[Form 4] Bowhead Specialty Holdings Inc. Insider Trading Activity

Rhea-AI Filing Summary

Bowhead Specialty Holdings Inc. (BOW) Form 4: Director and CEO Stephen J. Sills reported related-party transfers of common stock on 08/26/2025. The filing shows 163,185 shares disposed of (Code G) resulting in 861,000 shares held directly after the transaction. Simultaneously, 97,911 shares were recorded as acquired and held indirectly by the Stephen J. Sills 2024 I GRAT #3 grantor trust, and 65,274 shares were recorded as acquired and held indirectly by the Stephen J. Sills 2013 IRR Family GST EX grantor trust. The explanation states these entries reflect transfers to those two grantor trusts. The form is signed by an attorney-in-fact on 09/02/2025.

Positive

• Disclosed transfers to named grantor trusts are reported with specific share counts, showing transparency in insider ownership changes
• Form 4 filed and signed by attorney-in-fact, indicating compliance with Section 16 disclosure requirements

Negative

• None.

Insights

Financial Analyst

TL;DR: Insider transferred 163,185 shares into two named grantor trusts; direct holdings remain substantial.

The Form 4 documents an internal reallocation of equity by CEO and director Stephen J. Sills on 08/26/2025. The report shows a net disposal entry of 163,185 shares from his direct holdings and simultaneous recognition of 97,911 and 65,274 shares as indirect holdings within two grantor trusts. The filing provides explicit share counts before/after the transaction: 861,000 shares held directly after the reported disposal and identified indirect holdings in the specified trusts. For investors this is a change in beneficial ownership structure rather than an open-market sale; the filing contains no pricing information beyond $0 for these transfers and no derivative activity.

Corporate Governance Expert

TL;DR: Transaction appears to be estate/planning-related transfers to grantor trusts, formally disclosed via Form 4.

The disclosed transactions on 08/26/2025 are documented as transfers to the "Stephen J. Sills 2024 I GRAT #3" and the "Stephen J. Sills 2013 IRR Family GST EX" grantor trust, per the filer’s explanation. Code "G" is used for each line and the form records the movement of specific share amounts into indirect ownership. The report is properly signed by an attorney-in-fact and indicates compliance with Section 16 reporting. There are no derivative positions reported and no indications of sales to third parties or changes in executive status within this filing.

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
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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)
08/26/2025

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	08/26/2025		G		163,185(1)	D	$0	861,000	D
Common Stock	08/26/2025		G		97,911	A	$0	97,911	I	By Stephen J. Sills 2024 I GRAT #3
Common Stock	08/26/2025		G		65,274	A	$0	65,274	I	By Stephen J. Sills 2013 IRR Family GST EX

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 transfers of 97,911 shares to the Stephen J. Sills 2024 I Grant #3 grantor trust and 65,274 shares to the Stephen J. Sills 2013 IRR Family GST EX grantor trust.

Remarks:

	/s/ H. Matthew Crusey, as attorney-in-fact	09/02/2025
	** 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 did Stephen J. Sills report on the Form 4 for BOW?

He reported transfers on 08/26/2025 of 163,185 shares disposed from direct holdings and recognition of 97,911 and 65,274 shares as indirect holdings in two named grantor trusts.

How many shares does Stephen J. Sills hold directly after the reported transaction?

The Form 4 shows 861,000 shares held directly following the reported transactions.

Which trusts received shares according to the filing?

The filing names the Stephen J. Sills 2024 I GRAT #3 and the Stephen J. Sills 2013 IRR Family GST EX grantor trusts as recipients of transfers.

Were any derivative securities reported on this Form 4?

No. Table II for derivative securities contains no reported entries; only common stock transfers appear in Table I.

Did the filing report any cash proceeds or prices for the transfers?

Each transfer line lists a price of $0, and the explanation confirms these are transfers to grantor trusts rather than market sales.