Bowhead Specialty Holdings Inc.

In addition to the other information set forth in this Quarterly Report on Form 10-Q, you should carefully consider the risks and uncertainties described under the heading "Risk Factors" in Part I, Item 1A of our Annual Report on Form 10-K for the year ended December 31, 2025 and our Quarterly Report on Form 10-Q for the quarter ended June 30, 2026 (our “Q2 10-Q”), as updated and supplemented by the below risk factor. The below risk factors update the risk factors captioned “The completion of the Merger is subject to a number of conditions, including stockholder approval, and, if these conditions are not satisfied or waived, the Merger may not be completed within the expected timeframe or at all.” and “Failure to complete the Merger could adversely affect us, including in the event we are required to pay the termination fee.” in our Q2 10-Q. These risks and uncertainties are not the only ones facing us. There may be additional risks and uncertainties of which we are currently unaware or currently believe to be immaterial. The occurrence of any of these risks could materially and adversely affect our business, financial condition, liquidity, results of operations and prospects.

Risks Relating to the Proposed Merger

The completion of the Merger is subject to a number of conditions, including stockholder approval, and, if these conditions are not satisfied or waived, the Merger may not be completed within the expected timeframe or at all.

The completion of the Merger is subject to the satisfaction or waiver of certain conditions, including: (a) the approval of the Merger Agreement and the Merger by the affirmative vote of the holders of a majority of the outstanding shares of our common stock entitled to vote thereon at the Bowhead special stockholder meeting; (b) the approval of the Merger Agreement by the affirmative vote of the holders of a majority of the outstanding shares of our common stock entitled to vote thereon at such Bowhead special stockholder meeting, but excluding any outstanding shares of our common stock held by AFMIC or any of its affiliates or by certain recused directors of the Company; (c) the receipt of requisite regulatory approvals or clearances, including approval from the insurance regulator in Wisconsin; (d) the absence of governmental restraints or prohibitions preventing the consummation of the Merger; and (e) the absence of a “Company Material Adverse Effect” or “Burdensome Condition”, as each is defined in the Merger Agreement. In addition, the obligation of each party to complete the Merger is conditioned upon, among other things, the accuracy of the representations and warranties of each party (subject to certain materiality exceptions) and compliance in all material respects by each party with its obligations, covenants and agreements under the Merger Agreement.

There can be no assurance that the conditions to the completion of the Merger will be satisfied or waived on a timely basis or at all. In addition, no assurance can be given as to the terms, conditions and timing of any approvals or clearances. Any delay or noncompletion of the Merger would cause Bowhead stockholders not to receive on a timely basis, or at all, the Merger consideration. If the conditions to the completion of the Merger are not satisfied or waived, the Merger may not be completed within the expected timeframe or at all.

Failure to complete the Merger could adversely affect us, including in the event we are required to pay the termination fee.

We or AFMIC may terminate the Merger Agreement under specified circumstances and the Merger Agreement provides for the payment by us to AFMIC of a termination fee of $35 million under specified circumstances. If we are required to pay the termination fee, we may be required to use available cash that would have otherwise been available for general corporate purposes or other uses, which may materially and adversely affect our business, results of operations and financial condition.

If the Merger is not completed, our ongoing business may be adversely affected and will be subject to certain risks, including, among others, the following:

•the market price of our common stock (which may reflect a market assumption that the Merger will be completed) may decline, or we may experience other negative reactions from the financial markets;

•we will have incurred, and will continue to incur, significant expenses for professional services and other transaction costs in connection with the Merger for which we will have received little or no benefit if the Merger is not completed;

•we may experience negative reactions from our insured, broker partners, regulators and employees;

•failure to complete the Merger may result in negative publicity or result in a negative impression of us in the industry and with our insureds and other stakeholders; and

•matters relating to the Merger require substantial commitments of time and resources by our management, which would otherwise have been devoted to day-to-day operations and other opportunities that may have been beneficial to us.