X0609 4 2026-05-06 0001519449 Skyward Specialty Insurance Group, Inc. SKWD 0001415833 Robinson Andrew S false 800 GESSNER SUITE 600 HOUSTON TX 77024 true true false false Chairman & CEO, Skyward Group 0 Common Stock 2026-05-06 4 M 0 20150 0 A 187824 D Common Stock 2026-05-06 4 F 0 7930 43.68 D 179894 D 2023 LTIP - PSUs 2026-05-06 4 M 0 15151 0 D Common Stock 15151 0 D Represents the number of shares that were acquired by the Reporting Person in connection with the settlement of the Performance Share Units ("PSUs") listed in Line I of Table II. The disposition reported on this Form 4 represents shares withheld to cover tax withholding obligations in connection with the vesting and settlement of the PSUs listed in Line I of Table II. The disposition is mandated by the Issuer and does not represent a discretionary transaction by the Reporting Person. Each PSU represents the right to receive one share of the Issuer's Common Stock upon settlement. On February 27, 2023, the Reporting Person was awarded 15,151 PSUs. The PSUs are subject to obtaining specified performance criteria from January 1, 2023 through December 31, 2025. The number of PSUs subject to vest under this award can range from 0% to 150% of the amount shown. This award fully vested on December 31, 2025 and settled upon certification by the Compensation Committee of the Board of Directors. /s/ Stacy E. Skelton, Attorney-in-Fact 2026-05-08