Skyward Specialty Insurance Group, Inc. 10-Q

Item 1. Financial Statements SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES CONDENSED CONSOLIDATED BALANCE SHEETS (UNAUDITED) June 30, 2026 December 31, 2025 ($ in thousands, except share and per share amounts) (Unaudited) Assets Investments: Fixed maturity securities, available-for-sale, at fair value (net of allowance for credit losses of $ 6,228 and $ 7,000 , respectively) (amortized cost of $ 2,206,626 and $ 1,848,755 , respectively) $ 2,192,183 $ 1,856,303 Fixed maturity securities, held-to-maturity, at amortized cost (net of allowance for credit losses of $ 2,256 and $ 468 , respectively) 28,192 32,822 Equity securities, at fair value 1,141 1,174 Mortgage loans, at fair value 9,218 9,902 Equity method investments 62,725 77,365 Other long-term investments 52,295 58,650 Short-term investments, at fair value 392,634 264,299 Total investments 2,738,388 2,300,515 Cash and cash equivalents 219,221 168,544 Restricted cash 83,302 30,570 Funds at Lloyd’s 121,630 2,509 Options, at fair value 40,535 34,857 Premiums and commissions receivable, net 978,409 544,217 Reinsurance recoverables, net 1,411,648 1,119,880 Ceded unearned premium 337,180 238,948 Deferred policy acquisition costs and VOBA 186,491 136,100 Deferred tax assets 47,987 27,865 Goodwill and intangible assets, net 471,185 88,040 Other assets 145,163 99,807 Total assets $ 6,781,139 $ 4,791,852 Liabilities and stockholders’ equity Liabilities: Reserves for losses and loss adjustment expenses $ 3,070,598 $ 2,318,894 Unearned premiums 1,078,246 774,035 Deferred ceding commission 54,466 46,453 Reinsurance and premium payables 509,081 279,888 Funds held for others 169,051 128,003 Deferred tax liabilities 67,801 — Accounts payable and accrued liabilities 127,154 115,034 Notes payable 417,620 100,411 Subordinated debt, net of debt issuance costs 19,585 19,569 Total liabilities 5,513,602 3,782,287 Stockholders’ equity Common stock, $ 0.01 par value, 500,000,000 shares authorized, 44,827,499 shares issued and 44,396,493 shares outstanding at June 30, 2026; 40,511,222 shares issued and outstanding at December 31, 2025 448 405 Treasury stock, at cost, 431,006 and 0 shares, respectively ( 19,427 ) — Additional paid-in capital 927,690 730,555 Accumulated other comprehensive (loss) income ( 7,091 ) 11,457 Retained earnings 365,917 267,148 Total stockholders’ equity 1,267,537 1,009,565 Total liabilities and stockholders’ equity $ 6,781,139 $ 4,791,852 The accompanying notes are an integral part of the consolidated financial statements. 3 Table of Contents SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES CONDENSED CONSOLIDATED STATEMENTS OF OPERATIONS AND COMPREHENSIVE INCOME (UNAUDITED) Three months ended June 30, Six months ended June 30, ($ in thousands, except share and per share amounts) 2026 2025 2026 2025 Revenues: Net earned premiums $ 444,472 $ 295,542 $ 878,479 $ 595,908 Underwriting fee income 12,588 — 22,666 — Commission and fee income 2,334 2,560 3,861 4,536 Net investment income 30,727 18,704 57,782 38,126 Net investment (losses) gains ( 601 ) 3,090 2,584 9,840 Other income 13 7 28 20 Total revenues 489,533 319,903 965,400 648,430 Expenses: Losses and loss adjustment expenses 276,741 181,262 541,964 368,571 Underwriting, acquisition and insurance expenses 123,281 85,596 247,895 172,147 Fee‑based service expenses 4,562 — 8,732 — Interest expense 8,812 1,876 16,531 3,710 Amortization expense 8,843 372 17,686 709 Other expenses 3,737 1,002 6,959 2,063 Total expenses 425,976 270,108 839,767 547,200 Income before income taxes 63,557 49,795 125,633 101,230 Income tax expense 14,519 10,956 26,864 20,333 Net income $ 49,038 $ 38,839 $ 98,769 $ 80,897 Comprehensive income Net income $ 49,038 $ 38,839 $ 98,769 $ 80,897 Other comprehensive (loss) income: Unrealized gains and losses on investments: Net change in unrealized (losses) gains on investments, net of tax ( 625 ) 11,005 ( 17,842 ) 23,260 Reclassification adjustment for (losses) gains on securities no longer held, net of tax ( 490 ) ( 3,624 ) 12 ( 3,806 ) Foreign currency translation adjustment 150 — ( 718 ) — Total other comprehensive (loss) income ( 965 ) 7,381 ( 18,548 ) 19,454 Comprehensive income $ 48,073 $ 46,220 $ 80,221 $ 100,351 Per share data: Basic earnings per share $ 1.10 $ 0.96 $ 2.22 $ 2.01 Diluted earnings per share $ 1.07 $ 0.93 $ 2.17 $ 1.94 Weighted-average common shares outstanding Basic 44,521,162 40,445,391 44,492,608 40,322,051 Diluted 45,692,641 41,871,496 45,526,233 41,771,215 The accompanying notes are an integral part of the consolidated financial statements. 4 Table of Contents SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES CONDENSED CONSOLIDATED STATEMENTS OF STOCKHOLDERS’ EQUITY (UNAUDITED) Three months ended June 30, ($ in thousands, except share amounts) 2026 2025 Common shares: Balance at beginning of period 44,543,065 40,402,879 (Acquisition) issuance of common stock ( 146,572 ) 83,777 Balance at June 30, 44,396,493 40,486,656 Treasury shares: Balance at beginning of period ( 185,022 ) — Shares acquired ( 245,984 ) — Balance at June 30, ( 431,006 ) — Common stock: Balance at beginning of period $ 484 $ 404 (Acquisition) issuance of common stock ( 36 ) 1 Balance at June 30, $ 448 $ 405 Treasury stock: Balance at beginning of period $ ( 8,665 ) $ — Issuance of treasury stock ( 10,762 ) — Balance at June 30, $ ( 19,427 ) $ — Additional paid-in capital: Balance at beginning of period $ 922,311 $ 721,186 Issuance of common stock 5,379 2,973 Balance at June 30, $ 927,690 $ 724,159 Accumulated other comprehensive loss: Balance at beginning of period $ ( 6,126 ) $ ( 10,047 ) Other comprehensive (loss) income, net of tax ( 965 ) 7,381 Balance at June 30, $ ( 7,091 ) $ ( 2,666 ) Retained earnings: Balance at beginning of period $ 316,879 $ 139,178 Net income 49,038 38,839 Balance at June 30, $ 365,917 $ 178,017 Total stockholders’ equity $ 1,267,537 $ 899,915 The accompanying notes are an integral part of the consolidated financial statements. 5 Table of Contents SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES CONDENSED CONSOLIDATED STATEMENTS OF STOCKHOLDERS’ EQUITY (UNAUDITED) Six months ended June 30, ($ in thousands, except share amounts) 2026 2025 Common shares: Balance at beginning of year 40,511,222 40,127,908 Issuance of shares 3,885,271 358,748 Balance at June 30, 44,396,493 40,486,656 Treasury shares: Balance at beginning of year — — Shares acquired ( 431,006 ) — Balance at June 30, ( 431,006 ) — Common stock: Balance at beginning of year $ 405 $ 401 Issuance of common stock 43 4 Balance at June 30, $ 448 $ 405 Treasury stock: Balance at beginning of year $ — $ — Treasury stock acquired ( 19,427 ) — Balance at June 30, $ ( 19,427 ) $ — Additional paid-in capital: Balance at beginning of year $ 730,555 $ 718,598 Issuance of common stock 197,135 5,561 Balance at June 30, $ 927,690 $ 724,159 Accumulated other comprehensive loss: Balance at beginning of year $ 11,457 $ ( 22,120 ) Other comprehensive (loss) income, net of tax ( 18,548 ) 19,454 Balance at June 30, $ ( 7,091 ) $ ( 2,666 ) Retained earnings: Balance at beginning of year $ 267,148 $ 97,120 Net income 98,769 80,897 Balance at June 30, $ 365,917 $ 178,017 Total stockholders’ equity $ 1,267,537 $ 899,915 The accompanying notes are an integral part of the consolidated financial statements. 6 Table of Contents SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES CONDENSED CONSOLIDATED STATEMENTS OF CASH FLOWS (UNAUDITED) Six months ended June 30, ($ in thousands) 2026 2025 Cash flows from operating activities: Net income $ 98,769 $ 80,897 Adjustments to reconcile net income to net cash provided by operating activities 85,398 104,043 Net cash provided by operating activities 184,167 184,940 Cash flows from investing activities: Net cash paid in acquisition ( 303,035 ) ( 2,000 ) Purchase of fixed maturity securities, available-for-sale ( 480,843 ) ( 405,609 ) Purchase of equity securities — ( 12,626 ) Purchase of equity method investments and other long-term investments ( 485 ) ( 2,839 ) Investment in direct and indirect loans 3,164 13,435 Purchase of property and equipment ( 965 ) ( 1,287 ) Proceeds from the sales of fixed maturity securities, available-for-sale 237,986 25,524 Maturities, calls, transfers and paydowns of fixed maturity securities, available-for-sale 108,571 60,628 Maturities, calls and paydowns of fixed maturity securities held-to-maturity 1,695 3,459 Proceeds from the sales of equity securities — 67,495 Sales of and distributions from equity method and other long-term investments 16,469 8,730 Change in short-term investments 58,611 60,606 Change in receivable/payable for securities ( 15,762 ) — Cash (used in) provided by deposit accounting ( 8,026 ) 15,183 Net cash used in investing activities ( 382,620 ) ( 169,301 ) Cash flows from financing activities: Proceeds from issuance of common stock 200 — Proceeds from long term borrowings 371,089 — Payments on long term borrowings ( 50,000 ) — Treasury stock acquired ( 19,427 ) — Net cash provided by financing activities 301,862 — Net increase in cash and cash equivalents and restricted cash 103,409 15,639 Cash and cash equivalents and restricted cash at beginning of period (1) 199,114 157,525 Cash and cash equivalents and restricted cash at end of period (1) $ 302,523 $ 173,164 Supplemental disclosure of cash flow information: Cash paid for interest $ 14,013 $ 3,234 (1) The sum of cash and cash equivalents and restricted cash from the consolidated balance sheets The accompanying notes are an integral part of the consolidated financial statements. 7 Table of Contents SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED) 1. Summary of Significant Accounting Policies Basis of Presentation The unaudited condensed consolidated financial statements of Skyward Specialty Insurance Group, Inc. (the “Company”) have been prepared in accordance with generally accepted accounting principles (“GAAP”) in the United States of America for interim financial reporting and with the instructions to Form 10-Q and Regulation S-X. Accordingly, they do not include all the disclosures required by GAAP for complete consolidated financial statements. Readers are urged to review the Company’s Annual Report on Form 10-K for the year ended December 31, 2025 for a more complete description of the Company’s business and accounting policies. In the opinion of management, all adjustments necessary for a fair statement of the condensed consolidated financial statements have been included. Such adjustments consist only of normal recurring items. Interim results are not necessarily indicative of results of operations for the full year. The consolidated balance sheet as of December 31, 2025 was derived from the Company’s audited annual consolidated financial statements. Use of Estimates The preparation of consolidated financial statements in conformity with GAAP requires management to make estimates and assumptions that affect the reported amounts of assets and liabilities and disclosures of contingent assets and liabilities at the date of the consolidated financial statements and the reported amounts of revenue and expenses during the reporting period. Actual results could differ materially from these estimates. Updates to Significant Accounting Policies The following accounting policies have been updated following the Apollo Group Holdings Limited (“Apollo”) acquisition on January 1, 2026. Description of Business Skyward Specialty Insurance Group, Inc., an insurance holding company, is a Delaware corporation that was organized in 2006. It is a specialty insurance company operating in two segments delivering commercial property and casualty products insurance coverages. 