677847584bbb42b3e43b0a84d4e7 0 Advisory and professional services fees and expense reimbursements = 2024: USD 0.6m Other 195 Advisory and professional services fees, expense reimbursements, affiliated stockholders, directors, affiliated companies, related party transactions, common shares, preferred shares prose Skyward/2024/FY/Annual report# 7083ea4548d7e290503d7780dce4f2c2 0 Litigation 196 Legal actions, claims under insurance policies and contracts, bad faith claims, disputes with third parties, alleged errors and omissions prose Skyward/2024/FY/Annual report# 981c7a2cff824f5b18722c6d6946c312 0 Indemnification 197 Indemnifications, sale of business assets, subsidiaries, representations and warranties, performance responsibilities, sales contracts prose Skyward/2024/FY/Annual report# 86f323e43ba7cf28dca24a17d784a337 0 Statutory net income = 2024: USD 108.2m Statutory capital and surplus = December 31, 2024: USD 710.6m Lead insurance company = GMIC 23. Statutory Accounting Principles and Regulatory Matters 198 Statutory net income, statutory capital and surplus, GMIC, HSIC, IIC, OSIC, dividend payments, Texas state law, Risk Based Capital (RBC) requirements, National Association of Insurance Commissioners (NAIC) prose Skyward/2024/FY/Annual report# d11572230e43af1d4878495849c28efc 0 Commutation date = January 31, 2025 Cash received by Skyward Re = $11.7 million LPT loss reserves strengthened = December 31, 2024: $25.3 million Paid loss reinsurance recoverable increased = $25.3 million Allowance for estimated uncollectible reinsurance increased = $13.6 million Deferred gain recognized = $2.0 million 24. Subsequent Events 199 Skyward Re, Loss Portfolio Transfer, Adverse Development and Retrocession Agreement, R&Q, Commutation Agreement, LPT loss reserves, paid loss reinsurance recoverable, allowance for estimated uncollectible reinsurance, deferred gain prose Skyward/2024/FY/Annual report# 21007506d109f0eac3af96a67c57d176 0 Disclosure controls and procedures effectiveness = Not effective as of December 31, 2024 Evaluation of Disclosure Controls and Procedures 200 Disclosure controls and procedures, Securities Exchange Act of 1934, material weakness, internal control over financial reporting, financial statements, U.S. GAAP prose Skyward/2024/FY/Annual report# ea42b5bc891aae59e1823b319dc1a140 0 Internal control over financial reporting effectiveness = Not effective as of December 31, 2024 Management’s Report on Internal Control over Financial Reporting 201 Internal control over financial reporting, Securities Exchange Act of 1934, U.S. GAAP, COSO's Internal Control—Integrated Framework (2013), material weakness, information technology general controls prose Skyward/2024/FY/Annual report# 49bb695cddd39bb7abb7ee82c5366981 0 Planned Material Weakness Remediation Activities 202 Control deficiencies, material weakness, ITGCs, user access, IT compliance oversight function, training program, documentation, IT management review and testing plan, quarterly reporting, Audit Committee prose Skyward/2024/FY/Annual report# 2c0089297ccd119184fc74b5cb4334e0 0 Changes in Internal Control over Financial Reporting 203 Internal control over financial reporting, material weakness, Rule 13a-15(d), 15d-15(d), Exchange Act prose Skyward/2024/FY/Annual report# a35442e0476e4340c70575080192f4ed 0 Limitations on Effectiveness of Controls and Procedures 204 Disclosure controls and procedures, control objectives, resource constraints prose Skyward/2024/FY/Annual report# 75256e18490adf012d7cc64516930d3c 0 Exhibits filed with the document 205 Summary of Investments, Financial Information of Registrant (Parent Company), Supplementary Reinsurance Information, Valuation and Qualifying Accounts, Supplementary Information Concerning Property — Casualty Insurance Operations table Skyward/2024/FY/Annual report# d94b45bb191d214551ff9ed56b66733d 0 Exhibits 3.1 to 10.6 206 Amended and Restated Certificate of Incorporation, Amended and Restated Bylaws, Amended and Restated Stockholders’ Agreement, Description of Capital Stock, Share Purchase and Award Agreement, 2016 Equity Incentive Program, 2020 Long Term Incentive Plan table Skyward/2024/FY/Annual report# 1070e3d74f5322b96b2a5cf749568d24 0 Exhibits 10.7 to 10.16 207 Form of Restricted Stock Agreement, Form of Nonstatutory Stock Option Agreement, Form of Incentive Stock Option Agreement, Form of Performance-Based Restricted Stock Units Agreement, Performance-Based Restricted Stock Units Agreement, Performance Unit Agreement, 2022 Long-Term Incentive Plan table Skyward/2024/FY/Annual report# 816b4ecd6088ba5e37049039f6c8d1ef 0 Exhibits 10.25 to 23.1 208 Second Amendment Agreement, Investment Management Agreement, Arena Investors, LP, Houston Specialty Insurance Company, Imperium Insurance Company, Great Midwest Insurance