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    SEC Form 10-Q filed by Skyward Specialty Insurance Group Inc.

    5/7/25 3:40:46 PM ET
    $SKWD
    Property-Casualty Insurers
    Finance
    Get the next $SKWD alert in real time by email
    skwd-20250331
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    UNITED STATES
    SECURITIES AND EXCHANGE COMMISSION
    Washington, D.C. 20549
    __________________________________________
    FORM 10-Q
    __________________________________________
    (Mark One)
    ☒QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934
    For the quarterly period ended March 31, 2025
    OR
    ☐
    TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934
    For the transition period from ____________  to ____________

    Commission file number 001-41591

    SKYWARD SPECIALTY INSURANCE GROUP, INC.
    (Exact name of registrant as specified in its charter)
    Delaware
    14-1957288
    (State or other jurisdiction of incorporation or organization)
    (I.R.S. Employer
    Identification No.)
    800 Gessner Road, Suite 600
    Houston, Texas
    77024-4284
    (Address of Principal Executive Offices)(Zip Code)
    (713) 935-4800
    Registrant’s telephone number, including area code

    Securities registered pursuant to Section 12(b) of the Act:
    Title of each classTrading Symbol(s)Name of each exchange on which registered
    Common stock, par value $0.01SKWDThe Nasdaq Stock Market LLC

    Indicate by check mark whether the registrant: (1) has filed all reports required to be filed by Section 13 or 15(d) of the Securities Exchange Act of 1934 during the preceding 12 months (or for such shorter period that the registrant was required to file such reports); and (2) has been subject to such filing requirements for the past 90 days. Yes ☒    No  ☐
    Indicate by check mark whether the registrant has submitted electronically every Interactive Data File required to be submitted pursuant to Rule 405 of Regulation S-T (§232.405 of this chapter) during the preceding 12 months (or for such shorter period that the registrant was required to submit and post such files). Yes  ☒   No  ☐ 
    Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, a smaller reporting company, or an emerging growth company. See the definitions of “large accelerated filer,” “accelerated filer,” “smaller reporting company” and “emerging growth company” in Rule 12b-2 of the Exchange Act.
    Large accelerated filer
    ☒
    Accelerated filer
    ☐
    Non-accelerated filer  
    ☐
    Smaller reporting company
    ☐
    Emerging growth company
    ☐
    If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act. ☐
    Indicate by check mark whether the registrant is a shell company (as defined in Rule 12b-2 of the Act).     Yes ☐   No  ☒

    As of May 2, 2025, the registrant had 40,402,879 shares of common stock outstanding.


    Table of Contents

    TABLE OF CONTENTS
    Form 10-QItem and DescriptionPage
    Part I
    Item 1.
    Financial Statements
    3
    Condensed Consolidated Balance Sheets as of March 31, 2025 and December 31, 2024 (unaudited)
    3
    Condensed Consolidated Statements of Operations and Comprehensive Income for the Three-Month Periods Ended March 31, 2025 and 2024 (unaudited)
    4
    Condensed Consolidated Statements of Changes in Stockholders’ Equity for the Three-Month Periods Ended March 31, 2025 and 2024 (unaudited)
    5
    Condensed Consolidated Statements of Cash Flows for the Three-Month Periods Ended March 31, 2025 and 2024 (unaudited)
    6
    Notes to Condensed Consolidated Financial Statements (unaudited)
    7
    Item 2.
    Management's Discussion and Analysis of Financial Condition and Results of Operations
    27
    Item 3.
    Quantitative and Qualitative Disclosures About Market Risk
    36
    Item 4.
    Controls and Procedures
    36
    Part II
    Item 1.
    Legal Proceedings
    38
    Item 1A.
    Risk Factors
    38
    Item 2.
    Unregistered Sales of Equity Securities and Use of Proceeds
    38
    Item 3.
    Defaults Upon Senior Securities
    39
    Item 4.
    Mine Safety Disclosures
    39
    Item 5.
    Other Information
    40
    Item 6.
    Exhibits
    40
    Signatures
    41
    2

    Table of Contents

    PART I - FINANCIAL INFORMATION
    Item 1. Financial Statements
    SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES
    CONDENSED CONSOLIDATED BALANCE SHEETS (UNAUDITED)
    March 31, 2025December 31, 2024
    ($ in thousands, except share and per share amounts)(Unaudited)
    Assets
    Investments:
    Fixed maturity securities, available-for-sale, at fair value (amortized cost of $1,410,269 and $1,320,266, respectively)
    $1,397,508 $1,292,218 
    Fixed maturity securities, held-to-maturity, at amortized cost (net of allowance for credit losses of $250 and $243, respectively)
    37,519 39,153 
    Equity securities, at fair value108,075 106,254 
    Mortgage loans, at fair value16,012 26,490 
    Equity method investments88,588 98,594 
    Other long-term investments37,646 33,182 
    Short-term investments, at fair value308,042 274,929 
    Total investments1,993,390 1,870,820 
    Cash and cash equivalents112,916 121,603 
    Restricted cash40,590 35,922 
    Premiums receivable, net417,542 321,641 
    Reinsurance recoverables, net902,970 857,876 
    Ceded unearned premium232,147 203,901 
    Deferred policy acquisition costs126,439 113,183 
    Deferred income taxes26,984 30,486 
    Goodwill and intangible assets, net87,089 87,348 
    Other assets90,566 86,698 
    Total assets$4,030,633 $3,729,478 
    Liabilities and stockholders’ equity
    Liabilities:
    Reserves for losses and loss adjustment expenses$1,871,491 $1,782,383 
    Unearned premiums708,347 637,185 
    Deferred ceding commission45,544 40,434 
    Reinsurance and premium payables243,083 177,070 
    Funds held for others113,748 102,665 
    Accounts payable and accrued liabilities78,154 76,206 
    Notes payable100,000 100,000 
    Subordinated debt, net of debt issuance costs19,545 19,536 
    Total liabilities3,179,912 2,935,479 
    Stockholders’ equity
    Common stock, $0.01 par value, 500,000,000 shares authorized, 40,402,879 and 40,127,908 shares issued and outstanding, respectively
    404 401 
    Additional paid-in capital721,186 718,598 
    Accumulated other comprehensive loss(10,047)(22,120)
    Retained earnings139,178 97,120 
    Total stockholders’ equity850,721 793,999 
    Total liabilities and stockholders’ equity$4,030,633 $3,729,478 
    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 March 31,
    ($ in thousands, except share and per share amounts)20252024
    Revenues:
    Net earned premiums$300,366 $236,342 
    Commission and fee income1,976 2,026 
    Net investment income19,331 18,297 
    Net investment gains6,841 8,303 
    Other income13 — 
    Total revenues328,527 264,968 
    Expenses:
    Losses and loss adjustment expenses187,309 143,914 
    Underwriting, acquisition and insurance expenses86,551 69,774 
    Interest expense1,834 2,727 
    Amortization expense337 388 
    Other expenses1,061 1,188 
    Total expenses277,092 217,991 
    Income before income taxes51,435 46,977 
    Income tax expense9,377 10,193 
    Net income$42,058 $36,784 
    Comprehensive income
    Net income$42,058 $36,784 
    Other comprehensive income (loss):
    Unrealized gains and losses on investments:
    Net change in unrealized gains (losses) on investments, net of tax12,255 (5,418)
    Reclassification adjustment for losses on securities no longer held, net of tax(182)(908)
    Total other comprehensive income (loss)12,073 (6,326)
    Comprehensive income$54,131 $30,458 
    Per share data:
    Basic earnings per share$1.05 $0.94 
    Diluted earnings per share$1.01 $0.90 
    Weighted-average common shares outstanding
    Basic40,196,416 39,108,351 
    Diluted41,680,595 41,085,136 
    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 March 31,
    ($ in thousands, except share amounts)20252024
    Common shares:
    Balance at beginning of year40,127,908 39,863,756 
    Issuance of shares274,971 131,271 
    Balance at March 3140,402,879 39,995,027 
    Common stock:
    Balance at beginning of year$401 $399 
    Issuance of common stock3 1 
    Balance at March 31$404 $400 
    Additional paid-in capital:
    Balance at beginning of year$718,598 $710,855 
    Issuance of common stock2,588 454 
    Balance at March 31$721,186 $711,309 
    Stock notes receivable:
    Balance at beginning of year$— $(5,562)
    Employee equity transactions— 328 
    Balance at March 31$— $(5,234)
    Accumulated other comprehensive loss:
    Balance at beginning of year$(22,120)$(22,953)
    Other comprehensive income (loss), net of tax12,073 (6,326)
    Balance at March 31$(10,047)$(29,279)
    Retained earnings (accumulated deficit):
    Balance at beginning of year$97,120 $(21,708)
    Net income42,058 36,784 
    Balance at March 31$139,178 $15,076 
    Total stockholders’ equity$850,721 $692,272 
    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 CASH FLOWS (UNAUDITED)
    Three months ended March 31,
    ($ in thousands)20252024
    Cash flows from operating activities
    Net income$42,058 $36,784 
    Adjustments to reconcile net income to net cash provided by operating activities54,702 57,481 
    Net cash provided by operating activities96,760 94,265 
    Cash flows from investing activities:
    Purchase of fixed maturity securities, available-for-sale(126,827)(97,426)
    Purchase of equity securities(8,422)(2,035)
    Purchase of equity method investments(200)(261)
    Investment in direct and indirect loans13,829 10,816 
    Purchase of property and equipment(202)(260)
    Proceeds from the sales of fixed maturity securities, available-for-sale8,195 12,093 
    Maturities, calls, transfers and paydowns of fixed maturity securities, available-for-sale29,537 30,138 
    Maturities, calls and paydowns of fixed maturity securities held-to-maturity2,129 784 
    Proceeds from the sales of equity securities8,748 10,458 
    Sales of and distributions from equity method and other long-term investments4,396 4,871 
    Change in short-term investments(33,162)(27,706)
    Change in receivable/payable for securities— (13,755)
    Cash provided by deposit accounting1,200 2,417 
    Net cash used in investment activities(100,779)(69,866)
    Cash flows from financing activities:
    Repayment of stock notes receivable— 328 
    Proceeds from long term borrowings— 50,000 
    Payments on long term borrowings and trust preferred— (59,794)
    Net cash (used in) provided by financing activities— (9,466)
    Net increase (decrease) in cash and cash equivalents and restricted cash(4,019)14,933 
    Cash and cash equivalents and restricted cash at beginning of period(1)
    157,525 100,336 
    Cash and cash equivalents and restricted cash at end of period(1)
    $153,506 $115,269 
    Supplemental disclosure of cash flow information:
    Cash paid for interest$1,805 $2,656 
    (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.
    6

