Bowhead Specialty Holdings Inc.

Current report

On August 3, 2026, BOW entered into an Agreement and Plan of Merger (the “Merger Agreement”) with AmFam, Inc., a Wisconsin corporation (“American Family”), Superior Trident Inc., a Delaware corporation and a direct wholly-owned subsidiary of American Family (“Merger Sub”), and certain other affiliates of American Family and Merger Sub, solely for the purpose of certain provisions, pursuant to which, at the closing of the transactions contemplated by the Merger Agreement, Merger Sub will merge with and into BOW, with BOW surviving as a wholly-owned subsidiary of American Family (the “Merger”).

Current report

Risks Relating to the Proposed Merger

Current report

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.

Current report

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 American Family or any of its affiliates or by certain recused directors of BOW; (c) the receipt of requisite regulatory approvals or clearances, including the expiration or termination of the applicable waiting period under the Hart-Scott-Rodino Antitrust Improvements Act of 1976, as amended and approvals from insurance regulators in Wisconsin and Texas; (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.

Current report

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.

Current report

While the Merger is pending, we will be subject to business uncertainties and certain contractual restrictions that could adversely affect our business, results of operations or financial condition.

Current report

The Merger will happen only if the stated conditions are satisfied or waived, including, among others, 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 and 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 American Family or any of its affiliates or by certain recused directors of BOW.

Current report

Many of the conditions are outside our control, and both we and American Family have certain rights to terminate the Merger Agreement. Uncertainty regarding the outcome of the Merger or our prospects could disrupt our business relationships with our insureds, broker partners and other strategic or business partners, who may attempt to negotiate changes to existing business relationships, consider entering into business relationships with parties other than us or seek to delay or defer entering into contracts or other commercial arrangements with us, which could have a material adverse effect on our business, results of operations and financial condition, regardless of whether the Merger is ultimately completed. Such uncertainty could also adversely affect our ability to recruit and retain key personnel and other employees.

Current report

The Merger Agreement contains pre-closing covenants that requires us and our subsidiaries to conduct our business in the ordinary course of business consistent with past practice in all material respects, and restricts what we and our subsidiaries can do prior to completion of the Merger, including, during the pendency of the Merger, our ability to pursue strategic transactions, undertake certain significant financing transactions and other actions, even if such actions would prove beneficial and may cause us to forgo certain opportunities we might otherwise pursue.

Current report

We have expended, and continue to expend, significant management time and resources in an effort to complete the Merger, which may have a negative impact on our ongoing business and operations.

Current report

Litigation filed in connection with the Merger could prevent or delay the consummation of the mergers or result in the payment of damages following completion of the Merger.

Current report

Lawsuits in connection with the Merger may be filed against us, American Family, or Merger Sub and their respective affiliates, directors and officers, which could prevent or delay the consummation of the Merger, divert management’s attention and resources, and result in additional costs to us. The ultimate resolution of any lawsuits is uncertain, and an adverse ruling in any such lawsuit may cause the Merger to be delayed or not to be completed, which could cause us not to realize some or all of the anticipated benefits of the Merger.

Current report

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

Current report

We or American Family may terminate the Merger Agreement under specified circumstances and the Merger Agreement provides for the payment by us to American Family of a termination fee of $[●] 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.

Current report

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:

Current report

•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;

Current report

•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;

Current report

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

Current report

•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

Current report

•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.

Current report

In addition to the other information set forth in this Quarterly Report, you should carefully consider the risk factors discussed in “Risk Factors” in Bowhead’s Annual Report on Form 10-K for the fiscal year ended December 31, 2025, subsequent Quarterly Reports on Form 10-Q and other filings with the SEC.

Previous report

There have been no material changes in our risk factors in the quarter ended March 31, 2026 from those disclosed in our Annual Report on Form 10-K for the year ended December 31, 2025.