X0206 3 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 Common Stock 6176795 I (1)(2) Option (right to buy) 17 2027-05-23 2029-05-22 Common Stock 788235 D 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. 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. Pursuant to a Call Option Agreement, dated May 22, 2024, with GPC. 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. 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. American Family Mutual Insurance Company, S.I., By: /s/ Troy Van Beek, Chief Financial Officer 2024-05-23