Form 4 Filing for Stephen Jay Sills

Stephen Jay Sills, CEO and President of Bowhead Specialty Holdings Inc., reported a disposition of 24,353 shares of Common Stock on May 22, 2026. The transaction code "F" indicates shares were surrendered to cover tax withholdings due upon vesting of restricted stock units. The average price was $28.46 per share. Following this transaction, Mr. Sills directly holds 838,926 shares. The filing also details various indirect holdings through family trusts and GRATs, including 41,371 shares held by the Stephen J. Sills 2024 I GRAT #2, which were transferred to his direct holdings on May 15, 2026, exempt from reporting.