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, that is domiciled in the Cayman Islands. The Company has three non-risk bearing wholly owned subsidiaries, (i) Skyward Underwriters Agency, Inc. (“SUA”), a managing general insurance agent and reinsurance broker for property and casualty risks in specialty niche markets, (ii) Skyward Service Company, an entity which provides various administrative services to the Company’s subsidiaries, and (iii) Skyward Specialty No. 1 Limited, a Lloyd’s corporate member authorized to invest in Lloyd’s syndicates. 8 Table of Contents SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED) 1. Summary of Significant Accounting Policies (continued) On January 1, 2026, the Company completed its acquisition of Apollo Group Holdings Limited (“Apollo”), a Lloyd’s of London (“Lloyd’s”) specialist insurance and reinsurance group. Apollo includes a Lloyd’s of London Managing Agency, Apollo Syndicate Management Limited (“ASML”), which provides managing agency services to nine Lloyd’s syndicates. Syndicate 1969 underwrites a diversified specialty portfolio, Syndicate 1971 focuses on digital‑economy and technology‑enabled risks, and Syndicate 1972 provides reinsurance for Apollo managed syndicates and provides a quota share facility for Syndicates 1969 and 1971. Apollo participates in its wholly managed syndicates through its corporate member company, Apollo No. 16 Limited (“Apollo No. 16”) which has a quota share agreement in place with Apollo Bermuda Limited. Commission and Fee Income and Underwriting Fee Income Managing Agency Fees and Profit Commission ASML earns a fee for providing managing agency services (such as underwriting oversight, operational administration and regulatory compliance) to the syndicates it manages. These managing agency fees are based on each syndicate’s annual capacity and are recognized over the period of services provided. ASML may also earn profit commission under contractual arrangements with the capital providers to each syndicate. Profit commissions are contingent on syndicate profitability and are accrued in accordance with the contractual terms and the subsequent development of underwriting results at the balance sheet date. Amounts are generally not payable until the underlying underwriting results have substantially matured (typically around 36 months after inception), unless interim profit distributions permit earlier payments on account. Intra‑group managing agency fees and profit commission are eliminated on consolidation. Other Revenue From Management Services Apollo also earns other services revenue for other administrative and operational services performed for the syndicates it manages, including those supported primarily by third‑party capital providers. Such revenue is measured at the fair value of consideration received or receivable and includes service fees and consortium income. Consortium income represents fees charged to consortia members for whom ASML acts as consortium leader and is recognized at the point in time premiums are written; amounts related to underwriting services provided over multi‑year periods are deferred accordingly. Foreign Currency The Company transacts business in numerous currencies through business units located around the world. The functional currency for each business unit is determined by the local currency used for most economic activity in that area. Movements in exchange rates related to transactions in currencies other than a business unit’s functional currency for monetary assets and liabilities are remeasured through the consolidated statements of operations and comprehensive income (loss) in other income (expense), except for currency movements related to available for sale fixed maturities securities, which are excluded from net income (loss) and accumulated in stockholders’ equity, net of deferred taxes. The business units’ functional currency financial statements are translated to the Company’s reporting currency, U.S. dollars, using the exchange rates at the end of period for the balance sheets and the average exchange rates in effect for the reporting period for the statements of operations and comprehensive income. Gains and losses resulting from translating the foreign currency financial statements, net of deferred income taxes, are excluded from net income and accumulated as a separate component of accumulated other comprehensive income in stockholders’ equity. Reclassifications During the current period, the Company reclassified amounts previously included in “Other assets” to separate line items on the balance sheet for “Funds at Lloyd’s” and “Options, at fair value” to better reflect the nature of these balances. Prior period amounts have been reclassified to conform to the current presentation. 9 Table of Contents SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED) 2. Goodwill and Intangible Assets The following tables set forth the carrying amount and changes in the balance of goodwill by reporting unit at June 30, 2026 and 2025: ($ in thousands) Accident and Health Credit & Surety Energy Solutions Apollo Other Total Goodwill Gross balance at December 31, 2025 $ 91,577 $ 6,781 $ 10,204 $ — $ 3,879 $ 112,441 Accumulated impairment at December 31, 2025 ( 44,821 ) — — — ( 1,886 ) ( 46,707 ) Additions — — — 125,408 — 125,408 Net balance at June 30, 2026 $ 46,756 $ 6,781 $ 10,204 $ 125,408 $ 1,993 $ 191,142 ($ in thousands) Accident and Health Credit & Surety Energy Solutions Other Total Goodwill Gross balance at December 31, 2024 $ 91,577 $ 6,781 $ 10,204 $ 3,879 $ 112,441 Accumulated impairment at December 31, 2024 ( 44,821 ) — — ( 1,886 ) ( 46,707 ) Net balance at June 30, 2025 $ 46,756 $ 6,781 $ 10,204 $ 1,993 $ 65,734 The following tables set forth the carrying amount and changes in the balance of other intangible assets at June 30, 2026 and 2025: ($ in thousands) Agent Relationships Non-competes Trademarks Syndicate Capacity Licenses Total Other Intangible Assets Gross balance at December 31, 2025 $ 26,491 $ 1,117 $ 999 $ — $ 14,019 $ 42,626 Accumulated amortization at December 31, 2025 ( 19,203 ) ( 1,117 ) — — — ( 20,320 ) Additions 27,000 — 35,000 200,000 — 262,000 Amortization ( 2,513 ) — ( 1,750 ) — — ( 4,263 ) Net balance at June 30, 2026 $ 31,775 $ — $ 34,249 $ 200,000 $ 14,019 $ 280,043 ($ in thousands) Agent Relationships Non-competes Trademarks Licenses Total Other Intangible Assets Gross balance at December 31, 2024 $ 24,491 $ 1,117 $ 999 $ 14,019 $ 40,626 Accumulated amortization at December 31, 2024 ( 17,895 ) ( 1,117 ) — — ( 19,012 ) Additions 2,000 — — — 2,000 Amortization ( 553 ) — — — ( 553 ) Net balance at June 30, 2025 $ 8,043 $ — $ 999 $ 14,019 $ 23,061 The Company’s indefinite lived intangible assets relate to insurance licenses, trademarks and Lloyd’s syndicates capacity. Its finite lived intangible assets, which relate to policy renewals, agency relationships, within agent relationships, finite syndicates capacity relationships and non-compete/exclusivity agreements, within non-competes, have a weighted average useful life of approximately 9 years as of June 30, 2026. 10 Table of Contents SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED) 2. Goodwill and Intangible Assets (continued) During the three and six months ended June 30, 2026, the Company recognized approximately $ 2.2 million and $ 4.3 million, respectively, of amortization expense, compared to $ 0.3 million and $ 0.6 million, respectively, for the same 2025 periods. The following table sets forth the estimated future net amortization expense of intangible assets: ($ in thousands) Amount Remainder of 2026 $ 4,262 Year Ending December 31, 2027 8,525 Year Ending December 31, 2028 8,525 Year Ending December 31, 2029 8,233 Year Ending December 31, 2030 8,025 3. Investments The following tables set forth the amortized cost and the fair value by investment category at June 30, 2026 and December 31, 2025: ($ in thousands) Amortized Cost Gross Unrealized Gains Gross Unrealized Losses Allowance for Credit Losses Fair Value June 30, 2026 Fixed maturity securities, available-for-sale: U.S. government securities $ 128,460 $ 59 $ ( 1,455 ) $ — $ 127,064 Non U.S government securities 2,721 — ( 44 ) — 2,677 Corporate securities and miscellaneous 796,092 7,253 ( 6,310 ) ( 6,228 ) 790,807 Municipal securities 93,125 1,337 ( 2,249 ) — 92,213 Residential mortgage-backed securities 450,728 4,979 ( 10,496 ) — 445,211 Commercial mortgage-backed securities 84,645 539 ( 560 ) — 84,624 Other asset-backed securities 650,855 2,610 ( 3,878 ) — 649,587 Total fixed maturity securities, available-for-sale $ 2,206,626 $ 16,777 $ ( 24,992 ) $ ( 6,228 ) $ 2,192,183 Fixed maturity securities, held-to-maturity: Other asset-backed securities $ 30,448 $ 6,524 $ — $ ( 2,256 ) $ 34,716 Total fixed maturity securities, held-to-maturity $ 30,448 $ 6,524 $ — $ ( 2,256 ) $ 34,716 11 Table of Contents SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED) 3. Investments (continued) ($ in thousands) Amortized Cost Gross Unrealized Gains Gross Unrealized Loss Allowance for Credit Losses Fair Value December 31, 2025 Fixed maturity securities, available-for-sale: U.S. government securities $ 44,190 $ 292 $ ( 14 ) $ — $ 44,468 Corporate securities and miscellaneous 632,244 14,223 ( 3,080 ) ( 7,000 ) 636,387 Municipal securities 102,691 1,725 ( 2,300 ) — 102,116 Residential mortgage-backed securities 487,145 8,928 ( 9,486 ) — 486,587 Commercial mortgage-backed securities 72,631 1,016 ( 597 ) — 73,050 Other asset-backed securities 509,854 5,194 ( 1,353 ) — 513,695 Total fixed maturity securities, available-for-sale $ 1,848,755 $ 31,378 $ ( 16,830 ) $ ( 7,000 ) $ 1,856,303 Fixed maturity securities, held-to-maturity: Other asset-backed securities $ 33,290 $ 829 $ ( 48 ) $ ( 468 ) $ 33,603 Total fixed maturity securities, held-to-maturity $ 33,290 $ 829 $ ( 48 ) $ ( 468 ) $ 33,603 The following table sets forth the amortized cost and fair value of available-for-sale fixed maturity securities by contractual maturity at June 30, 2026: ($ in thousands) Amortized Cost Fair Value Due in less than one year $ 38,700 $ 38,794 Due after one year through five years 621,490 613,572 Due after five years through ten years 295,763 297,152 Due after ten years 64,445 63,243 Mortgage-backed securities 535,373 529,835 Other asset-backed securities 650,855 649,587 Total $ 2,206,626 $ 2,192,183 Expected maturities may differ from contractual maturities because borrowers have the right to call or prepay obligations with or without call or prepayment penalties. Also, changing interest rates, tax considerations or other factors may result in portfolio sales prior to maturity. The Company’s fixed maturity securities, held-to-maturity, at June 30, 2026 consisted entirely of asset-backed securities that were not due at a single maturity date. At June 30, 2026, the Company had U.S. government agencies mortgage-backed fixed maturity securities, with a carrying value of approximately $ 65.8 million pledged as collateral for a loan (the “FHLB Loan”) from the Federal Home Loan Bank of Dallas (“FHLB”) pursuant to an Advances and Security Agreement between the Company and FHLB (the “Advances and Security Agreement”). In accordance with the terms of the FHLB Loan, the Company retains all rights regarding these pledged securities. At June 30, 2026, the Company had assets with fair values of approximately $ 88.5 million pledged as collateral for performance obligations under reinsurance agreements. In accordance with the terms of the trust agreements, the Company retains all rights regarding these securities, of which $ 71.3 million are residential mortgage-backed securities, $ 15.0 million of cash and cash equivalents and other assets and $ 2.2 million of short-term investments. 