    Table of Contents
    SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES
    NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

    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, 2024 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, 2024 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.
    2.    Investments
    The following tables set forth the amortized cost and the fair value by investment category at March 31, 2025 and December 31, 2024:
    ($ in thousands)Amortized
    Cost
    Gross
    Unrealized
    Gains
    Gross
    Unrealized
    Losses
    Allowance for Credit LossesFair Value
    March 31, 2025
    Fixed maturity securities, available-for-sale:
    U.S. government securities$26,540 $212 $(70)$— $26,682 
    Corporate securities and miscellaneous494,356 7,340 (10,846)— 490,850 
    Municipal securities89,373 592 (4,134)— 85,831 
    Residential mortgage-backed securities410,080 4,658 (12,341)— 402,397 
    Commercial mortgage-backed securities76,802 652 (1,263)— 76,191 
    Other asset-backed securities313,118 3,863 (1,424)— 315,557 
    Total fixed maturity securities, available-for-sale$1,410,269 $17,317 $(30,078)$— $1,397,508 
    Fixed maturity securities, held-to-maturity:
    Other asset-backed securities$37,769 $97 $(6)$(250)$37,610 
    Total fixed maturity securities, held-to-maturity$37,769 $97 $(6)$(250)$37,610 
    7

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    SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES
    NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
    2.     Investments (continued)
    ($ in thousands)Amortized
    Cost
    Gross
    Unrealized
    Gains
    Gross
    Unrealized
    Loss
    Allowance for Credit LossesFair Value
    December 31, 2024
    Fixed maturity securities, available-for-sale:
    U.S. government securities$26,577 $35 $(126)$— $26,486 
    Corporate securities and miscellaneous433,298 5,618 (13,288)— 425,628 
    Municipal securities89,966 116 (5,366)— 84,716 
    Residential mortgage-backed securities408,585 1,875 (16,627)— 393,833 
    Commercial mortgage-backed securities70,262 545 (1,443)— 69,364 
    Other asset-backed securities291,578 2,447 (1,834)— 292,191 
    Total fixed maturity securities, available-for-sale$1,320,266 $10,636 $(38,684)$— $1,292,218 
    Fixed maturity securities, held-to-maturity:
    Other asset-backed securities$39,396 $— $(436)$(243)$38,717 
    Total fixed maturity securities, held-to-maturity$39,396 $— $(436)$(243)$38,717 
    The following table sets forth the amortized cost and fair value of available-for-sale fixed maturity securities by contractual maturity at March 31, 2025:
    ($ in thousands)Amortized
    Cost
    Fair Value
    Due in less than one year$26,394 $26,361 
    Due after one year through five years316,122 312,529 
    Due after five years through ten years222,978 221,809 
    Due after ten years44,775 42,664 
    Mortgage-backed securities486,882 478,588 
    Other asset-backed securities313,118 315,557 
    Total$1,410,269 $1,397,508 
    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 March 31, 2025 consisted entirely of asset backed securities that were not due at a single maturity date.
    At March 31, 2025, the Company had U.S. government agencies mortgage-backed fixed maturity securities, with a carrying value of approximately $68.1 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 March 31, 2025, the Company had assets with fair values of approximately $32.7 million pledged as collateral for the performance obligations under reinsurance agreements. In accordance with the terms of the trust agreements, the Company retains all rights regarding these securities, of which $28.2 million are residential mortgage-backed securities, $2.3 million of cash and cash equivalents and other assets and $2.2 million of short-term investments.
    8

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    SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES
    NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
    2.     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 March 31, 2025 and 2024:
    Less than 12 Months12 Months or MoreTotal
    ($ in thousands)Fair ValueGross Unrealized LossesFair ValueGross Unrealized LossesFair ValueGross Unrealized Losses
    March 31, 2025
    Fixed maturity securities, available-for-sale:
    U.S. government securities$5,350 $(2)$2,318 $(68)$7,668 $(70)
    Corporate securities and miscellaneous89,029 (1,179)80,321 (9,667)169,350 (10,846)
    Municipal securities25,337 (473)28,863 (3,661)54,200 (4,134)
    Residential mortgage-backed securities96,088 (984)83,406 (11,357)179,494 (12,341)
    Commercial mortgage-backed securities8,833 (216)12,372 (1,047)21,205 (1,263)
    Other asset-backed securities75,860 (507)25,644 (917)101,504 (1,424)
    Total fixed maturity securities, available-for-sale300,497 (3,361)232,924 (26,717)533,421 (30,078)
    Fixed maturity securities, held-to-maturity:
    Other asset-backed securities37,610 (6)— — 37,610 (6)
    Total fixed maturity securities, held-to-maturity:37,610 (6)— — 37,610 (6)
    Total$338,107 $(3,367)$232,924 $(26,717)$571,031 $(30,084)
    9

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    SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES
    NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
    2.     Investments (continued)
    Less than 12 Months12 Months or MoreTotal
    ($ in thousands)Fair ValueGross Unrealized LossesFair ValueGross Unrealized LossesFair ValueGross Unrealized Losses
    December 31, 2024
    Fixed maturity securities, available-for-sale:
    U.S. government securities$15,938 $(34)$2,297 $(92)$18,235 $(126)
    Corporate securities and miscellaneous136,888 (2,060)81,232 (11,228)218,120 (13,288)
    Municipal securities41,930 (1,046)27,687 (4,320)69,617 (5,366)
    Residential mortgage-backed securities201,407 (3,366)82,496 (13,261)283,903 (16,627)
    Commercial mortgage-backed securities9,411 (126)13,178 (1,317)22,589 (1,443)
    Other asset-backed securities75,119 (721)29,851 (1,113)104,970 (1,834)
    Total fixed maturity securities, available-for-sale480,693 (7,353)236,741 (31,331)717,434 (38,684)
    Fixed maturity securities, held-to-maturity:
    Other asset-backed securities2,144 (2)36,573 (434)38,717 (436)
    Total fixed maturity securities, held-to-maturity:2,144 (2)36,573 (434)38,717 (436)
    Total$482,837 $(7,355)$273,314 $(31,765)$756,151 $(39,120)
    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.
    As of March 31, 2025, the Company had 631 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 March 31, 2025 and determined that no 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.
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    SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES
    NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
    2.     Investments (continued)
    •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 components of net investment gains for the three months ended March 31, 2025 and 2024:
    Three months ended March 31,
    ($ in thousands)20252024
    Gross realized gains
    Fixed maturity securities, available-for sale$453 $499 
    Equity securities1,745 1,081 
    Other4 18 
    Total2,202 1,598 
    Gross realized losses
    Fixed maturity securities, available-for sale(120)(394)
    Equity securities(678)(1,874)
    Other(54)(18)
    Total(852)(2,286)
    Net unrealized gains (losses) on investments
    Equity securities1,080 8,020 
    Mortgage loans(66)971 
    Other4,477 — 
    Net investment gains
    $6,841 $8,303 
    The following table sets forth the proceeds from sales of available-for-sale fixed maturity securities and equity securities for the three months ended March 31, 2025 and 2024:
    Three months ended March 31,
    ($ in thousands)20252024
    Fixed maturity securities, available-for sale$8,195 $12,093 
    Equity securities8,748 10,458 
    11

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    SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES
    NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
    2.     Investments (continued)
    The following table sets forth the components of net investment income for the three months ended March 31, 2025 and 2024:
    Three months ended March 31,
    ($ in thousands)20252024
    Income:
    Fixed maturity securities, available-for sale$17,288 $12,231 
    Fixed maturity securities, held-to-maturity815 1,126 
    Equity securities617 627 
    Equity method investments(1,988)1,098 
    Mortgage loans661 1,419 
    Indirect loans(741)(1,694)
    Short-term investments and cash3,192 4,240 
    Other977 869 
    Total investment income20,821 19,916 
    Investment expenses(1,490)(1,619)
    Net investment income$19,331 $18,297 
    The following table sets forth the change in net unrealized gains (losses) on the Company’s investment portfolio, net of deferred income taxes, included in other comprehensive loss for the three months ended March 31, 2025 and 2024:
    Three months ended March 31,
    ($ in thousands)20252024
    Fixed maturity securities$15,284 $(7,989)
    Deferred income taxes(3,211)1,663 
    Total$12,073 $(6,326)
    12

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    SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES
    NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
    3.    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 and equity securities 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.
    13

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    SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES
    NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
    3.    Fair Value Measurements (continued)
    The following table sets forth the range of the discount rate as of March 31, 2025 and December 31, 2024:
    March 31, 2025December 31, 2024
    High7.98 %8.00 %
    Low5.43 %5.70 %
    Weighted average6.19 %6.60 %
    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 judgement and uncertainty.
    The following table sets forth the range and weighted average, weighted by relative fair value, of the spread as of March 31, 2025 and December 31, 2024:
    March 31, 2025December 31, 2024
    High7.93 %10.00 %
    Low7.59 %7.00 %
    Weighted average7.69 %7.93 %
    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 $32.6 million at March 31, 2025, 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 $24.4 million at March 31, 2025. 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.
    14

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    SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES
    NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
    3.    Fair Value Measurements (continued)
    The following tables set forth the Company’s investments within the fair value hierarchy at March 31, 2025 and December 31, 2024:
    March 31, 2025
    ($ in thousands)Level 1Level 2Level 3Total
    Fixed maturity securities, available-for-sale:
    U.S. government securities$26,682 $— $— $26,682 
    Corporate securities and miscellaneous— 415,528 75,322 490,850 
    Municipal securities— 85,831 — 85,831 
    Residential mortgage-backed securities— 402,397 — 402,397 
    Commercial mortgage-backed securities— 76,191 — 76,191 
    Other asset-backed securities— 307,422 8,135 315,557 
    Total fixed maturity securities, available-for-sale26,682 1,287,369 83,457 1,397,508 
    Fixed maturity securities, held-to-maturity:
    Other asset-backed securities— — 37,610 37,610 
    Total fixed maturity securities, held-to-maturity— — 37,610 37,610 
    Equity securities:
    Common stocks64,215 — — 64,215 
    Preferred stocks— 1,160 — 1,160 
    Mutual funds42,700 — — 42,700 
    Total equity securities106,915 1,160 — 108,075 
    Mortgage loans— — 16,012 16,012 
    Short-term investments308,042 — — 308,042 
    Total$441,639 $1,288,529 $137,079 $1,867,247 


