Duffy Sean W 4

What Happened
Sean W. Duffy, EVP & Chief Claims Officer of Skyward Specialty (SKWD), had performance share units (PSUs) settle on May 6, 2026. The PSUs converted into 3,805 shares (exercise/conversion), the issuer withheld 1,671 of those shares to satisfy tax withholding (proceeds = $72,989), and the original PSU derivative award (2,861 PSUs) was removed upon settlement. Net increase to his share position from the settlement was 3,805 − 1,671 = 2,134 shares.

Key Details

• Transaction date: May 6, 2026; Form filed May 8, 2026 (appears timely).
• Conversion/exercise: 3,805 shares acquired via settlement of PSUs (transaction code M) at $0 exercise price.
• Tax withholding: 1,671 shares withheld (transaction code F) at $43.68 per share = $72,989. This withholding was mandated by the issuer (not a discretionary sale).
• Derivative removal: 2,861 PSUs (original award) reported as converted/removed upon settlement.
• Footnotes: The 2,861 PSUs were awarded Feb 27, 2023, subject to 2023–2025 performance; they fully vested and settled following Compensation Committee certification. Each PSU equals one share; the vested payout implied a performance multiplier of roughly 133% (3,805/2,861).
• Shares owned after transaction: not specified in the excerpt; net newly acquired shares from this settlement = ~2,134.

Context
PSU settlements and issuer-mandated share withholding for taxes are routine compensation events and do not necessarily reflect a deliberate open‑market sale by the insider. Here, the filing documents a performance-based award that vested and converted to common stock, with a portion withheld to satisfy tax obligations.