12 Table of Contents SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED) 3. Investments (continued) The following tables set forth the gross unrealized losses and the corresponding fair values of investments, aggregated by length of time that individual securities had been in a continuous unrealized loss position as of June 30, 2026 and 2025: 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 June 30, 2026 Fixed maturity securities, available-for-sale: U.S. government securities $ 103,494 $ ( 1,455 ) $ — $ — $ 103,494 $ ( 1,455 ) Non-U.S. government securities 2,677 ( 44 ) — — 2,677 ( 44 ) Corporate securities and miscellaneous 347,196 ( 4,271 ) 40,383 ( 2,039 ) 387,579 ( 6,310 ) Municipal securities 21,859 ( 380 ) 19,056 ( 1,869 ) 40,915 ( 2,249 ) Residential mortgage-backed securities 151,044 ( 1,553 ) 61,911 ( 8,943 ) 212,955 ( 10,496 ) Commercial mortgage-backed securities 21,241 ( 53 ) 5,246 ( 507 ) 26,487 ( 560 ) Other asset-backed securities 292,691 ( 2,913 ) 8,394 ( 965 ) 301,085 ( 3,878 ) Total $ 940,202 $ ( 10,669 ) $ 134,990 $ ( 14,323 ) $ 1,075,192 $ ( 24,992 ) 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, 2025 Fixed maturity securities, available-for-sale: U.S. government securities $ 349 $ ( 1 ) $ 1,565 $ ( 13 ) $ 1,914 $ ( 14 ) Corporate securities and miscellaneous 67,644 ( 346 ) 63,575 ( 2,734 ) 131,219 ( 3,080 ) Municipal securities 19,157 ( 400 ) 22,004 ( 1,900 ) 41,161 ( 2,300 ) Residential mortgage-backed securities 56,147 ( 262 ) 74,075 ( 9,224 ) 130,222 ( 9,486 ) Commercial mortgage-backed securities 4,646 ( 3 ) 8,363 ( 594 ) 13,009 ( 597 ) Other asset-backed securities 85,098 ( 424 ) 16,081 ( 929 ) 101,179 ( 1,353 ) Total fixed maturity securities, available-for-sale 233,041 ( 1,436 ) 185,663 ( 15,394 ) 418,704 ( 16,830 ) Fixed maturity securities, held-to-maturity: Other asset-backed securities 1,912 ( 48 ) — — 1,912 ( 48 ) Total fixed maturity securities, held-to-maturity: 1,912 ( 48 ) — — 1,912 ( 48 ) Total $ 234,953 $ ( 1,484 ) $ 185,663 $ ( 15,394 ) $ 420,616 $ ( 16,878 ) The Company regularly monitors its available-for-sale fixed maturity securities that have fair values less than cost or amortized cost for signs of impairment, an assessment that requires significant management judgment regarding the evidence known. Such judgments could change in the future as more information becomes known, which could negatively impact the amounts reported. Among the factors that management considers for fixed maturity securities are the financial condition of the issuer including receipt of scheduled principal and interest cash flows, and intent to sell, including if it is more likely than not that the Company will be required to sell the investments before recovery. 13 Table of Contents SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED) 3. Investments (continued) As of June 30, 2026, the Company had 987 lots of fixed maturity securities in an unrealized loss position. The Company does not have an intent to sell these securities and it is not more likely than not that the Company will be required to sell these securities before maturity or recovery of its cost basis. The Company reviewed its investments at June 30, 2026 and determined that for two available-for-sale securities in the “corporate securities and miscellaneous” category, credit impairments existed, based on new recovery analysis that showed deteriorating conditions raising credit concerns. Other than the securities discussed previously, the Company determined that no other credit impairment existed in the gross unrealized holding losses, due to the reasons discussed below: • U.S. government securities and municipal securities : These securities were issued by the U.S. Treasury Department, Federal government-sponsored entities or by state and local governments. The decline in fair values was attributable to changes in interest rates and not credit quality. The Company does not intend to sell these securities and it is likely that it will not do so before their anticipated recovery. Therefore, the Company does not consider these impaired securities. • Corporate securities and miscellaneous : Corporations in various industries issued these securities. The decline in fair values was attributable to changes in interest rates and not credit quality. The Company reviewed the issuers of these securities to identify any significant adverse change in financial condition, a change in the quality of credit enhancement (if any), a ratings decrease, or negative outlook assignment from a major credit rating agency, and any failure to make interest or principal payments. After these reviews, the Company determined that the decline in fair values was attributable to changes in interest rates and not credit quality. The Company does not intend to sell these securities and it is likely that it will not do so before their anticipated recovery. Therefore, the Company does not consider these impaired securities. • Residential mortgage-backed securities, commercial mortgage-backed securities, and other asset-backed securities : The decline in fair values was attributable to changes in interest rates and not credit quality. The Company does not intend to sell these securities and it is likely that it will not do so before their anticipated recovery. Therefore, the Company does not consider these impaired securities. The following table sets forth the changes in the allowance for credit losses on available-for-sale securities and held-to-maturity securities during the six months ended June 30, 2026 and 2025: ($ in thousands) Fixed Maturity Securities, Available-For-Sale Fixed Maturity Securities, Held-to-Maturity Balance at December 31, 2025 $ 7,000 $ 468 Recoveries of amounts previously written off ( 500 ) ( 167 ) Balance at March 31, 2026 $ 6,500 $ 301 Write-offs — 1,955 Recoveries of amounts previously written off ( 272 ) — Balance at June 30, 2026 $ 6,228 $ 2,256 Fixed Maturity Securities, Available-For-Sale Fixed Maturity Securities, Held-to-Maturity Balance at December 31, 2024 $ — $ 243 Current period provision for credit losses — 7 Balance at March 31, 2025 $ — $ 250 Current period provision for credit losses 6,150 18 Balance at June 30, 2025 $ 6,150 $ 268 14 Table of Contents SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED) 3. Investments (continued) The following table sets forth the components of net investment (losses) gains for the three and six months ended June 30, 2026 and 2025: Three months ended June 30, Six months ended June 30, ($ in thousands) 2026 2025 2026 2025 Gross realized gains Fixed maturity securities, available-for-sale $ 1,339 $ 452 $ 2,971 $ 905 Equity securities — 15,441 — 17,186 Other ( 1,964 ) 596 ( 1,789 ) 626 Total ( 625 ) 16,489 1,182 18,717 Gross realized losses Fixed maturity securities, available-for-sale ( 1,347 ) ( 8,477 ) ( 1,605 ) ( 8,597 ) Equity securities — ( 1,577 ) — ( 2,255 ) Other ( 556 ) ( 164 ) ( 695 ) ( 335 ) Total ( 1,903 ) ( 10,218 ) ( 2,300 ) ( 11,187 ) Net unrealized gains (losses) on investments Equity securities — ( 9,429 ) ( 33 ) ( 8,349 ) Mortgage loans — 330 99 264 Other 1,927 5,918 3,636 10,395 Net investment (losses) gains $ ( 601 ) $ 3,090 $ 2,584 $ 9,840 The following table sets forth the proceeds from sales of available-for-sale fixed maturity securities and equity securities for the six months ended June 30, 2026 and 2025: Six months ended June 30, ($ in thousands) 2026 2025 Fixed maturity securities, available-for-sale $ 237,986 $ 25,524 Equity securities — 67,495 The following table sets forth the components of net investment income for the three and six months ended June 30, 2026 and 2025: Three months ended June 30, Six months ended June 30, ($ in thousands) 2026 2025 2026 2025 Income (loss): Fixed maturity securities, available-for-sale $ 25,879 $ 18,453 $ 55,290 $ 35,741 Fixed maturity securities, held-to-maturity 403 ( 822 ) ( 674 ) — Equity securities 19 492 37 1,109 Equity method investments ( 1,057 ) ( 898 ) ( 2,354 ) ( 2,886 ) Mortgage loans 291 270 ( 374 ) 931 Indirect loans ( 4,312 ) ( 4,249 ) ( 6,105 ) ( 4,990 ) Short-term investments and cash 2,463 3,707 5,937 6,899 Other 6,719 909 7,405 1,970 Total investment income 30,405 17,862 59,162 38,774 Investment expenses 322 842 ( 1,380 ) ( 648 ) Net investment income $ 30,727 $ 18,704 $ 57,782 $ 38,126 15 Table of Contents SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED) 3. Investments (continued) The following 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 three and six months ended June 30, 2026 and 2025: Three months ended June 30, Six months ended June 30, ($ in thousands) 2026 2025 2026 2025 Fixed maturity securities $ ( 1,609 ) $ 9,403 $ ( 22,762 ) $ 24,687 Deferred income taxes 644 ( 2,022 ) 4,214 ( 5,233 ) Total $ ( 965 ) $ 7,381 $ ( 18,548 ) $ 19,454 4. Fair Value Measurements The Company’s financial instruments include assets and liabilities carried at fair value, as well as assets and liabilities carried at cost or amortized cost but disclosed at fair value in its consolidated financial statements. In determining fair value, the market approach is generally applied, which uses prices and other relevant data based on market transactions involving identical or comparable assets and liabilities. The Company uses data primarily provided by third-party investment managers or pricing vendors to determine the fair value of its investments. Periodic analyses