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Bowhead Specialty Holdings Inc. Form 4 Filings

BOW NYSE

Every Form 4 that Bowhead Specialty Holdings Inc. (BOW) has filed with the SEC in the last 12 months is listed below, newest first, and each one links through to the document itself with the summary and the scores our analysis gives it.

A Form 4 covers the transactions officers, directors and large holders report, so if you follow BOW and want that one kind of document rather than the whole filing history, this is the page to keep. The company's other filings, of every form, are on the full BOW filings page.

Rhea-AI 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.

Rhea-AI Summary

Bowhead Specialty Holdings Inc. insider David John Newman reported a routine tax-related share disposition. He surrendered 2,118 shares of common stock at $28.30 per share to the company to cover required tax withholdings upon vesting of restricted stock units, and now directly holds 295,077 shares. This amended filing corrects an inadvertent error in a prior Form 4.

Rhea-AI Summary

Bowhead Specialty Holdings Inc. CFO Brad Mulcahey reported a routine tax-related share disposition. He surrendered 1,027 shares of Common Stock at $28.30 per share to the company to cover required tax withholdings upon vesting of restricted stock units, and now holds 135,300 shares directly. This amended filing corrects an inadvertent error in a prior Form 4 and does not reflect an open-market sale.

Rhea-AI Summary

Bowhead Specialty Holdings Inc. Chief Accounting Officer Shirley Shek Li Yap reported a tax-withholding share disposition. She surrendered 679 shares of common stock at $23.80 per share to the company to cover required tax withholdings upon vesting of restricted stock units, correcting an earlier Form 4. Following this, she directly holds 82,879 shares of common stock.

Rhea-AI 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.

Rhea-AI Summary

Bowhead Specialty Holdings Inc. reported a routine insider tax-withholding transaction by its CFO and Treasurer, Brad Mulcahey. On May 23, 2026, he surrendered 3,506 shares of common stock at $28.30 per share to cover required tax withholdings upon vesting of restricted stock units. After this non-market disposition, he directly holds 132,821 shares of Bowhead Specialty common stock.

Rhea-AI 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.

Rhea-AI Summary

Bowhead Specialty Holdings Inc. CEO and President Stephen Jay Sills reported a routine tax-withholding event related to equity compensation. He surrendered 24,353 shares of common stock at $28.46 per share to cover required tax withholdings upon vesting of restricted stock units, leaving 838,926 shares held directly plus additional indirect holdings through various trusts and an LLC.

Rhea-AI Summary

Baker Tom reported acquisition or exercise transactions in this Form 4 filing.

Bowhead Specialty Holdings Inc. director Tom Baker received a grant of 3,361 shares of Common Stock in the form of restricted stock units on April 30, 2026. The award was recorded at a price of $0.00 per share, reflecting a compensation grant rather than an open-market purchase. After this grant, Baker directly holds a total of 10,085 shares of the company’s common stock.

Rhea-AI Summary

Bowhead Specialty Holdings Inc. director Angela Brock-Kyle received an equity grant of 6,722 shares of Common Stock in the form of restricted stock units on April 30, 2026. The award was recorded at a price of $0.00 per share as a compensation grant, not a market purchase.

Following this grant, Brock-Kyle directly holds a total of 43,495 shares of Bowhead Specialty Holdings Inc. common stock. The filing classifies the transaction as a grant or award acquisition, highlighting ongoing stock-based compensation for the company’s board.

Rhea-AI Summary

Bowhead Specialty Holdings Inc. director David Thomas Foy received a grant of 3,361 shares of Common Stock in the form of restricted stock units on April 30, 2026. The award carried a stated price of $0.00 per share, consistent with a compensation grant rather than a market purchase.

After this award, Foy directly owns 10,085 shares of Bowhead Specialty Holdings common stock. The filing characterizes the transaction as a grant or other acquisition, reflecting routine equity-based director compensation rather than an open-market trade.

Rhea-AI Summary

Fondriest Fabian reported acquisition or exercise transactions in this Form 4 filing.

Bowhead Specialty Holdings Inc. director Fabian Fondriest received a grant of 6,722 shares of Common Stock in the form of restricted stock units. The award, dated April 30, 2026, was issued at no cash cost and increased his direct holdings to 49,818 shares.

Rhea-AI Summary

Bowhead Specialty Holdings Inc. director David Clifford Holman received a grant of 3,361 shares of Common Stock in the form of restricted stock units on April 30, 2026. The award was recorded at a price of $0.00 per share as a stock-based compensation grant, not an open-market purchase.

