SKWD / Skyward Specialty Insurance Group, Inc. - SEC-arkiveringar, Årsredovisning, Fullmaktsutlåtande

Skyward Specialty Insurance Group, Inc.
US ˙ NasdaqGS ˙ US8309401029

Grundläggande statistik
LEI 549300GXGXJG0YH4VN21
CIK 1519449
SEC Filings
All companies that sell securities in the United States must register with the Securities and Exchange Commission (SEC) and file reports on a regular basis. These reports include company annual reports (10K, 10Q), news updates (8K), investor presentations (found in 8Ks), insider trades (form 4), ownership reports (13D, and 13G), and reports related to the specific securities sold, such as registration statements and prospectus. This page shows recent SEC filings related to Skyward Specialty Insurance Group, Inc.
SEC Filings (Chronological Order)
Denna sida innehåller en komplett, kronologisk lista över SEC-arkiveringar, exklusive ägande-arkiveringar som vi tillhandahåller på andra ställen.
May 11, 2026 EX-10.1

FORM OF EXECUTIVE EMPLOYMENT AGREEMENT

EXHIBIT 10.1 FORM OF EXECUTIVE EMPLOYMENT AGREEMENT This EMPLOYMENT AGREEMENT (the “Agreement”) is entered into and effective as of [] (the “Effective Date”) by and between Skyward Specialty Insurance Group, Inc. (the “Company”), and [] (“Executive”). Each of the Company and Executive are a “Party,” and collectively, they are the “Parties.” WHEREAS, the Parties previously entered [] dated [] (the

May 11, 2026 EX-21.1

EX-21.1

EXHIBIT 21.1

May 11, 2026 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

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, 2026 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 SP

May 11, 2026 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 11, 2026 (May 5, 2026) Skywar

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 11, 2026 (May 5, 2026) Skyward Specialty Insurance Group, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or org

May 6, 2026 EX-99.1

Premiums ($ in thousands) Three months ended March 31, unaudited 2026 2025 Skyward Specialty Apollo Total Skyward Specialty Apollo(1) Total(1) Gross written premiums $ 581,804 $ 85,900 $ 667,704 $ 535,326 $ 72,390 $ 607,716 Ceded written premiums $ (

Exhibit 99.1 Skyward Group Reports First Quarter 2026 Results Houston, TX – May 6, 2026 – Skyward Specialty Insurance Group, Inc. (Nasdaq: SKWD) (“Skyward Group” or the “Company”) today reported first quarter 2026 net income of $49.7 million, or $1.09 per diluted share, compared to $42.1 million, or $1.01 per diluted share, for the same 2025 period. Operating income(1) for the first quarter of 202

May 6, 2026 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (date of earliest event reported): May 6, 2026 Skyward Specialty Ins

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (date of earliest event reported): May 6, 2026 Skyward Specialty Insurance Group, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-

March 26, 2026 DEFR14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Ru

March 26, 2026 DEFR14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Ru

March 25, 2026 ARS

ARS

ANNUAL REPORT Charting New Horizons 2025Shareholder Letter 2025 At a Glance Financial Summary Diversified & Balanced Portfolio The Bionic Underwriter Five Years of Community Impact Skyward Group Leadership pg.

March 25, 2026 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Ru

March 25, 2026 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Ru

March 17, 2026 EX-99.2

UNAUDITED PRO FORMA CONDENSED COMBINED FINANCIAL INFORMATION

EXHIBIT 99.2 UNAUDITED PRO FORMA CONDENSED COMBINED FINANCIAL INFORMATION The following unaudited pro forma condensed combined financial statements combine the separate historical financial information of Skyward Specialty Insurance Group, Inc. (the “Company”) and Apollo Group Holdings Limited (“Apollo”) after giving effect to the acquisition of Apollo by the Company (the “Transaction”), as descri

March 17, 2026 8-K/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 6, 2026 (December 30, 2

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 6, 2026 (December 30, 2025) Skyward Specialty Insurance Group, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorpora

March 17, 2026 EX-99.1

APOLLO GROUP HOLDINGS LIMITED GROUP CONSOLIDATED FINANCIAL STATEMENTS FOR THE YEAR ENDED 31 DECEMBER 2025

EXHIBIT 99.1 APOLLO GROUP HOLDINGS LIMITED GROUP CONSOLIDATED FINANCIAL STATEMENTS FOR THE YEAR ENDED 31 DECEMBER 2025 Registered Number: 12878158 APOLLO GROUP HOLDINGS LIMITED CONTENTS Page No. Directors and administration 3 Independent Auditor’s Report 4 Consolidated profit and loss account – Technical Account 7 Consolidated profit and loss account – Non-Technical Account 8 Consolidated statemen

March 4, 2026 EX-99.28

SKYWARD SPECIALTY INSURANCE GROUP, INC. (the Company) 800 Gessner Road, Suite 600 Houston, Texas 77024 United States of America

Exhibit 99.28 CERTAIN CONFIDENTIAL PORTIONS OF THIS EXHIBIT HAVE BEEN OMITTED AND REPLACED WITH “[***]”. SUCH IDENTIFIED INFORMATION HAS BEEN EXCLUDED FROM THIS EXHIBIT BECAUSE IT IS (I) NOT MATERIAL AND (II) WOULD LIKELY CAUSE COMPETITIVE HARM TO THE COMPANY IF DISCLOSED Apollo Management Incentive Program (“Apollo MIP”) SKYWARD SPECIALTY INSURANCE GROUP, INC. (the Company) 800 Gessner Road, Suit

March 4, 2026 EX-99.32

SKYWARD SPECIALTY INSURANCE GROUP, INC. “Bright Future” RESTRICTED STOCK UNITS NOTICE UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN

Exhibit 99.32 SKYWARD SPECIALTY INSURANCE GROUP, INC. “Bright Future” RESTRICTED STOCK UNITS NOTICE UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN Name of Grantee: /$ParticipantName$/ This Notice evidences the award of restricted stock units (each, an “RSU,” and collectively, the “RSUs”) of Skyward Specialty Insurance Group, Inc., a Delaware corporation (the “Compa

March 4, 2026 EX-99.36

SKYWARD SPECIALTY INSURANCE GROUP, INC. RESTRICTED STOCK UNITS NOTICE UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN

Exhibit 99.36 SKYWARD SPECIALTY INSURANCE GROUP, INC. RESTRICTED STOCK UNITS NOTICE UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN Name of Grantee: /$ParticipantName$/ This Notice evidences the award of restricted stock units (each, a “RSU,” and collectively, the “RSUs”) of Skyward Specialty Insurance Group, Inc., a Delaware corporation (the “Company”), that have b

March 4, 2026 EX-99.31

SKYWARD SPECIALTY INSURANCE GROUP, INC. “Bright Future” RESTRICTED STOCK UNITS NOTICE UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN

Exhibit 99.31 SKYWARD SPECIALTY INSURANCE GROUP, INC. “Bright Future” RESTRICTED STOCK UNITS NOTICE UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN Name of Grantee: /$ParticipantName$/ This Notice evidences the award of restricted stock units (each, an “RSU,” and collectively, the “RSUs”) of Skyward Specialty Insurance Group, Inc., a Delaware corporation (the “Compa

March 4, 2026 S-8

As filed with the Securities and Exchange Commission on March 3, 2026

As filed with the Securities and Exchange Commission on March 3, 2026 Registration No.

March 4, 2026 EX-FILING FEES

Table 1: Newly Registered Securities

Calculation of Filing Fee Tables S-8 Skyward Specialty Insurance Group, Inc. Table 1: Newly Registered Securities Security Type Security Class Title Fee Calculation Rule Amount Registered Proposed Maximum Offering Price Per Unit Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee 1 Equity Common Stock, $0.01 par value per share 457(a) 810,224 $ 45.96 $ 37,237,895.04 0.0001381 $ 5,

March 4, 2026 EX-99.30

SKYWARD SPECIALTY INSURANCE GROUP, INC. “Bright Future” RESTRICTED STOCK UNITS NOTICE UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN

Exhibit 99.30 SKYWARD SPECIALTY INSURANCE GROUP, INC. “Bright Future” RESTRICTED STOCK UNITS NOTICE UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN Name of Grantee: This Notice evidences the award of restricted stock units (each, a “RSU,” and collectively, the “RSUs”) of Skyward Specialty Insurance Group, Inc., a Delaware corporation (the “Company”), that have been

March 4, 2026 EX-99.33

SKYWARD SPECIALTY INSURANCE GROUP, INC. PERFORMANCE-BASED RESTRICTED STOCK UNITS AGREEMENT UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN (COMBINED RATIO)

Exhibit 99.33 SKYWARD SPECIALTY INSURANCE GROUP, INC. PERFORMANCE-BASED RESTRICTED STOCK UNITS AGREEMENT UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN (COMBINED RATIO) Name of Grantee: /$ParticipantName$/ This Notice evidences the award of performance-based restricted stock units (each, a “PSU,” and collectively, the “PSUs”) of Skyward Specialty Insurance Group, I

March 4, 2026 EX-99.35

SKYWARD SPECIALTY INSURANCE GROUP, INC. LONG-TERM CASH BONUS INCENTIVE PLAN As Effective February 25, 2026

Exhibit 99.35 SKYWARD SPECIALTY INSURANCE GROUP, INC. LONG-TERM CASH BONUS INCENTIVE PLAN As Effective February 25, 2026 I.              Purpose. The purpose of the Skyward Specialty Insurance Group, Inc. Long-Term Cash Bonus Incentive Plan is to promote the interests of Skyward Specialty Insurance Group, Inc., by providing both an incentive and a financial reward to certain senior leaders and oth

March 4, 2026 EX-99.29

SKYWARD SPECIALTY INSURANCE GROUP, INC. “BRIGHT FUTURE” RESTRICTED STOCK UNITS NOTICE UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN

Exhibit 99.29 Apollo Bright Future Awards SKYWARD SPECIALTY INSURANCE GROUP, INC. “BRIGHT FUTURE” RESTRICTED STOCK UNITS NOTICE UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN Name of Grantee: [Participant Name] This notice (the "Notice") evidences the award of restricted stock units (each, a “RSU,” and collectively, the “RSUs”) of Skyward Specialty Insurance Group,

March 4, 2026 EX-99.34

SKYWARD SPECIALTY INSURANCE GROUP, INC. PERFORMANCE-BASED RESTRICTED STOCK UNITS AGREEMENT UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN (Relative GBVPS)

Exhibit 99.34 SKYWARD SPECIALTY INSURANCE GROUP, INC. PERFORMANCE-BASED RESTRICTED STOCK UNITS AGREEMENT UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN (Relative GBVPS) Name of Grantee: /$ParticipantName$/ This Notice evidences the award of performance-based restricted stock units (each, a “PSU,” and collectively, the “PSUs”) of Skyward Specialty Insurance Group, I

March 2, 2026 EX-21.1

SKYWARD SPECIALTY INSURANCE GROUP, INC. ORGANIZATION CHART

EXHIBIT 21.1 SKYWARD SPECIALTY INSURANCE GROUP, INC. ORGANIZATION CHART

March 2, 2026 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 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 SPECIAL

March 2, 2026 EX-19.1

Securities Trading Policy

EXHIBIT 19.1 Securities Trading Policy Effective: January 12, 2023 Amended: November 5, 2025 Table of Contents 1. Introduction 3 2. Applicability 3 3. Policy Statement 3 4. Penalties for Insider Trading 3 5. Policy Violations Must Be Reported 3 6. Insider Trading Compliance Officers 4 7. Definition of Material Non-public Information 4 8. Covered Transactions 6 9. No Trading by Others on a Person's

February 26, 2026 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 26, 2026 (February 25, 2

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 26, 2026 (February 25, 2026) Skyward Specialty Insurance Group, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorpora

February 23, 2026 EX-99.1

Premiums ($ in thousands) Three months ended December 31, Twelve months ended December 31, unaudited 2025 2024 % Change 2025 2024 % Change Gross written premiums $ 439,487 $ 388,355 13.2% $ 2,166,236 $ 1,743,232 24.3% Ceded written premiums $ (156,90

Exhibit 99.1 Skyward Specialty Insurance Group Reports Fourth Quarter 2025 Results Houston, TX – February 23, 2026 – Skyward Specialty Insurance Group, Inc. (Nasdaq: SKWD) (“Skyward Group” or the “Company”), today reported fourth quarter 2025 net income of $43.2 million, or $1.03 per diluted share, compared to $14.4 million, or $0.35 per diluted share, for the same 2024 period. Net income for the

February 23, 2026 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (date of earliest event reported): February 23, 2026 Skyward Special

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (date of earliest event reported): February 23, 2026 Skyward Specialty Insurance Group, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization

