BOW · Bowhead Specialty Holdings Inc.

Represents shares surrendered to the Issuer by the Reporting Person to pay required tax withholdings due upon vesting of restricted stock units, correcting an inadvertent error in the Form 4 filed on May 27, 2026.

Represents shares surrendered to the Issuer by the Reporting Person to pay required tax withholdings due upon vesting of restricted stock units, correcting an inadvertent error in the Form 4 filed on May 26, 2026.

Represents shares surrendered to the Issuer by the Reporting Person to pay required tax withholdings due upon vesting of restricted stock units, correcting an inadvertent error in the Form 4 filed on May 26, 2026.

Represents shares surrendered to the Issuer by the Reporting Person to pay required tax withholdings due upon vesting of restricted stock units, correcting an inadvertent error in the Form 4 filed on May 26, 2026.

Includes 31,129 shares of common stock transferred on May 15, 2026, for no consideration, from the Stephen J. Sills 2024 I GRAT #2 to the direct holdings of the Reporting Person. Such transaction was exempt from reporting pursuant to Rule 16a-13 of the Securities Exchange Act of 1934, as amended.

Reflects restricted stock units.

Reflects restricted stock units.

Reflects restricted stock units.

Reflects restricted stock units.

Reflects restricted stock units.

Reflects restricted stock units.

Reflects restricted stock units.

Represents shares surrendered to the Issuer by the Reporting Person to pay required tax withholdings due upon vesting of restricted stock units.

Represents shares surrendered to the Issuer by the Reporting Person to pay required tax withholdings due upon vesting of restricted stock units.

Represents shares surrendered to the Issuer by the Reporting Person to pay required tax withholdings due upon vesting of restricted stock units.

Represents shares surrendered to the Issuer by the Reporting Person to pay required tax withholdings due upon vesting of restricted stock units.

Reflects a grant of restricted stock units.

Reflects a grant of restricted stock units.

Reflects a grant of performance stock units.

Reflects a grant of restricted stock units.

Reflects a grant of restricted stock units.

Reflects a transfer of 75,000 shares to the Stephen J. Sills 2024 I Grant #4 grantor trust.

Reflects transfers of 97,911 shares to the Stephen J. Sills 2024 I Grant #3 grantor trust and 65,274 shares to the Stephen J. Sills Irrevocable Family GST Exempt Trust.

The shares were sold in connection with an underwritten public offering of the Issuer's common stock at a price per share of $30.66.

Shares held by GPC Partners Investments (SPV III) LP ("GPC Fund"). Gallatin Point Capital LLC ("Gallatin Point") is the manager of GPC Partners GP LLC ("GPC GP"), which is the general partner of GPC Fund. The Reporting Person and Lewis (Lee) Sachs are the Co-Founders and Managing Partners of the ultimate parent of Gallatin Point and collectively make voting and investment decisions on behalf of GPC Fund. The Reporting Person disclaims beneficial ownership of the securities reported herein except to the extent of his pecuniary interest therein, if any, and the inclusion of these securities in this report shall not be deemed an admission that the Reporting Person is a beneficial owner of the securities reported in this filing for purposes of Section 16 of the Securities Exchange Act of 1934 (the "Exchange Act").

GPC Fund and American Family Mutual Insurance Company, S.I. ("AFMIC") are parties to a Voting Agreement dated as of May 22, 2024, and each may be deemed to be members of a "group," as defined in Rule 13d-5 under the Exchange Act. The share ownership reported herein does not include any shares of the common stock owned by AFMIC, and the Reporting Person disclaims beneficial ownership of any shares of the common stock owned by AFMIC to the extent GPC Fund and AFMIC may be deemed to be members of a group.

The shares were sold in connection with an underwritten public offering of the Issuer's common stock at a price per share of $30.66.

Shares held by GPC Partners Investments (SPV III) LP ("GPC Fund"). Gallatin Point Capital LLC ("Gallatin Point") is the manager of GPC Partners GP LLC ("GPC GP"), which is the general partner of GPC Fund. Matthew Botein and Lewis (Lee) Sachs are the Co-Founders and Managing Partners of the ultimate parent of Gallatin Point and collectively make voting and investment decisions on behalf of GPC Fund. Each Reporting Person disclaims Section 16 beneficial ownership of the securities reported herein except to the extent of his or its pecuniary interest therein, if any, and the inclusion of these securities in this report shall not be deemed an admission that any Reporting Person is a beneficial owner of the securities reported in this filing for purposes of Section 16 of the Securities Exchange Act of 1934 (the "Exchange Act").

GPC Fund and American Family Mutual Insurance Company, S.I. ("AFMIC") are parties to a Voting Agreement dated as of May 22, 2024, and each may be deemed to be members of a "group," as defined in Rule 13d-5 under the Exchange Act. The share ownership reported herein does not include any shares of the common stock owned by AFMIC, and each Reporting Person disclaims beneficial ownership of any shares of the common stock owned by AFMIC to the extent GPC Fund and AFMIC may be deemed to be members of a group.

Reflects restricted stock units.

Reflects the transfer of shares to six trusts for the benefit of certain members of the reporting person's family. The trustee for each of the trusts is a member of the reporting person's household.

Represents shares surrendered to the Issuer by the Reporting Person to pay required tax withholdings due upon vesting of restricted stock units.

Represents shares surrendered to the Issuer by the Reporting Person to pay required tax withholdings due upon vesting of restricted stock units.

Represents shares surrendered to the Issuer by the Reporting Person to pay required tax withholdings due upon vesting of restricted stock units.

Represents shares surrendered to the Issuer by the Reporting Person to pay required tax withholdings due upon vesting of restricted stock units.

Reflects a transfer of 72,500 shares to the Stephen J. Sills 2024 I Grant #2 grantor trust.