Bowhead Specialty Holdings Inc

Securities Trading Plans of Directors and Executive Officers

Transactions in our securities by our directors and executive officers are required to be made in accordance with our Insider Trading Policy (the “Insider Trading Policy”), which, among other things, requires that the transactions be in accordance with applicable U.S. federal securities laws that prohibit trading while in possession of material nonpublic information. Rule 10b5-1 under the Exchange Act provides an affirmative defense that enables prearranged transactions in securities in a manner that avoids concerns about initiating transactions at a future date while possibly in possession of material nonpublic information. Our Insider Trading Policy permits our directors and officers to enter into trading plans designed to comply with Rule 10b5-1.

During the fourth quarter of 2024, none of our directors or officers adopted, modified or terminated a Rule 10b5-1 trading plan oradopted, modified orterminated a non-Rule 10b5-1 trading arrangement (as defined in Item 408(c) of Regulation S-K).

Change in Control Severance Plan

On February 21, 2025, the Board approved and adopted the Bowhead Specialty Holding Inc. Change in Control Severance Plan (the “Severance Plan”), pursuant to which select employees of the Company (including each of its executive officers, but excluding the Chief Executive Officer of the Company), may become eligible to receive the following severance payments and benefits upon a qualifying termination within twenty-four months following the date of a change in control (each of qualifying termination and change in control as defined in the Severance Plan): (i) a cash payment payable in a lump sum equal to the sum of (x) one and one-half times the participant’s base salary and (y) pro-rata target annual bonus, and (ii) an additional cash payment payable in a lump sum equal to the product of twelve multiplied by the cost incurred by the Company for providing group health, dental and vision benefits to the participant and the participant’s eligible dependents in the month immediately prior to the month in which the qualifying termination date occurred.

The provision of payments and benefits described above is conditioned upon the participant’s execution and non-revocation of a release of claims in favor of the Company. The Severance Plan provides that if a participant receives any amount, whether under the Severance Plan or otherwise, that is subject to the excise tax imposed pursuant to Section 4999 of the Internal Revenue Code, the amount of the payments to be made to the participant will be reduced to the extent necessary to avoid imposition of the excise tax, but only if the net amount of the reduced payments exceeds the net amount that the participant would receive following imposition of the excise tax and all income and related taxes.

The foregoing description of the Severance Plan does not purport to be complete and is qualified in the entirety by reference to the Severance Plan, which is filed as Exhibit 10.17 to this Annual Report on Form 10-K and incorporated by reference herein.