Sec Form 4 Filing - Robinson Andrew S @ Skyward Specialty Insurance Group, Inc. - 2023-01-12

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 Robinson Andrew S 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) X __ Director _____ 10% Owner X __ Officer (give title below) _____ Other (specify below) CEO & PRESIDENT (Last) (First) (Middle) 800 GESSNER, SUITE 600 3. Date of Earliest Transaction (MM/DD/YY) 01/12/2023 (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 149,544( 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 2023 RSU Grant (3-Year) ( 2 ) 01/12/2023 A 100,000 ( 3 ) ( 3 ) Common Stock 100,000 $ 0 100,000 D 2023 RSU Grant (4-Year) ( 2 ) 01/12/2023 A 100,000 ( 4 ) ( 4 ) Common Stock 100,000 $ 0 100,000 D 2023 Stock Options (Right-to-Buy) $ 15 01/12/2023 A 400,000 ( 5 ) ( 5 ) Common Stock 400,000 $ 0 400,000 D

Reporting Owners Reporting Owner Name / Address Relationships Director 10% Owner Officer Other Robinson Andrew S 800 GESSNER SUITE 600 HOUSTON, TX77024 X CEO & PRESIDENT Signatures /s/ Stacy E. Skelton, Attorney-in-Fact 01/17/2023 Signature of Reporting Person Date

Explanation of Responses:

( 1 )The reporting person was granted 63,374 shares of Restricted Stock on March 17, 2021, as a match to shares purchased under the 2016 Employee Incentive Program. The first tranche vested on May 22, 2021. The second tranche vested on May 22, 2022. The third and final tranche of 21,124 shares immediately vested upon the closing of the Issuer's initial public offering on January 12, 2023. Also includes a Restricted Stock Award granted on January 1, 2022 in the amount of 22,796 shares. Each share is equivalent to one share of the Company's common stock. This award fully vests on January 1, 2025. ( 2 )Upon vesting, each Restricted Stock Unit ("RSU") settles for one share of Common Stock. ( 3 )Subject to the reporting person's continuous service through the vesting date, 50% of the RSUs shall vest on January 12, 2025, and the remaining 50% will vest on January 12, 2026. ( 4 )Subject to the reporting person's continuous service through the vesting date, 50% of the RSUs will vest on January 12, 2026, and the remaining 50% will vest on January 12, 2027. ( 5 )Subject to the reporting person's continuous service through the vesting date, 50% of the options will vest on January 12, 2026, and the remaining 50% will vest on January 12, 2027.

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).

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