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

Rhea-AI Filing Summary

Bowhead Specialty Holdings Inc. (BOW) insider report: This amended Form 4, filed for reporting person Stephen Jay Sills, records transactions dated 08/26/2025 that reallocate shares among Sills and several related trusts and entities. The filing shows a disposal of 163,185 shares (reported at $0), leaving 861,000 shares beneficially owned in the reported direct position. Simultaneously, transfers were recorded that add 97,911 shares to the "Stephen J. Sills 2024 I Grant #3" grantor trust and 65,274 shares to the "Stephen J. Sills Irrevocable Family GST Exempt Trust." The filing also lists small indirect holdings through multiple Sills family trusts and entities (several positions of 1,141 shares, 72,500, and 214,469 by related entities). The explanatory note confirms the transfers of 97,911 and 65,274 shares to the named trusts. The form is signed by an attorney-in-fact on 09/03/2025.

Positive

• Transfers recorded to named trusts ("Stephen J. Sills 2024 I Grant #3" and "Irrevocable Family GST Exempt Trust"), which clarifies beneficial ownership structure
• No cash proceeds (transactions reported at $0), indicating internal transfers rather than market sales

Negative

• Direct holdings decreased by 163,185 shares, reducing the reporting person's direct stake to 861,000 shares
• Reclassification of ownership from direct to indirect may complicate immediate transparency of voting/beneficial control

Insights

Corporate Governance Expert

TL;DR: Insider moved shares into grantor and irrevocable trusts, indicating estate or succession planning without cash proceeds.

The reported transactions show no cash consideration (price $0), suggesting transfers rather than market sales. Moving 97,911 and 65,274 shares into named trusts is consistent with estate planning or intra-family reallocation, and the filer retains substantial indirect holdings through several trusts and entities. For governance, these transfers do not indicate a change in control or an outward liquidity event, but they do reclassify beneficial ownership between direct and indirect positions. The filing is amended and properly signed by an attorney-in-fact.

Securities/Insider Transactions Analyst

TL;DR: Material share movements were recorded on 08/26/2025: 163,185 shares disposed from direct holding and significant transfers to related trusts.

Table I shows a net reported direct holding of 861,000 shares after a 163,185 disposal. The filing records acquisitions of 97,911 and 65,274 shares into two separate beneficiary vehicles, documented as indirect holdings thereafter. All transactions are coded "G" and priced at $0, and the issuer/ticker (BOW) is identified. From a market-impact perspective, these are internal transfers rather than open-market sales and therefore are unlikely to signal immediate liquidity pressure, though the decrease in direct holdings is notable for ownership classification purposes.

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

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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)
09/02/2025

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	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 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 Irrevocable Family GST Exempt Trust.

Remarks:

	/s/ H. Matthew Crusey, as attorney-in-fact	09/03/2025
	** 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.
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FAQ

What did Stephen J. Sills report on Form 4/A for BOW?

The filing reports transactions dated 08/26/2025 that show a 163,185 share disposal from direct holdings and transfers of 97,911 and 65,274 shares into two named trusts.

Were any shares sold for cash in the reported transactions?

No. All reported transactions show a price of $0, indicating transfers rather than cash sales.

How many shares does Sills directly own after the reported transactions?

The Form reports 861,000 shares beneficially owned in the direct position following the reported transactions.

Which trusts received transferred shares according to the filing?

The explanation states 97,911 shares were transferred to the "Stephen J. Sills 2024 I Grant #3" grantor trust and 65,274 shares to the "Stephen J. Sills Irrevocable Family GST Exempt Trust."

When was the amended Form 4 signed?

The form shows a signature by an attorney-in-fact on 09/03/2025.