are performed on prices received from third parties to determine whether the prices are reasonable estimates of fair value. The analyses include a review of month-to-month price fluctuations and, as needed, a comparison of pricing services’ valuations to other pricing services’ valuations for the identical security. The Company classifies its financial instruments into the following 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. The following methods and assumptions were used in estimating the fair value disclosures for financial instruments in the accompanying consolidated financial statements and in these notes: U.S. government securities, mutual funds and common stock The Company uses unadjusted quoted prices for identical instruments in an active exchange to measure fair value which represent Level 1 inputs. Preferred stocks, municipal securities, corporate securities and miscellaneous The Company uses a pricing model that utilizes market-based inputs such as trades in an illiquid market for a particular security or trades in active markets for securities with similar characteristics. The model considers other inputs such as benchmark yields, issuer spreads, security terms and conditions, and other market data. These represent Level 2 fair value inputs. Commercial mortgage-backed securities, residential mortgage-backed securities and other asset-backed securities The Company uses a pricing model that utilizes market-based inputs that may include dealer quotes, market spreads, and yield curves. It may evaluate individual tranches in a security by determining cash flows using the security’s terms and conditions, collateral performance, credit information benchmark yields and estimated prepayments. These represent Level 2 fair value inputs. Fixed maturity securities, available for sale classified as Level 3 The Company has corporate securities and miscellaneous, other asset-backed securities that are managed by an independent asset manager and priced by an independent pricing provider. The provider estimates the value of the securities using the discount net present value of cash flows method using an unobservable discount rate. The discount rate spread represents the risk associated with future cash flows, including inflation, opportunity cost and the time value of money. This rate represents Level 3 fair value inputs. 16 Table of Contents SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED) 4. Fair Value Measurements (continued) The following table sets forth the range of the discount rate as of June 30, 2026 and December 31, 2025: June 30, 2026 December 31, 2025 High 12.78 % 11.10 % Low 4.66 % 4.25 % Weighted average 7.99 % 6.40 % Mortgage loans Mortgage loans have variable interest rates and are collateralized by real property. The Company determines fair value of mortgage loans using the income approach utilizing inputs that are observable and unobservable (Level 3). The unobservable input consists of the spread applied to a prime rate used to discount cash flows. The spread represents the incremental cost of capital based on the borrower’s ability to make future payments and the value of the collateral relative to the loan balance and is subject to judgment and uncertainty. The following table sets forth the range and weighted average, weighted by relative fair value, of the spread as of June 30, 2026 and December 31, 2025: June 30, 2026 December 31, 2025 High 8.09 % 8.34 % Low 6.54 % 6.55 % Weighted average 7.65 % 7.74 % Derivatives Included in other assets are derivatives which consist of certain exchange traded options contracts entered into by the Company. The fair values of these options are measured using quoted prices in active markets on the relevant exchange, specifically utilizing either the volume-weighted average price of trades in similar contracts during a specified time window, or the last trade settlement price when no trades occur within that period. This method represents Level 1 inputs. 17 Table of Contents SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED) 4. Fair Value Measurements (continued) The following tables set forth the Company’s investments and derivatives within the fair value hierarchy at June 30, 2026 and December 31, 2025: June 30, 2026 ($ in thousands) Level 1 Level 2 Level 3 Total Fixed maturity securities, available-for-sale: U.S. government securities $ 127,064 $ — $ — $ 127,064 Non U.S government securities — 2,677 — 2,677 Corporate securities and miscellaneous — 650,362 140,445 790,807 Municipal securities — 92,213 — 92,213 Residential mortgage-backed securities — 445,211 — 445,211 Commercial mortgage-backed securities — 84,624 — 84,624 Other asset-backed securities — 632,209 17,378 649,587 Total fixed maturity securities, available-for-sale 127,064 1,907,296 157,823 2,192,183 Fixed maturity securities, held-to-maturity: Other asset-backed securities — — 34,716 34,716 Total fixed maturity securities, held-to-maturity — — 34,716 34,716 Equity securities: Preferred stocks — 1,141 — 1,141 Total equity securities — 1,141 — 1,141 Mortgage loans — — 9,218 9,218 Short-term investments 392,634 — — 392,634 Derivatives 40,535 — — 40,535 Total $ 560,233 $ 1,908,437 $ 201,757 $ 2,670,427 18 Table of Contents SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED) 4. Fair Value Measurements (continued) December 31, 2025 ($ in thousands) Level 1 Level 2 Level 3 Total Fixed maturity securities, available-for-sale: U.S. government securities $ 44,468 $ — $ — $ 44,468 Corporate securities and miscellaneous — 503,274 133,113 636,387 Municipal securities — 102,116 — 102,116 Residential mortgage-backed securities — 486,587 — 486,587 Commercial mortgage-backed securities — 73,050 — 73,050 Other asset-backed securities — 495,891 17,804 513,695 Total fixed maturity securities, available-for-sale 44,468 1,660,918 150,917 1,856,303 Fixed maturity securities, held-to-maturity: Other asset-backed securities — — 33,603 33,603 Total fixed maturity securities, held-to-maturity: — — 33,603 33,603 Equity securities: Preferred stocks — 1,174 — 1,174 Total equity securities — 1,174 — 1,174 Mortgage loans — — 9,902 9,902 Short-term investments 264,299 — — 264,299 Derivatives 34,857 — — 34,857 Total $ 343,624 $ 1,662,092 $ 194,422 $ 2,200,138 19 Table of Contents SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED) 4. Fair Value Measurements (continued) The following tables set forth the changes in the fair value of instruments carried at fair value with a Level 3 measurement during the six months ended June 30, 2026 and 2025: ($ in thousands) Fixed Maturity Securities, Available-For-Sale Mortgage Loans Balance at December 31, 2025 $ 150,917 $ 9,902 Total losses for the period recognized in net investment (losses) gains ( 62 ) ( 814 ) Purchases 11,266 — Sales/Disposals ( 334 ) — Total unrealized losses for the period recognized in accumulated comprehensive (loss) income ( 2,337 ) — Balance at March 31, 2026 $ 159,450 $ 9,088 Total (losses) gains for the period recognized in net investment gains ( 161 ) 130 Transfers into Level 3 643 — Purchases 3,458 — Sales/Disposals ( 5,518 ) — Total unrealized gains for the period recognized in accumulated comprehensive income (loss) ( 49 ) — Balance at June 30, 2026 $ 157,823 $ 9,218 ($ in thousands) Fixed Maturity Securities, Available-For-Sale Mortgage Loans Balance at December 31, 2024 $ 77,920 $ 26,490 Total losses for the period recognized in net investment gains ( 110 ) ( 66 ) Issuances — 5 Settlements — ( 10,417 ) Purchases 5,164 — Sales/Disposals ( 199 ) — Total unrealized gains for the period recognized in accumulated comprehensive income (loss) 682 — Balance at March 31, 2025 $ 83,457 $ 16,012 Total losses for the period recognized in net investment gains attributable to the change in unrealized gains or losses relating to assets held as of period end $ — $ ( 84 ) Total (losses) gains for the period recognized in net investment gains ( 4,081 ) 330 Issuances — 8 Settlements — ( 6,182 ) Transfers into Level 3 6,143 — Purchases 8,838 — Sales/Disposals ( 237 ) — Total unrealized gains for the period recognized in accumulated comprehensive income (loss) 747 — Balance at June 30, 2025 $ 94,867 $ 10,168 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 $ — $ 92 The transfers into Level 3 during the three and six months ended June 30, 2026 were the result of securities that began receiving valuations from asset managers that utilized unobservable inputs at the end of the period. 20 Table of Contents SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED) 4. Fair Value Measurements (continued) The Company measures certain assets, including investments in indirect loans and loan collateral, equity method investments and other invested assets, at fair value on a nonrecurring basis only when they are deemed to be impaired. In addition to the preceding disclosures on assets and liabilities recorded at fair value in the consolidated balance sheets, the Company is also required to disclose the fair values of certain other financial instruments for which it is practicable to estimate fair value. Estimated fair value amounts, defined as the quoted market price of a financial instrument, have been determined using available market information and other appropriate valuation methodologies. However, considerable judgments are required in developing the estimates of fair value where quoted market prices are not available. Accordingly, these estimates are not necessarily indicative of the amounts that could be realized in a current market exchange. The use of different market assumptions or estimating methodologies may have an effect on the estimated fair value amounts. The following methods and assumptions were used in estimating the fair value disclosures of other financial instruments: Fixed maturity securities, held-to-maturity: Fixed maturity securities, held-to-maturity consists of senior and junior notes with target rates of return. As of June 30, 2026, the Company determined the fair value of these instruments using the income approach utilizing inputs that are unobservable (Level 3). Investment in RedBird Capital Partners: Included in other long-term investments is an investment in a limited partnership with RedBird Capital Partners, which invests in Bishop Street Underwriters, LLC (“Bishop Street”), a managing general agent (MGA). The investment had a fair value of $ 49.1 million at June 30, 2026, which was determined using the net asset value. The Company employs procedures to assess the reasonableness of the fair value of the investment including obtaining and reviewing the audited financial statements. The unfunded commitment related to the investment was $ 18.3 million at June 30, 2026. The Company may sell its interest in the investment with the appropriate prior written notice and approval by the general partner. In accordance with Accounting Standard Codification 820-10, this investment is measured at fair value using the net asset value per share practical expedient and has not been classified in the fair value hierarchy. Notes payable: The carrying value approximates the estimated fair value for notes payable as the notes payable accrue interest at current market rates plus a spread. The Company determines fair value using the income approach utilizing inputs that are observable (Level 2). Subordinated debt: Subordinated debt consists of the Unsecured Subordinated Notes, due May 24, 2039 and have a fixed interest rate. The Company determines the fair value of these instruments using the income approach utilizing inputs that are observable (Level 2). The following table sets forth the Company’s carrying and fair values of notes payable and subordinated debt as of June 30, 2026 and December 31, 2025: June 30, 2026 December 31, 2025 ($ in thousands) Carrying Value Fair Value Carrying Value Fair Value Notes payable FHLB Loan $ 57,000 $ 56,737 $ 57,000 $ 57,458 Revolving Credit Facility 114,500 114,500 114,500 114,500 Term Loan Facility, net of debt issuance costs 246,120 246,073 300,000 300,000 Notes payable $ 417,620 $ 417,310 $ 471,500 $ 471,958 Subordinated debt Unsecured subordinated notes $ 19,585 $ 20,812 $ 19,569 $ 21,020 Subordinated debt, net of debt issuance costs $ 19,585 $ 20,812 $ 19,569 $ 21,020 Other financial instruments qualify as insurance-related products and are specifically exempted from fair value disclosure requirements. 