| Name | Relationship | Address | Signature | Signature date | CIK | 
|---|---|---|---|---|---|
| Sills Stephen Jay | CEO and President, Director | C/O BOWHEAD SPECIALTY HOLDINGS INC., 452 FIFTH AVENUE, NEW YORK | /s/ H. Matthew Crusey, as attorney-in-fact | 2025-05-23 | 0001362369 | 
| Type | Sym | Class | Transaction | Value $ | Shares | Change % | * Price $ | Shares After | Date | Ownership | Footnotes | 
|---|---|---|---|---|---|---|---|---|---|---|---|
| transaction | BOW | Common Stock | Tax liability | -$454K | -11.9K | -1.14% | $38.08 | 1.04M | May 22, 2025 | Direct | F1 | 
| holding | BOW | Common Stock | 214K | May 22, 2025 | By Sills 2024 LLC | ||||||
| holding | BOW | Common Stock | 72.5K | May 22, 2025 | By Stephen J. Sills 2024 I Grant #2 | 
| Id | Content | 
|---|---|
| F1 | Represents shares surrendered to the Issuer by the Reporting Person to pay required tax withholdings due upon vesting of restricted stock units. |