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Bowhead Specialty (NYSE: BOW) CEO surrenders 13,053 shares for RSU tax

Filing Impact
(Neutral)
Filing Sentiment
(Neutral)
Form Type
4/A

Rhea-AI Filing Summary

Bowhead Specialty Holdings CEO Stephen Jay Sills reported an amended Form 4 showing a tax-related share disposition. On May 22, 2026, 13,053 shares of common stock were surrendered to the company at $28.46 per share to cover required tax withholdings upon vesting of restricted stock units, correcting an earlier filing. Following this tax-withholding disposition, Sills directly held 850,226 common shares and also reported additional indirect holdings through multiple trusts and an LLC.

Positive

  • None.

Negative

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Insider Sills Stephen Jay
Role CEO and President
Type Security Shares Price Value
Tax Withholding Common Stock 13,053 $28.46 $371K
holding Common Stock -- -- --
holding Common Stock -- -- --
holding Common Stock -- -- --
holding Common Stock -- -- --
holding Common Stock -- -- --
holding Common Stock -- -- --
holding Common Stock -- -- --
holding Common Stock -- -- --
holding Common Stock -- -- --
holding Common Stock -- -- --
holding Common Stock -- -- --
Holdings After Transaction: Common Stock — 850,226 shares (Direct, null); Common Stock — 2,681 shares (Indirect, By Sills Family Trust 1)
Footnotes (1)
  1. Represents shares surrendered to the Issuer by the Reporting Person to pay required tax withholdings due upon vesting of restricted stock units, correcting an inadvertent error in the Form 4 filed on May 26, 2026. Includes 31,129 shares of common stock transferred on May 15, 2026, for no consideration, from the Stephen J. Sills 2024 I GRAT #2 to the direct holdings of the Reporting Person. Such transaction was exempt from reporting pursuant to Rule 16a-13 of the Securities Exchange Act of 1934, as amended.
Tax-withholding shares 13,053 shares Shares surrendered for tax withholdings on RSU vesting
Implied per-share value $28.46 per share Value used for 13,053-share tax-withholding disposition
Direct holdings after transaction 850,226 shares Common stock held directly following tax-withholding disposition
Sills 2024 LLC indirect holdings 214,469 shares Common stock held indirectly by Sills 2024 LLC
Irrevocable Family GST Exempt Trust holdings 72,000 shares Common stock held indirectly by Stephen J. Sills Irrevocable Family GST Exempt Trust
GRAT #2 indirect holdings 41,371 shares Common stock held indirectly by Stephen J. Sills 2024 I GRAT #2
restricted stock units financial
"due upon vesting of restricted stock units, correcting an inadvertent error"
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
"shares surrendered to the Issuer by the Reporting Person to pay required tax withholdings due"
Rule 16a-13 regulatory
"Such transaction was exempt from reporting pursuant to Rule 16a-13 of the Securities Exchange Act"
GRAT financial
"Includes 31,129 shares of common stock transferred on May 15, 2026, from the Stephen J. Sills 2024 I GRAT #2"
GST Exempt Trust financial
"By Stephen J. Sills Irrevocable Family GST Exempt Trust"
SEC Form 4
FORM 4UNITED 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 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)
XDirector10% Owner
XOfficer (give title below)Other (specify below)
CEO and President
2a. Foreign Trading Symbol
3. Date of Earliest Transaction (Month/Day/Year)
05/22/2026
6. Individual or Joint/Group Filing (Check Applicable Line)
XForm filed by One Reporting Person
Form filed by More than One Reporting Person
4. If Amendment, Date of Original Filed (Month/Day/Year)
05/26/2026
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)
CodeVAmount(A) or (D)Price
Common Stock05/22/2026F13,053(1)D$28.46850,226(2)D
Common Stock2,681IBy Sills Family Trust 1
Common Stock2,681IBy Sills Family Trust 2
Common Stock2,681IBy Sills Family Trust 3
Common Stock2,681IBy Sills Family Trust 4
Common Stock2,681IBy Sills Family Trust 5
Common Stock120,000IStephen J. Sills 2024 I GRAT #5
Common Stock75,000IBy Stephen J. Sills 2024 I GRAT #4
Common Stock97,911IBy Stephen J. Sills 2024 I GRAT #3
Common Stock72,000IBy Stephen J. Sills Irrevocable Family GST Exempt Trust
Common Stock214,469IBy Sills 2024 LLC
Common Stock41,371(2)IBy Stephen J. Sills 2024 I GRAT #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)
CodeV(A)(D)Date ExercisableExpiration DateTitleAmount 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, correcting an inadvertent error in the Form 4 filed on May 26, 2026.
2. Includes 31,129 shares of common stock transferred on May 15, 2026, for no consideration, from the Stephen J. Sills 2024 I GRAT #2 to the direct holdings of the Reporting Person. Such transaction was exempt from reporting pursuant to Rule 16a-13 of the Securities Exchange Act of 1934, as amended.
Remarks:
/s/ H. Matthew Crusey, as attorney-in-fact05/27/2026
** Signature of Reporting PersonDate
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 did Bowhead Specialty (BOW) CEO Stephen Sills report in this amended Form 4?

Stephen Sills reported an amended Form 4 showing shares used for tax withholding. He surrendered 13,053 Bowhead common shares to the company to pay required taxes on vested restricted stock units, correcting an inadvertent error in a prior Form 4 filed on May 26, 2026.

How many Bowhead (BOW) shares were used to cover Stephen Sills’ tax withholdings?

Stephen Sills used 13,053 Bowhead common shares to cover tax withholdings. These shares were surrendered to the issuer at a value of $28.46 per share in connection with the vesting of restricted stock units, according to the Form 4/A disclosure and related footnote.

What are Stephen Sills’ direct Bowhead (BOW) holdings after this tax-withholding transaction?

After the tax-withholding disposition, Stephen Sills directly held 850,226 Bowhead common shares. This figure reflects his remaining direct ownership following surrender of 13,053 shares to pay tax obligations related to vesting restricted stock units, as detailed in the amended Form 4 filing.

Does this Bowhead (BOW) Form 4/A involve open-market buying or selling by Stephen Sills?

The Form 4/A does not report open-market buying or selling by Stephen Sills. It shows a tax-withholding disposition coded “F,” where 13,053 shares were surrendered to the issuer to pay taxes on vested restricted stock units, a routine compensation-related event rather than a market trade.

What indirect Bowhead (BOW) holdings associated with Stephen Sills are disclosed in this filing?

The filing lists multiple indirect Bowhead holdings associated with Stephen Sills, including 214,469 shares held by Sills 2024 LLC and 72,000 shares held by the Stephen J. Sills Irrevocable Family GST Exempt Trust, along with several GRATs and family trusts each holding smaller share amounts.

Why was this Bowhead (BOW) Form 4 amended according to the footnotes?

The Form 4 was amended to correct an inadvertent error in the earlier May 26, 2026 filing. The footnote explains that 13,053 shares were surrendered to Bowhead to satisfy required tax withholdings on restricted stock unit vesting, and this correction aligns reported data with that event.