21 Table of Contents SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED) 5. Mortgage Loans The Company has invested in Separately Managed Accounts (“SMA1” and “SMA2”). As of June 30, 2026 and December 31, 2025, 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. The loans earn interest at a fixed spread above a prime rate and mature in approximately 2 to 4 years from loan origination. The principal amounts of the loans are approximately 64 % of the property’s appraised value at the time the loans were made. The following table sets forth the carrying value of the Company’s mortgage loans as of June 30, 2026 and 2025: ($ in thousands) June 30, 2026 December 31, 2025 Commercial $ 2,598 $ 3,334 Hospitality 6,620 6,568 $ 9,218 $ 9,902 The following table sets forth the Company’s gross investment income for mortgage loans for the three and six months ended June 30, 2026 and 2025: Three months ended June 30, Six months ended June 30, ($ in thousands) 2026 2025 2026 2025 Commercial $ 130 $ 109 $ ( 694 ) $ 217 Retail — — — 304 Hospitality 161 161 320 410 $ 291 $ 270 $ ( 374 ) $ 931 The uncollectible amounts on loans, on an individual loan basis, are determined based upon consultations and advice from the Company’s specialized investment manager and consideration of any adverse situations that could affect the borrower’s ability to repay, the estimated value of underlying collateral, and other relevant factors. The Company writes off the uncollectible amount in the period it was determined to be uncollectible. There was no write-off for uncollectible amounts during the three and six months ended June 30, 2026 and 2025, respectively. As of June 30, 2026 and as of December 31, 2025, $ 2.6 million mortgage loans were in the process of foreclosure and there was 1 mortgage loan that was not producing income for the previous 12 months. 6. Equity Method Investments and Other The following table sets forth the carrying value and ownership percentage of the Company’s equity method investments as of June 30, 2026 and 2025: ($ in thousands) June 30, 2026 December 31, 2025 Carrying Value Ownership % Carrying Value Ownership % Arena Special Opportunities Fund, LP units $ 22,399 13.1 % $ 26,936 14.0 % JVM Funds LLC units 12,856 10.1 % 14,911 10.1 % Hudson Ventures Fund 2 LP units 5,397 2.5 % 5,503 2.5 % RISCOM 2,952 20.0 % 3,307 20.0 % Brewer Lane Ventures Fund II LP units 2,662 2.4 % 2,251 2.4 % Dowling Capital Partners LP units 306 5.1 % 590 5.0 % Arena SOP LP units — 11.4 % — 11.2 % $ 46,572 $ 53,498 22 Table of Contents SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED) 6. Equity Method Investments and Other (continued) The following table sets forth the components of net investment income (loss) from equity method investments for the three and six months ended June 30, 2026 and 2025: Three months ended June 30, Six months ended June 30, ($ in thousands) 2026 2025 2026 2025 RISCOM $ 326 $ 1,055 $ 1,045 $ 927 Dowling Capital Partners LP units 14 203 189 216 Hudson Ventures Fund II LP units 1 90 ( 105 ) 65 Brewer Lane Ventures Fund II LP ( 25 ) ( 27 ) ( 37 ) 143 JVM Funds LLC ( 175 ) ( 304 ) ( 606 ) ( 515 ) Arena SOP LP units — ( 218 ) — ( 1,474 ) Arena Special Opportunities Fund, LP units ( 1,198 ) ( 1,697 ) ( 2,840 ) ( 2,248 ) $ ( 1,057 ) $ ( 898 ) $ ( 2,354 ) $ ( 2,886 ) The following table sets forth the unfunded commitment of equity method investments as of June 30, 2026 and December 31, 2025: ($ in thousands) June 30, 2026 December 31, 2025 Brewer Lane Ventures Fund II LP units $ 2,368 $ 3,237 Dowling Capital Partners LP units 386 386 Hudson Ventures Fund 2 LP units 166 166 $ 2,919 $ 3,789 The difference between the cost of an investment and its proportionate share of the underlying equity in net assets is allocated to the various assets and liabilities of the equity method investment. The Company amortizes the difference in net assets over the same useful life of a similar asset as the underlying equity method investment. For investment in RISCOM, a similar asset would be agent relationships. The Company amortizes this difference over a 15 -year useful life. The following table sets forth the Company’s recorded investment in RISCOM compared to its share of underlying equity as of June 30, 2026 and December 31, 2025: ($ in thousands) June 30, 2026 December 31, 2025 Investment in RISCOM: Underlying equity $ 2,059 $ 2,292 Difference 893 1,015 Recorded investment balance $ 2,952 $ 3,307 The following table sets forth the Company’s recorded investment in JVM Funds LLC compared to its share of underlying equity as of June 30, 2026 and December 31, 2025: ($ in thousands) June 30, 2026 December 31, 2025 Investment in JVM Funds LLC: Underlying equity $ 12,477 $ 14,457 Difference 379 454 Recorded investment balance $ 12,856 $ 14,911 Investment in Indirect Loans and Loan Collateral As of June 30, 2026 and December 31, 2025, the Company held indirect investments in collateralized loans and loan collateral through SMA1 and SMA2. 23 Table of Contents SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED) 6. Equity Method Investments and Other (continued) The carrying value of the SMA1 and SMA2 as of June 30, 2026 and December 31, 2025 were as follows: ($ in thousands) June 30, 2026 December 31, 2025 SMA1 $ 10,045 $ 15,418 SMA2 6,108 8,449 Investment in indirect loans and loan collateral $ 16,153 $ 23,867 7. Variable Interest Entity Pursuant to GAAP consolidation guidance, Skyward consolidates Separate Account HSIC-01 (“HSIC-01”), established by Mangrove Risk Solutions Bermuda Ltd. (“Mangrove”). HSIC-01 is a variable interest entity (“VIE”) for which the Company is the primary beneficiary. The purpose of the VIE is to hedge price volatility risks of certain insurance products by investing in dairy and livestock commodities. The Company directly manages the business; therefore, it considers itself the primary beneficiary. The Company does not provide performance guarantees and has no other financial obligation to provide funding to HSIC-01, other than its own capital commitments. The assets of consolidated variable interest entities may only be used to settle obligations of these entities. In addition, there is no recourse to the assets of HSIC-01 other than to satisfy associated liabilities. The following table presents the assets of HSIC-01, included in the condensed consolidated balance sheet as of June 30, 2026. The assets presented below only include third-party net assets and exclude any intercompany balances, which were eliminated in consolidation. ($ in thousands) June 30, 2026 Assets Cash and cash equivalents $ 10,564 Options, at fair value 40,534 Total assets $ 51,098 8 . Derivatives The Company uses derivatives as part of its financial risk management programs to mitigate price risk related to certain insurance contracts exposed to commodity price risk due to fluctuations in relevant market prices, including cattle and milk. To mitigate revenue volatility and support financial stability, the Company employs a hedging strategy that utilizes derivatives, specifically put options, as part of its risk management framework. The primary objective of holding these derivative instruments is to manage exposure to adverse price movements. The activity in these instruments generally reflects current market conditions and shifts in risk exposures throughout the year. The notional value of derivative contracts held and the degree of hedged exposure are actively managed and may vary depending on the prevailing pricing environment in cattle, hogs, and milk markets. The Company does not use derivatives for speculative or trading purposes. All derivative positions are intended to support the overall risk transfer objectives of the business. The Company has not elected hedge accounting for these derivatives. The following table presents the notional amounts and fair value of derivative assets in the condensed consolidated balance sheets at June 30, 2026: ($ in thousands) Derivative Assets Notional Amount Fair Value Economic hedges $ 197,991 $ 40,535 The Company presents the net gain (loss) recognized on derivative instruments in economic hedging relationships in “losses and loss adjustment expenses” on the condensed consolidated statements of operations. For the three and six months ended June 30, 2026, the Company recognized a pre-tax gain of $ 9.6 million and a pre-tax loss of $ 21.7 million, respectively, in losses and loss adjustment expenses. 