X0508 4 2026-01-12 0001519449 Skyward Specialty Insurance Group, Inc. SKWD 0001936023 Burkhart John A III 800 GESSNER SUITE 600 HOUSTON TX 77024 false true false false President, US P&C, Skyward Grp 0 Common Stock 2026-01-12 4 M 0 6665 0 A 31027 D Common Stock 2026-01-12 4 F 0 2798 46.10 D 28229 D Common Stock 2026-01-12 4 M 0 6665 0 A 34894 D Common Stock 2026-01-12 4 F 0 2623 46.10 D 32271 D 2023 IPO RSU Grant (4-Year) 2026-01-12 4 M 0 6665 0 D Common Stock 6665 6665 D 2023 IPO RSU Grant (3-Year) 2026-01-12 4 M 0 6665 0 D Common Stock 6665 0 D Represents the number of shares that were acquired by the Reporting Person in connection with the settlement of the Restricted Stock Units ("RSUs") listed in 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 RSUs listed in Table II. The disposition is mandated by the Issuer and does not represent a discretionary transaction by the Reporting Person. The number of shares withheld by the Issuer for the Reporting Owner was calculated using the closing price of the Issuer's Common Stock on the vesting date, January 12, 2026, pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Long Term Incentive Plan. Each RSU represents the right to receive one share of the Issuer's Common Stock upon settlement. On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 13,330 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2026. Subject to the Reporting Person's continuous service the remaining 50% of the RSUs will vest on January 12, 2027. On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 13,330 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2025, and the remaining 50% of the RSUs fully vested on January 12, 2026. /s/ Stacy E. Skelton, Attorney-in-Fact 2026-01-14