Item 9A. Controls and Procedures
Item 9A. Controls and Procedures
Evaluation of Disclosure Controls and Procedures
Our management, with the participation of our principal executive officer and our principal financial officer, evaluated, as of the end of the period covered by this Annual Report on Form 10-K, the effectiveness of our disclosure controls and procedures (as defined in Rules 13a-15(e) and 15d-15(e) under the Securities Exchange Act of 1934, as amended, or the Exchange Act). Based on that evaluation, our principal executive officer and principal financial officer have concluded that as of December 31, 2025, our disclosure controls and procedures were effective at the reasonable assurance level. Management recognizes that any controls and procedures, no matter how well designed and operated, can provide only reasonable assurance of achieving their objectives and our management necessarily applies its judgment in evaluating the cost-benefit relationship of possible controls and procedures.
Management’s Report on Internal Control over Financial Reporting
Our management is responsible for establishing and maintaining adequate internal control over financial reporting as defined in Rules 13a-15(f) and 15d-15(f) under the Securities Exchange Act of 1934, as amended. Our internal control over financial reporting is designed to provide reasonable assurance regarding the reliability of financial reporting and the preparation of financial statements for external purposes in accordance with generally accepted accounting principles in the United States of America. Our internal control over financial reporting includes those policies and procedures that:
(i) Pertain to the maintenance of records that, in reasonable detail, accurately and fairly reflect the transactions and dispositions of our assets;
(ii) Provide reasonable assurance that transactions are recorded as necessary to permit preparation of financial statements in accordance with generally accepted accounting principles, and that our receipts and expenditures are being made only in accordance with authorizations of our management and directors; and
(iii) Provide reasonable assurance regarding prevention or timely detection of unauthorized acquisition, use or disposition of our assets that could have a material effect on the financial statements.
Remediation of Material Weakness in Internal Control Over Financial Reporting
As previously disclosed in the Annual Report on Form 10-K for the fiscal year ended December 31, 2024, management concluded that its internal control over financial reporting was not effective because management identified material weaknesses in internal control over financial reporting. Our management concluded that a material weakness existed as of December 31, 2024 related to the ineffective implementation of information technology general controls (“ITGCs”) in the area of user access for systems that support our financial reporting processes. Further, our related process-level IT dependent manual and automated controls that rely upon the affected ITGCs, or information coming from IT systems with affected ITGCs, were also deemed ineffective.
During the year ended December 31, 2025, management took the following actions to remediate the aforementioned internal control deficiencies:
• enhanced our IT compliance oversight function and expanded our team to include team members with experience designing and implementing ITGC;
• developed a training program addressing ITGCs and policies, including educating control owners about the principles and requirements of each control;
• implemented procedures to develop and maintain documentation of underlying ITGCs to promote knowledge transfer upon IT personnel and function changes;
• implemented an IT management review and testing procedures to monitor ITGCs; and
• provided quarterly reporting on the remediation measures to the Audit Committee of our board of directors.
We believe the measures described above have remediated the material weakness previously identified and we have concluded our internal control over financial reporting was effective at a reasonable assurance level as of December 31, 2025.
Under the supervision and with the participation of our senior management, including our Chief Executive Officer and Chief Financial Officer, we assessed the effectiveness of our internal control over financial reporting as of December 31, 2025. In making this assessment, we used the criteria set forth by the Committee of Sponsoring Organizations of the
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Treadway Commission in the Internal Control — Integrated Framework (2013 Framework). Based on this assessment, management has concluded our internal control over financial reporting was effective as of December 31, 2025.
The effectiveness of our internal control over financial reporting as of December 31, 2025 has been audited by Ernst & Young, LLP, the Company’s independent registered public accounting firm, as stated in their report included herein titled “Report of Independent Registered Public Accounting Firm-Opinion on Internal Control over Financial Reporting.”