    15

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    SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES
    NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
    3.    Fair Value Measurements (continued)
    December 31, 2024
    ($ in thousands)Level 1Level 2Level 3Total
    Fixed maturity securities, available-for-sale:
    U.S. government securities$26,486 $— $— $26,486 
    Corporate securities and miscellaneous— 354,815 70,813 425,628 
    Municipal securities— 84,716 — 84,716 
    Residential mortgage-backed securities— 393,833 — 393,833 
    Commercial mortgage-backed securities— 69,364 — 69,364 
    Other asset-backed securities— 285,084 7,107 292,191 
    Total fixed maturity securities, available-for-sale26,486 1,187,812 77,920 1,292,218 
    Fixed maturity securities, held-to-maturity:
    Other asset-backed securities— — 38,717 38,717 
    Total fixed maturity securities, held-to-maturity:— — 38,717 38,717 
    Equity securities:
    Common stocks64,251 — — 64,251 
    Preferred stocks— 1,164 — 1,164 
    Mutual funds40,839 — — 40,839 
    Total equity securities105,090 1,164 — 106,254 
    Mortgage loans— — 26,490 26,490 
    Short-term investments274,929 — — 274,929 
    Total$406,505 $1,188,976 $143,127 $1,738,608 
    The following tables set forth the changes in the fair value of instruments carried at fair value with a Level 3 measurement during the three months ended March 31, 2025 and 2024:
    ($ in thousands)Fixed Maturity Securities, Available-For-SaleMortgage 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)
    Purchases5,164 — 
    Sales/Disposals(199)— 
    Total unrealized gains for the period recognized in accumulated comprehensive income (loss)682 — 
    Balance at March 31, 2025$83,457 $16,012 
    Total losses for the period recognized in net investment gains attributable to the change in unrealized gains or losses relating to assets held as of period end$— $(84)
    ($ in thousands)Mortgage Loans
    Balance at December 31, 2023$50,070 
    Total gains for the period recognized in net investment gains971 
    Issuances187 
    Settlements(6,919)
    Balance at March 31, 2024$44,309 
    Total gains 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$952 
    16

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    SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES
    NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
    3.    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 judgements 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 March 31, 2025, the Company determined the fair value of these instruments using the income approach utilizing inputs that are unobservable (Level 3).
    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 March 31, 2025 and December 31, 2024:
    March 31, 2025December 31, 2024
    ($ in thousands)Carrying
    Value
    Fair
    Value
    Carrying
    Value
    Fair
    Value
    Notes payable
    FHLB Loan$57,000 $57,089 $57,000 $56,200 
    Revolving credit facility43,000 43,000 43,000 43,000 
    Notes payable$100,000 $100,089 $100,000 $99,200 
    Subordinated debt
    Unsecured subordinated notes$19,545 $20,370 $19,536 $20,541 
    Subordinated debt, net of debt issuance costs$19,545 $20,370 $19,536 $20,541 
    Other financial instruments qualify as insurance-related products and are specifically exempted from fair value disclosure requirements.
    4.    Mortgage Loans
    The Company has invested in Separately Managed Accounts (“SMA1” and “SMA2”). As of March 31, 2025 and December 31, 2024, the Company held direct investments in mortgage loans from various creditors through SMA1 and SMA2.
    The Company’s mortgage loan portfolios are primarily senior loans on real estate across the U.S. The loans earn interest at a fixed spread above a prime rate, mature in approximately 2 years to 4 years from loan origination and the principal amounts of the loans range between 64% to 65% of the property’s appraised value at the time the loans were made.
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    SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES
    NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
    4.    Mortgage Loans (continued)
    The following table sets forth the carrying value of the Company’s mortgage loans as of March 31, 2025 and December 31, 2024:
    ($ in thousands)March 31, 2025December 31, 2024
    Commercial$8,016 $8,474 
    Retail— 10,032 
    Hospitality7,996 7,984 
    $16,012 $26,490 
    The following table sets forth the Company’s gross investment income for mortgage loans for the three months ended March 31, 2025 and 2024:
    Three months ended March 31,
    ($ in thousands)20252024
    Commercial$108 $458 
    Retail304 490 
    Hospitality249 471 
    $661 $1,419 
    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 months ended March 31, 2025 and 2024, respectively.
    As of March 31, 2025 $4.5 million of mortgage loans were in the process of foreclosure and there were no mortgage loans that were not producing income for the previous 12 months. As of December 31, 2024, no mortgage loans were in the process of foreclosure and there were no mortgage loans that were not producing income for the previous 12 months.
    5.    Equity Method Investments and Other
    The following table sets forth the carrying value and ownership percentage of the Company’s equity method investments as of March 31, 2025 and December 31, 2024:
    ($ in thousands)March 31, 2025December 31, 2024
    Carrying ValueOwnership %Carrying ValueOwnership %
    Arena Special Opportunities Fund, LP units$32,364 14.9 %$34,936 15.3 %
    JVM Funds LLC units16,692 10.1 %17,229 10.1 %
    Hudson Ventures Fund 2 LP units4,897 2.5 %4,967 2.5 %
    RISCOM2,886 20.0 %5,013 20.0 %
    Brewer Lane Ventures Fund II LP units1,410 2.4 %1,040 2.4 %
    Dowling Capital Partners LP units678 5.0 %666 5.0 %
    Arena SOP LP units218 11.1 %1,474 10.9 %
    $59,145 $65,325 
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    SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES
    NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
    5.    Equity Method Investments and Other (continued)
    The following table sets forth the components of net investment (loss) income from equity method investments for the three months ended March 31, 2025 and 2024:
    Three months ended March 31,
    ($ in thousands)20252024
    Brewer Lane Ventures Fund II LP$170 $(32)
    Dowling Capital Partners LP units13 1,342 
    Hudson Ventures Fund II LP units(25)(52)
    RISCOM(128)286 
    JVM Funds LLC(211)(484)
    Arena Special Opportunities Fund, LP units(551)(251)
    Arena SOP LP units(1,256)289 
    $(1,988)$1,098 
    The following table sets forth the unfunded commitment of equity method investments as of March 31, 2025 and December 31, 2024:
    ($ in thousands)March 31, 2025December 31, 2024
    Brewer Lane Ventures Fund II LP units$3,770 $4,077 
    Dowling Capital Partners LP units386 386 
    Hudson Ventures Fund 2 LP units266 397 
    $4,422 $4,860 
    The difference between the cost of an investment and its proportionate share of the underlying equity in net assets is allocated to the various assets and liabilities of the equity method investment. The Company amortizes the difference in net assets over the same useful life of a similar asset as the underlying equity method investment. For investment in RISCOM, a similar asset would be agent relationships. The Company amortizes this difference over a 15-year useful life.
    The following table sets forth the Company’s recorded investment in RISCOM compared to its share of underlying equity as of March 31, 2025 and December 31, 2024:
    ($ in thousands)March 31, 2025December 31, 2024
    Investment in RISCOM:
    Underlying equity$1,689 $3,756 
    Difference1,197 1,258 
    Recorded investment balance$2,886 $5,013 
    The following table sets forth the Company’s recorded investment in JVM Funds LLC compared to its share of underlying equity as of March 31, 2025 and December 31, 2024:
    ($ in thousands)March 31, 2025December 31, 2024
    Investment in JVM Funds LLC:
    Underlying equity$16,125 $16,624 
    Difference567 605 
    Recorded investment balance$16,692 $17,229 
    19

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    SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES
    NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
    5.    Equity Method Investments and Other (continued)
    Investment in Indirect Loans and Loan Collateral
    As of March 31, 2025 and December 31, 2024, the Company held indirect investments in collateralized loans and loan collateral through SMA1 and SMA2.
    The carrying value of the SMA1 and SMA2 as of March 31, 2025 and December 31, 2024 were as follows:
    ($ in thousands)March 31, 2025December 31, 2024
    SMA1$19,093 $20,296 
    SMA210,350 12,973 
    Investment in indirect loans and loan collateral$29,443 $33,269 
    6.     Segment
    The Company has one reportable segment through which it offers a broad array of commercial property and casualty products and solutions on a non-admitted (or E&S) and admitted basis, predominantly in the United States. The 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 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 segment 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, 2024. The CODM assesses performance for the segment and decides how to allocate resources based on gross written premiums by net underwriting division, underwriting income, and income before income taxes that also is reported on the condensed consolidated statements of operations as consolidated income before income taxes. The measure of segment assets is reported on the balance sheet as total consolidated assets.
    Gross written premiums by underwriting division, net underwriting income, and consolidated net income are used to monitor budget versus actual results. The chief operating decision maker also uses net underwriting income, annualized return on equity and growth in book value per share 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 segment and in establishing management’s compensation.
    20

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    SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES
    NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
    6.     Segment (continued)
    The following table presents gross written premiums by underwriting division for the three months ended March 31, 2025 and 2024:
    Three months ended March 31,
    ($ in thousands)20252024
    Accident & Health$63,169 $40,901 
    Agriculture and Credit (Re)insurance87,847 43,321 
    Captives68,401 68,408 
    Construction & Energy Solutions75,571 74,222 
    Global Property46,686 57,312 
    Professional Lines41,166 42,239 
    Programs62,675 52,178 
    Surety37,798 33,842 
    Transactional E&S52,006 46,232 
    Total continuing business535,319 458,655 
    Exited business7 (35)
    Total gross written premiums$535,326 $458,620 

