X0508 4 2024-10-25 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 Common Stock 2024-10-25 4 S 0 1362285 27.695 D 4700761 D The shares were sold in connection with an underwritten public offering of the Issuer's Common Stock (including pursuant to the underwriters' exercise of their over-allotment option) at a net price per share of $27.695, after underwriting discounts and commissions. Includes 117,679 shares that were distributed to American Family Mutual Insurance Company, S.I. ("AFMIC") in connection with the dissolution of Bowhead Insurance Holdings LP. 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. Troy Van Beek, the Enterprise Chief Financial Officer and Treasurer of 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 2024-10-28