Bowhead Specialty (NYSE: BOW) CAO surrenders shares to cover taxes

Rhea-AI Filing Summary

Bowhead Specialty Holdings Inc. Chief Accounting Officer Shirley Shek Li Yap surrendered 2,353 shares of common stock at $28.30 per share to cover tax withholdings due on vesting of restricted stock units. After this non-market, tax-related disposition, she directly holds 81,205 shares of Bowhead common stock.

Insider Trade Summary

1 transaction reported

Mixed 1 txn

Insider Yap Shirley Shek Li

Role Chief Accounting Officer

Type	Security	Shares	Price	Value
Tax Withholding	Common Stock	2,353	$28.30	$67K

Holdings After Transaction: Common Stock — 81,205 shares (Direct, null)

Footnotes (1)

1. [object Object]

Key Figures

Shares surrendered for taxes: 2,353 shares Reference price per share: $28.30 per share Shares held after transaction: 81,205 shares +1 more

4 metrics

Shares surrendered for taxes 2,353 shares Common stock surrendered for tax withholding on RSU vesting

Reference price per share $28.30 per share Value used for tax-withholding share surrender

Shares held after transaction 81,205 shares Direct common stock ownership after Form 4 event

Tax-withholding shares 2,353 shares Form 4 transaction code F, tax-withholding disposition

Key Terms

restricted stock units, tax withholdings, Form 4, transaction code F

4 terms

restricted stock units financial

"due upon vesting of restricted stock units"

Restricted stock units are a type of company reward where employees are promised shares of stock, but they only fully own these shares after meeting certain conditions, like staying with the company for a set time. They matter because they can become valuable assets and are often used to motivate employees to help the company succeed.

tax withholdings financial

"to pay required tax withholdings due upon vesting"

Form 4 regulatory

"according to a Form 4 insider filing"

Form 4 is a official document that company insiders, such as executives or major shareholders, file with regulators whenever they buy or sell company shares. It provides transparency about how those with inside knowledge are trading, helping investors see if insiders are confident in the company's prospects or may be selling for personal reasons. This information can influence investor decisions by revealing insiders' perspectives on the company's value.

transaction code F regulatory

"Transaction code F on the Bowhead Specialty Form 4"

Form 4 Insider Transactions: What Each Field Means →

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^*

Yap Shirley Shek Li

(Last) (First) (Middle)

C/O BOWHEAD SPECIALTY HOLDINGS INC.

452 FIFTH AVENUE

(Street)

NEW YORK NEW YORK 10018

(City) (State) (Zip)

UNITED STATES

(Country)

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

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

	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	Chief Accounting Officer

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
05/23/2026

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

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

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

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	05/23/2026		F		2,353(1)	D	$28.3	81,205	D

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. 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	05/27/2026
	** 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.
* Form 4: SEC 1474 (03-26)

FAQ

What insider transaction did Bowhead Specialty (BOW) report for its CAO?

Bowhead Specialty reported that Chief Accounting Officer Shirley Shek Li Yap surrendered 2,353 common shares to the company to satisfy tax withholdings due upon vesting of restricted stock units, according to a Form 4 insider filing.

Was the Bowhead Specialty (BOW) CAO transaction an open-market stock sale?

No. The Form 4 states the 2,353 shares were surrendered to Bowhead Specialty to pay required tax withholdings on vesting restricted stock units, not sold in the open market, making this a routine compensation-related tax transaction.

How many Bowhead Specialty (BOW) shares did the CAO surrender for taxes?

The Chief Accounting Officer surrendered 2,353 shares of Bowhead Specialty common stock at a reference price of $28.30 per share to cover required tax withholdings tied to the vesting of restricted stock units granted as compensation.

How many Bowhead Specialty (BOW) shares does the CAO hold after the Form 4 event?

Following the tax-withholding share surrender, Chief Accounting Officer Shirley Shek Li Yap directly holds 81,205 shares of Bowhead Specialty common stock, as disclosed in the Form 4’s post-transaction ownership line for non-derivative securities.

What does transaction code F mean in the Bowhead Specialty (BOW) Form 4?

Transaction code F on the Bowhead Specialty Form 4 indicates payment of tax liability or exercise cost by delivering securities. Here, it reflects shares surrendered by the CAO to satisfy required tax withholdings on vesting restricted stock units.