What changed in this filing

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Item 9A. Controls and Procedures

2026-03-02 compared with 2025-03-03 · 63 added, 40 removed, 283 unchanged (27% of the section changed)

2 unchanged sentences

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, 2024, the disclosure controls and procedures were not effective due to a material weakness in internal control over financial reporting, described below.

Notwithstanding the identified material weakness described below, management does not believe that the material weakness had an adverse effect on our reported operating results or financial condition and management has determined that the financial statements and other information included in this report and other periodic filings present fairly in all material respects our financial condition, results of operations, and cash flows at and for the periods presented in accordance with U.S.

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

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(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.

Management has assessed the effectiveness of our internal control over financial reporting as of December 31, 2024, using the criteria set forth by the Committee of Sponsoring Organizations of the Treadway Commission (COSO) in Internal Control—Integrated Framework (2013).

As a result of this assessment, management concluded that, as of December 31, 2024, its internal control over financial reporting was not effective because management identified a material weakness in internal control over financial reporting.

A material weakness is a deficiency, or a combination of deficiencies, in internal control over financial reporting, such that there is a reasonable possibility that a material misstatement of our annual or interim financial statements will not be prevented or detected on a timely basis.

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 the Company’s financial reporting processes.

Further, the Company’s 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.

This material weakness did not result in any material misstatements to the financial statements in this Form 10-K, and we have not identified any changes required to our previously issued financial statements.

We have completed substantive procedures for the year ended December 31, 2024.

Based on these procedures, management believes that our consolidated financial statements included in this Form 10-K have been prepared in accordance with U.S.

Our CEO and CFO have certified that, based on their knowledge, the financial statements, and other financial information included in this Form 10-K, 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-K.

Ernst & Young LLP has issued an unqualified opinion on our financial statements, which is included in Item 8 of this Form 10-K.

In addition, Ernst & Young LLP has issued a report on our internal control over financial reporting as of December 31, 2024, and its report appears in Item 8.

Planned Material Weakness Remediation Activities

Management is implementing measures designed to remediate the control deficiencies contributing to the material weakness described above.

The remediation actions for the material weakness related to the design of ITGCs in the area of user access over certain information technology include:

(1) enhancing our IT compliance oversight function and expanding our team members with experience designing and implementing ITGCs;

(2) developing and implementing a training program addressing ITGCs and policies, including educating control owners about the principles and requirements of each control;

(3) developing and maintaining documentation underlying ITGCs to promote knowledge transfer upon IT personnel and function changes;

(4) implementing an IT management review and testing plan to monitor ITGCs;

and (5) enhanced quarterly reporting on the remediation measures to the Audit Committee of our board of directors.

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.

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;

• 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

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 for changes relating to the material weakness 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 December 31, 2024 that have materially affected, or are reasonably likely to materially affect, our 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

19 unchanged sentences

The following consolidated financials statements of the Company are filed as part of this Form 10-K and are included in Item 8:

Reports of Independent Registered Public Accounting Firm

Report of Independent Registered Public Accounting Firm

Consolidated Balance Sheets as of December 31, 2025 and 2024

40 unchanged sentences

1 dated January 1, 2022 (incorporated by reference to Exhibit 10.7 to the Company's Registration Statement on Form S-1, filed with the SEC on November 14, 2022).

10.22+* Form of Non-Employee Director Deferred Restricted Stock Unit Agreement and Form of Notice Under the Company’s 2022 Long-Term Incentive Plan.

10.22+ 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 Investment Management Agreement by and among Arena Investors, LP, Houston Specialty Insurance Company, Imperium Insurance Company, and Great Midwest Insurance Company, dated November 6, 2015, with a Supplemental Acknowledgement dated January 13, 2016, a Supplemental Acknowledgement dated May 17, 2021, Supplemental Acknowledgement B dated May 17, 2021, an Amendment Agreement effective March 15, 2022, and a Supplemental Acknowledgement dated March 23, 2022 (incorporated by reference to Exhibit 10.15 to the Company's Registration Statement on Form S-1, filed with the SEC on November 14, 2022).

Number Exhibit Description

10.25 Second Amendment Agreement effective as of December 8, 2023, to that certain Investment Management Agreement dated November 6, 2015, by and among Arena Investors, LP, Houston Specialty Insurance Company, Imperium Insurance Company, and Great Midwest Insurance Company (incorporated by reference to Exhibit 10.26 to the Company’s Annual Report on Form 10-K, filed with the SEC on April 1, 2024).

10.24 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).

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.

1 unchanged sentence

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).

10.30+* Form of Severance Agreement between the Company and executive officers (other than the CEO)

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 .

19* Skyward Specialty Insurance Securities Trading Policy

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).

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

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Equity securities:

Common stocks 48,530 64,251 64,251

Preferred stocks 1,138 1,174 1,174

Mutual funds 33,643 40,839 40,839

Total equity securities 1,138 1,174 1,174

24 unchanged sentences

Total liabilities and stockholders’ equity $ 1,147,224 $ 916,645

See accompanying notes to financial statements.

SKYWARD SPECIALTY INSURANCE GROUP, INC.

5 unchanged sentences

Net investment income $ 3,371 $ 3,212 $ 3,822

Net investment (losses) gains 963 ( 963 ) ( 6 )

Net investment gains (losses) — 963 ( 963 )

Other loss — ( 2 ) ( 27 )

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Adjustments to reconcile net income to net cash used in operating activities ( 175,769 ) ( 121,563 ) ( 95,947 )

Net cash provided by operating activities ( 2,735 ) ( 9,963 ) ( 3,276 )

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 )

1 unchanged sentence

Change in short-term investments ( 513 ) ( 3,407 ) ( 10,569 )

Net cash (used in) provided by investing activities 5,093 ( 126,869 ) 4,000

Net cash provided by (used in) investing activities 5,887 5,093 ( 126,869 )

Cash flows from financing activities:

4 unchanged sentences

Proceeds from employee stock purchase plan — — 710

Net cash provided by financing activities ( 2,439 ) 130,947 2,180

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 )

3 unchanged sentences

Cash paid for interest $ 6,149 $ 8,573 $ 10,667

Cash paid for federal income taxes 36,980 15,800 —

See accompanying notes to financial statements.

14 unchanged sentences

The Promissory Note has been placed in Level 2 of the fair value hierarchy.

As of December 31, 2024, the carrying value and fair value of the Promissory Note were $ 57.0 million and $ 56.3 million, respectively.

The following table sets forth the Company’s carrying and fair values of the Promissory Note as of December 31, 2025 and 2024:

($ in thousands) Carrying

Value Carrying

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.

SKYWARD SPECIALTY INSURANCE GROUP, INC.

23 unchanged sentences

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

Cumulative effect of adoption of ASU 2016-13 at January 1, 2023 — 2,295 —

Charged to costs and expenses — 13,585 3,235

53 unchanged sentences

Michael Morrissey

/s/ Christopher L.

Peirce Director March 2, 2026

Christopher L.

/s/ Katharine Terry Director March 2, 2026

1 unchanged sentence

Compared sentence by sentence after normalising whitespace, quotation marks, case and digits, so re-formatting and restated figures do not read as changed language. Wording changes appear as one removal and one addition. The current filing and the prior one are authoritative.

What changed 10-K

Item 9A. Controls and Procedures