X0508 4 2024-05-28 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 2024-05-28 4 A 0 56471 0 A 2025-05-23 2034-05-23 Common Stock 56471 1670721 D Option (right to buy) 17 2024-05-28 4 A 0 28236 0 A 2027-05-23 2029-05-22 Common Stock 28236 816471 D Pursuant to a Warrant Agreement, dated May 23, 2024, with the Issuer. In accordance with its terms, the Warrant became exercisable for an additional 56,471 shares upon closing of the underwriters' over-allotment option on May 28, 2024. 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). Pursuant to a Call Option Agreement, dated May 22, 2024, with GPC Partners Investments (SPV III) LP. In accordance with its terms, the Option became exercisable for an additional 28,236 shares upon closing of the underwriters' over-allotment option on May 28, 2024. American Family Mutual Insurance Company, S.I., By: /s/ Troy Van Beek, Chief Financial Officer 2024-05-29