X0508 4 2024-05-23 0 0002002473 Bowhead Specialty Holdings Inc. BOW 0000351040 AMERICAN FAMILY MUTUAL INSURANCE COMPANY, S.I. 6000 AMERICAN PARKWAY MADISON WI 53783 1 0 1 1 See Remarks 0 Warrant to Purchase Common Stock 17 2024-05-23 4 A 0 1614250 0 A 2025-05-23 2034-05-23 Common Stock 1614250 1614250 D Pursuant to a Warrant Agreement, dated May 23, 2024, with the Issuer. 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. 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). 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. American Family Mutual Insurance Company, S.I., By: /s/ Troy Van Beek, Chief Financial Officer 2024-05-28