24 Table of Contents SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED) 9. Notes Payable & Subordinated Debt 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 in the principal amount of $ 57.0 million. The FHLB Loan provides for interest-only payments during its term, with principal due in full at maturity. The interest rate is fixed over the term of the loan at 4.00 %. The FHLB Loan is fully secured by a pledge of specific investment securities of HSIC. The Company used the proceeds to fund redemptions of the draws on its prior credit facility. Term Loan Facility During the fourth quarter of 2025, the Company entered into a Term Loan Credit Agreement (the “Term Loan Facility”) with a syndicate of participating banks. The Term Loan Facility includes (a) an unsecured senior delayed draw term loan facility (“DDTL”) in the aggregate principal amount of $ 150.0 million (the “Tranche A DDTL”) and (b) an additional unsecured senior DDTL in the aggregate principal amount of $ 150.0 million (the “Tranche B DDTL” and together with the Tranche A DDTL, the “Term Loan Facility”). The Term Loan Facility was used by the Company to fund a portion of the consideration of the Company’s acquisition of Apollo Group Holdings Limited (“Apollo”) and related transaction fees and expenses. Amounts drawn under the Term Loan Facility bear interest at either term SOFR plus a margin, which ranges from 150 basis points to 190 basis points, or the base rate plus a margin, which ranges from 50 basis points to 90 basis points, each depending on the Company’s debt to capitalization ratio. SOFR is calculated using a SOFR floor of 0.00 % and a credit spread adjustment of 0.10 %. The base rate is the highest of (i) the Agent’s then-current prime lending rate, (ii) the Federal Funds Rate plus 0.50 %, (iii) SOFR plus 1.00 % and (iv) zero percent (0%). In addition, the Company pays a fee ranging from 0.20 % to 0.35 % on average daily undrawn amounts under the Facility, depending on the Company’s debt to capitalization ratio. The Tranche A DDTL matures on January 1, 2028 and the Tranche B DDTL matures on July 2, 2029. On December 30, 2025, the Company drew $ 150.0 million of the Tranche A DDTL and $ 150.0 million of the Tranche B DDTL for the acquisition of Apollo on January 1, 2026. On June 26, 2026, the Company repaid $ 50.0 million of outstanding principal under the Tranche A DDTL. The Term Loan Facility includes customary covenants, including certain limitations on the incurrence by the Company of additional indebtedness exceeding $ 10.0 million and on the Company’s ability to make distributions to its stockholders, or redeem, repurchase or retire shares of stock, upon the occurrence of certain events and certain financial covenants, including financial covenants relating to our minimum consolidated net worth, maximum total debt to capitalization, minimum A.M. Best rating and minimum liquidity, as well as customary events of default. As of June 30, 2026, the Company was in compliance with all covenants. The Term Loan Facility is unsecured. In connection with the Revolving Credit Facility (defined below), during the fourth quarter of 2025, the Company and the subsidiary guarantors party thereto, entered into a guaranty agreement, pursuant to which the Company’s obligations under the Term Loan Facility are guaranteed by the Company and its existing wholly-owned subsidiaries and subsequently acquired or organized subsidiaries, excluding insurance company subsidiaries and subject to certain other exceptions. The Company reports debt related to the Term Loan Facility in its June 30, 2026 condensed consolidated balance sheet, net of debt issuance costs of approximately $ 3.9 million. These deferred financing costs are presented as a direct deduction from the carrying amount of the debt. Revolving Credit Facilities During the fourth quarter of 2025, the Company entered into a Credit Agreement (the “Revolving Credit Facility”) with a syndicate of participating banks. The Revolving Credit Facility is unsecured and provided the Company with up to an initial maximum principal amount of $ 150.0 million which was increased to $ 250.0 million on the closing date of the Company’s acquisition of Apollo. The Company initially drew $ 43.0 million, which was used to redeem the Company’s prior revolving credit facility (described below). On December 30, 2025, the company drew an additional $ 71.5 million which was used for the consideration paid for the acquisition of Apollo. The proceeds were used for the acquisition of Apollo on January 1, 2026. 25 Table of Contents SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED) 9. Notes Payable & Subordinated Debt (continued) Interest on the Revolving Credit Facility is payable quarterly. Amounts drawn under the Facility bear interest at either term SOFR plus a margin, which ranges from 150 and 190 basis points, or the base rate plus a margin, which ranges from 50 basis points to 90 basis points, each depending on the Company’s debt to capitalization ratio. SOFR is calculated using a SOFR floor of 0.00 % and a credit spread adjustment of 0.10 %. The base rate is the highest of (i) the Agent’s then current prime lending rate, (ii) the Federal Funds Rate plus 0.50 %, (iii) SOFR plus 1.00 % and (iv) zero percent (0%). In addition, the Company pays a fee ranging from 0.20 % to 0.35 % on average daily undrawn amounts under the Facility, depending on the Company’s debt to capitalization ratio. The availability period under the Facility will terminate on November 12, 2030. The Company is subject to covenants on the Revolving Credit Facility based on minimum net worth, maximum debt to capital ratio, minimum A.M. Best Rating and minimum liquidity, as well as customary events of default. As of June 30, 2026, the Company was in compliance with all covenants. Debentures In May 2019, the Company entered into an agreement to issue unsecured subordinated notes (the “Notes”) with an aggregate principal amount of $ 20.0 million. Interest on the Notes is fixed at 7.25 % for the first 8 years and fixed at 8.25 % thereafter. Early retirement of the debt ahead of 8 year commitment requires all interest payments to be paid in full as well as the return of outstanding principal. Principal 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 June 30, 2026 Condensed Consolidated Balance Sheet and its December 31, 2025 Consolidated Balance Sheet, net of debt issuance costs of approximately $ 0.4 million. These deferred financing costs are presented as a direct deduction from the carrying amount of the subordinated debt. 10. Stockholders' Equity Share Repurchase Program In October 2024, the Company’s Board of Directors (the “Board”) approved a share repurchase program authorizing the repurchase of up to $ 50.0 million of the Company’s common stock. On July 15, 2026, the Board authorized an increase to the share repurchase program authorizing the repurchase of up to an additional $ 50.0 million of the Company's common stock. As a result, the total amount authorized under the share repurchase program increased to $ 100.0 million. The shares may be repurchased from time to time in open market purchases, privately-negotiated transactions, block purchases, accelerated share repurchase agreements or a combination of methods, including through Rule 10b5-1 trading plans. The timing, manner, price and amount of any repurchases under the share repurchase program will be determined by the Company’s discretion. The share repurchase program does not require the Company to repurchase any specific number of shares, and may be modified, suspended or terminated at any time. During the three and six months ended June 30, 2026, the Company repurchased 222,635 shares for approximately $ 9.7 million under this plan. These shares represent the total repurchased under the plan as of June 30, 2026. 11. Segments The Company has two reportable segments, the Skyward Specialty segment and the Apollo segment, through which it offers a broad array of commercial property and casualty products and reinsurance solutions on a non-admitted (or E&S) and admitted basis, predominantly in the United States. The Company defines its segment on the basis of the way in which internally reported financial information is regularly reviewed by the Chief Operating Decision Maker (“CODM”) to analyze financial performance, make decisions and allocate resources. The Company’s CODM is the chief executive officer. The accounting policies of the segments are the same as those used for the preparation of the Company’s consolidated financial statements. Intersegment business is allocated to the segment accountable for the underwriting results. The Skyward Specialty segment is made up of nine distinct underwriting divisions, or “continuing business,” and has dedicated underwriting leadership supported by high-quality technical staff with deep experience in their respective niches. The Apollo segment consists of the operations of Apollo, a Lloyd’s‑based specialty insurance platform acquired by the Company on January 1, 2026, structured around two core divisions that collectively support its underwriting, specialty‑risk, and managing‑agency activities. Apollo operates within the Lloyd’s of London market, leveraging Lloyd’s global licensing, centralized underwriting infrastructure, and long‑standing distribution networks to access niche and emerging specialty classes across international markets. 26 Table of Contents SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED) 11. Segments (continued) The accounting policies of the segments are the same as those described in Note 1 “Summary of Significant Accounting Policies” of the Company’s Annual Report on Form 10-K for the year ended December 31, 2025. The CODM assesses performance for the segments and allocates resources based primarily on gross written premiums, managed premiums and underwriting contribution. The Company does not manage assets by segment, with the exception of goodwill and intangible assets. Investment results, interest expense, amortization expense, corporate expenses and other income and expenses are not allocated to the underwriting segments. Gross written premiums by underwriting division, managed premiums and underwriting contribution are used to monitor budget versus actual results. The CODM also uses underwriting contribution in competitive analysis by benchmarking to the Company’s competitors. The competitive analysis along with the monitoring of budgeted versus actual results are used in assessing performance of the segments and in establishing management’s compensation. The following table presents gross written premiums by underwriting division for the three and six months ended June 30, 2026 and 2025: Three months ended June 30, Six months ended June 30, ($ in thousands) 2026 2025 2026 2025 Skyward Specialty Segment Accident & Health $ 95,456 $ 60,489 $ 187,465 $ 123,658 Captives 64,251 76,994 122,165 143,923 Credit & Surety 63,759 55,131 127,933 100,159 Energy Solutions 62,690 74,822 111,556 150,416 Global Agriculture 111,939 57,179 214,291 137,796 Global Property 71,109 83,992 105,626 130,678 Professional Lines 34,978 37,555 71,206 77,772 Specialty Programs 111,441 85,955 206,208 148,630 Transactional E&S 52,296 53,461 102,360 105,467 Total continuing business 667,919 585,578 1,248,810 1,118,499 Exited business ( 146 ) ( 664 ) 767 1,741 Total Skyward Specialty Segment gross written premiums 667,773 584,914 1,249,577 1,120,240 Apollo Segment Syndicate 1969 59,431 — 124,439 — Syndicate 1971 13,350 — 34,242 — Total Apollo Segment gross written premiums 72,781 — 158,681 — Total gross written premiums $ 740,554 $ 584,914 $ 1,408,258 $ 1,120,240 The following table sets forth the Apollo segment’s managed premiums for the three and six months ended June 30, 2026: Three months ended June 30, Six months ended June 30, 2026 2026 Aligned Syndicates $ 217,196 $ 427,745 Partner Syndicates 100,925 190,381 Total managed premiums $ 318,121 $ 618,126 The following table presents information about reported segment net underwriting