Changes in Internal Control over Financial Reporting
Except in connection with the remediation of the material weakness identified in 2024 as discussed 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 December 31, 2025 that have materially affected, or are reasonably likely to materially affect, our internal control over financial reporting.
Limitations on Effectiveness of Controls and Procedures
In designing and evaluating the disclosure controls and procedures, management recognizes that any controls and procedures, no matter how well designed and operated, can provide only reasonable assurance of achieving the desired control objectives. In addition, the design of disclosure controls and procedures must reflect the fact that there are resource constraints and that management is required to apply judgment in evaluating the benefits of possible controls and procedures relative to their costs.
Item 9B. Other Information
During the quarter ended December 31, 2025, none of our directors or officers (as defined in Rule 16a-1(f) of the Securities Exchange Act of 1934) adopted , terminated or modified a Rule 10b5-1 trading arrangement or non-Rule 10b5-1 trading arrangement (as such terms are defined in Item 408 of Regulation S-K).
Item 9C. Disclosure Regarding Foreign Jurisdictions that Prevent Inspections - Not applicable.
PART III
Item 10. Directors, Executive Officers and Corporate Governance
The information required by this Item 10 of Form 10-K will be included in our 2026 Proxy Statement and is incorporated herein by reference.
Item 11. Executive Compensation
The information required by this Item 11 of Form 10-K will be included in our 2026 Proxy Statement and is incorporated herein by reference.
Item 12. Security Ownership of Certain Beneficial Owner and Management and Related Stockholder Matters
The information required by this Item 12 of Form 10-K will be included in our 2026 Proxy Statement and is incorporated herein by reference.
Item 13. Certain Relationships and Related Transactions, and Director Independence
The information required by this Item 13 of Form 10-K will be included in our 2026 Proxy Statement and is incorporated herein by reference.
Item 14. Principal Accounting Fees and Services
Our independent registered public accounting firm is Ernst & Young LLP , Houston, Texas . Auditor Firm ID: 42
The information required by this Item 14 of Form 10-K will be included in our 2026 Proxy Statement and is incorporated herein by reference.
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PART IV
Item 15. Exhibits, Financial Statement Schedules.
(a)(1) LISTING OF FINANCIAL STATEMENTS
The following consolidated financials statements of the Company are filed as part of this Form 10-K and are included in Item 8:
Report of Independent Registered Public Accounting Firm
Consolidated Balance Sheets as of December 31, 2025 and 2024
Consolidated Statements of Operations and Comprehensive Income (loss) for the three years in the periods ended December 31, 2025, 2024 and 2023
Consolidated Statements of Stockholders’ Equity for the three years in the period ended December 31, 2025, 2024 and 2023
Consolidated Statements of Cash Flows for the three years in the period ended December 31, 2025, 2024 and 2023
(a)(2)
Schedule Number Schedule Description Page
I. Summary of Investments — Other Than in Related Parties at December 31, 2025
113
II. Financial Information of Registrant (Parent Company) for the years ended December 31, 2025, 2024 and 2023
114
IV. Supplementary Reinsurance Information for the years ended December 31, 2025, 2024, and 2023
118
V. Valuation and Qualifying Accounts for the years ended December 31, 2025, 2024, and 2023
119
VI. Supplementary Information Concerning Property — Casualty Insurance Operations for the years ended December 31, 2025, 2024, and 2023
120
(a)(3) LISTING OF EXHIBITS
Exhibit
Number Exhibit Description
3.1 Amended and Restated Certificate of Incorporation (incorporated by reference to Exhibit 3.1 to the Company's Current Report on Form 8-K filed with the Commission on January 18, 2023).
3.2 Amended and Restated Bylaws (incorporated by reference to Exhibit 3.2 to the Company's Current Report on Form 8-K filed with the Commission on January 18, 2023).
4.1 Amended and Restated Stockholders’ Agreement, dated March 12, 2014, by and among the Company and the stockholders listed therein (incorporated by reference to Exhibit 4.1 to the Company's Registration Statement on Form S-1, filed with the SEC on November 14, 2022).