January 6, 2026 EX-99.1

Skyward Specialty Announces Completion of Apollo Acquisition

Exhibit 99.1 Skyward Specialty Announces Completion of Apollo Acquisition Houston, TX. – January 2, 2026 – Skyward Specialty Insurance Group, Inc. (Nasdaq: SKWD) (“Skyward Specialty” or the “Company”), today announced that it has completed its acquisition of Apollo Group Holdings Limited (“Apollo”) at the previously agreed upon terms. About Skyward Specialty Skyward Specialty is a rapidly growing

January 6, 2026 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 6, 2026 (December 30, 202

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 6, 2026 (December 30, 2025) Skyward Specialty Insurance Group, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporati

January 6, 2026 EX-10.3

FIRST AMENDMENT

Exhibit 10.3 FIRST AMENDMENT THIS FIRST AMENDMENT, dated as of December 30, 2025, (this “Agreement”), is by and among SKYWARD SPECIALTY INSURANCE GROUP, INC., a Delaware corporation (the “Borrower”), the Guarantors party hereto, the Lenders party hereto (which, for the avoidance of doubt, constitute each of the Lenders under the Existing Credit Agreement (as defined below)), and BARCLAYS BANK PLC,

January 6, 2026 EX-10.1

TERM LOAN CREDIT AGREEMENT DATED AS OF DECEMBER 30, 2025 SKYWARD SPECIALTY INSURANCE GROUP, INC., AS THE BORROWER THE LENDERS FROM TIME TO TIME PARTY HERETO BARCLAYS BANK PLC, AS ADMINISTRATIVE AGENT BARCLAYS BANK PLC as Sole Lead Arranger and Sole B

Exhibit 10.1 TERM LOAN CREDIT AGREEMENT DATED AS OF DECEMBER 30, 2025 AMONG SKYWARD SPECIALTY INSURANCE GROUP, INC., AS THE BORROWER THE LENDERS FROM TIME TO TIME PARTY HERETO AND BARCLAYS BANK PLC, AS ADMINISTRATIVE AGENT BARCLAYS BANK PLC as Sole Lead Arranger and Sole Book Runner for the Tranche A Term Facility and as Joint Lead Arranger and Joint Book Runner for the Tranche B Term Facility and

January 6, 2026 EX-10.2

GUARANTY AGREEMENT

Exhibit 10.2 GUARANTY AGREEMENT This GUARANTY AGREEMENT, dated as of December 30, 2025, is made by SKYWARD SERVICE COMPANY, a Delaware corporation (“Skyward Service”) and SKYWARD UNDERWRITERS AGENCY, INC., a Texas corporation (“Skyward Underwriters” and, together with Skyward Service and any Person who becomes a “Guarantor” pursuant to the terms hereof after the date hereof, collectively, the “Gua

December 3, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): December 3, 2025 (December 3, 202

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): December 3, 2025 (December 3, 2025) Skyward Specialty Insurance Group, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporati

December 3, 2025 EX-99.1

Skyward Specialty Insurance Group, Inc. Reconciliation of Non-GAAP Financial Measures

Exhibit 99.1 Regulatory Authorities and Minority Shareholders Approved Skyward Specialty Acquisition of Apollo Group; Skyward Specialty Provides Guidance for 2026 Houston, TX – December 3, 2025 – Skyward Specialty Insurance Group, Inc. (Nasdaq: SKWD) (“Skyward Specialty” or the “Company”) today announced that it has secured the required regulatory approvals and approvals of the minority shareholde

November 18, 2025 EX-10.2

GUARANTY AGREEMENT

GUARANTY AGREEMENT This GUARANTY AGREEMENT, dated as of November 13, 2025, is made by SKYWARD SERVICE COMPANY, a Delaware corporation (“Skyward Service”) and SKYWARD UNDERWRITERS AGENCY, INC.

November 18, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 18, 2025 (November 13, 2

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 18, 2025 (November 13, 2025) Skyward Specialty Insurance Group, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorpora

November 18, 2025 EX-10.1

CREDIT AGREEMENT DATED AS OF NOVEMBER 13, 2025 SKYWARD SPECIALTY INSURANCE GROUP, INC., AS THE BORROWER THE LENDERS FROM TIME TO TIME PARTY HERETO BARCLAYS BANK PLC, AS ADMINISTRATIVE AGENT BARCLAYS BANK PLC, TRUIST SECURITIES, INC., CITIZENS BANK, N

CREDIT AGREEMENT DATED AS OF NOVEMBER 13, 2025 AMONG SKYWARD SPECIALTY INSURANCE GROUP, INC.

November 12, 2025 EX-99.1

Skyward Specialty Welcomes Christopher Peirce to Board of Directors

Skyward Specialty Welcomes Christopher Peirce to Board of Directors HOUSTON, TX. – [November 11, 2025] – Skyward Specialty Insurance Group, Inc.TM (Nasdaq: SKWD) (“Skyward Specialty” or “the Company”), a leader in the specialty property and casualty market, is pleased to announce the addition of Christopher Peirce to its Board of Directors effective February 1, 2026. Peirce is a highly accomplishe

November 12, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 12, 2025 (November 5, 20

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 12, 2025 (November 5, 2025) Skyward Specialty Insurance Group, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporat

November 6, 2025 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

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 September 30, 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 SKYWAR

October 29, 2025 EX-99.1

Premiums ($ in thousands) Three months ended September 30, Nine months ended September 30, unaudited 2025 2024 % Change 2025 2024 % Change Gross written premiums $ 606,509 $ 400,014 51.6% $ 1,726,749 $ 1,354,877 27.4% Ceded written premiums $ (165,34

Exhibit 99.1 Skyward Specialty Insurance Group Reports Third Quarter 2025 Results Houston, TX – October 29, 2025 – Skyward Specialty Insurance Group, Inc. (Nasdaq: SKWD) (“Skyward Specialty” or the “Company”) today reported third quarter 2025 net income of $45.9 million, or $1.10 per diluted share, compared to $36.7 million, or $0.89 per diluted share, for the same 2024 period. Net income for the

October 29, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (date of earliest event reported): October 29, 2025 Skyward Specialt

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (date of earliest event reported): October 29, 2025 Skyward Specialty Insurance Group, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization)

September 8, 2025 EX-99.1

SKYWARD SPECIALTY INSURANCE GROUP TO ACQUIRE APOLLO GROUP HOLDINGS LIMITED, AMPLIFYING “RULE OUR NICHE” STRATEGY

SKYWARD SPECIALTY INSURANCE GROUP TO ACQUIRE APOLLO GROUP HOLDINGS LIMITED, AMPLIFYING “RULE OUR NICHE” STRATEGY Houston, TX - September 02, 2025 (Globe Newswire) - Skyward Specialty Insurance Group, Inc.

September 8, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): September 8, 2025 (September 2, 2

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): September 8, 2025 (September 2, 2025) Skyward Specialty Insurance Group, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorpora

September 8, 2025 EX-2.2

CERTAIN INFORMATION HAS BEEN EXCLUDED FROM THIS AGREEMENT (INDICATED BY [***]) BECAUSE SUCH INFORMATION IS BOTH NOT MATERIAL AND OF THE TYPE THAT THE REGISTRANT TREATS AS PRIVATE OR CONFIDENTIAL.

CERTAIN INFORMATION HAS BEEN EXCLUDED FROM THIS AGREEMENT (INDICATED BY [***]) BECAUSE SUCH INFORMATION IS BOTH NOT MATERIAL AND OF THE TYPE THAT THE REGISTRANT TREATS AS PRIVATE OR CONFIDENTIAL.

September 8, 2025 EX-2.1

CERTAIN INFORMATION HAS BEEN EXCLUDED FROM THIS AGREEMENT (INDICATED BY [***]) BECAUSE SUCH INFORMATION IS BOTH NOT MATERIAL AND OF THE TYPE THAT THE REGISTRANT TREATS AS PRIVATE OR CONFIDENTIAL.

CERTAIN INFORMATION HAS BEEN EXCLUDED FROM THIS AGREEMENT (INDICATED BY [***]) BECAUSE SUCH INFORMATION IS BOTH NOT MATERIAL AND OF THE TYPE THAT THE REGISTRANT TREATS AS PRIVATE OR CONFIDENTIAL.

September 5, 2025 10-K/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A (Mark One) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2024 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 SPECI

August 7, 2025 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

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 June 30, 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 SPE

August 7, 2025 10-K/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A (Mark One) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2024 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 SPECI

July 30, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (date of earliest event reported): July 30, 2025 Skyward Specialty I

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (date of earliest event reported): July 30, 2025 Skyward Specialty Insurance Group, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 00

July 30, 2025 EX-99.1

Premiums ($ in thousands) Three months ended June 30, Six months ended June 30, unaudited 2025 2024 % Change 2025 2024 % Change Gross written premiums $ 584,914 $ 496,243 17.9% $ 1,120,240 $ 954,863 17.3% Ceded written premiums $ (245,701) $ (199,114

Exhibit 99.1 Skyward Specialty Insurance Group Reports Second Quarter 2025 Results Houston, TX – July 30, 2025 – Skyward Specialty Insurance Group, Inc. (Nasdaq: SKWD) (“Skyward Specialty” or the “Company”) today reported second quarter 2025 net income of $38.8 million, or $0.93 per diluted share, compared to $31.0 million, or $0.75 per diluted share, for the same 2024 period. Net income for the f

May 13, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 13, 2025 (May 7, 2025) Skywar

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 13, 2025 (May 7, 2025) Skyward Specialty Insurance Group, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or org

May 7, 2025 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

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 SP

May 1, 2025 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (date of earliest event reported): May 1, 2025 Skyward Specialty Ins

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (date of earliest event reported): May 1, 2025 Skyward Specialty Insurance Group, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-

May 1, 2025 EX-99.1

Premiums ($ in thousands) Three months ended March 31, unaudited 2025 2024 % Change Gross written premiums $ 535,326 $ 458,620 16.7% Ceded written premiums $ (192,055) $ (171,520) 12.0% Net retention 64.1% 62.6% NM (1) Net written premiums $ 343,271

Exhibit 99.1 Skyward Specialty Insurance Group Reports First Quarter 2025 Results Houston, TX – May 1, 2025 – Skyward Specialty Insurance Group, Inc. (Nasdaq: SKWD) (“Skyward Specialty” or the “Company”) today reported first quarter 2025 net income of $42.1 million, or $1.01 per diluted share, compared to $36.8 million, or $0.90 per diluted share, for the same 2024 period. Adjusted operating incom

March 26, 2025 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Ru

March 26, 2025 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Ru

March 26, 2025 ARS

ARS

2024 Our Future is Bright ANNUAL REPORTANNUAL REPORT 2024 2 Andrew Robinson, Chairman & CEO FROM THE DESK OF THE CEO As we step into 2025 and I look back on 2024, I have immense pride at the accomplishments of our Skyward Specialty team.

March 5, 2025 EX-99.22

Amended Form of the Restricted Stock Unit (Others) Agreement under the Company’s 2022 Long-Term Incentive Plan.

Exhibit 99.22 SKYWARD SPECIALTY INSURANCE GROUP, INC. RESTRICTED STOCK UNITS NOTICE UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN Name of Grantee: This Notice evidences the award of restricted stock units (each, a “RSU,” and collectively, the “RSUs”) of Skyward Specialty Insurance Group, Inc., a Delaware corporation (the “Company”), that have been granted to you p

March 5, 2025 EX-FILING FEES

Filing Fee Table

Calculation of Filing Fee Tables S-8 Skyward Specialty Insurance Group, Inc. Table 1: Newly Registered Securities Security Type Security Class Title Fee Calculation Rule Amount Registered Proposed Maximum Offering Price Per Unit Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee 1 Equity Common Stock, $0.01 par value per share 457(a) 802,558 $ 51.28 $ 41,155,174.24 0.0001531 $ 6,

March 5, 2025 EX-99.25

Amended Form of Performance Share (GBVPS) (Executives) Agreement under the Company’s 2022 Long-Term Incentive Plan.

Exhibit 99.25 SKYWARD SPECIALTY INSURANCE GROUP, INC. PERFORMANCE-BASED RESTRICTED STOCK UNITS AGREEMENT UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN (Relative GBVPS) Name of Grantee: This Notice evidences the award of performance-based restricted stock units (each, a “PSU,” and collectively, the “PSUs”) of Skyward Specialty Insurance Group, Inc., a Delaware corp

March 5, 2025 EX-99.27

Amended Form of Long-Term Performance Cash Plan and Award Letter under the Company’s 2022 Long-Term Incentive Plan .

Exhibit 99.27 SKYWARD SPECIALTY INSURANCE GROUP, INC. LONG-TERM CASH BONUS INCENTIVE PLAN As Effective February 25, 2025 I.             Purpose. The purpose of the Skyward Specialty Insurance Group, Inc. Long-Term Cash Bonus Incentive Plan is to promote the interests of Skyward Specialty Insurance Group, Inc. by providing both an incentive and a financial reward to certain senior leaders and other

March 5, 2025 EX-99.23

Amended Form of Performance Share (Executives) Agreement under the Company’s 2022 Long-Term Incentive Plan.