Following this grant, Holman directly owns 5,716 shares of Bowhead Specialty Holdings Inc. common stock. The filing characterizes the transaction as a non-derivative acquisition through a grant or award, and a footnote clarifies that the reported amount reflects restricted stock units.

Rhea-AI Summary

Lowenstein Price reported acquisition or exercise transactions in this Form 4 filing.

Bowhead Specialty Holdings Inc. director Lowenstein Price received a grant of 3,361 shares of Common Stock in the form of restricted stock units. The award was recorded at a price of $0.00 per share, bringing Price’s directly owned stake to a total of 3,361 shares after the grant.

Rhea-AI Summary

Schnidman Ava reported acquisition or exercise transactions in this Form 4 filing.

Bowhead Specialty Holdings Inc. director Ava Schnidman reported equity compensation on a Form 4. She received a grant of 3,361 shares of common stock at a price of $0.00 per share, reflecting restricted stock units. After this grant, she directly holds 5,380 common shares and indirectly holds 1,893 shares through the Ava Schnidman Revocable Living Trust.

Rhea-AI Summary

Bowhead Specialty Holdings CEO Stephen J. Sills reported bona fide gifts of 255,400 shares of common stock on March 12–13. These G-code transactions reflect gift transfers from his direct holdings and several family trusts and GRATs. After these gifts, he holds 832,150 shares directly, along with multiple indirect trust and entity positions disclosed as of those dates.

Rhea-AI Summary

Bowhead Specialty Holdings Inc. CFO and Treasurer Brad Mulcahey reported equity compensation and related tax-withholding transactions in the company’s common stock.

On February 19, 2026, he acquired 25,145 shares through a grant of restricted stock units. On February 20, 2026, he disposed of 1,274 shares, surrendered to the issuer to cover required tax withholdings upon RSU vesting at $24.90 per share. Following these transactions, he directly owned 136,327 common shares.

Rhea-AI Summary

Bowhead Specialty Holdings Inc. Chief Underwriting Officer David John Newman reported two equity-related transactions in common stock. On February 19, 2026, he acquired 23,488 shares at a stated price of $0.00 per share as a grant of restricted stock units. On February 20, 2026, he disposed of 1,443 shares at $24.90 per share, surrendering them back to the company to cover required tax withholdings upon vesting. After these transactions, he directly held just under 300,000 shares.

Rhea-AI Summary

Bowhead Specialty Holdings Inc. CEO and President Stephen Jay Sills reported equity compensation grants and related tax withholding activity in Common Stock. On February 19, he received two stock awards totaling 90,703 and 88,566 shares, recorded as grant or award acquisitions at no cash cost.

On February 20, 5,419 shares were surrendered to the issuer to cover required tax withholdings due upon vesting of restricted stock units at $24.90 per share, a tax-withholding disposition rather than an open-market sale. He also reports additional indirect holdings through various family trusts and entities.

Rhea-AI Summary

Bowhead Specialty Holdings Inc. Chief Accounting Officer Shirley Shek Li Yap reported two stock-based compensation entries involving the company’s common stock. On February 19, 2026, she acquired 9,826 shares through a grant of restricted stock units at a stated price of $0.0000 per share, as noted in a footnote explaining it reflects an RSU grant. On February 20, 2026, she disposed of 524 shares at $24.90 per share to satisfy required tax withholdings upon vesting of restricted stock units, with a footnote clarifying these shares were surrendered to the issuer for tax purposes rather than sold in the open market.

Rhea-AI Summary

Bowhead Specialty Holdings Inc. director reported acquiring additional common stock in the company. On May 1, 2025, the reporting person acquired 4,038 shares of common stock at a stated price of $0, bringing their directly held beneficial ownership to 36,773 shares after the transaction.

The footnotes explain that this total includes 23,324 shares of common stock that were previously received on September 19, 2024 for no consideration, as part of a pro rata distribution connected to the dissolution of Bowhead Insurance Holdings LP. That earlier acquisition was treated as exempt from reporting under Rule 16a-9 of the Securities Exchange Act of 1934.

Rhea-AI Summary

Bowhead Specialty Holdings Inc. (BOW) CEO, President and Director Stephen J. Sills reported an internal transfer of company stock. On 11/26/2025, he moved 75,000 shares of common stock in a transaction coded "G" (a gift or similar transfer) at a price of $0 per share from his direct holdings to the Stephen J. Sills 2024 I GRAT #4 grantor trust. After this transfer, he directly held 786,000 shares and also reported additional indirect ownership through several trusts and an LLC, including the new 75,000-share position in the GRAT.