4.2 Description of Capital Stock (incorporated by reference to Exhibit 4.2 to the Company’s Annual Report on Form 10-K, filed with the SEC on March 28, 2023).
10.1+ Share Purchase and Award Agreement and form of agreements thereunder in use before 2016 (incorporated by reference to Exhibit 10.1 to the Company's Registration Statement on Form S-1, filed with the SEC on November 14, 2022).
10.2+ 2016 Equity Incentive Program and form of award agreements thereunder (incorporated by reference to Exhibit 10.2 to the Company's Registration Statement on Form S-1, filed with the SEC on November 14, 2022).
10.3+ 2020 Long Term Incentive Plan and form of award agreements thereunder (incorporated by reference to Exhibit 10.3 to the Company's Registration Statement on Form S-1, filed with the SEC on November 14, 2022).
10.4+ Skyward Specialty Insurance Group, Inc. 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 10.4 to the Company's Registration Statement on Form S-1, filed with the SEC on November 14, 2022).
10.5+ Skyward Specialty Insurance Group, Inc. 2022 Employee Stock Purchase Plan (incorporated by reference to Exhibit 10.5 to the Company's Registration Statement on Form S-1, filed with the SEC on November 14, 2022).
10.6+ Form of Restricted Stock Units Agreement and form of notice under the Company's 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 99.6 to the Company's Registration Statement on Form S-8, filed with the SEC on January 12, 2023).
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Exhibit
Number Exhibit Description
10.7+ Form of Restricted Stock Agreement under the Company’s 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 99.7 to the Company's Registration Statement on Form S-8, filed with the SEC on January 12, 2023).
10.8+ Form of Nonstatutory Stock Option Agreement and form of notice under the Company's 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 99.8 to the Company's Registration Statement on Form S-8, filed with the SEC on January 12, 2023).
10.9+ Form of Incentive Stock Option Agreement and form of notice under the Company's 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 99.9 to the Company's Registration Statement on Form S-8, filed with the SEC on January 12, 2023).
10.10+ Form of Performance-Based Restricted Stock Units Agreement under the Company’s 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 10.10 to the Company’s Annual Report on Form 10-K, filed with the SEC on March 28, 2023).
10.11+ Performance-Based Restricted Stock Units Agreement under the Company’s 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 10.11 to the Company’s Annual Report on Form 10-K, filed with the SEC on March 28, 2023).
10.12+ Performance Unit Agreement under the Company’s 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 10.12 to the Company’s Annual Report on Form 10-K, filed with the SEC on March 28, 2023).
10.13+ Amended Form of Performance Share (GBVPS) Agreement under the Company’s 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 10.13 to the Company’s Annual Report on Form 10-K, filed with the SEC on April 1, 2024).
10.14+ Amended Form of Performance Share (Executives) Agreement under the Company’s 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 10.14 to the Company’s Annual Report on Form 10-K, filed with the SEC on April 1, 2024).
10.15+ Amended Form of Performance Share (Others) Agreement under the Company’s 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 10.15 to the Company’s Annual Report on Form 10-K, filed with the SEC on April 1, 2024).
10.16+ Amended Form of Performance Cash Units Agreement under the Company’s Long-Term Incentive Plan. (incorporated by reference to Exhibit 10.16 to the Company’s Annual Report on Form 10-K, filed with the SEC on April 1, 2024).
10.17+ Amended Form of the Restricted Stock Unit (Executives) Agreement under the Company’s 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 10.17 to the Company’s Annual Report on Form 10-K, filed with the SEC on April 1, 2024).
10.18+ Amended Form of Restricted Stock Unit (Others) Agreement under the Company’s 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 10.18 to the Company’s Annual Report on Form 10-K, filed with the SEC on April 1, 2024).
10.19+ Amended Form of Long-Term Performance Cash Plan and Award Letter under the Company’s 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 10.19 to the Company’s Annual Report on Form 10-K, filed with the SEC on April 1, 2024).