Exhibit 99.23 SKYWARD SPECIALTY INSURANCE GROUP, INC. PERFORMANCE-BASED RESTRICTED STOCK UNITS AGREEMENT UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN (COMBINED RATIO) Name of Grantee: This Notice evidences the award of performance-based restricted stock units (each, a “PSU,” and collectively, the “PSUs”) of Skyward Specialty Insurance Group, Inc., a Delaware corp

March 5, 2025 EX-99.26

Amended Form of Performance Share (GBVPS) (Others) Agreement under the Company’s 2022 Long-Term Incentive Plan.

Exhibit 99.26 SKYWARD SPECIALTY INSURANCE GROUP, INC. PERFORMANCE-BASED RESTRICTED STOCK UNITS AGREEMENT UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN (Relative GBVPS) Name of Grantee:  This Notice evidences the award of performance-based restricted stock units (each, a “PSU,” and collectively, the “PSUs”) of Skyward Specialty Insurance Group, Inc., a Delaware cor

March 5, 2025 EX-99.21

Amended Form of the Restricted Stock Unit (Executives) Agreement under the Company’s 2022 Long-Term Incentive Plan.

Exhibit 99.21 SKYWARD SPECIALTY INSURANCE GROUP, INC. RESTRICTED STOCK UNITS NOTICE UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN Name of Grantee: This Notice evidences the award of restricted stock units (each, a “RSU,” and collectively, the “RSUs”) of Skyward Specialty Insurance Group, Inc., a Delaware corporation (the “Company”), that have been granted to you p

March 5, 2025 EX-99.24

Amended Form of Performance Share (Others) Agreement under the Company’s 2022 Long-Term Incentive Plan.

Exhibit 99.24 SKYWARD SPECIALTY INSURANCE GROUP, INC. PERFORMANCE-BASED RESTRICTED STOCK UNITS AGREEMENT UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN (COMBINED RATIO) Name of Grantee:  This Notice evidences the award of performance-based restricted stock units (each, a “PSU,” and collectively, the “PSUs”) of Skyward Specialty Insurance Group, Inc., a Delaware cor

March 5, 2025 S-8

As filed with the Securities and Exchange Commission on March 5, 2025

As filed with the Securities and Exchange Commission on March 5, 2025 Registration No.

March 3, 2025 EX-10.30

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

EXHIBIT 10.30 Severance Agreement For [] (“Employee”) If Skyward Service Company (the “Company”) terminates Employee’s employment without cause or Employee terminates his/her employment for “Good Reason,” the Company will pay the Employee an amount equal to twelve (12) months of Employee’s base salary, following the termination date, payable in roughly equal installments in accordance with the Com

March 3, 2025 EX-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.

EXHIBIT 10.22 SKYWARD SPECIALTY INSURANCE GROUP, INC. DEFERRED RESTRICTED STOCK UNITS NOTICE UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN Name of Grantee: This Notice evidences the award of deferred restricted stock units (each, an “DSU,” and collectively, the “DSUs”) of Skyward Specialty Insurance Group, Inc., a Delaware corporation (the “Company”), that have be

March 3, 2025 EX-21.1

List of Subsidiaries of the Company

EXHIBIT 21.1 SKYWARD SPECIALTY INSURANCE GROUP, INC. ORGANIZATION CHART

March 3, 2025 EX-19

Skyward Specialty Insurance Securities Trading Policy

Securities Trading Policy Adopted: 2023-01-12 Last Amended: 2024-11-07 Table of Contents 1.

March 3, 2025 EX-10.31

Amendment No. 2 to Employment Agreement between the Registrant and Andrew Robinson dated March 1, 2025

EXHIBIT 10.31 SECOND AMENDMENT TO EMPLOYMENT AGREEMENT This SECOND AMENDMENT TO EMPLOYMENT AGREEMENT (“First Amendment”) is effective as of the 1st day of March, 2025 by and among SKYWARD SPECIALTY INSURANCE GROUP, INC., SKYWARD SERVICE COMPANY, (together “Company’), and ANDREW ROBINSON, (“Executive”). WITNESSETH: WHEREAS, the Company and the Executive entered into that certain Employment Agreemen

March 3, 2025 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2024 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 SPECIAL

February 25, 2025 EX-99.1

Premiums ($ in thousands) Three months ended December 31, Twelve months ended December 31, unaudited 2024 2023 % Change 2024 2023 % Change Gross written premiums $ 388,355 $ 321,605 20.8% $ 1,743,232 $ 1,459,829 19.4% Ceded written premiums $ (117,32

Exhibit 99.1 Skyward Specialty Insurance Group Reports Fourth Quarter 2024 Results Houston, TX – February 25, 2025 – Skyward Specialty Insurance Group, Inc. (Nasdaq: SKWD) (“Skyward Specialty” or the “Company”) today reported fourth quarter 2024 net income of $14.4 million, or $0.35 per diluted share, compared to $29.3 million, or $0.74 per diluted share, for the same 2023 period. Net income for t

February 25, 2025 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (date of earliest event reported): February 25, 2025 Skyward Specialty Insurance Group, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization

February 5, 2025 8-K

Entry into a Material Definitive Agreement, Termination of a Material Definitive Agreement, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): February 5, 2025 (February 5, 2025) Skyward Specialty Insurance Group, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporati

February 5, 2025 EX-99.1

Skyward Specialty Insurance Group, Inc. Reconciliation of Non-GAAP Financial Measures

Exhibit 99.1 Skyward Specialty Commutes the LPT, Announces Preliminary Fourth Quarter 2024 Results and Provides Guidance for 2025 Houston, TX – February 05, 2025 – Skyward Specialty Insurance Group, Inc. (Nasdaq: SKWD) (“Skyward Specialty” or the “Company”) today announced that it commuted the Loss Portfolio Transfer and Adverse Development and Retrocession Agreement (“LPT”) with R&Q Re (Bermuda)

February 5, 2025 EX-10.1

Commutation Agreement dated January 31, 2025

EXHIBIT 10.1 COMMUTATION AND RELEASE AGREEMENT THIS COMMUTATION AND RELEASE AGREEMENT (the “Agreement”) is made on the 31st day of January 2025 BETWEEN: (1)R&Q Re (Bermuda) Ltd., acting in respect of the HIIG Segregated Account (in such capacity “RQRE”); (2)HIIG Re (k/n/a Skyward Re) (“SRE”); and (3)Houston Specialty Insurance Company, Imperium Insurance Company, and Great Midwest Insurance Compan

November 13, 2024 SC 13G

SKWD / Skyward Specialty Insurance Group, Inc. / Capital International Investors - SEC SCHEDULE 13G Passive Investment

SC 13G 1 SEC13GFiling.htm SEC SCHEDULE 13G UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* Skyward Specialty Insurance Group, Inc. (Name of Issuer) Common Stock (Title of Class of Securities) 830940102 (CUSIP Number) September 30, 2024 (Date of Event Which Requires Filing of this Statement) Check the a

November 12, 2024 SC 13G/A

SKWD / Skyward Specialty Insurance Group, Inc. / VANGUARD GROUP INC Passive Investment

SC 13G/A 1 UnitedStates13GSkywardSpe.txt 240.13d-102 Schedule 13G - Information to be included in statements filed pursuant to 240.13d-1(b), (c), and (d) and amendments thereto filed pursuant to 240.13d-2. Securities and Exchange Commission, Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No. 1)* (Name of Issuer) Skyward Specialty Insurance Group Inc (Title

November 12, 2024 SC 13G

SKWD / Skyward Specialty Insurance Group, Inc. / Hays James Charles - SCHEDULE 13G Passive Investment

SC 13G 1 jch20241107sc13g.htm SCHEDULE 13G UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13G UNDER THE SECURITIES EXCHANGE ACT OF 1934 Skyward Specialty Insurance Group, Inc. (Name of Issuer) Common Stock, $0.01 par value (Title of Class of Securities) 830940102 (CUSIP Number) September 30, 2024 (Date of Event Which Requires Filing of This Statement) Check the ap

November 8, 2024 SC 13G/A

SKWD / Skyward Specialty Insurance Group, Inc. / BlackRock, Inc. Passive Investment

SC 13G/A 1 us8309401029110824.txt us8309401029110824.txt SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No: 1) Skyward Specialty Insurance Group, Inc. - (Name of Issuer) Common Stock - (Title of Class of Securities) 830940102 - (CUSIP Number) September 30, 2024 - (Date of Event Which Requires Filing of this Statement) Che

November 7, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

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 September 30, 2024 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 SKYWAR

November 4, 2024 SC 13G/A

SKWD / Skyward Specialty Insurance Group, Inc. / VANGUARD GROUP INC Passive Investment

SC 13G/A 1 UnitedStates13GSkywardSpe.txt 240.13d-102 Schedule 13G - Information to be included in statements filed pursuant to 240.13d-1(b), (c), and (d) and amendments thereto filed pursuant to 240.13d-2. Securities and Exchange Commission, Washington, D.C. 20549 Schedule 13G Under the Securities Exchange Act of 1934 (Amendment No. )* (Name of Issuer) Skyward Specialty Insurance Group Inc (Title

October 29, 2024 EX-99.1

Premiums ($ in thousands) Three months ended September 30, Nine months ended September 30, unaudited 2024 2023 % Change 2024 2023 % Change Gross written premiums $ 400,014 $ 355,732 12.4% $ 1,354,877 $ 1,138,224 19.0% Ceded written premiums $ (131,69

Exhibit 99.1 Skyward Specialty Insurance Group Reports Third Quarter 2024 Results Houston, TX – October 29, 2024 – Skyward Specialty Insurance Group, Inc. (Nasdaq: SKWD) (“Skyward Specialty” or the “Company”) today reported third quarter 2024 net income of $36.7 million, or $0.89 per diluted share, compared to $21.7 million, or $0.57 per diluted share, for the same 2023 period. Net income for the

October 29, 2024 8-K

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (date of earliest event reported): October 29, 2024 Skyward Specialty Insurance Group, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization)

October 22, 2024 SC 13G/A

SKWD / Skyward Specialty Insurance Group, Inc. / BlackRock, Inc. Passive Investment

SC 13G/A 1 us8309401029102224.txt us8309401029102224.txt SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No: 1) Skyward Specialty Insurance Group, Inc. - (Name of Issuer) Common Stock - (Title of Class of Securities) 830940102 - (CUSIP Number) September 30, 2024 - (Date of Event Which Requires Filing of this Statement) Che

September 9, 2024 EX-10.1

Advances and Security Agreement by and between HSIC and FHLB

Exhibit 10.1 ADVANCES AND SECURITY AGREEMENT This Advances and Security Agreement (“Agreement”) is made as of August 1st, 2023 , between the Federal Home Loan Bank of Dallas (“Bank”), with its principal office located at 8500 Freeport Parkway South, Suite 600, Irving, Texas 75063, mailing address: P.O. Box 619026, Dallas, Texas 75261-9026 and Houston Specialty Insurance Company a Insurance Company

September 9, 2024 8-K

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): September 6, 2024 (August 30, 2024) Skyward Specialty Insurance Group, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporati

August 8, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

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 June 30, 2024 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 SPE

August 8, 2024 EX-10.1

Form of Restricted Stock Units Agreement for Nonemployee Directors and form of notice under the Company's 2022 Long-Term Incentive Plan.

