Bowhead Specialty (BOW) CEO awarded stock units, surrenders shares for taxes

Rhea-AI Filing Summary

Bowhead Specialty Holdings Inc. CEO and President Stephen Jay Sills reported equity compensation grants and related tax withholding activity in Common Stock. On February 19, he received two stock awards totaling 90,703 and 88,566 shares, recorded as grant or award acquisitions at no cash cost.

On February 20, 5,419 shares were surrendered to the issuer to cover required tax withholdings due upon vesting of restricted stock units at $24.90 per share, a tax-withholding disposition rather than an open-market sale. He also reports additional indirect holdings through various family trusts and entities.

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

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

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)
02/19/2026

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	02/19/2026		A		90,703(1)	A	$0	876,703	D
Common Stock	02/19/2026		A		88,566(2)	A	$0	965,269	D
Common Stock	02/20/2026		F		5,419(3)	D	$24.9	959,850	D
Common Stock								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 grant of restricted stock units.

2. Reflects a grant of performance stock units.

3. Represents shares surrendered to the Issuer by the Reporting Person to pay required tax withholdings due upon vesting of restricted stock units.

Remarks:

	/s/ H. Matthew Crusey, as attorney-in-fact	02/23/2026
	** 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 transactions did Bowhead Specialty (BOW) CEO Stephen J. Sills report on this Form 4?

Stephen J. Sills reported equity compensation activity, including two stock awards and one tax-withholding share surrender. The awards increased his direct Common Stock holdings, while a smaller portion was surrendered back to the issuer to cover required tax withholdings on vested restricted stock units.

How many Bowhead Specialty (BOW) shares were granted to CEO Stephen J. Sills?

Sills received two equity grants of Bowhead Specialty Common Stock totaling 90,703 and 88,566 shares. Footnotes describe these as restricted stock units and performance stock units, both awarded at zero dollar price per share as part of his stock-based compensation program.

Did Bowhead Specialty (BOW) CEO Stephen J. Sills sell shares in the open market?

The Form 4 shows no open-market sales by Sills. Instead, 5,419 shares were surrendered to the issuer at $24.90 per share to satisfy tax withholding obligations arising from the vesting of restricted stock units, a non-market, tax-related disposition transaction.

What does the tax-withholding disposition on Bowhead Specialty (BOW) shares represent?

The 5,419-share disposition reflects shares surrendered to Bowhead Specialty to pay required tax withholdings on vested restricted stock units. This transaction uses existing shares to settle tax liabilities, rather than involving a traditional buy or sell order in the open market.

What indirect Bowhead Specialty (BOW) holdings are reported for Stephen J. Sills?

The filing lists indirect ownership in Bowhead Specialty Common Stock through several trusts and an LLC, including vehicles such as the Sills 2024 LLC, multiple Sills Family Trusts, and GRATs, each with its own reported share balance following the reported holding entries.

How did Stephen J. Sills’ direct ownership in Bowhead Specialty (BOW) change after these transactions?

Direct ownership increased due to the two stock awards and then decreased slightly from the tax-withholding surrender. After the 5,419-share surrender, his directly held Common Stock balance is reported as 959,850 shares following the final transaction in the sequence.