| 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 | 13 Mar 2026 | 0001362369 |
| Type | Sym | Class | Transaction | Value $ | Shares | Change % | * Price $ | Shares After | Date | Ownership | Footnotes |
|---|---|---|---|---|---|---|---|---|---|---|---|
| transaction | BOW | Common Stock | Gift | -7,700 | -0.8% | $0.000000* | 952,150 | 12 Mar 2026 | Direct | ||
| transaction | BOW | Common Stock | Gift | +1,540 | +135% | $0.000000* | 2,681 | 12 Mar 2026 | By Sills Family Trust 1 | ||
| transaction | BOW | Common Stock | Gift | +1,540 | +135% | $0.000000* | 2,681 | 12 Mar 2026 | By Sills Family Trust 2 | ||
| transaction | BOW | Common Stock | Gift | +1,540 | +135% | $0.000000* | 2,681 | 12 Mar 2026 | By Sills Family Trust 3 | ||
| transaction | BOW | Common Stock | Gift | +1,540 | +135% | $0.000000* | 2,681 | 12 Mar 2026 | By Sills Family Trust 4 | ||
| transaction | BOW | Common Stock | Gift | +1,540 | +135% | $0.000000* | 2,681 | 12 Mar 2026 | By Sills Family Trust 5 | ||
| transaction | BOW | Common Stock | Gift | -120,000 | -13% | $0.000000* | 832,150 | 13 Mar 2026 | Direct | ||
| transaction | BOW | Common Stock | Gift | +120,000 | $0.000000* | 120,000 | 13 Mar 2026 | Stephen J. Sills 2024 I GRAT #5 | |||
| holding | BOW | Common Stock | 75,000 | 12 Mar 2026 | By Stephen J. Sills 2024 I GRAT #4 | ||||||
| holding | BOW | Common Stock | 97,911 | 12 Mar 2026 | By Stephen J. Sills 2024 I GRAT #3 | ||||||
| holding | BOW | Common Stock | 72,000 | 12 Mar 2026 | By Stephen J. Sills Irrevocable Family GST Exempt Trust | ||||||
| holding | BOW | Common Stock | 214,469 | 12 Mar 2026 | By Sills 2024 LLC | ||||||
| holding | BOW | Common Stock | 72,500 | 12 Mar 2026 | By Stephen J. Sills 2024 I Grant #2 |