EXHIBIT 10.1 SKYWARD SPECIALTY INSURANCE GROUP, INC. RESTRICTED STOCK UNITS NOTICE UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN Name of Grantee: /Participant Name/ This Notice evidences the award of restricted stock units (each, an “RSU,” and collectively, the “RSUs”) of Skyward Specialty Insurance Group, Inc., a Delaware corporation (the “Company”), that have be

August 5, 2024 EX-99.1

Premiums ($ in thousands) Three months ended June 30, Six months ended June 30, unaudited 2024 2023 % Change 2024 2023 % Change Gross written premiums $ 496,243 $ 421,994 17.6% $ 954,863 $ 782,492 22.0% Ceded written premiums $ (199,114) $ (208,257)

Exhibit 99.1 Skyward Specialty Insurance Group Reports Second Quarter 2024 Results Houston, TX – August 5, 2024 – Skyward Specialty Insurance Group, Inc. (Nasdaq: SKWD) (“Skyward Specialty” or the “Company”) today reported second quarter 2024 net income of $31.0 million, or $0.75 per diluted share, compared to $19.5 million, or $0.51 per diluted share, for the same 2023 period. Net income for the

August 5, 2024 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (date of earliest event reported): August 5, 2024 Skyward Specialty Insurance Group, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 0

May 14, 2024 8-K

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 14, 2024 (May 9, 2024) Skyward Specialty Insurance Group, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or org

May 13, 2024 SC 13G/A

SKWD / Skyward Specialty Insurance Group, Inc. / WESTAIM Corp - AMENDMENT NO. 1 TO SCHEDULE 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 1) Skyward Specialty Insurance Group, Inc. (Name of Issuer) Common Stock, par value $0.01 per share (Title of Class of Securities) 830940102 (CUSIP Number) May 9, 2024 (Date of Event which Requires Filing of this Statement) Check the appropriate box to desig

May 7, 2024 EX-1.1

Underwriting Agreement, dated as of May 6, 2024 by and among Skyward Specialty Insurance Group, Inc., Westaim HIIG GP Inc. and Barclays Capital Inc., Keefe, Bruyette & Woods, Inc. and Jefferies LLC, as representatives of the several underwriters named therein

Exhibit 1.1 4,400,000 shares of Common Stock SKYWARD SPECIALTY INSURANCE GROUP, INC. UNDERWRITING AGREEMENT May 6, 2024 Barclays Capital Inc. Keefe, Bruyette & Woods, Inc. Jefferies LLC, As Representatives of the several Underwriters named in Schedule I attached hereto, c/o Barclays Capital Inc. 745 Seventh Avenue New York, New York 10019 c/o Keefe, Bruyette & Woods, Inc. 787 Seventh Avenue New Yo

May 7, 2024 424B7

4,400,000 Shares Skyward Specialty Insurance Group, Inc. Common Stock

TABLE OF CONTENTS  Filed Pursuant to Rule 424(b)(7)   Registration File No. 333-279129 PROSPECTUS SUPPLEMENT (To Prospectus dated May 6, 2024) 4,400,000 Shares Skyward Specialty Insurance Group, Inc. Common Stock The selling stockholder named in this prospectus supplement is offering 4,400,000 shares of our common stock. We will not receive any proceeds from the sale of shares by the selling stock

May 7, 2024 8-K

Entry into a Material Definitive Agreement, Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): May 6, 2024 Skyward Specialty Insurance Group, Inc. (Exact Name of Registrant as Specified in Charter) Delaware (State of Incorporation) 001-41591 14-1957288 Commission File Number (I

May 7, 2024 EX-99.1

Skyward Specialty ANNOUNCES secondary offering of its common stock

Exhibit 99.1 Skyward Specialty ANNOUNCES secondary offering of its common stock HOUSTON, TX. – May 6, 2024 –Skyward Specialty Insurance Group, Inc. (NASDAQ: SKWD) (“Skyward Specialty” or the “Company”) a leader in the specialty property and casualty (“P&C”) market, announced that The Westaim Corporation (“Westaim”), through its wholly-owned subsidiary, Westaim HIIG GP Inc. (the “Selling Stockholde

May 7, 2024 EX-FILING FEES

CALCULATION OF FILING FEE TABLE (Form Type) Skyward Specialty Insurance Group, Inc. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered Securities

Exhibit 107 CALCULATION OF FILING FEE TABLE 424(b)(7) (Form Type) Skyward Specialty Insurance Group, Inc.

May 7, 2024 EX-99.2

Skyward Specialty ANNOUNCES PRICING OF its secondary offering of its common stock

Exhibit 99.2 Skyward Specialty ANNOUNCES PRICING OF its secondary offering of its common stock HOUSTON, TX. – May 6, 2024 –Skyward Specialty Insurance Group, Inc. (NASDAQ: SKWD) (“Skyward Specialty” or the “Company”) a leader in the specialty property and casualty (“P&C”) market, announced the pricing of its secondary offering of 4,400,000 shares being offered by The Westaim Corporation, through i

May 6, 2024 EX-FILING FEES

Filing Fee Table (filed herewith).

Exhibit 107 Calculation of Filing Fee Tables Form S-3ASR (Form Type) Skyward Specialty Insurance Group, Inc.

May 6, 2024 S-3ASR

As filed with the Securities and Exchange Commission on May 6, 2024

TABLE OF CONTENTS As filed with the Securities and Exchange Commission on May 6, 2024 Registration No.

May 6, 2024 424B7

Subject to Completion, Dated May 6, 2024 4,400,000 Shares Skyward Specialty Insurance Group, Inc. Common Stock

TABLE OF CONTENTS The information in this preliminary prospectus is not complete and may be changed.

May 6, 2024 EX-4.2

Form of Indenture (filed herewith).

Exhibit 4.2 SKYWARD SPECIALTY INSURANCE GROUP, INC. INDENTURE Dated as of [·] [·] Trustee TABLE OF CONTENTS Page ARTICLE 1 DEFINITIONS 1 Section 1.01. Certain Terms Defined 1 Section 1.02. Other Definitions 6 Section 1.03. Rules of Construction 6 ARTICLE 2 SECURITY FORMS 6 Section 2.01. Forms Generally 6 Section 2.02. Guarantees by Guarantor; Form of Guarantee; Release of Guarantee 7 Section 2.03.

May 3, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

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, 2024 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 SP

May 1, 2024 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (date of earliest event reported): May 1, 2024 Skyward Specialty Insurance Group, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-

May 1, 2024 EX-99.1

Premiums ($ in thousands) Three months ended March 31, unaudited 2024 2023 % Change Gross written premiums $ 458,620 $ 360,498 27.2% Ceded written premiums $ (171,520) $ (158,357) 8.3% Net retention 62.6% 56.1% NM (1) Net written premiums $ 287,100 $

Exhibit 99.1 Skyward Specialty Insurance Group Reports First Quarter 2024 Results Houston, TX – May 1, 2024 – Skyward Specialty Insurance Group, Inc. (Nasdaq: SKWD) (“Skyward Specialty” or the “Company”) today reported first quarter 2024 net income of $36.8 million, or $0.90 per diluted share, compared to $15.6 million, or $0.42 per diluted share. for the same 2023 period. Adjusted operating incom

April 8, 2024 DEFR14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. 1)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. 1) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (

April 5, 2024 EX-FILING FEES

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Table Form S-8 (Form Type) Skyward Specialty Insurance Group, Inc.

April 5, 2024 S-8

As filed with the Securities and Exchange Commission on April 5, 2024

As filed with the Securities and Exchange Commission on April 5, 2024 Registration No.

April 2, 2024 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (as permitted by Ru

April 1, 2024 EX-10.13

Amended Form of Performance Share (GBVPS) Agreement under the Company’s 2022 Long-Term Incentive Plan.

EXHIBIT 10.13 SKYWARD SPECIALTY INSURANCE GROUP, INC. PERFORMANCE-BASED RESTRICTED STOCK UNITS AGREEMENT UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN (Relative GBVPS) Name of Grantee: This Notice evidences the award of performance-based restricted stock units (each, a “PSU,” and collectively, the “PSUs”) of Skyward Specialty Insurance Group, Inc., a Delaware corp

April 1, 2024 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a Party other than the Registrant o Check the appropriate box: o Preliminary Proxy Statement o Confidential, for Use of the Commission Only (

April 1, 2024 EX-10.14

Amended Form of Performance Share (Executives) Agreement under the Company’s 2022 Long-Term Incentive Plan.

EXHIBIT 10.14 SKYWARD SPECIALTY INSURANCE GROUP, INC. PERFORMANCE-BASED RESTRICTED STOCK UNITS AGREEMENT UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN (COMBINED RATIO) Name of Grantee: This Notice evidences the award of performance-based restricted stock units (each, a “PSU,” and collectively, the “PSUs”) of Skyward Specialty Insurance Group, Inc., a Delaware corp

April 1, 2024 EX-97

Policy for Recovery of Erroneously Awarded Incentive Compensation (“Clawback Policy”)

EXHIBIT 97 SKYWARD SPECIALTY INSURANCE GROUP, INC. POLICY FOR RECOVERY OF ERRONEOUSLY AWARDED INCENTIVE COMPENSATION (Adopted November 9, 2023) 1. INTRODUCTION Skyward Specialty Insurance Group, Inc. (the “Company”) is adopting this policy (this “Policy”) to provide for the Company’s recovery of certain Incentive Compensation (as defined below) erroneously awarded to Affected Officers (as defined

April 1, 2024 EX-10.18

Amended Form of Restricted Stock Unit (Others) Agreement under the Company’s 2022 Long-Term Incentive Plan.

EXHIBIT 10.18 SKYWARD SPECIALTY INSURANCE GROUP, INC. RESTRICTED STOCK UNITS NOTICE UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN Name of Grantee: This Notice evidences the award of restricted stock units (each, a “RSU,” and collectively, the “RSUs”) of Skyward Specialty Insurance Group, Inc., a Delaware corporation (the “Company”), that have been granted to you p

April 1, 2024 EX-10.15

Amended Form of Performance Share (Others) Agreement under the Company’s 2022 Long-Term Incentive Plan.

EXHIBIT 10.15 SKYWARD SPECIALTY INSURANCE GROUP, INC. PERFORMANCE-BASED RESTRICTED STOCK UNITS AGREEMENT UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN (COMBINED RATIO) Name of Grantee: This Notice evidences the award of performance-based restricted stock units (each, a “PSU,” and collectively, the “PSUs”) of Skyward Specialty Insurance Group, Inc., a Delaware corp

April 1, 2024 EX-10.16

Amended Form of Performance Cash Units Agreement under the Company’s Long-Term Incentive Plan.

EXHIBIT 10.16 SKYWARD SPECIALTY INSURANCE GROUP, INC. PERFORMANCE UNIT AGREEMENT UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN (COMBINED RATIO) Name of Grantee: This Notice evidences the award of cash-settled performance stock units (each, a “PU,” and collectively, the “PUs”) of Skyward Specialty Insurance Group, Inc., a Delaware corporation (the “Company”), that

April 1, 2024 EX-10.19

Amended Form of Long-Term Performance Cash Plan and Award Letter under the Company’s 2022 Long-Term Incentive Plan.

EXHIBIT 10.19 SKYWARD SPECIALTY INSURANCE GROUP, INC. LONG-TERM CASH BONUS INCENTIVE PLAN Effective as of February , 2024 I.Purpose. The purpose of the Skyward Specialty Insurance Group, Inc. Long-Term Cash Bonus Incentive Plan is to promote the interests of Skyward Specialty Insurance Group, Inc. by providing both an incentive and a financial reward to Underwriting Division Leaders and certain se

April 1, 2024 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2023 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 SPECIAL

April 1, 2024 EX-10.26

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.

EXHIBIT 10.26 SECOND AMENDMENT AGREEMENT TO THE INVESTMENT MANAGEMENT AGREEMENT THIS SECOND AMENDMENT AGREEMENT TO THE INVESTMENT MANAGEMENT AGREEMENT (the “Second Amendment Agreement”) is entered into this December 8, 2023, with an effective date as of December 8, 2023, between Houston Specialty Insurance Company, Imperium Insurance Company and Great Midwest Insurance Company (collectively the “C

April 1, 2024 EX-10.17

Amended Form of the Restricted Stock Unit (Executives) Agreement under the Company’s 2022 Long-Term Incentive Plan.

EXHIBIT 10.17 SKYWARD SPECIALTY INSURANCE GROUP, INC. RESTRICTED STOCK UNITS NOTICE UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN Name of Grantee: This Notice evidences the award of restricted stock units (each, a “RSU,” and collectively, the “RSUs”) of Skyward Specialty Insurance Group, Inc., a Delaware corporation (the “Company”), that have been granted to you p

April 1, 2024 ARS

ARS

23 2023 2023 annual report2 Dear Shareholders, As I reflect on our progress in my second shareholder letter to you following what was a remarkable and historic year for Skyward Specialty, I find myself energized and inspired by what we have accomplished in such a short time.

April 1, 2024 EX-10.28

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.