income, significant segment expenses and a reconciliation of net underwriting income to net income for the three and six months ended June 30, 2026 and 2025: 27 Table of Contents SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED) 11. Segments (continued) Three months ended June 30, 2026 2025 ($ in thousands) Skyward Specialty Apollo Total Skyward Specialty Total Underwriting income Revenues: Net earned premiums $ 378,346 $ 66,126 $ 444,472 $ 295,542 $ 295,542 Underwriting fee income — 12,588 12,588 — — Commission and fee income 2,334 — 2,334 2,560 2,560 Total underwriting revenues 380,680 78,714 459,394 298,102 298,102 Expenses: Losses and LAE 236,967 39,774 276,741 181,262 181,262 Amortization of policy acquisition costs 52,927 18,227 71,154 44,636 44,636 Other operating and general expenses 41,204 6,551 47,755 37,730 37,730 Corporate expenses — — 4,372 — 3,230 Fee‑based service expenses — 4,562 4,562 — — Total underwriting expenses 331,098 69,114 404,584 263,628 266,858 Underwriting income $ 49,582 $ 9,600 $ 54,810 $ 34,474 $ 31,244 Reconciliation of underwriting income to net income: Underwriting income $ 54,810 $ 31,244 Add: Net investment income 30,727 18,704 Net investment (losses) gains ( 601 ) 3,090 Other income 13 7 Less: Interest expense 8,812 1,876 Amortization expense 8,843 372 Other expenses 3,737 1,002 Income before income taxes 63,557 49,795 Income tax expense 14,519 10,956 Net income $ 49,038 $ 38,839 28 Table of Contents SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED) 11. Segments (continued) Six months ended June 30, 2026 2025 ($ in thousands) Skyward Specialty Apollo Total Skyward Specialty Total Underwriting income Revenues: Net earned premiums $ 742,289 $ 136,190 $ 878,479 $ 595,908 $ 595,908 Underwriting fee income — 22,666 22,666 — — Commission and fee income 3,861 — 3,861 4,536 4,536 Total underwriting revenues 746,150 158,856 905,006 600,444 600,444 Expenses: Losses and LAE 465,198 76,766 541,964 368,571 368,571 Amortization of policy acquisition costs 103,986 26,784 130,770 89,126 89,126 Other operating and general expenses 87,108 20,736 107,844 75,878 75,878 Corporate expenses — — 9,281 — 7,143 Fee‑based service expenses — 8,732 8,732 — — Total underwriting expenses 656,292 133,018 798,591 533,575 540,718 Underwriting income $ 89,858 $ 25,838 $ 106,415 $ 66,869 $ 59,726 Reconciliation of underwriting income to net income: Underwriting income $ 106,415 $ 59,726 Add: Net investment income 57,782 38,126 Net investment gains 2,584 9,840 Other income 28 20 Less: Interest expense 16,531 3,710 Amortization expense 17,686 709 Other expenses 6,959 2,063 Income before income taxes 125,633 101,230 Income tax expense 26,864 20,333 Net income $ 98,769 $ 80,897 29 Table of Contents SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED) 12. Income Taxes The following table sets forth the Company’s income tax expense and effective tax rates for the three and six months ended June 30, 2026 and 2025: Three months ended June 30, Six months ended June 30, ($ in thousands) 2026 2025 2026 2025 Income tax expense $ 14,519 $ 10,956 $ 26,864 $ 20,333 Effective tax rate 22.8 % 22.0 % 21.4 % 20.1 % The effective tax rate will differ from the statutory rate of 21 percent due to tax charges associated with the effect of foreign operations, permanent differences for disallowed expenses for tax and beneficial adjustments for tax-exempt income, dividends-received deduction, and discrete items. The effect of foreign operations is primarily related to income of our foreign operations taxed at statutory tax rates of 15 % in Bermuda and 25 % in UK. The increase in the effective tax rate for the three months ended June 30, 2026, was primarily driven by state taxes. The increase in the effective tax rate for the six months ended June 30, 2026 was primarily attributable to foreign taxes associated with the Apollo acquisition, partially offset by discrete tax benefits, primarily from stock-based compensation. The Company paid income taxes of $ 27.4 million and $ 30.3 million during the three and six months ended June 30, 2026, respectively, and paid $ 20.3 million during the three and six months ended 2025. 13. Losses and Loss Adjustment Expenses The following table sets forth the reconciliation of unpaid losses and loss adjustment expenses (“LAE”) as reported in the condensed consolidated balance sheets as of and for the six months ended June 30, 2026 and 2025: Six months ended June 30, ($ in thousands) 2026 2025 Reserves for losses and LAE, beginning of period $ 2,796,491 $ 1,782,383 Less: reinsurance recoverable on unpaid claims, beginning of period ( 1,067,551 ) ( 670,846 ) Reserves for losses and LAE, beginning of period, net of reinsurance 1,728,940 1,111,537 Incurred, net of reinsurance, related to: Current period 520,304 368,571 Prior years — — Total incurred, net of reinsurance 520,304 368,571 Paid, net of reinsurance, related to: Current period 56,539 42,153 Prior years 284,591 230,232 Total paid 341,130 272,385 Net reserves for losses and LAE, end of period 1,908,114 1,207,723 Plus: reinsurance recoverable on unpaid claims, end of period 1,162,484 711,030 Reserves for losses and LAE, end of period $ 3,070,598 $ 1,918,753 30 Table of Contents SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED) 14. Commission and Fee Income and Underwriting Fee Income Skyward Underwriters Agency, Inc. (“SUA”), a subsidiary of the Company, is a managing general insurance agent and reinsurance broker for property and casualty and accident and health risks in specialty niche markets. Commission and fee income is primarily generated from SUA for the placement of insurance policies on either a third-party insurance or reinsurance company. The following table sets forth the Company’s disaggregated revenues from contracts with customers for the three and six months ended June 30, 2026 and 2025: Three months ended June 30, Six months ended June 30, ($ in thousands) 2026 2025 2026 2025 SUA commission revenue $ 2,778 $ 3,090 $ 5,059 $ 4,927 SUA fee income 342 608 797 1,785 Other 1,461 397 2,054 407 Total commission and fee revenue 4,581 4,095 7,910 7,119 Commission and fee expenses ( 2,247 ) ( 1,535 ) ( 4,049 ) ( 2,583 ) Net commission and fee income $ 2,334 $ 2,560 $ 3,861 $ 4,536 The Company’s contract assets from commission and fee income as of June 30, 2026 and December 31, 2025 were $ 1.0 million. Through its Apollo subsidiary ASML, the Company earns revenue for services performed in its capacity as managing agent to both its wholly owned and third‑party capitalized Lloyd’s syndicates. These revenues primarily consist of managing agency fees, which compensate the Company for underwriting oversight, operational administration, and regulatory and compliance support, as well as profit commissions, which is contingent upon the underwriting and investment performance of certain syndicates. ASML receives (i) managing agency fees from managed syndicates, including 1969, 1971 and 1972 (collectively the “Managed Syndicates”) at a rate of 0.9 % of the managed stamp capacity and for SPA1925 at 1.0 %, which is fully recognized over the period the services are rendered, (ii) profit commissions from certain syndicates, subject to a two-year deficit clause, and (iii) a share of the leader’s fee for managing consortium arrangements. Managing agency fees and services revenue are recognized over time as services are rendered, while profit commission is recognized only when it becomes probable that no significant reversal will occur. This revenue is disclosed in underwriting fee income. The following table sets forth Apollo’s revenues from contracts with customers for the three and six months ended June 30, 2026: Three months ended June 30, Six months ended June 30, ($ in thousands) 2026 2026 Managing agents fees $ 3,508 $ 7,035 Profit commission & consortium overrider charged to Managed Syndicates 8,072 14,623 Miscellaneous fee income 1,008 1,008 Underwriting fee income $ 12,588 $ 22,666 31 Table of Contents SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED) 15. Underwriting, Acquisition and Insurance Expenses The following table sets forth the components of underwriting, acquisition and insurance expenses for the three and six months ended June 30, 2026 and 2025: Three months ended June 30, Six months ended June 30, ($ in thousands) 2026 2025 2026 2025 Amortization of policy acquisition costs $ 71,154 $ 44,636 $ 130,770 $ 89,126 Other operating and general expenses 47,755 37,730 107,844 75,878 Corporate expenses 4,372 3,230 9,281 7,143 Total underwriting, acquisition and insurance expenses $ 123,281 $ 85,596 $ 247,895 $ 172,147 16. Reinsurance Certain premiums and benefits are assumed from and ceded to other insurance companies under various reinsurance agreements. The reinsurance agreements provide the Company with increased capacity to write larger risks and maintain its exposure to loss within its risk tolerance. The Company remains obligated for amounts ceded in the event that the reinsurers do not meet their obligations. The following tables set forth the effects of reinsurance on written and earned premiums and losses and loss adjustment expenses for the three and six months ended June 30, 2026 and 2025: Three months ended June 30, 2026 2025 ($ in thousands) Written Earned Written Earned Direct premiums $ 558,375 $ 529,263 $ 461,081 $ 392,777 Assumed premiums 182,179 144,737 123,833 86,420 Ceded premiums ( 254,938 ) ( 229,528 ) ( 245,701 ) ( 183,655 ) Net premiums $ 485,616 $ 444,472 $ 339,213 $ 295,542 Ceded losses and LAE incurred $ 183,466 $ 138,438 Six months ended June 30, 2026 2025 ($ in thousands) Written Earned Written Earned Direct premiums $ 1,065,509 $ 1,044,752 $ 869,391 $ 778,215 Assumed premiums 342,749 294,293 250,849 165,147 Ceded premiums ( 489,759 ) ( 460,566 ) ( 437,756 ) ( 347,454 ) Net premiums $ 918,499 $ 878,479 $ 682,484 $ 595,908 Ceded losses and LAE incurred $ 336,039 $ 273,905 The following table sets forth the components of reinsurance recoverables and ceded unearned premium as of June 30, 2026 and December 31, 2025: ($ in thousands) June 30, 2026 December 31, 2025 Ceded unpaid losses and LAE $ 1,162,484 $ 921,165 Ceded paid losses and LAE 251,459 201,010 Allowance for credit losses ( 2,295 ) ( 2,295 ) Reinsurance recoverables $ 1,411,648 $ 1,119,880 Ceded unearned premium $ 337,180 $ 238,948 32 Table of Contents SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED) 16. Reinsurance (continued) The Company entered into agreements with several of its reinsurers, whereby the reinsurer established funded trust accounts with the Company as the sole beneficiary. These trust accounts provide the Company additional security to collect claim recoverables under reinsurance contracts and the Company does not carry these on the balance sheet because the Company will only have custody over these accounts upon the failure of the reinsurer to pay amounts due. At June 30, 2026, the market value of these accounts was approximately $ 224.0 million. The trust amount will be adjusted periodically, by mutual agreement, based on claim payments and loss reserve recoverables. Certain ceded reinsurance contracts that transfer only significant timing risk and do not transfer sufficient underwriting risk are accounted for using the deposit method of accounting. The Company’s deposit asset at June 30, 2026 and December 31, 2025 was $ 30.7 million and $ 22.7 million, respectively, and was included in other assets on the condensed consolidated balance sheets. 