Bowhead Specialty Holdings Inc. (NYSE: BOW) (the “Company”, “Bowhead Specialty”, “we” or “our”) announced the launch of a proposed underwritten secondary public offering of 4,000,000 shares of its common stock by certain of its stockholders (the “Selling Stockholders”). In connection with the proposed offering, certain of the Selling Stockholders intend to grant the underwriters a 30-day option to purchase up to an additional 600,000 shares of the Company’s common stock. The proposed offering is subject to market and other conditions.

The Company is not selling any shares of its common stock in the proposed offering and will not receive any of the proceeds from the sale.

J.P. Morgan, Morgan Stanley and Keefe, Bruyette & Woods, A Stifel Company are acting as joint lead bookrunning managers for the proposed offering.

The proposed offering is being made only by means of a prospectus. Copies of the preliminary prospectus relating to the proposed offering may be obtained from: J.P. Morgan Securities LLC, c/o Broadridge Financial Solutions, 1155 Long Island Avenue, Edgewood, NY 11717 or by email at prospectus-eq_fi@jpmchase.com and postsalemanualrequests@broadridge.com; Morgan Stanley & Co. LLC, Attention: Prospectus Department, 180 Varick Street, 2nd Floor, New York, NY 10014; or Keefe, Bruyette & Woods, Inc., Attention: Capital Markets, 787 Seventh Avenue, 4th Floor, New York, NY 10019, or by email at uscapitalmarkets@kbw.com, or by telephone at (800) 966 1559.

A registration statement on Form S-1, including a preliminary prospectus, relating to these securities has been filed with the Securities and Exchange Commission (the “SEC”) but has not yet become effective. These securities may not be sold nor may offers to buy be accepted prior to the time the registration statement becomes effective. This press release shall not constitute an offer to sell or the solicitation of an offer to buy securities, nor shall there be any sale of securities in any state or other jurisdiction in which such offer, solicitation or sale would be unlawful prior to registration or qualification under the securities laws of any such state or jurisdiction.

About Bowhead Specialty Holdings Inc.

Bowhead Specialty is a growing specialty insurance business providing casualty, professional liability and healthcare liability insurance products. We were founded and are led by industry veteran Stephen Sills. The team is composed of highly experienced and respected industry veterans with decades of individual, successful underwriting and management experience. We focus on providing “craft” solutions in our specialty lines and classes of business that we believe require deep underwriting and claims expertise in order to produce attractive financial results.

We pride ourselves on the quality and experience of our people, who are committed to exceeding our partners’ expectations through excellent service and expertise. Our collaborative culture spans all functions of our business and allows us to provide a consistent, positive experience for all of our partners.

Forward-Looking Statements

This press release contains forward-looking statements as that term is defined in the Private Securities Litigation Reform Act of 1995. All statements other than statements of historical facts contained in press release are forward-looking statements. In some cases, forward-looking statements can be identified by terms such as “anticipates,” “believes,” “estimates,” “expects,” “intends,” “plans,” “predicts,” “projects,” “seeks,” “future,” “outlook,” “prospects” “will,” “would,” “should,” “could,” “may,” “can have” or similar words. Forward-looking statements involve risks and uncertainties that could cause actual results to differ materially from those contemplated by the forward-looking statements. These risks and uncertainties include, but are not limited to, risks and uncertainties associated with the consummation of the proposed offering and other risks described in the Company’s registration statement on Form S-1 as it may be amended from time to time, and Quarterly Report on Form 10-Q for the quarterly period ended June 30, 2024 and any subsequent filings with the SEC. Forward-looking statements speak only as of the date of this press release and the Company does not undertake any obligation to update or revise any forward-looking information to reflect changes in assumptions, the occurrence of unanticipated events or otherwise.

Investor Relations Shirley Yap, Head of Investor Relations investorrelations@bowheadspecialty.com

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