American Family to buy Bowhead (NYSE: BOW) in $1.2B all-cash deal

Rhea-AI Filing Summary

Bowhead Specialty Holdings Inc. agreed to be acquired by American Family Mutual Insurance Company for $34.00 per share in cash, valuing the company at approximately $1.2 billion, an 11% premium to the July 31, 2026 closing price. The merger will be effected via a subsidiary, after approval by a majority of all shares and a majority of unaffiliated shares, required HSR and insurance regulatory clearances, and other customary conditions. Either party may terminate if not closed by April 2, 2027, extendable to June 2, 2027, and American Family may receive a $35 million termination fee in specified circumstances.

Equity awards will be cashed out or converted into cash-based escrow interests that generally follow existing vesting, with special treatment for the CEO’s RSUs and PSUs. For the quarter ended June 30, 2026, Bowhead reported gross written premiums of $297.9 million (up 28.2%), net income of $16.1 million or $0.48 per diluted share, adjusted net income of $16.1 million, a combined ratio of 95.9%, and book value per share of $14.39. Net investment income rose 37.6% to $18.8 million. In light of the pending transaction, the company cancelled its planned earnings call.

Positive

• American Family agreed to acquire Bowhead for $34.00 per share in cash, valuing the company at approximately $1.2 billion and representing an 11% premium to Bowhead’s July 31, 2026 closing share price.
• Second-quarter 2026 performance was strong, with gross written premiums up 28.2% to $297.9 million, net income up 30.8% to $16.1 million, adjusted net income up 26.5%, and a combined ratio of 95.9% versus 96.8% a year earlier.

Negative

• None.

Filing Explained

Unvested awards convert to cash-based interests, while the company warrant ends without payment before closing.

The August 3, 2026 Form 8-K reports an agreement dated August 2, 2026; closing is still conditional, and Bowhead would become American Family’s direct wholly owned subsidiary if it occurs.

The agreement adds that the Company Warrant will terminate immediately before closing with no payment or other consideration.

For non-CEO unvested RSUs, the consideration becomes a cash-based escrow interest that keeps the underlying vesting and forfeiture conditions, with payment within 15 business days after each vesting date.

The CEO’s unvested RSUs and PSUs instead become a cash-based escrow interest generally payable on the first anniversary of closing, but specified termination events can make it fully vested and payable sooner.

The transaction-specific documents that will further resolve the pending state are the stockholder vote and required HSR, Wisconsin, and Texas insurance approvals; the company says these materials will be provided in a proxy statement and Schedule 13E-3.

8-K Event Classification

4 items: 1.01, 2.02, 8.01, 9.01

4 items

Item 1.01 Entry into a Material Definitive Agreement Business

The company signed a significant contract such as a merger agreement, credit facility, or major partnership.

Item 2.02 Results of Operations and Financial Condition Financial

Disclosure of earnings results, typically an earnings press release or preliminary financials.

Item 8.01 Other Events Other

Voluntary disclosure of events the company deems important to shareholders but not covered by other items.

Item 9.01 Financial Statements and Exhibits Exhibits

Financial statements, pro forma financial information, and exhibit attachments filed with this report.

Key Figures

Per-share merger price: $34.00 per share Transaction equity value: $1.2 billion Offer premium: 11% +5 more

8 metrics

Per-share merger price $34.00 per share Cash consideration for each share of Bowhead common stock in American Family merger

Transaction equity value $1.2 billion Approximate value of Bowhead implied by the all-cash acquisition

Offer premium 11% Premium to Bowhead’s July 31, 2026 closing share price

Q2 2026 gross written premiums $297.9 million Three months ended June 30, 2026; up 28.2% year-over-year

Q2 2026 net income $16.1 million Three months ended June 30, 2026; 30.8% increase year-over-year

Q2 2026 combined ratio 95.9% Three months ended June 30, 2026; compared with 96.8% in Q2 2025