EXHIBIT 10.28 FIRST AMENDMENT THIS FIRST AMENDMENT, dated as of February 26, 2024 (this “Agreement”), is by and among SKYWARD SPECIALTY INSURANCE GROUP, INC., a Delaware corporation (the “Borrower”), the Lenders party hereto (which, for the avoidance of doubt, constitute the Required Lenders), and TRUIST BANK, in its capacities as administrative agent for the Lenders (in such capacity, the “Admini

February 20, 2024 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (date of earliest event reported): February 20, 2024 Skyward Specialty Insurance Group, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization

February 20, 2024 EX-99.1

Premiums ($ in thousands) Three months ended December 31 Twelve months ended December 31 unaudited 2023 2022 % Change 2023 2022 % Change Gross written premiums $ 321,605 $ 264,832 21.4% $ 1,459,829 $ 1,143,952 27.6% Ceded written premiums $ (107,488)

Exhibit 99.1 Skyward Specialty Insurance Group Reports Fourth Quarter 2023 Results Houston, TX – February 20, 2024 – Skyward Specialty Insurance Group, Inc.TM (Nasdaq: SKWD) (“Skyward Specialty” or the “Company”) today reported fourth quarter 2023 net income of $29.3 million, or $0.74 per diluted share, compared to $20.4 million, or $0.63 per diluted share, for the same 2022 period. Net income for

February 8, 2024 SC 13G

US8309401029 / Skyward Specialty Insurance Group, Inc. / WESTAIM Corp - SCHEDULE 13G Passive Investment

SC 13G 1 ea193235-13gwestaimskyward.htm SCHEDULE 13G UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 Skyward Specialty Insurance Group, Inc. (Name of Issuer) Common Stock, par value $0.01 per share (Title of Class of Securities) 830940102 (CUSIP Number) December 31, 2023 (Date of Event which Requires Filing of this Stat

February 8, 2024 EX-99.1

Joint Filing Agreement, dated as of February 8, 2024, by and among the Reporting Persons

EX-99.1 2 ea193235ex99-1skyward.htm JOINT FILING AGREEMENT, DATED AS OF FEBRUARY 8, 2024, BY AND AMONG THE REPORTING PERSONS EXHIBIT 99.1 JOINT FILING AGREEMENT Each of the undersigned hereby acknowledges and agrees, in compliance with the provisions of Rule 13d-1(k)(1)(iii) promulgated under the Securities Exchange Act of 1934, as amended, that the Schedule 13G to which this agreement is attached

January 29, 2024 SC 13G

US8309401029 / Skyward Specialty Insurance Group, Inc. / BlackRock Inc. Passive Investment

SC 13G 1 us8309401029012924.txt us8309401029012924.txt SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No: ) Skyward Specialty Insurance Group, Inc. - (Name of Issuer) Common Stock - (Title of Class of Securities) 830940102 - (CUSIP Number) December 31, 2023 - (Date of Event Which Requires Filing of this Statement) Check t

December 14, 2023 EX-99.1

SKYWARD SPECIALTY ADDS MICHAEL MORRISSEY TO ITS BOARD OF DIRECTORS

Exhibit 99.1 SKYWARD SPECIALTY ADDS MICHAEL MORRISSEY TO ITS BOARD OF DIRECTORS HOUSTON, TX. – December 14, 2023 – Skyward Specialty Insurance Group Inc.TM (NASDAQ: SKWD) (“Skyward Specialty” or “the Company”), a leader in the specialty property and casualty (“P&C”) market, is pleased to announce the addition of Mike Morrissey, CFA to its Board of Directors effective December 14, 2023. During his

December 14, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): December 14, 2023 Skyward Special

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): December 14, 2023 Skyward Specialty Insurance Group, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization

November 30, 2023 8-K

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): November 30, 2023 Skyward Specialty Insurance Group, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization

November 30, 2023 EX-99.1

Skyward Specialty announces leadership changes to its board of directors

Exhibit 99.1 Skyward Specialty announces leadership changes to its board of directors HOUSTON, TX. – November 30, 2023 –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 a series of changes to its Board of Directors (the “Board”) effective Thursday, November 30, 2023. Cameron MacDo

November 16, 2023 424B4

5,000,000 Shares Skyward Specialty Insurance Group, Inc. Common Stock

TABLE OF CONTENTS  Filed Pursuant to Rule 424(b)(4)  Registration No. 333-275500 5,000,000 Shares Skyward Specialty Insurance Group, Inc. Common Stock This is a public offering of shares of common stock of Skyward Specialty Insurance Group, Inc. We are offering 2,150,000 shares of our common stock. The selling stockholder identified in this prospectus is offering an additional 2,850,000 shares of

November 15, 2023 EX-FILING FEES

Filing Fee Table.

Exhibit 107 Calculation of Filing Fee Tables Form S-1 (Form Type) Skyward Specialty Insurance Group, Inc.

November 15, 2023 S-1MEF

As filed with the Securities and Exchange Commission on November 15, 2023.

As filed with the Securities and Exchange Commission on November 15, 2023. Registration No. 333- UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM S-1 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 SKYWARD SPECIALTY INSURANCE GROUP, INC. (Exact name of Registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization)

November 13, 2023 CORRESP

VIA EDGAR

VIA EDGAR Securities and Exchange Commission Division of Corporation Finance 100 F Street, N.

November 13, 2023 EX-FILING FEES

Filing Fee Table.

Exhibit 107 Calculation of Filing Fee Tables Form S-1 (Form Type) Skyward Specialty Insurance Group, Inc.

November 13, 2023 EX-1.1

Form of Underwriting Agreement.

Exhibit 1.1 shares of Common Stock SKYWARD SPECIALTY INSURANCE GROUP, INC. UNDERWRITING AGREEMENT , 2023 Barclays Capital Inc. Keefe, Bruyette & Woods, Inc. Jefferies LLC, As Representatives of the several Underwriters named in Schedule I attached hereto, c/o Barclays Capital Inc. 745 Seventh Avenue New York, New York 10019 c/o Keefe, Bruyette & Woods, Inc. 787 Seventh Avenue New York, New York 10

November 13, 2023 CORRESP

[Signature Page Follows]

Barclays Capital Inc. 745 Seventh Avenue New York, New York 10019 Keefe, Bruyette & Woods, Inc. 787 Seventh Avenue New York, New York 10019 Jefferies LLC 520 Madison Avenue New York, New York 10022 November 13, 2023 VIA EDGAR Securities and Exchange Commission Division of Corporation Finance 100 F Street, N.E. Washington, D.C. 20549 Attention: Robert Arzonetti Re: Skyward Specialty Insurance Group

November 13, 2023 S-1

As filed with the Securities and Exchange Commission on November 13, 2023.

TABLE OF CONTENTS As filed with the Securities and Exchange Commission on November 13, 2023.

November 9, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

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 September 30, 2023 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 SKYWAR

November 6, 2023 EX-99.1

Premiums ($ in thousands) Three months ended September 30, Nine months ended September 30, unaudited 2023 2022 % Change 2023 2022 % Change Gross written premiums $ 355,732 $ 270,250 31.6% $ 1,138,224 $ 879,119 29.5% Ceded written premiums $ (75,036)

Exhibit 99.1 Skyward Specialty Insurance Group Reports Third Quarter 2023 Results Houston, TX – November 6, 2023 – Skyward Specialty Insurance Group, Inc. (Nasdaq: SKWD) (“Skyward Specialty” or the “Company”) today reported third quarter 2023 net income of $21.7 million, or $0.57 per diluted share, compared to a net loss of $2.4 million, or $0.15 per diluted share, for the same 2022 period. Net in

November 6, 2023 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (date of earliest event reported): November 6, 2023 Skyward Specialty Insurance Group, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization)

October 19, 2023 LETTER

LETTER

United States securities and exchange commission logo October 19, 2023 Andrew Robinson Chief Executive Officer Skyward Specialty Insurance Group, Inc.

October 11, 2023 DRS

As confidentially submitted to the Securities and Exchange Commission on October 11, 2023. This draft registration statement has not been publicly filed with the Securities and Exchange Commission and all information herein remains strictly confident

TABLE OF CONTENTS As confidentially submitted to the Securities and Exchange Commission on October 11, 2023.

August 15, 2023 EX-99.1

Skyward Specialty Welcomes Gena Ashe to Board of Directors

Exhibit 99.1 Skyward Specialty Welcomes Gena Ashe to Board of Directors HOUSTON, TX. – August 15, 2023 –Skyward Specialty Insurance Group Inc.TM (NASDAQ: SKWD) ("Skyward Specialty" or "the Company"), a leader and innovator in the specialty property and casualty market, is pleased to announce the addition of Gena Ashe to its Board of Directors as an independent director effective August 14, 2023. M

August 15, 2023 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (date of earliest event reported): August 15, 2023 (August 14, 2023) Skyward Specialty Insurance Group, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41591 14-1957288 (State or other jurisdic

August 10, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

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 June 30, 2023 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 SPE

August 8, 2023 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (date of earliest event reported): August 8, 2023 Skyward Specialty Insurance Group, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 0

August 8, 2023 EX-99.1

Premiums ($ in thousands) Three months ended June 30, Six months ended June 30, unaudited 2023 2022 % Change 2023 2022 % Change Gross written premiums $ 421,994 $ 326,227 29.4% $ 782,492 $ 608,869 28.5% Ceded written premiums $ (208,257) $ (137,496)

Exhibit 99.1 Skyward Specialty Insurance Group Reports Second Quarter 2023 Results Houston, TX – August 8, 2023 – Skyward Specialty Insurance Group, Inc. (Nasdaq: SKWD) (“Skyward Specialty” or the “Company”) today reported second quarter 2023 net income of $19.5 million, or $0.51 per diluted share, compared to $5.1 million, or $0.16 per diluted share, for the same 2022 period. Net income for the f

June 8, 2023 424B4

3,850,000 Shares Skyward Specialty Insurance Group, Inc. Common Stock

TABLE OF CONTENTS  Filed Pursuant to Rule 424(b)(4)  Registration No. 333-272427 3,850,000 Shares Skyward Specialty Insurance Group, Inc. Common Stock The selling stockholders are offering 3,850,000 shares of our common stock. We will not receive any proceeds from the sale of shares by the selling stockholders. Our common stock is listed on the Nasdaq Global Select Market (“Nasdaq”) under the symb

June 6, 2023 S-1/A

As filed with the Securities and Exchange Commission on June 6, 2023.

As filed with the Securities and Exchange Commission on June 6, 2023. Registration No. 333-272427 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 AMENDMENT NO. 1 FORM S-1 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 SKYWARD SPECIALTY INSURANCE GROUP, INC. (Exact name of Registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation

June 5, 2023 EX-1.1

Form of Underwriting Agreement.

Exhibit 1.1 shares of Common Stock SKYWARD SPECIALTY INSURANCE GROUP, INC. UNDERWRITING AGREEMENT , 2023 Barclays Capital Inc. Keefe, Bruyette & Woods, Inc., As Representatives of the several Underwriters named in Schedule I attached hereto, c/o Barclays Capital Inc. 745 Seventh Avenue New York, New York 10019 c/o Keefe, Bruyette & Woods, Inc. 787 Seventh Avenue New York, New York 10019 Ladies and

June 5, 2023 S-1

As filed with the Securities and Exchange Commission on June 5, 2023.

TABLE OF CONTENTS As filed with the Securities and Exchange Commission on June 5, 2023.

June 5, 2023 EX-FILING FEES

Filing Fee Table.

Exhibit 107 Calculation of Filing Fee Tables Form S-1 (Form Type) Skyward Specialty Insurance Group, Inc.

June 5, 2023 CORRESP

[Signature Page Follows]

Barclays Capital Inc. 745 Seventh Avenue New York, New York 10019 Keefe, Bruyette & Woods, Inc. 787 Seventh Avenue New York, New York 10019 June 5, 2023 VIA EDGAR Securities and Exchange Commission Division of Corporation Finance 100 F Street, N.E. Washington, D.C. 20549 Attention: Madeline Mateo Re: Skyward Specialty Insurance Group, Inc. Registration Statement on Form S-1 File No. 333-272427 Acc

June 5, 2023 CORRESP

June 5, 2023

June 5, 2023 VIA EDGAR Securities and Exchange Commission Division of Corporation Finance 100 F Street, N.

June 2, 2023 LETTER

LETTER

United States securities and exchange commission logo June 2, 2023 Andrew Robinson Chief Executive Officer Skyward Specialty Insurance Group, Inc.

May 30, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 25, 2023 Skyward Specialty In

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 25, 2023 Skyward Specialty Insurance Group, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001

May 25, 2023 DRS

Confidential Treatment Requested by Skyward Specialty Insurance Group, Inc. Pursuant to 17 C.F.R. Section 200.83 As confidentially submitted to the Securities and Exchange Commission on May 25, 2023.

DRS 1 filename1.htm TABLE OF CONTENTS Confidential Treatment Requested by Skyward Specialty Insurance Group, Inc. Pursuant to 17 C.F.R. Section 200.83 As confidentially submitted to the Securities and Exchange Commission on May 25, 2023. Registration No. 333-268326 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM S-1 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 19

May 16, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (date of earliest event reported): May 15, 2023 Skyward Specialty In

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (date of earliest event reported): May 15, 2023 Skyward Specialty Insurance Group, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41591 14-1957288 (State or other jurisdiction of incorporation

May 16, 2023 EX-99.1

Skyward Specialty Adds Anthony J. Kuczinski to Board of Directors

Exhibit 99.1 Skyward Specialty Adds Anthony J. Kuczinski to Board of Directors May 16, 2023 HOUSTON, May 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, is pleased to announce the addition of Anthony J. Kuczinski to its Board of Directors effective August 1, 2023. Wit

May 11, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

Table of Contents 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, 2023 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 00

May 9, 2023 EX-99.1

Premiums ($ in thousands) Three months ended March 31 unaudited 2023 2022 % Change Gross written premiums $ 360,498 $ 282,642 27.5% Ceded written premiums $ (158,357) $ (147,241) 7.5% Net retention 56.1% 47.9% NM (1) Net written premiums $ 202,141 $

Exhibit 99.1 Skyward Specialty Insurance Group Reports First Quarter 2023 Results Houston, TX – May 9, 2023 – Skyward Specialty Insurance Group, Inc. (Nasdaq: SKWD) (“Skyward Specialty” or the “Company”) today reported first quarter 2023 net income of $15.6 million, or $0.42 per diluted share, compared to $16.3 million, or $0.50 per diluted share, for the same 2022 period. Adjusted operating incom

May 9, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (date of earliest event reported): May 9, 2023 Skyward Specialty Ins

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (date of earliest event reported): May 9, 2023 Skyward Specialty Insurance Group, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 001-

April 19, 2023 DEFR14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. 1)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. 1) Filed by the Registrant x Filed by a Party other than the Registrant ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission Only (

April 14, 2023 DEF 14A

our Definitive Proxy Statement on Schedule 14A, filed on April 14, 2023

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (

April 14, 2023 ARS

ARS

T his letter, our first as a public Company, follows an extraordinary year for Skyward Specialty.

