BOW insider Stephen Sills gifts 75,000 shares to 2024 GRAT

Rhea-AI Filing Summary

Bowhead Specialty Holdings Inc. (BOW) CEO, President and Director Stephen J. Sills reported an internal transfer of company stock. On 11/26/2025, he moved 75,000 shares of common stock in a transaction coded "G" (a gift or similar transfer) at a price of $0 per share from his direct holdings to the Stephen J. Sills 2024 I GRAT #4 grantor trust. After this transfer, he directly held 786,000 shares and also reported additional indirect ownership through several trusts and an LLC, including the new 75,000-share position in the GRAT.

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

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Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Sills Stephen Jay

(Last) (First) (Middle)

C/O BOWHEAD SPECIALTY HOLDINGS INC.

452 FIFTH AVENUE

(Street)

NEW YORK NY 10018

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
Bowhead Specialty Holdings Inc. [ BOW ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

X	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	CEO and President

3. Date of Earliest Transaction (Month/Day/Year)
11/26/2025

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
			Code	V	Amount	(A) or (D)	Price
Common Stock	11/26/2025		G		75,000(1)	D	$0	786,000	D
Common Stock	11/26/2025		G		75,000	A	$0	75,000	I	By Stephen J. Sills 2024 I GRAT #4
Common Stock								97,911	I	By Stephen J. Sills 2024 I GRAT #3
Common Stock								72,000	I	By Stephen J. Sills Irrevocable Family GST Exempt Trust
Common Stock								1,141	I	By Sills Family Trust 1
Common Stock								1,141	I	By Sills Family Trust 2
Common Stock								1,141	I	By Sills Family Trust 3
Common Stock								1,141	I	By Sills Family Trust 4
Common Stock								1,141	I	By Sills Family Trust 5
Common Stock								214,469	I	By Sills 2024 LLC
Common Stock								72,500	I	By Stephen J. Sills 2024 I Grant #2

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares

Explanation of Responses:

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

Remarks:

	/s/ H. Matthew Crusey, as attorney-in-fact	11/26/2025
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

FAQ

What insider transaction did Bowhead Specialty (BOW) report on this Form 4?

Stephen J. Sills, Bowhead Specialty Holdings Inc.'s CEO, President and Director, reported a transfer coded "G" involving 75,000 shares of common stock on 11/26/2025.

How many Bowhead (BOW) shares did Stephen J. Sills transfer and at what price?

He transferred 75,000 shares of Bowhead common stock at a reported price of $0 per share in a transaction coded as a gift or similar transfer.

Where were the 75,000 Bowhead (BOW) shares transferred by Stephen J. Sills?

The 75,000 shares of Bowhead common stock were transferred to the Stephen J. Sills 2024 I GRAT #4 grantor trust, as noted in the explanation of responses.

How many Bowhead (BOW) shares does Stephen J. Sills hold directly after this transaction?

Following the reported transfer, Stephen J. Sills beneficially owned 786,000 shares of Bowhead common stock in direct ownership.

Does Stephen J. Sills report indirect ownership of Bowhead (BOW) shares?

Yes. In addition to his direct holdings, he reported indirect ownership of Bowhead common stock through multiple entities, including the Stephen J. Sills 2024 I GRAT #4 and other trusts and an LLC.

What is Stephen J. Sillss relationship to Bowhead Specialty Holdings Inc. (BOW)?

Stephen J. Sills is reported as both a Director and an Officer, serving as CEO and President of Bowhead Specialty Holdings Inc.