Return on equity 13.8% Q2 2026 annualized return on equity based on net income

Book value per share $14.39 Book value per share as of June 30, 2026

Key Terms

Merger Consideration, Company Termination Fee, combined ratio, Hart-Scott-Rodino Antitrust Improvements Act of 1976, +1 more

5 terms

Merger Consideration financial

"each share of common stock will be converted into the right to receive $34.00 per share in cash (the "Merger Consideration")"

Merger consideration is the total payment a company or buyer offers to shareholders of a target company in exchange for combining the two businesses, and can include cash, shares in the surviving company, debt assumption, or a mix of these. Investors care because the form and amount affect the deal’s value, tax consequences, immediate cash received versus future ownership, and the risk and upside of holding new shares — similar to choosing between cash now or stock that could grow later.

Company Termination Fee financial

"Parent will have the right to receive a termination fee of $35 million (the "Company Termination Fee")"

combined ratio financial

"Key metrics included a loss ratio, expense ratio and a combined ratio of 95.9% for Q2 2026"

The combined ratio is a way insurance companies measure how well they are doing by adding up all their costs and claims and comparing them to the money they earn from premiums. If the ratio is below 100%, it means the company is making a profit; if it's above 100%, they are losing money. It helps see if an insurance company is financially healthy or not.

Hart-Scott-Rodino Antitrust Improvements Act of 1976 regulatory

"closing is conditioned on expiration or termination of the waiting period under the Hart-Scott-Rodino Antitrust Improvements Act of 1976"

Company Required Vote regulatory

"consummation of the Merger is subject to obtaining the Company Required Vote at a special meeting of stockholders"

Earnings Snapshot

Gross written premiums: $297.9 million

quarter ended June 30, 2026

Gross written premiums $297.9 million up 28.2% year-over-year

Net income $16.1 million up 30.8% year-over-year

Adjusted net income $16.1 million up 26.5% year-over-year

Combined ratio 95.9% improved from 96.8% in Q2 2025

Book value per share $14.39 reported as of June 30, 2026

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Available on EDGAR 08/03/2026 - 08:03 AM Accepted by SEC EDGAR 08/03/2026 - 08:03 AM Learn about SEC filing dates

FAQ

What are Bowhead Specialty (BOW) stockholders receiving in the American Family acquisition?

Bowhead stockholders will receive $34.00 per share in cash for each share they own, valuing Bowhead at approximately $1.2 billion. The price represents an 11% premium to Bowhead’s closing share price on July 31, 2026.

What conditions must be satisfied for the Bowhead (BOW) and American Family merger to close?

Closing requires the Company Required Vote (majority of all shares and majority of unaffiliated shares), expiration or termination of the HSR Act waiting period, specified insurance regulatory approvals, no blocking legal orders, and satisfaction of customary covenants and representation conditions.

How did Bowhead Specialty (BOW) perform financially in Q2 2026?

For Q2 2026, Bowhead reported gross written premiums of $297.9 million (up 28.2%), net income of $16.1 million, adjusted net income of $16.1 million, diluted EPS of $0.48, and a combined ratio of 95.9%, reflecting both premium growth and solid underwriting performance.

What happens to Bowhead (BOW) equity awards such as RSUs and PSUs in the merger?

Vested RSUs will be cashed out for $34.00 per underlying share. Most unvested RSUs convert into cash-funded escrow interests that keep their vesting schedules. The CEO’s RSUs and PSUs convert into a cash escrow amount that generally vests after one year of continued employment or upon certain qualifying terminations.

Is there a termination fee in the Bowhead (BOW) merger agreement with American Family?

Yes. Under specified circumstances, including an Adverse Recommendation Change or terminating to enter a Superior Proposal, American Family is entitled to a $35 million Company Termination Fee, payable by Bowhead upon such termination events.

Why did Bowhead Specialty (BOW) cancel its Q2 2026 earnings conference call?

Bowhead cancelled its previously scheduled Q2 2026 earnings call after announcing the definitive merger agreement with American Family. The company still released full second-quarter 2026 financial results and made them available via a press release and its investor relations website.