10.20+ Form of Indemnification Agreement (incorporated by reference to Exhibit 10.6 to the Company's Registration Statement on Form S-1, filed with the SEC on November 14, 2022).
10.21+ Employment Agreement, dated May 22, 2020, by and between the Registrant and Andrew Robinson, with Amendment No. 1 dated January 1, 2022 (incorporated by reference to Exhibit 10.7 to the Company's Registration Statement on Form S-1, filed with the SEC on November 14, 2022).
10.22+ Form of Non-Employee Director Deferred Restricted Stock Unit Agreement and Form of Notice Under the Company’s 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 10.22 to the Company’s Annual Report on Form 10-K, filed with the SEC on March 3, 2025).
10.23 Commutation and Release Agreement by and among R&Q Re (Bermuda) Ltd., Skyward Re, Houston Specialty Insurance Company, Imperium Insurance Company, and Great Midwest Insurance Company, dated January 31, 2025 (incorporated by reference to Exhibit 10.1 to the Company's Current Report on Form 8-K filed with the Commission on February 5, 2025).
10.24 Credit Agreement, dated March 29, 2023, by and among Skyward Specialty Insurance Group, Inc., the lenders from time to time party thereto and Truist Bank, as administrative agent (incorporated by reference to Exhibit 10.1 to the Company's Current Report on Form 8-K filed with the Commission on April 3, 2023).
10.25 First Amendment dated as of February 26, 2024, to that certain Credit Agreement, dated March 29, 2023, by and among Skyward Specialty Inc., the lenders from time to time party thereto and Truist Bank, as administrative agent (incorporated by reference to Exhibit 10.28 to the Company’s Annual Report on Form 10-K, filed with the SEC on April 1, 2024).
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Exhibit
Number Exhibit Description
10.26 Guaranty Agreement, dated March 29, 2023, by and among Skyward Service Company, Skyward Underwriters Agency, Inc., the loan parties identified on the signature pages thereto and Truist Bank. (incorporated by reference to Exhibit 10.2 to the Company's Current Report on Form 8-K filed with the Commission on April 3, 2023).
10.27 Advances and Security Agreement, dated August 1, 2024, by and between Houston Specialty Insurance Company, a wholly owned insurance company subsidiary of the Company and the Federal Home Loan Bank of Dallas (incorporated by reference to Exhibit 10.1 to the Company’s Current Report on Form 8-K filed with the Commission on September 6, 2024).
10.28+ Form of Severance Agreement between the Company and executive officers (other than the CEO) (incorporated by reference to Exhibit 10.30 to the Company’s Annual Report on Form 10-K, filed with the SEC on March 3, 2025).
10.29+ Amendment No. 2 to Employment Agreement between the Registrant and Andrew Robinson dated March 1, 2025 (incorporated by reference to Exhibit 10.31 to the Company’s Annual Report on Form 10-K, filed with the SEC on March 3, 2025).
10.30+ Amended Form of Restricted Stock Unit (Executives) Agreement under the Company’s 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 99.21 to the Company’s Registration Statement on Form S-8, filed with the SEC on March 5, 2025).
10.31+ Amended Form of the Restricted Stock Unit (Others) Agreement under the Company’s 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 99.22 to the Company’s Registration Statement on Form S-8, filed with the SEC on March 5, 2025).
10.32+ Amended Form of Performance Share (Executives) Agreement under the Company’s 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 99.23 to the Company’s Registration Statement on Form S-8, filed with the SEC on March 5, 2025).
10.33+ Amended Form of Performance Share (Others) Agreement under the Company’s 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 99.24 to the Company’s Registration Statement on Form S-8, filed with the SEC on March 5, 2025).
10.34+ Amended Form of Performance Share (GBVPS) (Executives) Agreement under the Company’s 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 99.25 to the Company’s Registration Statement on Form S-8, filed with the SEC on March 5, 2025).
