Sec Form 4 Filing - AMERICAN FAMILY MUTUAL INSURANCE COMPANY, S.I. @ Bowhead Specialty Holdings Inc. - 2024-05-23

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 AMERICAN FAMILY MUTUAL INSURANCE COMPANY, S.I. 2. Issuer Name and Ticker or Trading Symbol Bowhead Specialty Holdings Inc. [ BOW] 5. Relationship of Reporting Person(s) to Issuer (Check all applicable) X __ Director X __ 10% Owner _____ Officer (give title below) X __ Other (specify below) See Remarks (Last) (First) (Middle) 6000 AMERICAN PARKWAY 3. Date of Earliest Transaction (MM/DD/YY) 05/23/2024 (Street) MADISON, WI53783 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

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 Warrant to Purchase Common Stock ( 1 ) $ 17 05/23/2024 A 1,614,250 ( 2 ) 05/23/2025( 3 ) 05/23/2034( 3 ) Common Stock 1,614,250 ( 2 ) $ 0 1,614,250 ( 2 ) D

Reporting Owners Reporting Owner Name / Address Relationships Director 10% Owner Officer Other AMERICAN FAMILY MUTUAL INSURANCE COMPANY, S.I. 6000 AMERICAN PARKWAY MADISON, WI53783 X X See Remarks Signatures American Family Mutual Insurance Company, S.I., By: /s/ Troy Van Beek, Chief Financial Officer 05/28/2024 Signature of Reporting Person Date

Explanation of Responses:

( 1 )Pursuant to a Warrant Agreement, dated May 23, 2024, with the Issuer. ( 2 )This assumes that the over-allotment option granted by the Issuer to the underwriters will not be exercised. To the extent it is exercised, the Warrant will be increased by a number of shares equal to 5% of such additional shares issued, up to a maximum of 1,670,721. ( 3 )This Warrant will vest as to 20% of the total number of shares subject to the Warrant on the first, second, third, fourth and fifth anniversaries of the vesting commencement date (05/23/2024).

Remarks: Troy Van Beek, the Chief Financial Officer and Treasurer of American Family Mutual Insurance Company, S.I. (AFMIC), was nominated as a director of the Issuer pursuant to the Investor Matters Agreement, dated May 23, 2024, between AFMIC and the Issuer. Accordingly, AFMIC may be deemed to be a director by deputization for purposes of Section 16 under the Securities Exchange Act of 1934, as amended.

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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