    21

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    SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES
    NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
    6.     Segment (continued)
    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 months ended March 31, 2025 and 2024:
    Three months ended March 31,
    ($ in thousands)20252024
    Underwriting income
    Revenues:
    Net earned premiums$300,366 $236,342 
    Commission and fee income1,976 2,026 
    Total underwriting revenues302,342 238,368 
    Expenses:
    Losses and LAE187,309 143,914 
    Amortization of policy acquisition costs44,490 31,977 
    Other operating and general expenses42,061 37,797 
    Total underwriting expenses273,860 213,688 
    Net underwriting income$28,482 $24,680 
    Reconciliation of net underwriting income to net income:
    Net underwriting income$28,482 $24,680 
    Add:
    Net investment income19,331 18,297 
    Net investment gains6,841 8,303 
    Other income13 — 
    Less:
    Interest expense1,834 2,727 
    Amortization expense337 388 
    Other expenses1,061 1,188 
    Income before income taxes51,435 46,977 
    Income tax expense9,377 10,193 
    Net income$42,058 $36,784 
    The following table presents annualized return on equity for the three months ended March 31, 2025 and 2024 and book value per share as of March 31, 2025 and December 31, 2024:
    Three months ended March 31,
    20252024
    Annualized return on equity20.5 %21.7 %
    March 31, 2025December 31, 2024
    Book value per share$21.06$19.79
    22

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    SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES
    NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
    7.    Income Taxes
    The following table sets forth the Company’s income tax expense and effective tax rates for the three months ended March 31, 2025 and 2024:
    Three months ended March 31,
    ($ in thousands)20252024
    Income tax expense$9,377 $10,193 
    Effective tax rate18.2 %21.7 %
    The effective tax rate will differ from the statutory rate of 21 percent due to permanent differences for disallowed expenses for tax and beneficial adjustments for tax-exempt income, dividends-received deduction, non-deductible expenses and discrete items. The effective tax rate for the three months ended March 31, 2025 was impacted by certain discrete tax items, primarily tax benefits from stock-based compensation, which reduced the effective tax rate by 3.9%.
    8.    Losses and Loss Adjustment Expenses
    The following table sets forth the reconciliation of unpaid losses and loss adjustment expenses (“LAE”) as reported in the condensed consolidated balance sheets as of and for the three months ended March 31, 2025 and 2024:
    Three months ended March 31,
    ($ in thousands)20252024
    Reserves for losses and LAE, beginning of period$1,782,383 $1,314,501 
    Less: reinsurance recoverable on unpaid claims, beginning of period(670,846)(455,484)
    Reserves for losses and LAE, beginning of period, net of reinsurance1,111,537 859,017 
    Incurred, net of reinsurance, related to:
    Current period187,309 144,155 
    Prior years— — 
    Total incurred, net of reinsurance187,309 144,155 
    Paid, net of reinsurance, related to:
    Current period15,256 11,805 
    Prior years118,900 80,516 
    Total paid134,156 92,321 
    Net reserves for losses and LAE, end of period1,164,690 910,851 
    Plus: reinsurance recoverable on unpaid claims, end of period706,801 466,095 
    Reserves for losses and LAE, end of period$1,871,491 $1,376,946 
    23

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    SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES
    NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

    9.    Commission and 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 months ended March 31, 2025 and 2024:
    Three months ended March 31,
    ($ in thousands)20252024
    SUA commission revenue$865 $990 
    SUA fee income1,629 846 
    Other(518)190 
    Total commission and fee income$1,976 $2,026 
    The Company’s contract assets from commission and fee income as of March 31, 2025 and December 31, 2024 were $1.9 million and $1.4 million, respectively.
    10.    Underwriting, Acquisition and Insurance Expenses
    The following table sets forth the components of underwriting, acquisition and insurance expenses for the three months ended March 31, 2025 and 2024:
    Three months ended March 31,
    ($ in thousands)20252024
    Amortization of policy acquisition costs$44,490 $31,977 
    Other operating and general expenses42,061 37,797 
    Total underwriting, acquisition and insurance expenses$86,551 $69,774 
    11.    Reinsurance
    Certain premiums and benefits are assumed from and ceded to other insurance companies under various reinsurance agreements. The reinsurance agreements provide the Company with increased capacity to write larger risks and maintain its exposure to loss within its capital resources. The Company remains obligated for amounts ceded in the event that the reinsurers do not meet their obligations.
    The following tables set forth the effects of reinsurance on written and earned premiums and losses and loss adjustment expenses for the three months ended March 31, 2025 and 2024:
    20252024
    ($ in thousands)WrittenEarnedWrittenEarned
    Direct premiums$408,310 $385,438 $366,796 $327,172 
    Assumed premiums127,016 78,727 91,824 62,186 
    Ceded premiums(192,055)(163,799)(171,520)(153,016)
    Net premiums$343,271 $300,366 $287,100 $236,342 
    Ceded losses and LAE incurred$135,467 $85,619 
    24

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    SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES
    NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
    11.     Reinsurance (continued)
    The following table sets forth the components of reinsurance recoverables and ceded unearned premium as of March 31, 2025 and December 31, 2024:
    ($ in thousands)March 31, 2025December 31, 2024
    Ceded unpaid losses and LAE$706,801 $670,846 
    Ceded paid losses and LAE198,464 166,663 
    Loss portfolio transfer— 22,662 
    Allowance for credit losses(2,295)(2,295)
    Reinsurance recoverables$902,970 $857,876 
    Ceded unearned premium$232,147 $203,901 
    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 March 31, 2025, the market value of these accounts was approximately $212.8 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 March 31, 2025 and December 31, 2024 was $24.7 million and $25.9 million, respectively, and was included in other assets on the condensed consolidated balance sheets.
    12.    Earnings Per Share
    The following table sets forth the compilation of basic and diluted net earnings per share for the three months ended March 31, 2025 and 2024:
    Three months ended March 31,
    ($ in thousands, except for share and per share amounts)20252024
    Numerator
    Net income$42,058 $36,784 
    Denominator
    Basic weighted-average common shares40,196,41639,108,351
    Dilutive effect of stock notes—711,752
    Dilutive effect of stock units1,004,585935,890
    Dilutive effect of options479,594329,143
    Diluted weighted-average common share equivalents41,680,59541,085,136
    Basic earnings per share$1.05 $0.94 
    Diluted earnings per share$1.01 $0.90 
    The following table presents anti-dilutive instruments that were excluded from the calculation of diluted weighted-average common share equivalents during the three months ended March 31, 2025 and 2024:
    Three months ended March 31,
    20252024
    Stock units56,15570,671
    Options2,51248
    25

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    SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES
    NOTES TO (UNAUDITED) CONDENSED CONSOLIDATED FINANCIAL STATEMENTS
    12.    Earnings Per Share (continued)
    The following table presents common share equivalents of contingently issuable instruments that were excluded from basic earnings per share in the three months ended March 31, 2025 and 2024:
    Three months ended March 31,
    20252024
    Common shares—866,428
      Total —866,428
    13.    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 months ended March 31, 2025 and 2024 were as follows:
    Three months ended March 31,
    ($ in thousands)20252024
    Net earned premium$28,960 $25,894 
    Commissions7,632 6,887 
    Premiums receivable as of March 31, 2025 and December 31, 2024 were $18.6 million and $12.6 million, respectively.
    Other
    Advisory and professional services fees and expense reimbursements paid to various affiliated stockholders and directors for the three months ended March 31, 2025 were $0.2 million, compared to $2.0 million for the three months ended March 31, 2024.
    See Note 4 and 5 for investments involving affiliated companies and additional related party transactions.
    14.    Commitments and Contingencies
    Litigation
    The Company is named as a defendant 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.
    26

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    Item 2. Management’s Discussion and Analysis of Financial Condition and Results of Operations
    The term “Skyward Specialty” as used below refers only to Skyward Specialty Insurance Group, Inc. and the terms “our Company,” “we,” “us,” and “our” as used below refer to Skyward Specialty Insurance Group and its consolidated subsidiaries. The term “first quarter” as used below refers to the three months ended March 31 for the time period then ended. We discuss certain key metrics which provide useful information about our business and the operational factors underlying our financial performance. Many of these metrics are generally standard among insurance companies and help to provide comparability with our peers. Select insurance, accounting, operating and financial terms for Skyward Specialty are defined in the sections entitled “Select Insurance and Financial Terms” and “Key Operating and Financial Metrics” included in our 2024 Form 10-K for the year ended December 31, 2024 (the “2024 Form 10-K”).
    The discussion and analysis below include certain forward-looking statements that are subject to risks, uncertainties and other factors described in “Risk Factors” in our 2024 Form 10-K. Our actual results could differ materially from those anticipated in these forward-looking statements as a result of many factors.
    The results of operations for the three months ended March 31, 2025 are not necessarily indicative of the results that may be expected for the full year ended December 31, 2025, or for any other future period. The following discussion should be read in conjunction with the unaudited condensed consolidated financial statements and the notes thereto included in Part I, Item 1 of this Quarterly Report, and in conjunction with our audited consolidated financial statements and the notes thereto included in our 2024 Form 10-K.
    The accompanying condensed consolidated financial statements and related notes have been prepared in accordance with United States (“U.S.”) generally accepted accounting principles (“GAAP”).
    Overview
    Founded in 2006, Skyward Specialty is a specialty insurance holding company incorporated in Delaware. We have one reportable segment through which we offer a broad array of commercial property and casualty products and solutions on a non-admitted (or E&S) and admitted basis, predominantly in the United States. We focus our business on markets that are underserved, dislocated and/or for which standard insurance coverages are insufficient or inadequate to meet the needs of businesses, including our customers and prospective customers operating in these markets. Our customers typically require highly specialized, customized underwriting solutions and claims capabilities. As such, we develop and deliver tailored insurance products and services to address each of the niche markets we serve.
    During the first quarter of 2025, the Company updated its underwriting divisions to align with how management currently oversees the business, allocates resources and evaluates operating performance. The Company added a ninth division, Agriculture and Credit (Re)insurance, which includes the Global Agriculture unit, previously reported with Global Property, and the Mortgage and Credit units, and focuses on specialty classes for which reinsurance provides a more attractive market entry. The Industry Solutions division is now the Construction & Energy Solutions division and the Inland Marine unit is now included in the Transactional E&S division. Programs is now Specialty Programs. Prior reporting periods have been conformed to reflect the new presentation.
    All of our insurance company subsidiaries are group rated and have financial strength ratings of “A” (Excellent) with stable outlook from the A.M. Best Company.
    27

