Sec Form 3 Filing - AMERICAN FAMILY MUTUAL INSURANCE COMPANY, S.I. @ Bowhead Specialty Holdings Inc. - 2024-05-23

FORM 3 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 Common Stock 6,176,795 I (1)(2) ( 1 ) ( 2 )

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 Option (right to buy) ( 3 ) $ 17 05/23/2027 05/22/2029 Common Stock 788, 235 ( 4 ) 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 05/23/2024 Signature of Reporting Person Date

Explanation of Responses:

( 1 )American Family Mutual Insurance Company, SI's (AFMIC) pecuniary interest in the shares is held through its limited partnership interest in Bowhead Insurance Holdings LP, which directly owns the shares. ( 2 )GPC Partners Investments (SPV III) LP (GPC) and AMFIC are parties to a Voting Agreement, dated May 22, 2024, and each may be deemed to be members of a "group," as defined in Rule 13d-5 of the Securities Exchange Act of 1934, as amended. The share ownership reported herein does not include any shares owned by GPC, and AFMIC disclaims membership in a group with GPC and disclaims beneficial ownership of any shares owned by GPC. ( 3 )Pursuant to a Call Option Agreement, dated May 22, 2024, with GPC. ( 4 )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 option will be increased by 2.5% of such additional shares issued, up to a maximum of 816,471 shares.

Remarks: Troy Van Beek, the Chief Financial Officer and Treasurer of AFMIC, was nominated as a director of the Issuer in accordance with an Investor Matters Agreement 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).

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