Sec Form 4 Filing - Khan Shakoor @ Skyward Specialty Insurance Group, Inc. - 2026-02-25

FORM 4 Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934, Section 17(a) of the Public Utility Holding Company Act of 1935 or Section 30(h) of the Investment Company Act of 1940

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1. Name and Address of Reporting Person Khan Shakoor 2. Issuer Name and Ticker or Trading Symbol Skyward Specialty Insurance Group, Inc. [ SKWD] 5. Relationship of Reporting Person(s) to Issuer (Check all applicable) _____ Director _____ 10% Owner X __ Officer (give title below) _____ Other (specify below) Corp. Dev. Officer (Last) (First) (Middle) 800 GESSNER ROAD, SUITE 600 3. Date of Earliest Transaction (MM/DD/YY) 02/25/2026 (Street) HOUSTON, TX77024 4. If Amendment, Date Original Filed (MM/DD/YY) 6. Individual or Joint/Group Filing (Check Applicable Line) __ X __ Form filed by One Reporting Person _____ Form filed by More than One Reporting Person (City) (State) (Zip)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned 1.Title of Security (Instr. 3) 2. Transaction Date (MM/DD/YY) 2A. Deemed Execution Date, if any (MM/DD/YY) 3. Transaction Code (Instr. 8) 4. Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5) 5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4) 6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4) Code V Amount (A) or (D) Price Common Stock 694 ( 1 ) D

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned ( e.g. , puts, calls, warrants, options, convertible securities) 1. Title of Derivative Security (Instr. 3) 2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (MM/DD/YY) 3A. Deemed Execution Date, if any (MM/DD/YY) 4. Transaction Code (Instr. 8) 5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4, and 5) 6. Date Exercisable and Expiration Date (MM/DD/YY) 7. Title and Amount of Underlying Securities (Instr. 3 and 4) 8. Price of Derivative Security (Instr. 5) 9. Number of Derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form of Derivative Security: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4) Code V (A) (D) Date Exercisable Expiration Date Title Amount or Number of Shares 2026 LTIP - RSUs ( 2 ) 02/25/2026 A 1,261 ( 3 ) ( 3 ) Common Stock 1,261 $ 0 1,261 D 2026 LTIP - PSUs ( 4 ) 02/25/2026 A 1,261 ( 4 ) ( 4 ) Common Stock 1,261 $ 0 1,261 D 2026 LTIP - PSUs ( 5 ) 02/25/2026 A 1,261 ( 5 ) ( 5 ) Common Stock 1,261 $ 0 1,261 D 2026 Bright Future - RSUs ( 2 ) 02/25/2026 A 4,326 ( 6 ) ( 6 ) Common Stock 4,326 $ 0 4,326 D

Reporting Owners Reporting Owner Name / Address Relationships Director 10% Owner Officer Other Khan Shakoor 800 GESSNER ROAD, SUITE 600 HOUSTON, TX77024 Corp. Dev. Officer Signatures /s/ Stacy E. Skelton, Attorney-in-Fact 02/27/2026 Signature of Reporting Person Date

Explanation of Responses:

( 1 )The number of securities reported reflects the June 1, 2025 acquisition of 134 shares and the December 1, 2025 acquisition of 156 shares of the Company's Common Stock pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Employee Stock Purchase Plan ("ESPP") for the ESPP purchase periods of December 1, 2024 through May 31, 2025, and June 1, 2025 through November 30, 2025, respectively. ( 2 )Each Restricted Stock Unit ("RSU") represents the right to receive one share of the Issuer's Common Stock upon settlement. ( 3 )On February 25, 2026, the Reporting Person was granted an RSU Award in the amount of 1,261 RSUs. Subject to the Reporting Person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2029. ( 4 )On February 25, 2026, the Reporting Person was granted 1,261 Performance Stock Units ("PSUs"). Each PSU is equivalent to one share of the Issuer's Common Stock. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on December 31, 2028. ( 5 )On February 25, 2026, the Reporting Person was granted 1,261 PSUs. Each PSU is equivalent to one share of the Issuer's Common Stock. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on December 31, 2028. ( 6 )On February 25, 2026, the Reporting Person was granted an RSU Award in the amount of 4,326 RSUs. Subject to the terms of the RSU Agreement and the Reporting Person's continuous service through the vesting dates, 50% of the RSUs shall vest on January 1, 2029 and the remaining 50% of the RSUs will vest on January 1, 2030.

Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.

* If the form is filed by more than one reporting person, see Instruction 4(b)(v).

** Intentional misstatements or omissions of facts constitute Federal Criminal Violations. See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).

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