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    Results of Operations
    The following table summarizes our results for the three months ended March 31, 2025 and 2024:
    Three months ended March 31,
    ($ in thousands)20252024
    Gross written premiums$535,326 $458,620 
    Ceded written premiums(192,055)(171,520)
    Net written premiums$343,271 $287,100 
    Net earned premiums$300,366 $236,342 
    Commission and fee income1,976 2,026 
    Losses and LAE187,309 143,914 
    Underwriting, acquisition and insurance expenses86,551 69,774 
    Underwriting income(1)
    $28,482 $24,680 
    Net investment income$19,331 $18,297 
    Net investment gains$6,841 $8,303 
    Income before income taxes$51,435 $46,977 
    Net income$42,058 $36,784 
    Adjusted operating income(1)
    $37,321 $31,024 
    Loss and LAE ratio62.4 %60.9 %
    Expense ratio28.1 %28.7 %
    Combined ratio90.5 %89.6 %
    Annualized return on equity20.5 %21.7 %
    Annualized return on tangible equity(1)
    22.9 %25.0 %
    Annualized adjusted return on equity(1)
    18.2 %18.3 %
    Annualized adjusted return on tangible equity(1)
    20.3 %21.1 %
    (1) See “Reconciliation of Non-GAAP Financial Measures” in this Item 2
    Reconciliation of Non-GAAP Financial Measures
    Adjusted Operating Income
    The following table provides a reconciliation of adjusted operating income to net income for the three months ended March 31, 2025 and 2024:
    Three months ended March 31,
    20252024
    ($ in thousands)Pre-taxAfter-taxPre-taxAfter-tax
    Income as reported$51,435 $42,058 $46,977 $36,784 
    Less (add):
    Net investment gains6,841 5,594 8,303 6,501 
    Net impact of LPT— — 241 189 
    Other income13 11 — — 
    Other expenses(1,061)(868)(1,188)(930)
    Adjusted operating income$45,642 $37,321 $39,621 $31,024 
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    Underwriting Income
    The following table provides a reconciliation of underwriting income to income before federal income tax expense for the three months ended March 31, 2025 and 2024:
    Three months ended March 31,
    ($ in thousands)20252024
    Income before income taxes$51,435$46,977
    Add:
    Interest expense1,8342,727 
    Amortization expense337388
    Other expenses1,0611,188
    Less:  
    Net investment income19,33118,297
    Net investment gains6,8418,303
    Other income13—
    Underwriting income$28,482$24,680
    Tangible Stockholders’ Equity
    The following table provides a reconciliation of tangible stockholders’ equity to stockholders’ equity for the periods ended March 31, 2025 and 2024:
    Three months ended March 31,
    ($ in thousands)20252024
    Stockholders’ equity$850,721$692,272
    Less: Goodwill and intangible assets87,08988,137
    Tangible stockholders’ equity$763,632$604,135
    Annualized Adjusted Return on Equity
    The following table provides a reconciliation of annualized adjusted return on equity to annualized return on equity for the three months ended March 31, 2025 and 2024:
    Three months ended March 31,
    ($ in thousands)20252024
    Numerator: annualized adjusted operating income$149,284 $123,896 
    Denominator: average stockholders’ equity$822,360 $676,652 
    Annualized adjusted return on equity
    18.2 %18.3 %
    Annualized Return on Tangible Equity
    Annualized return on tangible equity for the three months ended March 31, 2025 and 2024 reconciles to annualized return on equity as follows:
    Three months ended March 31,
    ($ in thousands)20252024
    Numerator: annualized net income$168,232 $147,136 
    Denominator: average tangible stockholders’ equity$735,142 $588,366 
    Annualized return on tangible equity
    22.9 %25.0 %
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    Annualized Adjusted Return on Tangible Equity
    Annualized adjusted return on tangible equity for the three months ended March 31, 2025 and 2024 reconciles to annualized return on equity as follows:
    Three months ended March 31,
    ($ in thousands)20252024
    Numerator: annualized adjusted operating income$149,284 $123,896 
    Denominator: average tangible stockholders’ equity$735,142 $588,366 
    Annualized adjusted return on tangible equity
    20.3 %21.1 %
    Underwriting Results
    Premiums
    The following tables present gross written premiums by underwriting division for the three months ended March 31, 2025 and 2024:
    Three months ended March 31,
    ($ in thousands)20252024Change% Change
    Accident & Health$63,169 $40,901 $22,268 54.4 %
    Agriculture and Credit (Re)insurance87,847 43,321 44,526 102.8 %
    Captives68,401 68,408 (7)— %
    Construction & Energy Solutions75,571 74,222 1,349 1.8 %
    Global Property46,686 57,312 (10,626)(18.5 %)
    Professional Lines41,166 42,239 (1,073)(2.5 %)
    Specialty Programs62,675 52,178 10,497 20.1 %
    Surety37,798 33,842 3,956 11.7 %
    Transactional E&S52,006 46,232 5,774 12.5 %
    Total gross written premiums(1)
    $535,319 $458,655 $76,664 16.7 %
    (1) Excludes exited business
    The increase in gross written premiums for the first quarter of 2025, when compared to the same 2024 period, was driven by double-digit premium growth primarily from the agriculture and credit (re)insurance, accident & health and specialty programs divisions, partially offset by a decrease in gross written premiums in the global property division.
    Net written premiums for the first quarter of 2025 were $343.3 million, an increase of $56.2 million or 19.6%, when compared to $287.1 million for the same 2024 period. The increase in net written premiums was primarily driven by the same reasons that drove the increases in gross written premiums discussed above.
    Net earned premiums for the first quarter of 2025 were $300.4 million, an increase of $64.1 million or 27.1% when compared to $236.3 million for the same 2024 period. The increase in net earned premiums was primarily driven by the same reasons that drove the increases in gross written premiums discussed above.
    For additional information regarding our reinsurance programs, see the “Reinsurance” discussion included in this Item 2.
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    Losses and LAE
    The following tables set forth the components of the loss and LAE ratios and adjusted loss and LAE ratios for the three months ended March 31, 2025 and 2024:
    Three months ended March 31,
    20252024
    ($ in thousands)
    Losses
    and LAE
    % of
    Net Earned
    Premiums
    Losses
    and LAE
    % of
    Net Earned
    Premiums
    Losses and LAE:
    Non-cat loss and LAE
    $180,809 60.2 %$143,155 60.6 %
    Cat loss and LAE(1)
    6,500 2.2 %1,000 0.4 %
    Prior accident year development - LPT
    — — %(241)(0.1)%
    Total losses and LAE$187,309 62.4 %$143,914 60.9 %
    (1) Current accident year
    The loss ratio for the first quarter of 2025 increased 1.5 points when compared to the same 2024 period, due to higher catastrophe losses, primarily from convective storms in the Midwest and the California wildfires. The improvement in the non-catastrophe loss and LAE ratio for the first quarter of 2025 when compared to the same 2024 period, was driven by the business mix shift.
    Expense Ratio
    The following tables set forth the components of the expense ratios for the three months ended March 31, 2025 and 2024:
    Three months ended March 31,
    20252024
    ($ in thousands)Expenses% of
    Net Earned Premiums
    Expenses% of
    Net Earned Premiums
    Net policy acquisition expenses $44,490 14.8 %$31,977 13.6 %
    Other operating and general expenses 42,061 14.0 %37,797 16.0 %
    Underwriting, acquisition and insurance expenses 86,551 28.8 %69,774 29.6 %
    Less: commission and fee income (1,976)(0.7 %)(2,026)(0.9 %)
    Total net expenses $84,575 28.1 %$67,748 28.7 %
    The expense ratio for the first quarter improved 0.6 points when compared to the same 2024 period primarily due to earnings leverage partially offset by higher acquisition costs due to the business mix shift.
    The expense ratios for the first quarters of 2025 and 2024 exclude the impact of IPO related stock compensation and secondary offering expenses, which are reported in other expenses in our condensed consolidated statements of operations and comprehensive income.
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    Investment Results
    The following table sets forth the components of net investment income and net investment gains (losses) for the three months ended March 31, 2025 and 2024:
    Three months ended March 31,
    $ in thousands20252024
    Short-term investments & cash and cash equivalents $4,041 $5,088 
    Fixed income16,73012,478
    Equities657627
    Alternative and strategic investments(2,097)104
    Net investment income$19,331 $18,297 
    Net unrealized gains on securities still held
    $5,491$8,991
    Net realized gains (losses)1,350(688)
    Net investment gains$6,841 $8,303 
    Net investment income for the first quarter of 2025 increased $1.0 million when compared to the same 2024 period.
    The increase in income from our fixed income portfolio for the first quarter of 2025, when compared to the same 2024 period, was due to (i) a larger asset base as we continued to increase our allocation to this part of our investment portfolio and (ii) a higher book yield of 5.2% at March 31, 2025 compared to 4.7% at March 31, 2024. The decrease in income from short-term investments for the first quarter of 2025 when compared to the same 2024 period, was due to a lower book yield. The losses from alternative and strategic investments for the first quarter of 2025 was driven by the decline in the fair value of limited partnership investments.
    When a fixed maturity has been determined to have an impairment, the impairment charge is separated into an amount representing the credit loss, which is recognized in earnings as a realized loss and on the balance sheet as an allowance for credit losses netted with the amortized cost of fixed maturities. Future increases in fair value, if related to credit factors, are recognized through earnings limited to the amount previously recognized as an allowance for credit losses. The amount related to non-credit factors is recognized in accumulated other comprehensive income and future increases or decreases in fair value, if not credit losses, are included in accumulated other comprehensive (loss) income. We reviewed our available-for-sale fixed maturities at March 31, 2025 and determined that no credit impairment existed in the gross unrealized holding losses. See Note 2, “Investments” to our condensed consolidated financial statements included in Item 1 of this Form 10-Q for additional information.
    Investments
    Composition of Investment Portfolio
    The following table sets forth the components of our investment portfolio at carrying value at March 31, 2025 and December 31, 2024:
    20252024
    ($ in thousands)
    Carrying Value
    % of Total
    Carrying Value
    % of Total
    Cash and cash equivalents$112,916 5.4 %$121,603 6.1 %
    Short-term investments308,042 14.6 %274,929 13.8 %
    Fixed income1,413,520 67.1 %1,318,708 66.2 %
    Equities108,075 5.1 %106,254 5.3 %
    Alternative and strategic investments163,753 7.8 %170,929 8.6 %
    Total portfolio$2,106,306 100.0 %$1,992,423 100.0 %
    32