April 14, 2023 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

DEFA14A 1 tm237395d2defa14a.htm DEFA14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a Party other than the Registrant ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of

April 3, 2023 EX-10.2

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).

EXHIBIT 10.2 Execution Version GUARANTY AGREEMENT This GUARANTY AGREEMENT, dated as of March 29, 2023, is made by SKYWARD SERVICE COMPANY, a Delaware corporation (“Skyward Service”) and SKYWARD UNDERWRITERS AGENCY, INC., a Texas corporation (“Skyward Underwriters”; and together with Skyward Service and any Person who becomes a “Guarantor” pursuant to the terms hereof after the date hereof, collect

April 3, 2023 EX-10.1

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).

EXHIBIT 10.1 Execution Version Deal CUSIP: 83089LAA1 Revolver CUSIP: 83089LAB9 CREDIT AGREEMENT dated as of March 29, 2023 among SKYWARD SPECIALTY INSURANCE GROUP, INC., as the Borrower THE LENDERS FROM TIME TO TIME PARTY HERETO and TRUIST BANK, as Administrative Agent TRUIST SECURITIES, INC. as Left Lead Arranger and Joint Book Runner and CITIZENS BANK, N.A., and BMO HARRIS BANK N.A. as Joint Lea

April 3, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): March 29, 2023 Skyward Specialty

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): March 29, 2023 Skyward Specialty Insurance Group, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization) 0

March 28, 2023 EX-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).

EXHIBIT 10.10 SKYWARD SPECIALTY INSURANCE GROUP, INC. PERFORMANCE-BASED RESTRICTED STOCK UNITS AGREEMENT UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN (COMBINED RATIO) Name of Grantee: This Notice evidences the award of performance-based restricted stock units (each, an “PSU,” and collectively, the “PSUs”) of Skyward Specialty Insurance Group, Inc., a Delaware cor

March 28, 2023 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) x ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2022 OR o 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 001-415

March 28, 2023 EX-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).

EXHIBIT 10.12 SKYWARD SPECIALTY INSURANCE GROUP, INC. PERFORMANCE UNIT AGREEMENT UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN (COMBINED RATIO) Name of Grantee: This Notice evidences the award of cash-settled performance stock units (each, an “PU,” and collectively, the “PUs”) of Skyward Specialty Insurance Group, Inc., a Delaware corporation (the “Company”), that

March 28, 2023 EX-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).

EXHIBIT 10.11 SKYWARD SPECIALTY INSURANCE GROUP, INC. PERFORMANCE-BASED RESTRICTED STOCK UNITS AGREEMENT UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN (Relative GBVPS) Name of Grantee: This Notice evidences the award of performance-based restricted stock units (each, an “PSU,” and collectively, the “PSUs”) of Skyward Specialty Insurance Group, Inc., a Delaware cor

March 28, 2023 EX-4.2

Description of Capital Stock

EXHIBIT 4.2 DESCRIPTION OF CAPITAL STOCK REGISTERED PURSUANT TO SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934 The following description of the capital stock of Skyward Specialty Insurance Group, Inc. (“we,” “us” and “our”) is a summary and does not purport to be complete. It is subject to, and qualified in its entirety by reference to, our Amended and Restated Certificate of Incorporation (“Ce

February 28, 2023 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (date of earliest event reported): February 28, 2023 Skyward Special

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (date of earliest event reported): February 28, 2023 Skyward Specialty Insurance Group, Inc. (Exact name of registrant as specified in its charter) Delaware (State or other jurisdiction of incorporation or organization

February 28, 2023 EX-99.1

Premiums ($ in thousands) Three months ended December 31 Twelve months ended December 31 unaudited 2022 2021 % Change 2022 2021 % Change Total continuing business $ 263,880 $ 217,346 21.4% $ 1,138,627 $ 867,906 31.2 % Exited business 952 6,837 (86.1)

Exhibit 99.1 Skyward Specialty Insurance Group Reports Fourth Quarter 2022 Results Houston, TX – February 28, 2023 – Skyward Specialty Insurance Group, Inc. (Nasdaq: SKWD) (“Skyward Specialty” or the “Company”) today reported fourth quarter 2022 net income of $20.4 million, or $0.63 per diluted share, compared to $1.3 million, or $0.04 per diluted share, for the same 2021 period. Adjusted operatin

January 18, 2023 8-K

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): January 18, 2023 Skyward Specialty Insurance Group, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41591 14-1957288 (State or other jurisdiction of incorpora

January 18, 2023 EX-99.1

SKYWARD SPECIALTY ANNOUNCES PRICING OF UPSIZED INITIAL PUBLIC OFFERING

Exhibit 99.1 SKYWARD SPECIALTY ANNOUNCES PRICING OF UPSIZED INITIAL PUBLIC OFFERING Houston, TX – (January 12, 2023) - Skyward Specialty Insurance Group, Inc. ("Skyward Specialty" or the “Company") announced today that it has priced its upsized initial public offering of 8,952,383 shares of its common stock, with 4,750,000 shares being offered by Skyward Specialty and 4,202,383 shares being sold b

January 18, 2023 EX-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).

EX-3.1 2 tm233575d1ex3-1.htm EXHIBIT 3.1 Exhibit 3.1 AMENDED AND RESTATED CERTIFICATE OF INCORPORATION OF SKYWARD SPECIALTY INSURANCE GROUP, INC. a Delaware corporation (Pursuant to Sections 242 and 245 of the General Corporation Law of the State of Delaware) Skyward Specialty Insurance Group, Inc., (the “Corporation”) a corporation organized and existing under and by virtue of the provisions of t

January 18, 2023 EX-99.2

SKYWARD SPECIALTY ANNOUNCES CLOSING OF INITIAL PUBLIC OFFERING

Exhibit 99.2 SKYWARD SPECIALTY ANNOUNCES CLOSING OF INITIAL PUBLIC OFFERING Houston, TX – (January 18, 2023) - Skyward Specialty Insurance Group, Inc. ("Skyward Specialty" or the "Company") announced today the closing of its upsized initial public offering of 8,952,383 shares of its common stock, consisting of 4,750,000 shares sold by Skyward Specialty and 4,202,383 shares sold by selling stockhol

January 18, 2023 EX-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).

Exhibit 3.2 AMENDED AND RESTATED Bylaws of SKYWARD SPECIALTY INSURANCE GROUP, INC. Effective as of January 18, 2023 ARTICLE I CORPORATE OFFICES 1.1 Registered Office. The address of the registered office of Skyward Specialty Insurance Group, Inc. (the “Corporation”) in the State of Delaware, and the name of its registered agent at such address, shall be as set forth in the Corporation’s certificat

January 13, 2023 424B4

8,952,383 Shares Skyward Specialty Insurance Group, Inc. Common Stock

TABLE OF CONTENTS  Filed Pursuant to Rule 424(b)(4)  Registration No. 333-268326 8,952,383 Shares Skyward Specialty Insurance Group, Inc. Common Stock This is an initial public offering of shares of common stock of Skyward Specialty Insurance Group, Inc. We are offering 4,750,000 shares of common stock. The selling stockholders identified in this prospectus are offering an additional 4,202,383 sha

January 12, 2023 EX-99.9

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).

Exhibit 99.9 Grant No.: SKYWARD SPECIALTY INSURANCE GROUP, INC. INCENTIVE STOCK OPTION NOTICE This Notice evidences the award of stock options (each, an “Option” or collectively, the “Options”) that have been granted to you, [NAME], subject to and conditioned upon your agreement to the terms of the attached Incentive Stock Option Agreement (the “Agreement”). The Options entitle you to purchase sha

January 12, 2023 S-8

As filed with the Securities and Exchange Commission on January 12, 2023

As filed with the Securities and Exchange Commission on January 12, 2023 Registration No.

January 12, 2023 8-A12B/A

The description of the Registrant’s common stock contained in the Registrant’s Registration Statement on Form 8-A (File No. 001-41591), filed by the Registrant with the SEC under Section 12(b) of the Exchange Act, on January 12, 2023, including any amendments or reports filed for the purpose of updating such description; and

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-A/A Amendment No. 1 FOR REGISTRATION OF CERTAIN CLASSES OF SECURITIES PURSUANT TO SECTION 12(b) OR (g) OF THE SECURITIES EXCHANGE ACT OF 1934 SKYWARD SPECIALTY INSURANCE GROUP, INC. (Exact name of registrant as specified in its charter) Delaware 14-1957288 (State of incorporation or organization) (I.R.S. Employer Identi

January 12, 2023 EX-99.7

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).

Exhibit 99.7 FORM Restricted Stock Agreement under the Skyward Specialty Insurance Group, Inc. 2022 Long-Term Incentive Plan Grantee: No. of Shares: This Agreement (the “Agreement”) evidences the award of restricted shares (each, an “Award Share,” and collectively, the “Award Shares”) of the common stock of Skyward Specialty Insurance Group, Inc., a Delaware corporation (the “Company”), granted to

January 12, 2023 CERT

CERT

The Nasdaq Stock Market LLC, 805 King Farm Blvd., Rockville, MD 20850 Eun Ah Choi Senior Vice President U.S. Listing Qualifications & Market Surveillance By Electronic Mail January 12, 2023 Division of Corporation Finance U.S. Securities and Exchange Commission 100 F Street, N.E. Washington, D.C. 20549 Division of Corporation Finance: This is to certify that on January 12, 2023, The Nasdaq Stock M

January 12, 2023 EX-99.8

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).

Exhibit 99.8 Grant No.: SKYWARD SPECIALTY INSURANCE GROUP, INC. NONSTATUTORY STOCK OPTION NOTICE This Notice evidences the award of nonstatutory stock options (each, an “Option” or collectively, the “Options”) that have been granted to you, [NAME], subject to and conditioned upon your agreement to the terms of the attached Nonstatutory Stock Option Agreement (the “Agreement”). The Options entitle

January 12, 2023 EX-99.4

Skyward Specialty Insurance Group, Inc. 2022 Long-Term Incentive Plan (incorporated by reference to Exhibit 99.4 to the Registrant’s Registration Statement on Form S-8 filed with the Commission on January 12, 2023).

Exhibit 99.4 SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN TABLE OF CONTENTS 1. History; Existence of the Plan 1 2. Purposes of the Plan 1 3. Terminology 1 4. Administration 1 (a) Administration of the Plan 1 (b) Powers of the Administrator 1 (c) Delegation of Administrative Authority 3 (d) Non-Uniform Determinations 3 (e) Limited Liability; Advisors 3 (f) Indemnification 3

January 12, 2023 EX-99.5

Skyward Specialty Insurance Group, Inc. 2022 Employee Stock Purchase Plan (incorporated by reference to Exhibit 99.5 to the Registrant’s Registration Statement on Form S-8 filed with the Commission on January 12, 2023).

EX-99.5 5 tm233124d1ex99-5.htm EXHIBIT 99.5 Exhibit 99.5 SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 EMPLOYEE STOCK PURCHASE PLAN Table of Contents Page 1. Establishment, Purpose and Term of Plan 1 1.1 Establishment 1 1.2 Purpose 1 1.3 Term of Plan 1 2. Definitions and Construction 1 2.1 Definitions 1 2.2 Construction 5 3. Administration 5 3.1 Administration by the Committee 5 3.2 Authority of Of

January 12, 2023 EX-99.6

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).

Exhibit 99.6 SKYWARD SPECIALTY INSURANCE GROUP, INC. RESTRICTED STOCK UNITS NOTICE UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN Name of Grantee: This Notice evidences the award of restricted stock units (each, an “RSU,” and collectively, the “RSUs”) of Skyward Specialty Insurance Group, Inc., a Delaware corporation (the “Company”), that have been granted to you p

January 12, 2023 EX-FILING FEES

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Table Form S-8 (Form Type) Skyward Specialty Insurance Group, Inc.

January 12, 2023 8-A12B

the Form 8-A, filed on January 12, 2023.

