Bowhead Specialty Holdings Inc.

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FORWARD-LOOKING STATEMENTS

All references to the “Company,” “Bowhead,” “we,” “our” and “us,” unless the context otherwise requires, are to Bowhead Specialty Holdings Inc., a Delaware corporation, and its consolidated subsidiaries.

This Annual Report on Form 10-K contains forward-looking statements within the meaning of the Private Securities Litigation Reform Act of 1995. All statements other than statements of historical facts contained in this Annual Report on Form 10-K, including statements regarding our future results of operations or financial condition, business strategy and plans, and objectives of management for future operations are forward-looking statements.

Some of the forward-looking statements can be identified by the use of terms such as “believes”, “expects”, “may”, “will”, “should”, “could”, “seeks”, “intends”, “plans”, “estimates”, “anticipates” or other comparable terms. However, not all forward-looking statements contain these identifying words. These forward-looking statements include all matters that are not related to present facts or current conditions or that are not historical facts. They appear in a number of places throughout this Annual Report on Form 10-K and include statements regarding our intentions, beliefs or current expectations concerning, among other things, our consolidated results of operations, financial condition, liquidity, prospects and growth strategies, management’s expectations with respect to any regulatory actions related to Insurance Regulatory Information System (“IRIS”) ratio results, the industries in which we operate, and other statements relating to our future performance.

Forward-looking statements are subject to known and unknown risks and uncertainties, many of which are beyond our control. Our actual results may differ materially from those expressed in, or implied by, the forward-looking statements included in this Annual Report on Form 10-K as a result of various factors, including, among others:

•our inability to accurately assess our underwriting risk;

•intense competition for business in our industry;

•our inability to maintain our strategic relationship with American Family Mutual Insurance Company, S.I. (“AFMIC” and, together with its subsidiaries, “AmFam”);

•a decline in AmFam’s financial strength rating or financial size category;

•exposure to certain risks arising out of our reliance on insurance retail agents, brokers and wholesalers as distribution channels;

•inadequate losses and loss expense reserves to cover our actual losses;

•unexpected changes in the interpretation of our coverage or provisions, including loss limitations and exclusions, in our policies;

•our reinsurers’ failure to reimburse us for claims on a timely basis, or at all;

•adverse economic factors and their impact on our growth and profitability;

•existing or future regulation and our ability to comply with these regulations;

•changes to trade policies, retaliatory measures, or prolonged uncertainty in trade relationships;

•the loss of one or more key personnel;

•disruptions of our operations due to security breaches, loss of data, cyber-attacks and other information technology failures;

•increased costs as a result of operating as a public company; and

•other risks and uncertainties discussed in Part I, Item 1A of this Annual Report on Form 10-K.

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Forward-looking statements speak only as of the date on which they are made. Except as expressly required under federal securities laws or the rules and regulations of the Securities and Exchange Commission ("SEC"), we do not assume any obligation to update or revise any forward-looking statement, whether as a result of new information, future events or otherwise. You should not place undue reliance on forward-looking statements. All forward-looking statements attributable to us are expressly qualified by these cautionary statements.

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