Kestrel Group, Ltd.

Item 5.02 Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangement of Certain Officers On May 8, 2026, the Compensation Committee (the “Committee”) of the Board of Directors (the “Board”) of Kestrel Group Ltd, a Bermuda company (the “Company”) adopted a new form of performance-based restricted stock agreement (the “Performance Award Agreement”) used in the grant of performance awards on May 13, 2026 in an amount of $650,000 each to Terry Ledbetter, the Company’s Executive Chairman, Bradford Luke Ledbetter, the Company’s Chief Executive Officer, and Patrick Haveron, the Company’s President and Chief Financial Officer (together, the “Executives”) for fiscal year 2026 pursuant to the Kestrel Group Ltd. 2025 Equity Incentive Plan (the “Plan”). The number of performance-based restricted shares was determined by dividing $650,000 by the 20-day volume weighted average price of the Company’s common stock immediately preceding the grant date resulting in a grant of 61,588 performance-based restricted shares to each of the Executives. Shares of restricted stock granted pursuant to the Performance Award Agreement (the “Performance Award”) are subject to performance- and time-based vesting conditions. The Performance Award is subject to a one-year performance period beginning on January 1, 2026 and ending on December 31, 2026 (the “Performance Period”), during which the designated performance goal must be achieved. The performance goal for the Performance Period will be based upon the EBITDA of our program services segment. If the threshold level of performance is not met, the Performance Award will be forfeited immediately upon certification by the Committee. Earned shares vest ratably in one-third (1/3) increments with the first one-third (1/3) vesting upon the Committee’s confirmation that the performance goal has been achieved and the remaining two‑thirds (2/3) of the shares vest in equal installments, with one‑third (1/3) vesting on the first anniversary of such confirmation and one‑third (1/3) vesting on the second anniversary of such confirmation (each date, a "Vesting Date"). In addition, each Performance Award is subject to the Executive’s continuous employment with the Company through the applicable Vesting Date. In the event the Executive’s employment is terminated by the Company for “Cause” (as defined in the Plan) or by the Executive’s voluntary resignation (other than for “Good Reason” following a “Change in Control” (each as defined in the Plan)), the Performance Award and any unvested shares will be forfeited without compensation. If, following the end of the Performance Period but prior to a Vesting Date, the Executive’s employment is terminated due to death, “Disability” (as defined in the Performance Award Agreement), or by the Company without Cause, the shares deemed earned based on the satisfaction of the performance goal will remain outstanding and vest upon the earlier of the applicable Vesting Date or a Change in Control. If such termination occurs prior to the end of the Performance Period, the performance goal will be deemed achieved based on the greater of target performance or actual performance. In the event of a Change in Control prior to a Vesting Date, the shares deemed earned pursuant to the performance goal will continue to be subject to time-based vesting through the applicable Vesting Date(s); provided, however, that if the Executive’s employment is terminated by the Company without Cause or by the Executive for Good Reason within twenty-four months following the Change in Control, the Performance Award will vest in full as of the date of such termination. If the Change in Control occurs prior to the end of the Performance Period, the performance goal will be deemed achieved based on the greater of target performance or actual performance. The description of the new form of Performance Award Agreement is qualified in its entirety by reference to the form of Performance Award Agreement which is included as Exhibit 10.1 and is incorporated in this Item 5.01 by reference.