Company, Credit Agreement, Skyward Specialty Insurance Group, Inc., Truist Bank, Guaranty Agreement, Skyward Service Company, Skyward Underwriters Agency, Inc., Advances and Security Agreement table Skyward/2024/FY/Annual report# 23cc970189a8731681ac925b56cd9bdf 0 Fixed maturity securities as of December 31, 2024 209 Fixed maturity securities, U.S. government securities, corporate securities, municipal securities, residential mortgage-backed securities, commercial mortgage-backed securities, other asset-backed securities table Skyward/2024/FY/Annual report# 69c418f1dae42396ee4968f88e1e0993 0 Cash and cash equivalents = December 31, 2023: USD 10.0m Investments available-for-sale = December 31, 2023: USD 1,000.0m Investments held-to-maturity = December 31, 2023: USD 1,000.0m Investments, at fair value = December 31, 2023: USD 1,000.0m Total investments = December 31, 2023: USD 3,000.0m Balance sheets (parent company) 210 Cash and cash equivalents, investments available-for-sale, investments held-to-maturity, investments at fair value, total investments, premiums receivable, reinsurance recoverable on paid and unpaid losses, deferred acquisition costs, prepaid expenses and other assets, goodwill, intangible assets prose Skyward/2024/FY/Annual report# 0f0fd33949f6d6d04ee923371204b0b1 0 Assets, liabilities, and stockholders' equity 211 Investments, investment in subsidiaries, short-term investments, cash and cash equivalents, deferred income taxes, goodwill and intangible assets, other assets, accounts payable and accrued liabilities, notes payable, subordinated debt table Skyward/2024/FY/Annual report# 85372ff136aea018a2b49826c1f67281 0 (parent company) 212 Notes to financial statements prose Skyward/2024/FY/Annual report# fec94b404157c4e5f9fb2ee87d849f79 0 Consolidated statements of comprehensive income 213 Net investment income, net investment losses, other loss, total revenues, operating expenses, interest expense, amortization expense, other expenses, total expenses, loss before income tax expense table Skyward/2024/FY/Annual report# c86136be70ff12d5392a123d276143fc 0 Schedule ii — statements of cash flows (parent company) 214 Notes to financial statements prose Skyward/2024/FY/Annual report# 9df1e671bfde4dbeba6f9ac1e37f5357 0 Consolidated statements of cash flows 215 Cash flows from operating activities, net income, adjustments to reconcile net income to net cash used in operating activities, net cash provided by operating activities, capital contributions to subsidiaries, distributions from investment in subsidiaries, change in short-term investments, net cash used in investing activities, repayment of stock notes receivable table Skyward/2024/FY/Annual report# 4de0583e03305aa530feabc9ef6d470d 0 Promissory Note date = September 30, 2024 Amount borrowed by Skyward Specialty = USD 57.0 million Interest rate = 4.00% Notes to Financial Statements 216 Intercompany Loan Promissory Note, Houston Specialty Insurance Company (HSIC), Skyward Specialty, Skyward Specialty No. 1 Limited Company, Lloyd’s corporate member, Lloyd’s syndicates prose Skyward/2024/FY/Annual report# c89e5db09e008b0589e586252aae3fcc 0 Carrying value of Promissory Note = December 31, 2024: USD 57.0 million Fair value of Promissory Note = December 31, 2024: USD 56.3 million Promissory Note classification = Level 2 Financial Instruments Disclosed, But Not Carried, At Fair Value 217 Promissory Note, Skyward Specialty, HSIC, fair value hierarchy prose Skyward/2024/FY/Annual report# 2f72eeeaffd32fbf425b1c93e3a50821 0 Reinsurance activity and promissory note details 218 Reinsurance activity, promissory note details table Skyward/2024/FY/Annual report# aedc513e5a7e7f7ae843441053b3e33a 0 Valuation allowances and uncollectible amounts 219 Valuation allowances, uncollectible amounts, deferred tax assets, uncollectible reinsurance recoverable, uncollectible premiums receivable table Skyward/2024/FY/Annual report# 62c7f91a26804714f2f7ccc001bca31b 0 Deferred policy acquisition costs and reserves 220 Deferred policy acquisition costs, reserves, unearned premiums, net earned premium, net investment income, losses and loss adjustment expenses, amortization of policy acquisition costs, paid claims and claim adjustment expenses table Skyward/2024/FY/Annual report# db10f006c3ed301770aac7560f0b82fd 0 Signatures 221 Registrant signatures, Securities Exchange Act of 1934 prose Skyward/2024/FY/Annual report# fab9ef5a4cf4852ed08c0476c3582576 0 Signatures on behalf of the registrant 222 Registrant signatures, Andrew Robinson table Skyward/2024/FY/Annual report# e838b2d4ce3b99c23a07e791150c26a6 0 Signatures, titles, and dates 223 Signatures, titles, dates, Andrew Robinson, Mark Haushill, Gena Ashe, Robert Creager, Marcia Dall table Skyward/2024/FY/Annual report# a5d8193663a528a69a994ec82bf92184