8-A12B 1 tm228594d208a12b.htm 8-A12B UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-A FOR REGISTRATION OF CERTAIN CLASSES OF SECURITIES PURSUANT TO SECTION 12(b) OR (g) OF THE SECURITIES EXCHANGE ACT OF 1934 SKYWARD SPECIALTY INSURANCE GROUP, INC. (Exact name of registrant as specified in its charter) Delaware 14-1957288 (State of incorporation or organization) (I.R

January 10, 2023 CORRESP

[Signature Page Follows]

Barclays Capital Inc. 745 Seventh Avenue New York, New York 10019 Keefe, Bruyette & Woods, Inc. 787 Seventh Avenue New York, New York 10019 January 10, 2023 VIA EDGAR Securities and Exchange Commission Division of Corporation Finance 100 F Street, N.E. Washington, D.C. 20549 Attention: Tonya K. Aldave Susan Block Rolf Sundwall Mark Brunhofer Re: Skyward Specialty Insurance Group, Inc. Registration

January 10, 2023 CORRESP

January 10, 2023

January 10, 2023 VIA EDGAR U.S. Securities and Exchange Commission Division of Corporation Finance 100 F Street, N.E. Washington, D.C. 20549 Attention: Tonya K. Aldave Susan Block Rolf Sundwall Mark Brunhofer Re: Skyward Specialty Insurance Group, Inc. Registration Statement on Form S-1 File No. 333-268326 Acceleration Request Requested Date:         January 12, 2023 Requested Time:        4:00 p.

January 4, 2023 EX-1.1

Form of Underwriting Agreement.

EX-1.1 2 tm228594d16ex1-1.htm EXHIBIT 1.1 Exhibit 1.1 shares of Common Stock SKYWARD SPECIALTY INSURANCE GROUP, INC. UNDERWRITING AGREEMENT , 2023 Barclays Capital Inc. Keefe, Bruyette & Woods, Inc., As Representatives of the several Underwriters named in Schedule I attached hereto, c/o Barclays Capital Inc. 745 Seventh Avenue New York, New York 10019 c/o Keefe, Bruyette & Woods, Inc. 787 Seventh

January 4, 2023 EX-FILING FEES

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables Form S-1 (Form Type) Skyward Specialty Insurance Group, Inc.

January 4, 2023 S-1/A

As filed with the Securities and Exchange Commission on January 4, 2023.

TABLE OF CONTENTS As filed with the Securities and Exchange Commission on January 4, 2023.

November 14, 2022 EX-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).

EX-3.1 2 tm228594d12ex3-1.htm EXHIBIT 3.1 Exhibit 3.1 AMENDED AND RESTATED CERTIFICATE OF INCORPORATION OF SKYWARD SPECIALTY INSURANCE GROUP, INC. a Delaware corporation (Pursuant to Sections 242 and 245 of the General Corporation Law of the State of Delaware) Skyward Specialty Insurance Group, Inc., (the “Corporation”) a corporation organized and existing under and by virtue of the provisions of

November 14, 2022 EX-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).

Exhibit 10.2 EXECUTIVE SUMMARY OF DOCUMENTATION FOR HOUSTON INTERNATIONAL INSURANCE GROUP, LTD. SHARE PURCHASE AND AWARD AGREEMENTS FOR Share Purchase Agreement ? (?Executive?) purchasing shares of Houston International Insurance Group, Ltd. (?HIIG?) common stock (calculated based upon book value as of . ? Purchase price payable 30% ($.00) in cash and 70% ($.00) with a Note. Promissory Note ? Prin

November 14, 2022 EX-10.8

Form of Promissory Note.

EX-10.8 14 tm228594d12ex10-8.htm EXHIBIT 10.8 Exhibit 10.8 PROMISSORY NOTE $. 00 , 2020 Houston, Texas FOR VALUE RECEIVED, the undersigned, (“Participant”), hereby promises to pay to the order of HOUSTON INTERNATIONAL INSURANCE GROUP, LTD., a Delaware corporation (“Company”), at its designated office, in lawful money of the United States of America, the principal sum of AND NO/100 DOLLARS ($.00),

November 14, 2022 EX-10.9

Lease Agreement by and between Memorial City Towers, Ltd. and Southwest Insurance Partners, Inc., dated December 1, 2008, with Amendment No. 1, dated February 16, 2009, Lease Commencement Agreement, dated August 24, 2009, Supplemental Parking Agreement, dated September 24, 2009, Amendment No. 2, dated August 17, 2010, Supplemental Letter Agreement dated August 26, 2010, Supplemental Lease Commencement Agreement, dated November 8, 2010, Amendment No. 3, dated February 20, 2013, Supplemental Commencement Agreement, dated September 25, 2013, Amendment No. 4, dated April 21, 2015, Amendment No. 5, dated July 27, 2015, Supplemental Commencement Agreement, dated October 7, 2015, Supplemental Commencement Agreement, dated April 7, 2016, Amendment No. 6, dated May 9, 2016, Supplemental Commencement Agreement, dated February 24, 2017, Amendment No. 7, dated November 6, 2017, and Supplemental Commencement Agreement, dated October 3, 2018.

EX-10.9 15 tm228594d12ex10-9.htm EXHIBIT 10.9 Exhibit 10.9 LEASE AGREEMENT This Lease Agreement (“Lease”) is entered into on this 10th day of December 2008 (the “Effective Date”), by and between MEMORIAL CITY TOWERS, LTD., a Texas limited partnership (“Landlord”) and SOUTHWEST INSURANCE PARTNERS, INC., a Texas corporation (whether one or more, “Tenant”). ARTICLE 1 Reference Provisions Section 1.1 

November 14, 2022 EX-3.4

Amended and Restated Bylaws, to be effective immediately prior to closing of this offering.

Exhibit 3.4 AMENDED AND RESTATED BYLAWS OF HOUSTON INTERNATIONAL INSURANCE GROUP, LTD. AS AMENDED AND RESTATED ON JULY 31, 2014 Capitalized terms used but not defined herein shall have the respective meanings set forth in the Amended and Restated Stockholders? Agreement, dated as of March 12, 2014, among the Company and its stockholders (the ?Stockholders? Agreement?). ARTICLE I Stockholders Secti

November 14, 2022 EX-10.13

Consulting Agreement by and between Stephen Way and Skyward Specialty Insurance Group, Inc., dated January 1, 2022.

Exhibit 10.13 CERTAIN CONFIDENTIAL PORTIONS OF THIS EXHIBIT HAVE BEEN OMITTED AND REPLACED WITH ?[***]?. SUCH IDENTIFIED INFORMATION HAS BEEN EXCLUDED FROM THIS EXHIBIT BECAUSE IT IS (I) NOT MATERIAL AND (II) WOULD LIKELY CAUSE COMPETITIVE HARM TO THE COMPANY IF DISCLOSED. CONSULTING AGREEMENT This CONSULTING AGREEMENT AND EXHIBITS (collectively, this ?Agreement?) is made and entered into effectiv

November 14, 2022 EX-10.6

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).

EX-10.6 12 tm228594d12ex10-6.htm EXHIBIT 10.6 Exhibit 10.6 Skyward Specialty Insurance Group, Inc. INDEMNIFICATION AGREEMENT This Indemnification Agreement, dated [], 2021, is made between Skyward Specialty Insurance Group, Inc., a Delaware corporation (the “Company”), and [] (the “Indemnitee”). RECITALS WHEREAS, the Company desires to attract and retain the services of talented and experienced in

November 14, 2022 EX-3.3

Amended and Restated Certificate of Incorporation, to be effective immediately prior to closing of this offering.

Exhibit 3.3

November 14, 2022 EX-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).

EX-4.1 6 tm228594d12ex4-1.htm EXHIBIT 4.1 Exhibit 4.1 Execution Version AMENDED AND RESTATED STOCKHOLDERS’ AGREEMENT By and Among THE STOCKHOLDERS LISTED IN ANNEX A and HOUSTON INTERNATIONAL INSURANCE GROUP, LTD. DATED AS OF MARCH 12, 2014 EXHIBITS Annex A        Stockholders Annex B        Capitalization Table Annex C        Defined Terms Annex D        Charter Annex E         Bylaws Annex F     

November 14, 2022 EX-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).

Exhibit 10.1 Houston International Insurance Group, Ltd. 2016 Equity Incentive Program 1. PURPOSE This Program is intended to foster and promote the long-term financial success of Houston International Insurance Group, Ltd., a Delaware corporation (“Company”), by providing stock purchase and matching stock grant opportunities for its key employees and directors. There are two components to the Pro

November 14, 2022 EX-10.11

Management Services Agreement by and between Westaim HIIG GP Inc. and Houston International Insurance Group, Ltd., dated August 1, 2019.

Exhibit 10.11 MANAGEMENT SERVICES AGREEMENT This MANAGEMENT SERVICES AGREEMENT made as of August 1, 2019 (this ?Agreement?) is between Houston International Insurance Group, Ltd., a Delaware corporation (the ?Company?), and Westaim HIIG GP Inc. (the ?Manager?). BACKGROUND 1.????????Westaim IRIG Limited Partnership, an Ontario, Canada limited partnership (the ?Partnership?) owns approximately 71% o

November 14, 2022 S-1

As filed with the Securities and Exchange Commission on November 14, 2022.

TABLE OF CONTENTS As filed with the Securities and Exchange Commission on November 14, 2022.

November 14, 2022 EX-21.1

List of Subsidiaries of the Company (incorporated by reference to Exhibit 21.1 to the Company's Registration Statement on Form S-1, filed with the SEC on November 14, 2022).

EX-21.1 22 tm228594d12ex21-1.htm EXHIBIT 21.1 Exhibit 21.1 SKYWARD SPECIALTY INSURANCE GROUP, INC. ORGANIZATION CHART As of January 31, 2022

November 14, 2022 EX-10.14

Loss Portfolio Transfer and Adverse Development Retrocession Agreement by and among R&Q Bermuda (SAC) Limited acting in respect of the HIIG Segregated Account, HIIG Re, Houston Specialty Insurance Company, Imperium Insurance Company, and Great Midwest Insurance Company, dated April 1, 2020.

Exhibit 10.14 CERTAIN CONFIDENTIAL PORTIONS OF THIS EXHIBIT HAVE BEEN OMITTED AND REPLACED WITH ?[***]?. SUCH IDENTIFIED INFORMATION HAS BEEN EXCLUDED FROM THIS EXHIBIT BECAUSE IT IS (I) NOT MATERIAL AND (II) WOULD LIKELY CAUSE COMPETITIVE HARM TO THE COMPANY IF DISCLOSED. CONFIDENTIAL INFORMATION Execution Version LOSS PORTFOLIO TRANSFER AND ADVERSE DEVELOPMENT RETROCESSION AGREEMENT by and among

November 14, 2022 EX-10.12

Surety Excess of Loss Reinsurance Contract by and among Everest Reinsurance Company, Houston Specialty Insurance Company, Imperium Insurance Company, Great Midwest Insurance Company, Oklahoma Specialty Insurance Company and Boston Indemnity Company, Inc., dated June 1, 2021.

Exhibit 10.12 JUNE 1, 2021 SUBSURETYSHIP, POWER OF ATTORNEY, AND INDEMNIFICATION AGREEMENT This June 1, 2021 SUBSURETYSHIP, POWER OF ATTORNEY, AND INDEMNIFICATION AGREEMENT (?the June 1, 2021 Agreement?) is made this 1st day of June 2021 by and between EVEREST REINSURANCE COMPANY (?EVEREST?), a Delaware domiciled company with its principal offices at 100 Everest Way, Warren, New Jersey, 07059 and

November 14, 2022 EX-10.15

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).

Exhibit 10.15 CERTAIN CONFIDENTIAL PORTIONS OF THIS EXHIBIT HAVE BEEN OMITTED AND REPLACED WITH ?[***]?. SUCH IDENTIFIED INFORMATION HAS BEEN EXCLUDED FROM THIS EXHIBIT BECAUSE IT IS (I) NOT MATERIAL AND (II) WOULD LIKELY CAUSE COMPETITIVE HARM TO THE COMPANY IF DISCLOSED. INVESTMENT MANAGEMENT AGREEMENT INVESTMENT MANAGEMENT AGREEMENT (the ?Agreement?), made as of the 6th day of November, 2015, a

November 14, 2022 EX-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).

Exhibit 10.3 SKYWARD SPECIALTY INSURANCE GROUP, INC. LONG-TERM INCENTIVE PLAN 1.                  Purpose   The purpose of this Plan is to promote the interests of the Company and its participating Affiliates and Shareholders by enabling the Company and its participating Affiliates to attract, motivate and retain Participants by offering them incentive awards that recognize the creation of value f

November 14, 2022 EX-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).

Exhibit 3.2 AMENDED AND RESTATED Bylaws of SKYWARD SPECIALTY INSURANCE GROUP, INC. Effective as of ARTICLE I CORPORATE OFFICES 1.1 Registered Office. The address of the registered office of Skyward Specialty Insurance Group, Inc. (the ?Corporation?) in the State of Delaware, and the name of its registered agent at such address, shall be as set forth in the Corporation?s certificate of incorporatio

November 14, 2022 EX-10.7

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).

