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Bowhead Specialty Holdings Inc.·4

Nov 26, 4:06 PM ET

Sills Stephen Jay 4

4 · Bowhead Specialty Holdings Inc. · Filed Nov 26, 2025

Insider Transaction Report

Form 4

Period: 2025-11-26

Bowhead Specialty Holdings Inc.BOW

Sills Stephen Jay

DirectorCEO and President

Transactions

Gift
Common Stock
[F1]
2025-11-26−75,000→ 786,000 total
Gift
Common Stock
2025-11-26+75,000→ 75,000 total(indirect: By Stephen J. Sills 2024 I GRAT #4)

Holdings

Common Stock
(indirect: By Stephen J. Sills 2024 I GRAT #3)
97,911
Common Stock
(indirect: By Trust)
72,000
Common Stock
(indirect: By Trust)
1,141
Common Stock
(indirect: By Trust)
1,141
Common Stock
(indirect: By Trust)
1,141
Common Stock
(indirect: By Trust)
1,141
Common Stock
(indirect: By Trust)
1,141
Common Stock
(indirect: By LLC)
214,469
Common Stock
(indirect: By Stephen J. Sills 2024 I Grant #2)
72,500

Footnotes (1)

[F1]Reflects a transfer of 75,000 shares to the Stephen J. Sills 2024 I Grant #4 grantor trust.

Signature

/s/ H. Matthew Crusey, as attorney-in-fact|2025-11-26

Documents

1 file

4
wk-form4_1764191202.xmlPrimary
FORM 4