When is the Bowhead (BOW) and American Family transaction expected to close and what is the outside date?

The transaction is targeted to close before the end of 2026, subject to approvals and closing conditions. Either party may terminate if it has not closed by April 2, 2027, with a potential extension to June 2, 2027 under specified regulatory-related circumstances.

0002002473false00020024732026-08-022026-08-02

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

FORM 8-K

CURRENT REPORT

Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934

Date of Report (Date of earliest event reported): August 2, 2026

Bowhead Specialty Holdings Inc.

(Exact name of registrant as specified in its charter)

Delaware			001-42111			87-1433334
(State or other jurisdiction of incorporation)			(Commission File Number)			(IRS Employer Identification No.)
			452 Fifth Avenue New York, New York 10018
			(Address of principal executive offices)
			(212) 970-0269
			(Registrant’s telephone number, including area code)

Check the appropriate box below if the Form 8-K filing is intended to simultaneously satisfy the filing obligation of the registrant under any of the following provisions:

£    Written communications pursuant to Rule 425 under the Securities Act (17 CFR 230.425)

T    Soliciting material pursuant to Rule 14a-12 under the Exchange Act (17 CFR 240.14a-12)

£    Pre-commencement communications pursuant to Rule 14d-2(b) under the Exchange Act (17 CFR 240.14d-2(b))

£    Pre-commencement communications pursuant to Rule 13e-4(c) under the Exchange Act (17 CFR 240.13e-4(c))

Securities registered pursuant to Section 12(b) of the Act:

Title of each class			Trading Symbol(s)			Name of each exchange on which registered
Common Stock, par value $0.01 per share			BOW			New York Stock Exchange

Indicate by check mark whether the registrant is an emerging growth company as defined in Rule 405 under the Securities Act of 1933 (§230.405 of this chapter) or Rule 12b-2 under the Securities Exchange Act of 1934 (§240.12b-2 of this chapter).

Emerging growth company T

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act. £

Item 1.01     Entry into a Material Definitive Agreement.

On August 2, 2026, Bowhead Specialty Holdings Inc. (the “Company”), a Delaware corporation, American Family Mutual Insurance Company, S.I., a Wisconsin insurance company (“Parent”), and Trident Superior Inc., a Delaware corporation and a wholly-owned direct subsidiary of Parent (“Merger Sub”), entered into an Agreement and Plan of Merger (the “Merger Agreement”), pursuant to which, at the closing of the transactions contemplated by the Merger Agreement (the “Closing”), Merger Sub will merge with and into the Company, with the Company surviving as a direct wholly-owned subsidiary of Parent (the “Merger”).

Pursuant to the Merger Agreement, at the effective time of the Merger (the “Effective Time”), each share of common stock of the Company, par value $0.01 per share (the “Common Stock”), issued and outstanding immediately prior to the Effective Time will be converted into the right to receive $34.00 per share in cash, without interest and less any amounts that are required to be deducted or withheld under applicable law (the “Merger Consideration”). Shares of Common Stock owned by the Company, Parent, Merger Sub or any other subsidiary of Parent will not be converted into the Merger Consideration, nor will shares of Common Stock held by stockholders who have properly demanded and not withdrawn their appraisal rights under Delaware law.

At the Effective Time, each restricted stock unit award (“Company RSU”) that is outstanding and vested as of immediately prior to the Effective Time, will, as of immediately prior to the Effective Time, automatically be converted into the right to receive, as promptly as practicable following the Effective Time, an amount in cash, without interest and subject to applicable withholding taxes, equal to the product of (a) the Merger Consideration and (b) the total number of shares of Common Stock subject to such Company RSU as of immediately prior to the Effective Time.