10.35+ Amended Form of Performance Share (GBVPS) (Others) Agreement under the Company’s 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 99.26 to the Company’s Registration Statement on Form S-8, filed with the SEC on March 5, 2025).
10.36+ Amended Form of Long-Term Performance Cash Plan and Award Letter under the Company’s 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 99.27 to the Company’s Registration Statement on Form S-8, filed with the SEC on March 5, 2025).
10.37 Share Purchase Agreement, dated September 2, 2025, by and between Skyward Specialty Insurance Group, Inc. and Apollo institutional shareholders, of Apollo Group Holdings Limited (incorporated by reference to Exhibit 2.1 to the Company’s Current Report on Form 8-K filed with the Commission on September 8, 2025).
10.38 Share Purchase Agreement, dated September 2, 2025, by and between Skyward Specialty Insurance Group, Inc. and Apollo management shareholders, of Apollo Group Holdings Limited (incorporated by reference to Exhibit 2.2 to the Company’s Current Report on Form 8-K filed with the Commission on September 8, 2025).
10.39 Credit Agreement, dated November 13, 2025, by and between Skyward Specialty Insurance Group, Inc. and Barclays Bank PLC, as Administrative Agent, Truist Securities, Inc., Citizens Bank, N.A. and Texas Capital Bank (incorporated by reference to Exhibit 10.1 to the Company's Current Report on Form 8-K filed with the Commission on November 18, 2025).
10.40 Guaranty Agreement, dated November 13, 2025, by and among Skyward Specialty Insurance Group, Inc., Skyward Service Company, Skyward Underwriters Agency, Inc., the loan parties identified on the signature pages thereto and Barclays Bank PLC. Barclays Bank PLC (incorporated by reference to Exhibit 10.2 to the Company's Current Report on Form 8-K filed with the Commission on November 18, 2025).
10.41 Term Loan Credit Agreement, dated December 30, 2025, by and among Skyward Specialty Insurance Group, Inc., and Barclays Bank PLC, as Administrative Agent, Truist Securities, Inc., Citizens Bank, N.A. and Texas Capital Bank (incorporated by reference to Exhibit 10.1 to the Company's Current Report on Form 8-K filed with the Commission on January 6, 2026).
10.42 Guaranty Agreement, dated December 30, 2025, by and among Skyward Specialty Insurance Group, Inc., Skyward Service Company, Skyward Underwriters Agency, Inc., the loan parties identified on the signature pages and Barclays Bank PLC (incorporated by reference to Exhibit 10.2 to the Company's Current Report on Form 8-K filed with the Commission on January 6, 2026).
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Exhibit
Number Exhibit Description
10.43 First Amendment, dated December 30, 2025, by and among Skyward Specialty Insurance Group, Inc., Skyward Service Company, Skyward Underwriters Agency, Inc., the loan parties identified on the signature pages and Barclays Bank PLC (incorporated by reference to Exhibit 10.3 to the Company's Current Report on Form 8-K filed with the Commission on January 6, 2026).
19 Skyward Specialty Insurance Securities Trading Policy (incorporated by reference to Exhibit 19 to the Company ’ s Annual Report on Form 10-K, filed with the SEC on March 3, 2025).
19.1* Skyward Specialty Insurance Securities Trading Policy amended November 5, 2025.
21.1* List of Subsidiaries of the Company
23.1* Consent of Ernst & Young LLP, Independent Registered Public Accounting Firm.
31.1* Certification of Principal Executive Officer pursuant to Rule 13a-14(a) or Rule 15d-14(a) of the Securities Exchange Act of 1934, as adopted pursuant to Section 302 of the Sarbanes-Oxley Act of 2002.
31.2* Certification of Principal Financial and Accounting Officer pursuant to Rule 13a 14(a) or Rule 15d 14(a) of the Securities Exchange Act of 1934, as adopted pursuant to Section 302 of the Sarbanes-Oxley Act of 2002.
