X0508 4 2025-12-12 0001519449 Skyward Specialty Insurance Group, Inc. SKWD 0001937132 Kapadia Sandip A 800 GESSNER SUITE 600 HOUSTON TX 77024 false true false false Head of Actuarial 1 Common Stock 2025-12-12 4 S 0 1486 50.03 D 14289 D Common Stock 2025-12-12 4 S 0 1200 50.01 D 13089 D Sales reported were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on September 8, 2025. The number of securities reported reflects the June 1, 2025 acquisition of 231 shares and the December 1, 2025 acquisition of 197 shares of the Company's Common Stock pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Employee Stock Purchase Plan ("ESPP") for the ESPP purchase periods of December 1, 2024 through May 31, 2025, and June 1, 2025 through November 30, 2025, respectively. /s/ Stacy E. Skelton, Attorney-in-Fact 2025-12-16