At the Effective Time, each Company RSU (other than the Company RSUs granted to the Company’s Chief Executive Officer, Stephen Sills (the “CEO”)) that is outstanding and unvested as of immediately prior to the Effective Time will, as of immediately prior to the Effective Time, be automatically assumed by Parent and converted into a beneficial interest security in a special escrow subaccount funded by Parent with an amount in cash equal to the product of (a) the Merger Consideration and (b) the total number of shares of Common Stock subject to such Company RSU as of immediately prior to the Effective Time (the “RSU Consideration”), which will be subject to the same vesting and forfeiture conditions as the underlying Company RSUs and will entitle the holder thereof to receive an amount in cash, subject to applicable withholding taxes, within fifteen (15) business days of each applicable vesting date, equal to the applicable portion of the RSU Consideration that has vested, plus accrued interest thereon from the Effective Time through each applicable settlement date.

At the Effective Time, each Company RSU and each performance stock unit award (“Company PSU”) granted to the CEO that is outstanding and unvested as of immediately prior to the Effective Time will, as of immediately prior to the Effective Time, be automatically assumed by Parent and converted into a beneficial interest security in a special escrow subaccount funded by Parent with an amount in cash equal to any amounts that otherwise would be payable with respect to such Company RSUs and Company PSUs at the Effective Time (the “CEO Award Amount”), which will vest subject to the CEO’s continued employment through the first anniversary of the Effective Time. On the first anniversary of the Effective Time, the CEO will be entitled to receive an amount in cash, subject to applicable withholding taxes, equal to the CEO Award Amount plus accrued interest thereon from the Effective Time through the applicable settlement date, provided that if the CEO’s employment is terminated by Parent, the Company or any of their respective subsidiaries or affiliates without Cause, by the CEO for Good Reason or due to the CEO’s death or Disability (as each such capitalized term is defined in the CEO’s employment agreement with the Company, dated as of May 22, 2024 (incorporated by reference to Exhibit 10.9 to the Company’s Quarterly Report on Form 10-Q filed with the SEC on August 8, 2024)), the CEO Award Amount plus accrued interest thereon will become fully vested and payable, subject to applicable withholding taxes, within five (5) business days following such termination.

Immediately prior to the Effective Time, the Common Stock Purchase Warrant, dated May 23, 2024, issued by the Company to Parent (the “Company Warrant”), will automatically terminate and be of no further force or effect, with no payment or other consideration payable in respect thereof.

The Company’s Board of Directors (the “Board”) adopted resolutions (a) determining that the Merger Agreement, the Merger and the other transactions contemplated thereby are fair, advisable and in the best interests of the Company and its stockholders (the “Company Stockholders”), (b) approving the Merger Agreement, the Merger and the other transactions contemplated thereby, and (c) declaring its advisability and recommending the adoption by the Company Stockholders of the Merger Agreement, the Merger and the other transactions contemplated thereby (the “Company Recommendation”).

The consummation of the Merger is subject to the satisfaction or waiver of customary closing conditions, including, among others, (a) the adoption of the Merger Agreement, the Merger, and the other transactions contemplated thereby by the affirmative vote of (i) the holders of a majority of the issued and outstanding shares of Common Stock entitled to vote thereon and (ii) the holders of a majority of the issued and outstanding shares of Common Stock entitled to vote thereon held by stockholders other than Parent and its subsidiaries and the Recused Directors (as defined in the Merger Agreement), in each case at a special meeting of the Company’s stockholders (collectively, the “Company Required Vote”), (b) the absence of any law or governmental order (whether temporary, preliminary or permanent) that is in effect and prevents or prohibits consummation of the Merger, (c) the expiration or termination of the applicable waiting period under the Hart-Scott-Rodino Antitrust Improvements Act of 1976, as amended (the “HSR Act”), and the receipt of required regulatory approvals from insurance regulators in Wisconsin and Texas, (d) the performance in all material respects by each party of its obligations, covenants and agreements under the Merger Agreement and (e) the accuracy of the representations and warranties of each party (subject to certain materiality qualifiers). Parent’s and Merger Sub’s obligations are also conditioned upon the absence of a Company Material Adverse Effect (as defined in the Merger Agreement) and the absence of a Burdensome

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Condition (as defined in the Merger Agreement). The receipt of financing by Parent is not a condition precedent to the completion of the Merger.