32.1* Certification of Principal Executive Officer pursuant to 18 U.S.C. Section 1350, as adopted pursuant to Section 906 of the Sarbanes-Oxley Act of 2002.
97 Policy for Recovery of Erroneously Awarded Incentive Compensation (“Clawback Policy”) (incorporated by reference to Exhibit 97 to the Company’s Annual Report on Form 10-K, filed with the SEC on April 1, 2024).
101.INS Inline XBRL Instance Document – the instance document does not appear in the Interactive Data File because XBRL tags are embedded within the Inline XBRL document.
101.SCH Inline XBRL Taxonomy Extension Schema With Embedded Linkbase Documents
104 Cover Page Interactive Date File (embedded within the Inline XBRL document)
____________________
* Filed herewith.
+ Management contract or compensatory plan or arrangement.
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SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES
SCHEDULE I — SUMMARY OF INVESTMENTS — OTHER THAN IN RELATED PARTIES
($ in thousands) Cost Fair Value (if applicable) Amount on
Balance Sheet
December 31, 2025
Fixed maturity securities, available for sale:
U.S. government securities $ 44,190 $ 44,468 $ 44,468
Corporate securities and miscellaneous 632,244 636,387 636,387
Municipal securities 102,691 102,116 102,116
Residential mortgage-backed securities 487,145 486,587 486,587
Commercial mortgage-backed securities 72,631 73,050 73,050
Other asset-backed securities 509,854 513,695 513,695
Total fixed maturity securities, available for sale 1,848,755 1,856,303 1,856,303
Fixed maturity securities, held to maturity:
Other asset-backed securities 33,290 33,603 32,822
Total fixed maturity securities, held to maturity 33,290 33,603 32,822
Equity securities:
Preferred stocks 1,138 1,174 1,174
Total equity securities 1,138 1,174 1,174
Mortgage loans 10,093 9,902 9,902
Other long-term investments 37,290 58,650 58,650
Short-term investments 264,299 264,299 264,299
Total $ 2,194,865 $ 2,223,931 $ 2,223,150
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SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES
SCHEDULE II — FINANCIAL INFORMATION OF REGISTRANT
BALANCE SHEETS (PARENT COMPANY)
December 31,
($ in thousands) 2025 2024
Assets
Investments:
Investment in subsidiaries $ 1,076,288 $ 853,670
Short-term investments, at fair value 14,513 14,000
Total investments 1,090,801 867,670
Cash and cash equivalents 3,500 2,943
Deferred income taxes 27,865 30,486
Goodwill and intangible assets, net 14,349 12,641
Other assets 10,709 2,905
Total assets $ 1,147,224 $ 916,645
Liabilities and Stockholders’ Equity
Liabilities:
Accounts payable and accrued liabilities $ 17,680 $ 3,110
Notes payable 100,410 100,000
Subordinated debt, net of debt issuance costs 19,569 19,536
Total liabilities 137,659 122,646
Stockholders’ Equity:
Stockholders’ equity 1,009,565 793,999
Total liabilities and stockholders’ equity $ 1,147,224 $ 916,645
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SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES
SCHEDULE II — STATEMENTS OF OPERATIONS
(PARENT COMPANY)
Years Ended December 31,
($ in thousands) 2025 2024 2023
Revenues:
Net investment income $ 3,371 $ 3,212 $ 3,822
Net investment gains (losses) — 963 ( 963 )
Other loss — ( 2 ) ( 27 )
Total revenues 3,371 4,173 2,832
Expenses
Operating expenses 7,899 10,632 —
Interest expense 6,762 8,140 9,815
Amortization expense 620 920 313
Other expenses 17,962 9,646 451
Total expenses 33,243 29,338 10,579
Loss before income tax expense ( 29,872 ) ( 25,165 ) ( 7,747 )
Income tax expense 45,860 33,578 6,808
Loss before equity in earnings of subsidiaries ( 75,732 ) ( 58,743 ) ( 14,555 )
Equity in undistributed earnings of subsidiaries 245,760 177,571 100,539
Net income $ 170,028 $ 118,828 $ 85,984
See accompanying notes to financial statements.