    Table of Contents
    Fixed income
    Our fixed income portfolio primarily consists of investment grade fixed income securities, which are predominantly highly-rated and liquid bonds, and commercial mortgage loans.
    The following table sets forth the components of our fixed income securities at March 31, 2025 and December 31, 2024:
    20252024
    ($ in thousands)Carrying Value
    % of Total
    Carrying Value
    % of Total
    U.S. government securities$26,682 1.9 %$26,486 2.0 %
    Corporate securities and miscellaneous490,850 34.7 %425,628 32.3 %
    Municipal securities85,831 6.1 %84,716 6.4 %
    Residential mortgage-backed securities402,397 28.5 %393,833 29.9 %
    Commercial mortgage-backed securities76,191 5.4 %69,364 5.2 %
    Other asset-backed securities315,557 22.3 %292,191 22.2 %
    Total fixed income portfolio, available-for-sale1,397,508 98.9 %1,292,218 98.0 %
    Commercial mortgage loans$16,012 1.1 %$26,490 2.0 %
    Total fixed income portfolio$1,413,520 100.0 %$1,318,708 100.0 %
    The weighted average credit rating of our available-for-sale fixed income portfolio was “A+” by Standard & Poor’s Financial Services, LLC (“Standard & Poor’s”) at March 31, 2025 and “AA-” at December 31, 2024. The following table sets forth the credit quality of our available-for-sale fixed income portfolio at March 31, 2025 and December 31, 2024, as rated by Standard & Poor’s or equivalent designation:
    20252024
    ($ in thousands)Fair Value% of TotalFair Value% of Total
    AAA$479,479 34.2 %$483,099 37.3 %
    AA158,996 11.4 %141,177 10.9 %
    A480,478 34.4 %429,703 33.3 %
    BBB255,335 18.3 %216,602 16.8 %
    BB and Lower23,220 1.7 %21,637 1.7 %
    Total fixed income portfolio, available-for-sale$1,397,508 100.0 %$1,292,218 100.0 %
    Our commercial mortgage loans are primarily senior loans on real estate across the U.S.
    The average duration of our fixed income portfolio was approximately 4.29 years and 4.34 years, respectively, as of March 31, 2025 and December 31, 2024.
    Equities
    The equities portfolio primarily consists of domestic preferred stocks, common equities, exchange traded funds, limited partnerships, limited liability corporations and other types of equity interests, 100.0% of which are publicly traded.
    Alternative and strategic investments
    Alternative investments consists of promissory notes, limited partnerships, joint ventures and equity interests. The underlying investments are primarily floating rate senior secured loans, comprised of short duration, collateralized, asset-oriented credit investments. The limited partnerships and joint ventures are subject to future increases or decreases in asset value as asset values are monetized and the income is distributed. Strategic investments consists of equity interests in private entities within the insurance industry.
    Other Items
    Income Taxes
    Income tax expense for the three months ended March 31, 2025 was $9.4 million compared to $10.2 million for the same 2024 period. Our effective tax rate for the three months ended March 31, 2025 was 18.2%, compared to 21.7% for the same 2024 period. The effective tax rate for the three months ended March 31, 2025 was impacted by certain discrete tax items, primarily tax benefits from stock-based compensation, which reduced the effective tax rate by 3.9%. For
    33

    Table of Contents
    additional information, see Note 7 of our condensed consolidated financial statements included in Item 1 of this Form 10-Q.
    Liquidity and Capital Resources
    Sources and Uses of Funds
    Our most significant source of cash is from premiums received from our insureds, which, for most policies, we receive at the beginning of the coverage period, net of the related commission amount for the policies. Our most significant cash outflow is for claims that arise when a policyholder incurs an insured loss. Because the payment of claims occurs after the receipt of the premium, often years later, we invest the cash in various investment securities that generally earn interest and dividends. We also use cash to pay for operating expenses such as salaries, rent and taxes and capital expenditures such as technology systems. We use reinsurance to manage the risk that we take on our policies. We cede, or pay out, part of the premiums we receive to our reinsurers and collect cash back when losses subject to our reinsurance coverage are paid.
    The timing of our cash flows from operating activities can vary among periods due to the timing by which payments are made or received. Some of our payments and receipts, including loss settlements and subsequent reinsurance receipts, can be significant, and as a result their timing can influence cash flows from operating activities in any given period. Management believes that cash receipts from premiums and proceeds from investment income are sufficient to cover cash outflows in the foreseeable future.
    Our cash flows for the three months ended March 31, 2025 and 2024:
    ($ in thousands)20252024
    Cash and cash equivalents provided by (used in):
    Operating activities $96,760 $94,265 
    Investing activities (100,779)(69,866)
    Financing activities — (9,466)
    Change in cash and cash equivalents and restricted cash$(4,019)$14,933 
    The increase in cash provided by operating activities in 2025 when compared to 2024 was primarily due to positive cash flow from our insurance operations. Cash from operations can vary from period to period due to the timing of premium receipts, claim payments and reinsurance activity. Cash flows from operations in each of the past two years were used primarily to fund investing activities.
    Net cash used in investing activities in 2025 and 2024 were primarily driven by purchases of fixed maturity securities and short-term investments. Net cash used in financing activities in 2024 was driven by net payments on debt.
    Credit Agreements
    FHLB Loan
    On August 30, 2024, we entered into a loan (the “FHLB Loan”) with the Federal Home Loan Bank of Dallas (the “FHLB”) pursuant to its 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. We used the proceeds to fund the redemption of the March 15, 2024 draw on the Revolving Credit Facility and redeemed $7.0 million of the March 29, 2023 draw on the Revolving Credit Facility (see “Revolving Credit Facility” below for additional information regarding the redemption).
    Revolving Credit Facility
    On March 29, 2023, we entered into an unsecured revolving credit facility (the “Revolving Credit Facility”) with a syndicate of participating banks. The Revolving Credit Facility provides us with up to a $150.0 million revolving credit facility and a letter of credit sub-facility of up to $30.0 million.
    On March 14, 2024, we drew $50.0 million on the Revolving Credit Facility and used the proceeds and existing cash to fund the redemption of the Debentures (see “Debentures” below for additional information regarding the redemption).
    On August 30, 2024, we fully redeemed the March 15, 2024 draw on the Revolving Credit Facility and redeemed $7.0 million of the March 29, 2023 draw on the Revolving Credit Facility. As of March 31, 2025, we had $43.0 million outstanding under the Revolving Credit Facility with another $107.0 million of undrawn capacity.
    34

    Table of Contents
    Interest on the Revolving Credit Facility is payable quarterly. The interest rate on the Revolving Credit Facility is the SOFR plus a margin of between 150 and 190 basis points based on the ratio of debt to total capital and a credit spread adjustment of 10 basis points. At March 31, 2025, the six-month SOFR on the Revolving Credit Facility was 4.22%, plus a margin of 1.60%.
    We are 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 of March 31, 2025, we are in compliance with all covenants.
    Debentures
    In August 2006, we received $58.0 million of proceeds from a debenture offering through a statutory trust, Delos Capital Trust (the “Trust”). The sole asset of the Trust consists of Fixed/Floating Rate Junior Subordinated Deferrable Interest Debentures (the “Trust Preferred”) with a principal amount of $59.8 million issued by us and cash of $1.8 million from the issuance of Trust common shares purchased by us equal to 3% of the Trust capitalization. On March 15, 2024, the Company redeemed the Debentures and paid $1.4 million of accrued interest.
    Subordinated Debt
    In May 2019, we issued unsecured subordinated notes (the “Notes”) with an aggregate principal amount of $20.0 million. Interest on the subordinated notes is 7.25% fixed for the first eight years and 8.25% fixed thereafter. Early retirement of the debt ahead of the eight-year commitment requires all interest payments to be paid in full, as well as the return of all capital. Principal payment is due at maturity on May 24, 2039 and interest is payable quarterly.
    At March 31, 2025 the ratio of total debt outstanding, including the FHLB Loan, the Revolving Credit Facility and the Notes, to total capitalization (defined as total debt plus stockholders’ equity) was 12.3% and at December 31, 2024, the ratio of total debt outstanding, including the Term Loan, the Revolver, the Trust Preferred and the Notes, to total capitalization was 13.1%.
    Share Repurchase Program
    In October 2024, the Board of Directors approved a share repurchase program authorizing the repurchase of up to $50.0 million of our common stock. 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 us in our discretion. The share repurchase program does not require us to repurchase any specific number of shares, and may be modified, suspended or terminated at any time. As of March 31, 2025, no shares had been repurchased under this plan.
    Reinsurance
    We strategically purchase reinsurance from third parties which enhances our business by protecting capital from severity events (either large single event losses or catastrophes) and reducing volatility in our earnings. Our reinsurance contracts are predominantly one year in length and renew annually throughout the year, primarily in January and April. At each annual renewal, we consider several factors that influence any changes to our reinsurance purchases, including any plans to change the underlying insurance coverage we offer, updated loss activity, the level of our capital and surplus, changes in our risk appetite and the cost and availability of reinsurance treaties.
    We purchase quota share reinsurance, excess of loss reinsurance, and facultative reinsurance coverage to limit our exposure from losses on any one occurrence. The mix of reinsurance purchased considers efficiency, cost, our risk appetite and specific factors of the underlying risks we underwrite.
    •Quota share reinsurance refers to a reinsurance contract whereby the reinsurer agrees to assume a specified percentage of the ceding company’s losses arising out of a defined class of business in exchange for a corresponding percentage of premiums, net of a ceding commission.
    •Excess of loss reinsurance refers to a reinsurance contract whereby the reinsurer agrees to assume all or a portion of the ceding company’s losses for an individual claim or an event in excess of a specified amount in exchange for a premium payable amount negotiated between the parties, which includes our catastrophe reinsurance program.
    •Facultative coverage refers to a reinsurance contract on individual risks as opposed to a group or class of business. It is used for a variety of reasons, including supplementing the limits provided by the treaty coverage or covering risks or perils excluded from treaty reinsurance.
    For the three months ended March 31, 2025 our net retention on a written basis (calculated as net written premiums as a percentage of gross written premiums) was 64.1%, compared to 62.6% for the same 2024 period.
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    Table of Contents
    The following is a summary of our reinsurance programs as of March 31, 2025:
    Line of BusinessMaximum Company Retention
    Accident & Health$0.90 million per occurrence
    Commercial Auto(1)
    $1.00 million per occurrence
    Excess Casualty(1)(2)
    $1.69 million per occurrence
    General Liability(1)
    $1.68 million per occurrence
    Ocean Marine(2)
    $2.50 million per occurrence
    Professional Lines(2)
    $5.19 million per occurrence
    Property(3)
    $4.00 million per occurrence
    Representation and Warranty$5.00 million per occurrence
    Surety(2)
    $4.00 million per occurrence
    Workers’ Compensation(2)
    $2.33 million per occurrence
    (1) Legal defense expenses can force exposure above the maximum company retention for Excess Casualty, Commercial Auto and General Liability.
    (2) Reinsurance is subject to a loss ratio cap or aggregate level of loss cover that exceeds a modeled 1:250-year PML event.
    (3) Catastrophe loss protection is purchased up to $36.0 million in excess of $12.0 million retention, which provides cover for a 1:250-year PML event.
    Credit and Financial Strength Ratings
    On August 1, 2024, A.M. Best upgraded Skyward Specialty’s financial strength rating to A (Excellent) from A- (Excellent) and revised the outlook to stable from positive.
    Item 3. Quantitative and Qualitative Disclosures About Market Risk
    There have been no material changes in market risk from the information provided in our Annual Report on Form 10-K for the year ended December 31, 2024.
    Item 4. Controls and Procedures
    Evaluation of Disclosure Controls and Procedures
    We maintain disclosure controls and procedures that are designed to ensure that information required to be disclosed in the reports we file under the Securities Exchange Act of 1934, as amended (the “Exchange Act”), is recorded, processed, summarized and reported within the time periods specified in the SEC’s rules and forms, and that such information is accumulated and communicated to our management, including our Chief Executive Officer (“CEO”) and Chief Financial Officer (“CFO”), as appropriate, to allow timely decisions regarding required financial disclosure.
    As previously disclosed within Item 9A. Controls and Procedures of our 2024 Form 10-K, management concluded that a material weakness existed related to the ineffective implementation of information technology general controls (“ITGCs”) in the area of user access for systems that support the Company’s financial reporting processes as well as the related process-level IT dependent manual and automated controls that rely upon the affected ITGCs, or information coming from IT systems with affected ITGCs. As part of our efforts to remediate the material weakness, new controls and procedures have been designed and are in process of being implemented as previously disclosed within Item 9A. Controls and Procedures of our 2024 Form 10-K. Therefore, our CEO and CFO concluded that, as of March 31, 2025, our disclosure controls and procedures were not effective. Despite the foregoing, our CEO and CFO have certified that, based on their knowledge, the financial statements, and other financial information included in this Form 10-Q, fairly present in all material respects our financial condition, results of operations and cash flows as of, and for, the periods presented in this Form 10-Q.
    Status of Remediation Activities
    With the oversight of the Audit Committee, our management has implemented, and is in process of implementing, additional measures to improve our internal control over ITGCs to remediate the material weakness identified above, including (i) conducting a thorough review of existing ITGCs to identify areas of weakness, (ii) enhancing access controls, (iii) strengthening system access procedures and (iv) providing regular training and awareness programs for employees to ensure they understand ITGC policies and procedures and adhere to best practices for maintaining data integrity and security. We are committed to continuing to improve our ITGCs.
    We cannot assure you that the measures we have taken to date, and are continuing to implement, will be sufficient to remediate the identified material weakness, or to avoid potential future material weaknesses or significant deficiencies. While we believe our efforts have improved our internal control over ITGCs, remediation of the material weakness will require further validation and testing of the design and operating effectiveness of internal controls over a sustained period
    36