EX-10.7 13 tm228594d12ex10-7.htm EXHIBIT 10.7 Exhibit 10.7 Execution Copy EMPLOYMENT AGREEMENT THIS EMPLOYMENT AGREEMENT (“Agreement”) is made on May 22, 2020 by and between HIIG SERVICE COMPANY and HOUSTON INTERNATIONAL INSURANCE GROUP, Ltd. (“HIIG”), both organized under the laws of the state of Delaware (collectively, the “Company”), and Andrew Robinson (“Executive”). W I T N E S S E T H: WHERE

November 14, 2022 EX-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).

Exhibit 10.5 SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 EMPLOYEE STOCK PURCHASE PLAN Table of Contents Page 1. Establishment, Purpose and Term of Plan 1? 1.1 Establishment 1 1.2 Purpose 1 1.3 Term of Plan 1 2. Definitions and Construction 1 2.1 Definitions 1 2.2 Construction 5 3. Administration 5 3.1 Administration by the Committee 5 3.2 Authority of Officers 6 3.3 Power to Adopt Sub-Plans or Va

November 14, 2022 EX-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).

EX-10.4 10 tm228594d12ex10-4.htm EXHIBIT 10.4 Exhibit 10.4 SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN TABLE OF CONTENTS 1. History; Existence of the Plan 1 2. Purposes of the Plan 1 3. Terminology 1 4. Administration 1 (a) Administration of the Plan 1 (b) Powers of the Administrator 1 (c) Delegation of Administrative Authority 3 (d) Non-Uniform Determinations 3 (e) Limit

November 14, 2022 EX-10.10

Credit Agreement by and between Prosperity Bank and Houston International Insurance Group, Ltd., dated December 11, 2019.

? Exhibit 10.10 ? CLOSING BINDER INDEX ? $100,000,000.00 Credit Facilities from? Prosperity Bank to? Houston International Insurance Group, Ltd. ? Closing Date: December 11, 2019 ? ? ? ? Borrower - Houston International Insurance Group, Ltd. ? ? ? Guarantors - HIIG Service Company HIIG Underwriters Agency, Inc. ? ? ? Borrower?s Counsel - Leslie Shaunty, Vice President-Legal, HIIG Service Company ?

November 14, 2022 CORRESP

CONFIDENTIAL TREATMENT

CONFIDENTIAL TREATMENT REQUESTED BY SKYWARD SPECIALTY INSURANCE GROUP, INC. November 14, 2022 VIA EDGAR Division of Corporation Finance United States Securities and Exchange Commission 100 F Street NE Washington, D.C. 20549 Attention: Tonya K. Aldave Susan Block Rolf Sundwall Mark Brunhofer Re: Skyward Specialty Insurance Group, Inc. Registration Statement on Form S-1 CIK No. 0001519449 Ladies and

November 14, 2022 EX-FILING FEES

Filing Fee Table

EX-FILING FEES 24 tm228594d12ex-fillingfees.htm EX-FILING FEES Exhibit 107 Calculation of Filing Fee Tables Form S-1 (Form Type) Skyward Specialty Insurance Group, Inc. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered Securities Security Type Security Class Title Fee Calculation or Carry Forward Rule Maximum Aggregate Offering Price(1)(2) Fee Rate Amount of Registra

August 22, 2022 DRSLTR

[Remainder of page intentionally blank. Signature page follows.]

August 22, 2022 VIA EDGAR Office of Finance Division of Corporation Finance Securities and Exchange Commission 100 F Street, N.

August 19, 2022 DRS/A

As confidentially submitted to the Securities and Exchange Commission on August 19, 2022. This draft registration statement has not been publicly filed with the Securities and Exchange Commission and all information herein remains strictly confidenti

DRS/A 1 filename1.htm TABLE OF CONTENTS As confidentially submitted to the Securities and Exchange Commission on August 19, 2022. This draft registration statement has not been publicly filed with the Securities and Exchange Commission and all information herein remains strictly confidential. Registration No. 333-       UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 AMENDM

July 8, 2022 DRS/A

As confidentially submitted to the Securities and Exchange Commission on July 8, 2022. This draft registration statement has not been publicly filed with the Securities and Exchange Commission and all information herein remains strictly confidential.

TABLE OF CONTENTS As confidentially submitted to the Securities and Exchange Commission on July 8, 2022.

July 8, 2022 DRSLTR

[Remainder of page intentionally blank. Signature page follows.]

July 8, 2022 VIA EDGAR AND OVERNIGHT COURIER Office of Finance Division of Corporation Finance Securities and Exchange Commission 100 F Street, N.

June 23, 2022 LETTER

LETTER

United States securities and exchange commission logo June 23, 2022 Andrew Robinson Chief Executive Officer Skyward Specialty Insurance Group, Inc.

June 8, 2022 EX-10.7

EMPLOYMENT AGREEMENT

Exhibit 10.7 Execution Copy EMPLOYMENT AGREEMENT THIS EMPLOYMENT AGREEMENT (?Agreement?) is made on May 22, 2020 by and between HIIG SERVICE COMPANY and HOUSTON INTERNATIONAL INSURANCE GROUP, Ltd. (?HIIG?), both organized under the laws of the state of Delaware (collectively, the ?Company?), and Andrew Robinson (?Executive?). W?I?T?N?E?S?S?E?T?H: WHEREAS, the Company desires to employ Executive as

June 8, 2022 EX-10.14

LOSS PORTFOLIO TRANSFER AND ADVERSE DEVELOPMENT RETROCESSION AGREEMENT by and among R&Q BERMUDA (SAC) LIMITED ACTING IN RESPECT OF THE HIIG SEGREGATED ACCOUNT HIIG RE solely for purposes of Article 7, Article 11, Article 12, Article 23, and Article 2

Exhibit 10.14 CONFIDENTIAL INFORMATION Execution Version LOSS PORTFOLIO TRANSFER AND ADVERSE DEVELOPMENT RETROCESSION AGREEMENT by and among R&Q BERMUDA (SAC) LIMITED ACTING IN RESPECT OF THE HIIG SEGREGATED ACCOUNT and HIIG RE and solely for purposes of Article 7, Article 11, Article 12, Article 23, and Article 28 (and Article 2 and Article 30 to the extent relating to any of the foregoing) HOUST

June 8, 2022 DRS/A

As confidentially submitted to the Securities and Exchange Commission on June 8, 2022. This draft registration statement has not been publicly filed with the Securities and Exchange Commission and all information herein remains strictly confidential.

DRS/A 1 filename1.htm TABLE OF CONTENTS As confidentially submitted to the Securities and Exchange Commission on June 8, 2022. This draft registration statement has not been publicly filed with the Securities and Exchange Commission and all information herein remains strictly confidential. Registration No. 333-       UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 AMENDMENT

June 8, 2022 EX-10.15

INVESTMENT MANAGEMENT AGREEMENT

EX-10.15 4 filename4.htm Exhibit 10.15 EXECUTION VERSION INVESTMENT MANAGEMENT AGREEMENT INVESTMENT MANAGEMENT AGREEMENT (the "Agreement"), made as of the 13th day of January, 2016, among Houston Specialty Insurance Company, Imperium Insurance Company and Great Midwest Insurance Company (collectively, the "Client") and Arena Investors, LP, a Delaware limited partnership, as investment adviser (ref

June 8, 2022 DRSLTR

[Remainder of page intentionally blank. Signature page follows.]

June 8, 2022 VIA EDGAR AND OVERNIGHT COURIER Office of Finance Division of Corporation Finance Securities and Exchange Commission 100 F Street, N.

May 19, 2022 LETTER

LETTER

United States securities and exchange commission logo May 19, 2022 Andrew Robinson Chief Executive Officer Skyward Specialty Insurance Group, Inc.

April 22, 2022 EX-10.6

Skyward Specialty Insurance Group, Inc. INDEMNIFICATION AGREEMENT

Exhibit 10.6 Skyward Specialty Insurance Group, Inc. INDEMNIFICATION AGREEMENT This Indemnification Agreement, dated [], 2021, is made between Skyward Specialty Insurance Group, Inc., a Delaware corporation (the ?Company?), and [] (the ?Indemnitee?). RECITALS WHEREAS, the Company desires to attract and retain the services of talented and experienced individuals, such as Indemnitee, to serve as dir

April 22, 2022 EX-10.12

JUNE 1, 2021 SUBSURETYSHIP, POWER OF ATTORNEY, AND INDEMNIFICATION AGREEMENT

Exhibit 10.12 JUNE 1, 2021 SUBSURETYSHIP, POWER OF ATTORNEY, AND INDEMNIFICATION AGREEMENT This June 1, 2021 SUBSURETYSHIP, POWER OF ATTORNEY, AND INDEMNIFICATION AGREEMENT (?the June 1, 2021 Agreement?) is made this 1st day of June 2021 by and between EVEREST REINSURANCE COMPANY (?EVEREST?), a Delaware domiciled company with its principal offices at 100 Everest Way, Warren, New Jersey, 07059 and

April 22, 2022 EX-10.13

CONSULTING AGREEMENT

EX-10.13 15 filename15.htm Exhibit 10.13 CONSULTING AGREEMENT This CONSULTING AGREEMENT AND EXHIBITS (collectively, this “Agreement”) is made and entered into effective as of January 1, 2022 (the “Effective Date”), by and between SKYWARD SPECIALTY INSURANCE GROUP, INC., a Delaware corporation (the “Company”), on the one hand, and SLW INTERNATIONAL, LLC (“Consultant”), and for the limited purposes

April 22, 2022 EX-10.7

EMPLOYMENT AGREEMENT

EX-10.7 9 filename9.htm Exhibit 10.7 Execution Copy EMPLOYMENT AGREEMENT THIS EMPLOYMENT AGREEMENT (“Agreement”) is made on May 22, 2020 by and between HIIG SERVICE COMPANY and HOUSTON INTERNATIONAL INSURANCE GROUP, Ltd. (“HIIG”), both organized under the laws of the state of Delaware (collectively, the “Company”), and Andrew Robinson (“Executive”). W I T N E S S E T H: WHEREAS, the Company desire

April 22, 2022 EX-10.2

EXECUTIVE SUMMARY OF DOCUMENTATION FOR HOUSTON INTERNATIONAL INSURANCE GROUP, LTD. SHARE PURCHASE AND AWARD AGREEMENTS FOR ______________

EX-10.2 6 filename6.htm Exhibit 10.2 EXECUTIVE SUMMARY OF DOCUMENTATION FOR HOUSTON INTERNATIONAL INSURANCE GROUP, LTD. SHARE PURCHASE AND AWARD AGREEMENTS FOR Share Purchase Agreement ● (“Executive”) purchasing shares of Houston International Insurance Group, Ltd. (“HIIG”) common stock (calculated based upon book value as of . ● Purchase price payable 30% ($.00) in cash and 70% ($.00) with a Note

April 22, 2022 EX-10.10

CLOSING BINDER INDEX

? Exhibit 10.10 ? CLOSING BINDER INDEX ? $100,000,000.00 Credit Facilities from? Prosperity Bank to? Houston International Insurance Group, Ltd. ? Closing Date: December 11, 2019 ? ? ? ? Borrower - Houston International Insurance Group, Ltd. ? ? ? Guarantors - HIIG Service Company HIIG Underwriters Agency, Inc. ? ? ? Borrower?s Counsel - Leslie Shaunty, Vice President-Legal, HIIG Service Company ?

April 22, 2022 EX-10.3

SKYWARD SPECIALTY INSURANCE GROUP, INC. LONG-TERM INCENTIVE PLAN

Exhibit 10.3 SKYWARD SPECIALTY INSURANCE GROUP, INC. LONG-TERM INCENTIVE PLAN 1.????????????????? Purpose ? The purpose of this Plan is to promote the interests of the Company and its participating Affiliates and Shareholders by enabling the Company and its participating Affiliates to attract, motivate and retain Participants by offering them incentive awards that recognize the creation of value f

April 22, 2022 EX-4.1

AMENDED AND RESTATED STOCKHOLDERS’ AGREEMENT By and Among THE STOCKHOLDERS LISTED IN ANNEX A HOUSTON INTERNATIONAL INSURANCE GROUP, LTD. DATED AS OF MARCH 12, 2014

Exhibit 4.1 Execution Version AMENDED AND RESTATED STOCKHOLDERS? AGREEMENT By and Among THE STOCKHOLDERS LISTED IN ANNEX A and HOUSTON INTERNATIONAL INSURANCE GROUP, LTD. DATED AS OF MARCH 12, 2014 EXHIBITS Annex A????????Stockholders Annex B????????Capitalization Table Annex C????????Defined Terms Annex D????????Charter Annex E?????????Bylaws Annex F?????????Management Rights Letter Annex G??????

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