The Merger Agreement also contains customary representations, warranties and covenants by each of Parent, Merger Sub and the Company, including, among others, covenants by the Company to conduct its business in the ordinary course consistent with past practice in all material respects and to refrain from taking certain actions prior to the Effective Time, in each case except with Parent’s prior written consent (not to be unreasonably withheld, delayed or conditioned) or as set forth as exceptions to the interim operating covenants in the disclosure schedules to the Merger Agreement.

The Company has agreed not to solicit any Takeover Proposal (as defined in the Merger Agreement) from third parties or to engage in discussions with any third party regarding any Takeover Proposal. Prior to the receipt of the Company Required Vote, the Board may change its recommendation that Company Stockholders vote to approve the Merger Agreement (an “Adverse Recommendation Change”) following certain changes in circumstance or receipt of a Superior Proposal (as defined in the Merger Agreement), or terminate the Merger Agreement in order to enter into an agreement providing for a Superior Proposal, subject to the Company paying the Company Termination Fee (as defined below), if, after consulting with its financial advisor and outside counsel, the Board determines that failure to take such action would be inconsistent with the Board’s fiduciary duties under applicable law.

If the Merger has not closed by April 2, 2027 (as may be extended as described below, the “Outside Termination Date”), the Company or Parent may terminate the Merger Agreement; however, if the Closing has not occurred solely because (i) the applicable waiting period under the HSR Act relating to the Merger has not expired or been terminated or the required regulatory approvals from insurance regulators in Wisconsin and Texas have not been obtained and (ii) all other conditions to Closing have been satisfied (other than those conditions that by their nature are to be satisfied at the Closing, each of which is capable of being satisfied at the Closing) or waived, then either the Company or Parent may unilaterally extend the Outside Termination Date to June 2, 2027.

The Merger Agreement contains certain additional termination rights for Parent and the Company and further provides that, upon termination of the Merger Agreement under specified circumstances, including, termination by Parent in the event of an Adverse Recommendation Change or termination by the Company in order to enter into an agreement providing for a Superior Proposal, Parent will have the right to receive a termination fee of $35 million (the “Company Termination Fee”).

The foregoing description of the Merger Agreement and the transactions contemplated thereby does not purport to be complete, and is subject to, and qualified in its entirety by reference to, the full text of the Merger Agreement, which is attached as Exhibit 2.1 to this Current Report on Form 8-K and is incorporated herein by reference. The Merger Agreement and the foregoing description have been included to provide investors and stockholders with information regarding its terms. It is not intended to provide any other factual information about Parent, Merger Sub or the Company. The representations, warranties and covenants contained in the Merger Agreement were made only for purposes of the Merger Agreement as of the dates specified therein, were solely for the benefit of the parties to the Merger Agreement, may be subject to limitations agreed upon by the contracting parties, including being qualified by confidential disclosures made for the purposes of allocating contractual risk between the parties to the Merger Agreement instead of establishing these matters as facts, and may be subject to standards of materiality applicable to the contracting parties that differ from those applicable to investors. Investors and stockholders are not third-party beneficiaries under the Merger Agreement and should not rely on the representations, warranties and covenants or any descriptions thereof as characterizations of the actual state of facts or condition of Parent, Merger Sub or the Company. Moreover, information concerning the subject matter of the representations and warranties may change after the date of the Merger Agreement, which subsequent information may or may not be fully reflected in the parties’ public disclosures.

Item 2.02     Results of Operations and Financial Condition.

On August 3, 2026, the Company issued a press release announcing its financial results for the three months ended June 30, 2026. A copy of the press release is furnished as Exhibit 99.1 to this Current Report on Form 8-K.

In light of the announced Merger, on August 3, 2026, the Company announced that it will not be hosting its earnings conference call to discuss its financial results for the three months ended June 30, 2026, which was previously scheduled for 8:30 a.m. Eastern Time on August 4, 2026.