17. Earnings Per Share The following table sets forth the computation of basic and diluted net earnings per share for the three and six months ended June 30, 2026 and 2025: Three months ended June 30, Six months ended June 30, ($ in thousands, except for share and per share amounts) 2026 2025 2026 2025 Numerator Net income $ 49,038 $ 38,839 $ 98,769 $ 80,897 Denominator Basic weighted-average common shares 44,521,162 40,445,391 44,492,608 40,322,051 Dilutive effect of stock units 687,512 893,067 555,233 940,951 Dilutive effect of options 483,967 533,038 478,392 508,213 Diluted weighted-average common share equivalents 45,692,641 41,871,496 45,526,233 41,771,215 Basic earnings per share $ 1.10 $ 0.96 $ 2.22 $ 2.01 Diluted earnings per share $ 1.07 $ 0.93 $ 2.17 $ 1.94 The following table presents anti-dilutive instruments that were excluded from the calculation of diluted weighted-average common share equivalents during the three and six months ended June 30, 2026 and 2025: Three months ended June 30, Six months ended June 30, 2026 2025 2026 2025 Stock units 348,788 49,540 344,753 109,359 Options 179 868 220 834 18. Related Party Transactions RISCOM RISCOM provides the Company with wholesale brokerage services. RISCOM and the Company also 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 three and six months ended June 30, 2026 and 2025 were as follows: Three months ended June 30, Six months ended June 30, ($ in thousands) 2026 2025 2026 2025 Net earned premium $ 32,525 $ 29,886 $ 63,449 $ 58,846 Commissions 7,647 7,533 15,835 15,165 Premiums receivable as of June 30, 2026 and December 31, 2025 were $ 17.2 million and $ 13.9 million, respectively. 33 Table of Contents SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED) 18. Related Party Transactions (continued) See Note 6 for investments involving affiliated companies and additional related party transactions. 19. Acquisitions On January 1, 2026 (the “Acquisition Date”), the Company completed the acquisition of Apollo Group Holdings Limited (“Apollo”) pursuant to the Apollo share purchase agreements and acquired 100 % of the issued and outstanding share capital of Apollo. Apollo is a U.K.-based specialty underwriting platform operating at Lloyd’s of London. Apollo underwrites a multi-class specialty insurance portfolio and offers products across Property, Casualty, Marine, Energy & Transportation, Specialty and Reinsurance, as well as digital and embedded risk programs. The Company acquired Apollo to broaden its specialty insurance platform, expand into additional specialty niches, enhance its innovation and technology capabilities, and strengthen its market position. The fair value of the consideration transferred, or the purchase price, is approximately $ 559.1 million. This amount is based on (i) the issuance of 3,679,332 shares of common stock of the Company, using the closing price of Skyward common stock of $ 51.11 per share on December 31, 2025, the last trading day prior to the Acquisition Date, and (ii) $ 371.1 million in cash (the “Cash Consideration”). The table below presents the components of the fair value of consideration transferred: ($ in thousands, except for share and per share amounts) Share consideration Skyward Specialty Insurance Group, Inc. common stock issued to existing Apollo common stockholders 3,679,332 Skyward Specialty Insurance Group, Inc. closing stock price on December 31, 2025 $ 51.11 Consideration of Skyward Specialty Insurance Group, Inc. issued common stock $ 188,051 Cash consideration 371,089 Total consideration $ 559,140 The Company accounted for the transaction as a business combination under ASC 805, Business Combinations (“ASC 805”). The purchase price has been preliminarily allocated to the assets acquired and liabilities assumed based on their estimated fair values as of the Acquisition Date. The Company is considered the accounting acquirer in the transaction. 34 Table of Contents SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED) 19. Acquisitions (continued) The following table summarizes the preliminary purchase price allocation as of the Acquisition Date: ($ in thousands) January 1, 2026 Assets acquired, excluding goodwill Fixed maturity securities, available-for-sale, at fair value $ 222,460 Short-term investments, at fair value 187,178 Cash and cash equivalents 68,054 Funds at Lloyd's 106,336 Premiums receivable, net 272,803 Reinsurance recoverables, net 165,540 Ceded unearned premium 69,097 Deferred policy acquisition costs and VOBA 56,128 Deferred income taxes 13,966 Intangible assets, excluding goodwill, net 262,000 Other assets 25,830 Total assets acquired, excluding goodwill 1,449,392 Liabilities assumed Reserves for losses and loss adjustment expenses 477,596 Unearned premiums 233,501 Reinsurance and premium payables 144,536 Funds held for others 18,684 Accounts payable and accrued liabilities 71,506 Deferred income taxes 69,837 Total liabilities assumed 1,015,660 Fair value of net assets acquired, excluding goodwill $ 433,732 Total consideration $ 559,140 Preliminary allocation to goodwill $ 125,408 The Apollo acquisition was accounted for as a business combination using the acquisition method of accounting in accordance with ASC 805. The purchase price was allocated to assets acquired and liabilities assumed based on the estimated fair values at the Acquisition Date. Goodwill recognized in the transaction represents the excess of consideration transferred over the fair value of identifiable net assets acquired and will not be deductible for tax purposes and is fully allocated to the U.K. segment. Goodwill primarily represents the expected future economic benefits arising from the acquisition, including anticipated synergies from the integration of operations, Apollo’s established specialty underwriting platform, and access to its distribution network and Lloyd’s market presence. The identifiable intangible assets primarily relate to syndicate capacity, cover holder relationships, strategic partner syndicates and trade names. The amounts, based on preliminary valuations and subject to final adjustment, allocated to intangible assets are as follows: ($ in thousands) Estimated fair value Estimated average useful life (in years) Estimated Annual Amortization Expense Syndicate 1969 capacity - with fees $ 90,000 Indefinite N/A, indefinite lived asset Syndicate 1971 capacity - with fees 110,000 Indefinite N/A, indefinite lived asset Cover holder relationships 25,000 7 $ 3,571 Strategic partner syndicates 2,000 5 400 Trade name 35,000 10 3,500 Total $ 262,000 $ 7,471 35 Table of Contents SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS (UNAUDITED) 19. Acquisitions (continued) The Company also recognized value of business acquired (“VOBA”), which represents the estimated fair value of the deferred acquisition costs of acquired in‑force insurance contracts. VOBA is amortized over one year, reflecting the expected runoff of the acquired in‑force contracts. VOBA is aggregated with deferred policy acquisition costs and included within deferred policy acquisition costs and VOBA on the consolidated balance sheets. For the three and six months ended June 30, 2026 the Company recognized $ 7.3 million and $ 14.6 million, respectively, in underwriting, acquisition and insurance expenses, and $ 6.7 million and $ 13.4 million, respectively, in amortization expense on the consolidated statements of operations related to the amortization of VOBA. Estimated fair values of assets acquired and liabilities assumed from Apollo are subject to change as additional information is obtained, and will be updated and finalized within the measurement period that will not extend beyond 12 months from the Acquisition Date. Any measurement period adjustments will be recorded in the period in which the adjustments are identified, as if they had been recognized as of the acquisition date. The results of operations for Apollo of $ 78.7 million and $ 158.9 million of revenue for the three and six months ended June 30, 2026, respectively, and $ 15.4 million and $ 37.6 million of net income for the three and six months ended June 30, 2026, respectively, have been included within the accompanying consolidated statements of operations and comprehensive loss. All transaction expenses incurred by the Company were expensed as incurred and reflected in the Company’s results of operations for the period ended December 31, 2025 in accordance with ASC 805. No material transaction expenses were incurred for the period ended June 30, 2026. The Company has not presented the unaudited supplemental pro forma financial information required by ASC 805-10-50-2(h) as it is impractical to do so, as Apollo did not historically prepare quarterly financial statements and its historical financial information was prepared under U.K. GAAP rather than U.S. GAAP. 20. Commitments and Contingencies Litigation The Company is named as a party in various legal actions arising from claims made under insurance policies and contracts. Those actions are considered by the Company in estimating the losses and loss adjustment expense reserves. Also, from time to time, the Company is a defendant in various legal actions that relate to bad faith claims, disputes with third parties or that involve alleged errors and omissions. The Company records accruals for these items to the extent the losses are probable and reasonably estimable. Although the ultimate outcome of these matters cannot be determined at this time, based on present information, the availability of insurance coverage and advice received from outside legal counsel, the Company believes the resolution of any such matters will not, individually or in the aggregate, have a material adverse effect on the Company’s consolidated financial position, results of operations or cash flows. Indemnification In conjunction with the sale of business assets and subsidiaries, the Company has provided indemnifications to certain buyers. Certain indemnifications cover typical representations and warranties related to the responsibilities to perform under the sales contracts. The amount of potential exposure covered by the indemnifications is difficult to determine because the indemnifications cover a variety of matters, operations and scenarios. Certain of these indemnifications have no time limit. At this time, the Company does not have reason to believe any such significant claims exist. 36 Table of Contents