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SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES
SCHEDULE II — STATEMENTS OF CASH FLOWS (PARENT COMPANY)
Years Ended December 31,
($ in thousands) 2025 2024 2023
Cash flows from operating activities:
Net income $ 170,028 $ 118,828 $ 85,984
Adjustments to reconcile net income to net cash used in operating activities ( 175,769 ) ( 121,563 ) ( 95,947 )
Net cash used in operating activities ( 5,741 ) ( 2,735 ) ( 9,963 )
Cash flows from investing activities:
Purchase of intangible assets and goodwill ( 2,000 ) — —
Capital contributions to subsidiaries ( 100 ) — ( 122,800 )
Distributions from investment in subsidiaries 8,500 8,500 6,500
Change in short-term investments ( 513 ) ( 3,407 ) ( 10,569 )
Net cash provided by (used in) investing activities 5,887 5,093 ( 126,869 )
Cash flows from financing activities:
Repayment of stock notes receivable — 5,561 1,350
Proceeds from long term borrowings 43,411 107,000 50,000
Payments on long term borrowings and trust preferred ( 43,000 ) ( 115,000 ) ( 50,000 )
Proceeds from equity offerings — — 128,887
Proceeds from employee stock purchase plan — — 710
Net cash provided by (used in) financing activities 411 ( 2,439 ) 130,947
Net increase (decrease) in cash and cash equivalents and restricted cash 557 ( 81 ) ( 5,885 )
Cash and cash equivalents and restricted cash at beginning of year 2,943 3,024 8,909
Cash and cash equivalents and restricted cash at end of year $ 3,500 $ 2,943 $ 3,024
Supplemental disclosure of cash flow information:
Cash paid for interest $ 6,149 $ 8,573 $ 10,667
See accompanying notes to financial statements.
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SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES
SCHEDULE II — FINANCIAL INFORMATION OF REGISTRANT
CONTINUED
Notes to Financial Statements
On September 30, 2024, Skyward Specialty entered into an Intercompany Loan Promissory Note (“the Promissory Note”) with Houston Specialty Insurance Company (“HSIC”). Under the terms of the Promissory Note, Skyward Specialty borrowed $ 57.0 million from HSIC. Under the terms of the Promissory Note, interest is payable monthly at a fixed annual interest rate of 4.00 %, with the principal due at the maturity date. There are no prepayment penalties and no collateral was given as security for the payment of the Promissory Note.
During the year ended December 31, 2024, Skyward Specialty provided funds for a new subsidiary, Skyward Specialty No. 1 Limited Company, a UK company authorized as a Lloyd’s corporate member to invest in Lloyd’s syndicates.
Financial Instruments Disclosed, But Not Carried, At Fair Value
Notes Payable
Included in notes payable is the Promissory Note described above between Skyward Specialty and HSIC. Skyward Specialty determined its fair value using the income approach utilizing inputs that are observable. The Promissory Note has been placed in Level 2 of the fair value hierarchy.
The following table sets forth the Company’s carrying and fair values of the Promissory Note as of December 31, 2025 and 2024:
2025 2024
($ in thousands) Carrying
Value Fair
Value Carrying
Value Fair
Value
Notes payable
Promissory Note $ 57,000 $ 57,401 $ 57,000 $ 56,300
Other financial instruments qualify as insurance-related products and are specifically exempted from fair value disclosure requirements.