    Table of Contents
    of financial reporting cycles. We have invested, and expect to continue to invest, significant resources to improve our ITGCs.
    Changes in Internal Control over Financial Reporting
    Except for the ongoing remediation efforts relating to the material weaknesses identified above, there has been no change in our internal control over financial reporting identified in connection with the evaluation required by Rule 13a-15(d) and 15d-15(d) of the Exchange Act that occurred during the year ended March 31, 2025 that have materially affected, or are reasonably likely to materially affect, our internal control over financial reporting.
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    Table of Contents
    PART II - OTHER INFORMATION
    Item 1. Legal Proceedings
    We are party to legal proceedings which arise in the ordinary course of business. We believe that the outcome of such matters, individually and in the aggregate, will not have a material adverse effect on our consolidated financial position.
    Item 1A. Risk Factors
    In addition to the other information set forth in this Quarterly Report on Form 10-Q, you should carefully consider the risks and uncertainties described under the heading “Risk Factors” in Part I, Item 1A of our Annual Report on Form 10-K for the year ended December 31, 2024 (our “2024 Form 10-K”), as supplemented by the below risk factor update. The below risk factor updates the risk factor captioned “Security breaches, loss of data, cyberattacks, and other information technology failures could disrupt our operations, damage our reputation, and adversely affect our business, operations, and financial results.” in our 2024 Form 10-K. There have been no other material changes in our risk factors in the quarter ended March 31, 2025 from those disclosed in our 2024 Form 10-K.
    Security breaches, loss of data, cyberattacks, and other information technology failures could disrupt our operations, damage our reputation, and adversely affect our business, operations, and financial results.
    Our business is highly dependent upon our information technology and telecommunications systems, including our underwriting and claims systems. We rely on these systems to interact with brokers and insureds, to underwrite business, to prepare policies and process premiums, to perform actuarial and other modeling functions, to process claims and make claims payments, and to prepare internal and external financial statements. Some of these systems may include or rely on third-party systems not located on our premises or under our control. Events such as natural catastrophes, terrorist attacks, industrial accidents, computer viruses and other cyber-attacks may cause our systems to fail or be inaccessible for extended periods of time. While we have implemented business contingency plans and other reasonable plans to protect our systems, whether housed internally or through third-party cloud services, sustained or repeated system failures or service denials could severely limit our ability to write and process new and renewal business, provide customer service, pay claims in a timely manner or otherwise operate in the ordinary course of business.
    Computer viruses, hackers, employee misconduct, and other external hazards could expose our systems to security breaches, cyber-attacks or other disruptions. While we have implemented security measures designed to protect against breaches of security and other interference with our systems and networks, our systems and networks may be subject to breaches or interference and we, and our third-party service providers, will likely continue to experience cybersecurity incidents of varying degrees. For instance, we recently experienced a data incident in which attackers acquired certain of our data. We currently believe the breach is immaterial in nature, but we are continuing to investigate. At this time, there is no evidence that a nation-state actor or global hacker was involved or that there has been any misuse of this information. In the event that our investigation results in more significant exposure than we currently believe, our business may be adversely impacted. Any such event may result in operational disruptions as well as unauthorized access to, the disclosure of, or loss of our proprietary information or our customers’ data and information, which in turn may result in legal claims, regulatory scrutiny and liability, reputational damage, the incurrence of costs to eliminate or mitigate further exposure, the loss of customers or affiliated advisors, or other damage to our business. In addition, SEC and state law requirements regarding general public notification of such incidents could exacerbate the harm to our business, financial condition and results of operations. Even if we successfully protect our technology infrastructure and the confidentiality of sensitive data, we could suffer harm to our business and reputation if attempted security breaches are publicized. We cannot be certain that advances in criminal capabilities, discovery of new vulnerabilities, attempts to exploit vulnerabilities in our systems, data thefts, physical system or network break-ins or inappropriate access, or other developments will not compromise or breach the technology or other security measures protecting the networks and systems used in connection with our business.
    Third parties to whom we outsource certain of our functions are also subject to these risks. While we review and assess our third-party providers’ cybersecurity controls, as appropriate, and make changes to our business processes to manage these risks, we cannot ensure that our attempts to keep systems from being compromised and confidential information from being disclosed will always be successful. Moreover, our increased use of third-party services (e.g. cloud technology and software as a service) can make it more difficult to identify and respond to cyberattacks in any of the above situations due to the dynamic nature of these technologies. These risks could increase as vendors adopt and use more cloud-based software services rather than software services which can be run within our data centers.
    Item 2. Unregistered Sales of Equity Securities and Use of Proceeds
    None.
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    Table of Contents
    Item 3. Defaults Upon Senior Securities
    None.
    Item 4. Mine Safety Disclosures
    None.
    39

    Table of Contents
    Item 5. Other Information
    During the quarter ended March 31, 2025, certain of our executives entered into or amended existing written plans during an open insider trading window for the purchase or sale of our securities that are intended to satisfy the affirmative defense of Rule 10b5-1(c) under the Exchange Act and our policies regarding transactions in our securities.
    On March 6, 2025, Andrew Robinson, Chief Executive Officer, modified his Rule 10b5-1 Trading Arrangement, originally adopted on September 10, 2024, to change the start date of the second tranche from May 9, 2025 to June 6, 2025. The modified plan provides for the sale of up to an aggregate of 36,271 shares of our common stock that remain available for sell.
    On March 12, 2025, Mark Haushill entered into a new Rule 10b5-1 Trading Arrangement. The material terms of these trading plans are set forth in the table below.
    Disclosure Events
    Name (Title)
    Date of AdoptionNature of Trading ArrangementDuration of Trading ArrangementAggregate Number of Securities
    1
    Andrew Robinson (Chief Executive Officer)
    September 10, 2024; Amended second order of plan on March 6, 2025Rule 10b5-1(c) Trading Arrangement
    1/2/2025 – 6/30/2025
    Up to 60,358 shares
    2
    Mark Haushill (Chief Financial Officer)
    March 12, 2025Rule 10b5-1(c) Trading Arrangement
    6/13/2025 – 3/31/2026
    Up to 75,000 shares
    Item 6. Exhibits
    (a)Exhibits.
    Exhibit NumberExhibit Description
    3.1
    Amended and Restated Certificate of Incorporation (incorporated by reference to Exhibit 3.1 to the Company’s Current Report on Form 8-K filed with the Commission on January 18, 2023).
    3.2
    Amended and Restated Bylaws (incorporated by reference to Exhibit 3.2 to the Company’s Current Report on Form 8-K filed with the Commission on January 18, 2023).
    4.1
    Amended and Restated Stockholders’ Agreement, by and among the Company and the stockholders listed therein (incorporated by reference to Exhibit 4.1 to the Company’s Registration Statement on Form S-1, filed with the SEC on November 14, 2022).
    31.1
    Certification of Principal Executive Officer pursuant to Rule 13a-14(a) or Rule 15d-14(a) of the Securities Exchange Act of 1934, as adopted pursuant to Section 302 of the Sarbanes-Oxley Act of 2002.
    31.2
    Certification of Principal Financial and Accounting Officer pursuant to Rule 13a-14(a) or Rule 15d-14(a) of the Securities Exchange Act of 1934, as adopted pursuant to Section 302 of the Sarbanes-Oxley Act of 2002.
    32.1
    Certification of Principal Executive Officer pursuant to 18 U.S.C. Section 1350, as adopted pursuant to Section 906 of the Sarbanes-Oxley Act of 2002.
    101.INSInline XBRL Instance Document - the instance document does not appear in the Interactive Data File because XBRL tags are embedded within the Inline XBRL document.
    101.SCHInline XBRL Taxonomy Extension Schema with Embedded Linkbase Documents
    104Cover Page Interactive Data File (embedded within the Inline XBRL document)

