Bowhead (NYSE: BOW) CUO surrenders 4,506 shares for tax withholding

Rhea-AI Filing Summary

Bowhead Specialty Holdings Inc. Chief Underwriting Officer David John Newman surrendered 4,506 shares of common stock to the company at $28.30 per share to cover required tax withholdings on vested restricted stock units. This was a tax-withholding disposition rather than an open-market sale. After the transaction, he directly holds 292,689 shares of Bowhead common stock.

Insider Trade Summary

1 transaction reported

Mixed 1 txn

Insider Newman David John

Role Chief Underwriting Officer

Type	Security	Shares	Price	Value
Tax Withholding	Common Stock	4,506	$28.30	$128K

Holdings After Transaction: Common Stock — 292,689 shares (Direct, null)

Footnotes (1)

1. [object Object]

Key Figures

Shares surrendered for taxes: 4,506 shares Tax-withholding price: $28.30 per share Shares held after transaction: 292,689 shares +1 more

4 metrics

Shares surrendered for taxes 4,506 shares Tax-withholding disposition on 2026-05-23

Tax-withholding price $28.30 per share Value used for surrendered shares

Shares held after transaction 292,689 shares Direct ownership following Form 4 transaction

Transaction code F Payment of tax liability by delivering securities

Key Terms

restricted stock units, tax withholdings, Form 4, tax-withholding disposition

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

"after this Form 4 transaction"

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.

tax-withholding disposition financial

"transaction_action: tax-withholding disposition"

A tax-withholding disposition is an event or transaction—such as selling or transferring securities, exercising options, or receiving compensation—that triggers a requirement to hold back part of the payment and remit it to tax authorities. It matters to investors because it reduces the cash they receive immediately and can change the timing and amount of taxable income, like a cashier taking a portion of your sale proceeds to pay taxes before you get the rest.

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^*

Newman David John

(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 Underwriting 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		4,506(1)	D	$28.3	292,689	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	05/26/2026
	** 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 (BOW) report for David John Newman?

Bowhead reported that Chief Underwriting Officer David John Newman surrendered 4,506 common shares to the company. The shares were used to pay tax withholdings triggered by the vesting of restricted stock units, rather than being sold in the open market.

Was the Bowhead (BOW) insider transaction an open-market sale?

No, the transaction was not an open-market sale. The 4,506 shares were surrendered back to Bowhead Specialty Holdings to satisfy required tax withholdings upon RSU vesting, a common non-discretionary mechanism rather than a voluntary sale of shares into the market.

How many Bowhead (BOW) shares does David John Newman hold after this Form 4?

After the tax-withholding disposition, David John Newman directly holds 292,689 shares of Bowhead common stock. This figure reflects his remaining ownership position following the surrender of 4,506 shares to cover tax obligations from restricted stock unit vesting.

What price per share was used in the Bowhead (BOW) tax-withholding transaction?

The tax-withholding disposition used a price of $28.30 per Bowhead common share. This price is applied solely for calculating the value of the 4,506 surrendered shares used to satisfy the reporting person’s tax obligations on vested restricted stock units.

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

Transaction code “F” indicates payment of an exercise price or tax liability by delivering securities. In this Bowhead filing, it reflects shares surrendered by the insider to cover required tax withholdings related to the vesting of restricted stock units, not a discretionary share sale.

What do the footnotes in the Bowhead (BOW) Form 4 explain?

The footnote clarifies that the 4,506 shares were surrendered to Bowhead Specialty Holdings to pay required tax withholdings due upon vesting of restricted stock units. It confirms the disposition was a tax event, providing important context for interpreting the insider’s reported transaction.