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SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES
SCHEDULE IV — REINSURANCE
Years Ended December 31,
2025 2024 2023
($ in thousands) Accident &
Health Property &
Casualty Accident &
Health Property &
Casualty Accident &
Health Property &
Casualty
Gross amount $ 254,102 $ 1,430,309 $ 173,073 $ 1,285,564 $ 151,702 $ 1,089,478
Ceded to other companies ( 143,811 ) ( 616,193 ) ( 86,503 ) ( 533,151 ) ( 79,091 ) ( 470,047 )
Assumed from other companies — 481,825 — 284,595 — 218,649
Net amount $ 110,291 $ 1,295,941 $ 86,570 $ 1,037,008 $ 72,611 $ 838,080
Percentage of amount assumed to net — % 37.2 % — % 27.4 % — % 26.1 %
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SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES
SCHEDULE V — VALUATION AND QUALIFYING ACCOUNTS
($ in thousands) Valuation
Allowance
For Deferred
Tax Assets Allowance for
Uncollectible
Reinsurance
Recoverable Allowance for
Uncollectible
Premiums
Receivable
Balance at January 1, 2023 586 — 629
Cumulative effect of adoption of ASU 2016-13 at January 1, 2023 — 2,295 —
Charged to costs and expenses — — 748
Amounts written off — — ( 513 )
Recoveries of amounts previously written off — — 100
Balance at December 31, 2023 586 2,295 964
Charged to costs and expenses — 13,585 3,235
Amounts written off — ( 13,585 ) ( 1,895 )
Recoveries of amounts previously written off — — 128
Balance at December 31, 2024 586 2,295 2,432
Charged to costs and expenses 68 — 2,351
Amounts written off — — ( 2,141 )
Recoveries of amounts previously written off — — 498
Balance at December 31, 2025 $ 654 $ 2,295 $ 3,140
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SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES
SCHEDULE VI — SUPPLEMENTAL INFORMATION CONCERNING PROPERTY-CASUALTY
INSURANCE OPERATIONS
As of and Years Ended December 31,
($ in thousands) 2025 2024 2023
Deferred policy acquisition costs $ 136,100 $ 113,183 $ 91,955
Reserve for losses and loss adjustment expenses 2,318,894 1,782,383 1,314,501
Unearned premiums 774,035 637,185 552,532
Net earned premium (1)
1,304,505 1,056,722 829,143
Net investment income 83,619 80,686 40,322
Losses and loss adjustment expenses (current year) (1)
810,375 657,783 516,664
Losses and loss adjustment expenses (prior years) (1)(2)
( 7,471 ) 25,728 —
Amortization of policy acquisition costs (1)
195,422 149,975 108,514
Paid claims and claim adjustment expenses (1)
516,712 430,991 363,418
Net premiums written (1)
1,406,232 1,123,578 910,691
Ceded unearned premium 238,948 203,901 186,121
Deferred ceding commission 46,453 40,434 37,057
(1) Amount is presented net of reinsurance
(2) Amount does not include gain on retroactive reinsurance which is included in losses and loss adjustment expenses presented on the Consolidated Statements of Operations
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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.
Dated: March 2, 2026
/s/ Andrew Robinson
Andrew Robinson
Chairman and Chief Executive Officer
Pursuant to the requirements of the Securities Exchange Act of 1934, this report has been signed by the following persons on behalf of the Registrant and in the capacities and on the dates indicated.
Signature Title Date
/s/ Andrew Robinson Chairman and Chief Executive Officer March 2, 2026
Andrew Robinson (Principal Executive Officer)
/s/ Mark Haushill Chief Financial Officer March 2, 2026
Mark Haushill (Principal Financial and Accounting Officer)
/s/ Gena Ashe Director March 2, 2026
Gena Ashe
/s/ Robert Creager Director March 2, 2026
Robert Creager
/s/ Marcia Dall Director March 2, 2026
Marcia Dall
/s/ James Hays Director March 2, 2026
James Hays
/s/ Anthony J. Kuczinski Director March 2, 2026
Anthony J. Kuczinski
/s/ Michael Morrissey Director March 2, 2026
Michael Morrissey
/s/ Christopher L. Peirce Director March 2, 2026
Christopher L. Peirce
/s/ Katharine Terry Director March 2, 2026
Katharine Terry
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