    (b)Financial Statement Schedules. All financial statement schedules are omitted because the information called for is not required or is shown either in the consolidated financial statements or in the notes thereto.
    40

    Table of Contents
    SIGNATURES
    Pursuant to the requirements of Section 13 or 15(d) of the Securities Exchange Act of 1934, the registrant has duly caused this report to be signed on its behalf by the undersigned, thereunto duly authorized.
    Skyward Specialty Insurance Group, Inc.
    Date: May 7, 2025
    By:/s/ Andrew Robinson
    Andrew Robinson
    Chairman and Chief Executive Officer
    (Principal Executive Officer)
    Date: May 7, 2025
    By:/s/ Mark Haushill
    Mark Haushill
    Chief Financial Officer
    (Principal Financial and Accounting Officer)
    41
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    • Skyward Specialty Insurance Group downgraded by Wolfe Research

      Wolfe Research downgraded Skyward Specialty Insurance Group from Outperform to Peer Perform

      2/28/25 7:29:43 AM ET
      $SKWD
      Property-Casualty Insurers
      Finance

    $SKWD
    Insider Purchases

    Insider purchases reveal critical bullish sentiment about the company from key stakeholders. See them live in this feed.

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    • Kuczinski Anthony J bought $14,468 worth of shares (400 units at $36.17), increasing direct ownership by 11% to 4,124 units (SEC Form 4)

      4 - Skyward Specialty Insurance Group, Inc. (0001519449) (Issuer)

      3/5/24 4:23:01 PM ET
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      Property-Casualty Insurers
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    $SKWD
    Large Ownership Changes

    This live feed shows all institutional transactions in real time.

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    • SEC Form SC 13G filed by Skyward Specialty Insurance Group Inc.

      SC 13G - Skyward Specialty Insurance Group, Inc. (0001519449) (Subject)

      11/13/24 11:08:40 AM ET
      $SKWD
      Property-Casualty Insurers
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    • Amendment: SEC Form SC 13G/A filed by Skyward Specialty Insurance Group Inc.

      SC 13G/A - Skyward Specialty Insurance Group, Inc. (0001519449) (Subject)

      11/12/24 5:59:53 PM ET
      $SKWD
      Property-Casualty Insurers
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    • SEC Form SC 13G filed by Skyward Specialty Insurance Group Inc.

      SC 13G - Skyward Specialty Insurance Group, Inc. (0001519449) (Subject)

      11/12/24 3:29:14 PM ET
      $SKWD
      Property-Casualty Insurers
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    Financials

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    • Skyward Specialty Announces Time Change for First Quarter Earnings Call on Friday, May 2, 2025

      HOUSTON, April 28, 2025 (GLOBE NEWSWIRE) -- Skyward Specialty Insurance Group, Inc.™ (NASDAQ:SKWD) ("Skyward Specialty" or "the Company") today announced a time change of its previously announced first quarter earnings call. The conference call and webcast will be held on Friday, May 2 at 9:30 a.m. EDT. Skyward Specialty will issue its first quarter 2025 earnings results after the market closes on Thursday, May 1. The earnings results will be available on the Company website at investors.skywardinsurance.com/ under Quarterly Results. Investors may access the live audio webcast via the link on the Company's investor site at investors.skywardinsurance.com/ under Events & Presentations. Add

      4/28/25 4:01:20 PM ET
      $SKWD
      Property-Casualty Insurers
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    • Skyward Specialty to Host First Quarter 2025 Earnings Call Friday, MAY 2, 2025

      HOUSTON, April 10, 2025 (GLOBE NEWSWIRE) -- Skyward Specialty Insurance Group, Inc.™ (NASDAQ:SKWD) ("Skyward Specialty" or "the Company") expects to issue its first quarter 2025 earnings results after the market closes on Thursday, May 1 which will be available on the Company website at investors.skywardinsurance.com/ under Quarterly Results. Skyward Specialty will host its earnings call to review the first quarter 2025 financial results on Friday, May 2 at 9:00 a.m. EST. Investors may access the live audio webcast via the link on the Company's investor site at investors.skywardinsurance.com/ under Events & Presentations. Additionally, investors can access the earnings call via conferenc

      4/10/25 4:00:00 PM ET
      $SKWD
      Property-Casualty Insurers
      Finance
    • Skyward Specialty to Host Fourth Quarter 2024 Earnings Call Wednesday, February 26, 2025

      HOUSTON, Feb. 03, 2025 (GLOBE NEWSWIRE) -- Skyward Specialty Insurance Group, Inc.™ (NASDAQ:SKWD) ("Skyward Specialty" or "the Company") expects to issue its fourth quarter 2024 earnings results after the market closes on Tuesday, February 25th which will be available on the Company website at investors.skywardinsurance.com/ under Quarterly Results. Skyward Specialty will host its earnings call to review the fourth quarter 2024 financial results on Wednesday, February 26 at 9:30 a.m. EDT. Investors may access the live audio webcast via the link on the Company's investor site at investors.skywardinsurance.com/ under Events & Presentations. Additionally, investors can access the earnings c

      2/3/25 12:00:00 PM ET
      $SKWD
      Property-Casualty Insurers
      Finance

    $SKWD
    Insider Trading

    Insider transactions reveal critical sentiment about the company from key stakeholders. See them live in this feed.

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    SEC Filings

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    • Director Hays James Charles converted options into 2,779 shares, increasing direct ownership by 10% to 30,397 units (SEC Form 4)

      4 - Skyward Specialty Insurance Group, Inc. (0001519449) (Issuer)

      5/9/25 4:05:26 PM ET
      $SKWD
      Property-Casualty Insurers
      Finance
    • Director Kuczinski Anthony J converted options into 2,779 shares, increasing direct ownership by 67% to 6,903 units (SEC Form 4)

      4 - Skyward Specialty Insurance Group, Inc. (0001519449) (Issuer)

      5/9/25 4:05:17 PM ET
      $SKWD
      Property-Casualty Insurers
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    • Director Morrissey Michael J. converted options into 2,779 shares, increasing direct ownership by 376% to 3,519 units (SEC Form 4)

      4 - Skyward Specialty Insurance Group, Inc. (0001519449) (Issuer)

      5/9/25 4:05:20 PM ET
      $SKWD
      Property-Casualty Insurers
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    • SEC Form 144 filed by Skyward Specialty Insurance Group Inc.

      144 - Skyward Specialty Insurance Group, Inc. (0001519449) (Subject)

      5/8/25 5:02:37 PM ET
      $SKWD
      Property-Casualty Insurers
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    • SEC Form 144 filed by Skyward Specialty Insurance Group Inc.

      144 - Skyward Specialty Insurance Group, Inc. (0001519449) (Subject)

      5/8/25 4:50:53 PM ET
      $SKWD
      Property-Casualty Insurers
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    • SEC Form 10-Q filed by Skyward Specialty Insurance Group Inc.

      10-Q - Skyward Specialty Insurance Group, Inc. (0001519449) (Filer)

      5/7/25 3:40:46 PM ET
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      Property-Casualty Insurers
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    Leadership Updates

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    • Skyward Specialty Enters Media Liability With Addition of New Team

      HOUSTON, Jan. 17, 2024 (GLOBE NEWSWIRE) -- Skyward Specialty Insurance Group, Inc.TM (NASDAQ:SKWD) ("Skyward Specialty" or "the Company") a leader in the specialty property and casualty (P&C) market, announced the expansion of its Professional Lines division into the media liability market focusing on multimedia, film and ad agencies. Regina Williams, who joins Skyward Specialty as vice president, Media Liability, will be leading the new underwriting unit. Based in Kansas City, MO, the birthplace of media liability, Ms. Williams is an industry veteran with unparalleled hands-on expertise and knowledge in this sector. Prior to joining Skyward Specialty, Ms. Williams began her career at Med

      1/17/24 8:30:00 AM ET
      $SKWD
      Property-Casualty Insurers
      Finance
    • Skyward Specialty Appoints Global Agriculture Expert James Tran to Spearhead Entry Into Market

      HOUSTON, March 21, 2023 (GLOBE NEWSWIRE) -- Skyward Specialty Insurance Group, Inc.™ (NASDAQ:SKWD) ("Skyward Specialty" or "the Company"), a leader in the specialty property and casualty market, announced today it has entered the global agriculture market. The Company appointed James Tran, a seasoned global agriculture underwriting leader, as Senior Vice President, Global Agriculture, to spearhead its entry into this market. With more than two decades of experience in global agriculture, Tran has held various leadership roles at Tokyo Marine Kiln, XL Catlin, and Catlin Group, most recently serving as the Managing Partner at Jasperian Consulting, Inc. Global Agriculture. Skyward Specialty

      3/21/23 8:30:00 AM ET
      $SKWD
      Property-Casualty Insurers
      Finance
    • Skyward Specialty Launches New Inland Marine Underwriting Unit led by Havis Wright

      HOUSTON, Feb. 16, 2023 (GLOBE NEWSWIRE) -- Skyward Specialty Insurance Group Inc.TM (NASDAQ:SKWD) ("Skyward Specialty" or "the Company"), a leader in the specialty property and casualty market, announces the appointment of Havis Wright to lead the expansion of the Company's industry solutions division with the launch of a new dedicated inland marine underwriting unit. Based in Richmond, VA, Wright will oversee the growth and development of Skyward Specialty's inland marine solutions. Wright brings nearly 20 years of underwriting leadership experience in inland marine and property. He began his career at Hartford Insurance Group and then Travelers. More recently he spent nearly seven years

      2/16/23 8:30:00 AM ET
      $SKWD
      Property-Casualty Insurers
      Finance