The information furnished pursuant to this Item 2.02 and Exhibit 99.1 shall not be deemed “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or otherwise subject to the liabilities under that Section and shall not be deemed to be incorporated by reference into any filing of the Company under the Securities Act of 1933, as amended (the “Securities Act”), or the Exchange Act.

Item 8.01     Other Events.

On August 3, 2026, the Company issued a press release announcing its entry into the Merger Agreement. A copy of the Company’s press release is filed herewith as Exhibit 99.2 and is incorporated herein by reference.

3

Forward-Looking Statements

Statements in this Current Report on Form 8-K, and any related oral statements, contain forward-looking statements within the meaning of the Private Securities Litigation Reform Act of 1995. 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 or the converse of such 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 Current Report on Form 8-K and include statements regarding intentions, beliefs or current expectations concerning, among other things, the transaction, regulatory approvals, and the timing of the transaction, the industries in which the Company operates, and other statements relating to the Company’s future performance.

The transaction is subject to risks and uncertainties, including: that the Company and American Family may be unable to complete the transaction because, among other reasons, conditions to the closing of the transaction may not be satisfied or waived; uncertainty as to the timing of completion of the transaction; the inability to complete the transaction due to the failure to obtain the Company stockholder approvals for the transaction or the failure to satisfy other conditions to completion of the transaction, including that a governmental entity may prohibit, delay or refuse to grant approval for the consummation of the transaction; interloper risk; the occurrence of any event, change or other circumstances that could give rise to the termination of the merger agreement; risks related to disruption of management’s attention from the Company’s ongoing business operations due to the transaction; the effect of the announcement of the transaction on the Company’s relationships with its insureds, operating results and business generally; and the outcome of any legal proceedings to the extent initiated against the Company, American Family or others following the announcement of the transaction, as well as the Company’s and American Family management’s response to any of the aforementioned factors.

A more fulsome discussion of the risks related to the transaction will be included in the Company’s proxy statement for the transaction. For a discussion of factors that could cause actual results to differ materially from those contemplated by forward-looking statements, see the section captioned “Risk Factors” in the Company’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 Securities and Exchange Commission (“SEC”). Should one or more of these risks or uncertainties materialize, or should underlying assumptions prove incorrect, actual results may vary materially from those indicated or anticipated by such forward-looking statements. While the list of factors presented here is, and the list of factors presented in the proxy statement will be, considered representative, no such list should be considered to be a complete statement of all potential risks and uncertainties. Unlisted factors may present significant additional obstacles to the realization of forward-looking statements.

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 SEC, the Company does 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 the Company are expressly qualified by these cautionary statements.

The information contained on or connected to any websites referenced in this Form 8-K is not incorporated by reference into this Form 8-K.

Additional Information and Where to Find It

In connection with the transaction, the Company will file with the SEC a proxy statement on Schedule 14A, the definitive version of which will be sent or provided to the Company’s stockholders. The Company and affiliates of the Company intend to jointly file a transaction statement on Schedule 13E-3 (the “Schedule 13E-3”). The Company may also file or furnish other documents with the SEC regarding the transaction. This material is not a substitute for the proxy statement, the Schedule 13E-3 or any other document that the Company may file with, or furnish to, the SEC. INVESTORS IN AND STOCKHOLDERS OF THE COMPANY ARE URGED TO READ THE PROXY STATEMENT, THE SCHEDULE 13E-3 AND ANY OTHER RELEVANT DOCUMENTS THAT ARE FILED OR FURNISHED OR WILL BE FILED WITH OR WILL BE FURNISHED TO THE SEC, AS WELL AS ANY AMENDMENTS OR SUPPLEMENTS TO THESE DOCUMENTS, CAREFULLY AND IN THEIR ENTIRETY (IF AND WHEN THEY BECOME AVAILABLE) BECAUSE THEY CONTAIN OR WILL CONTAIN IMPORTANT INFORMATION ABOUT THE TRANSACTION AND RELATED MATTERS. Investors and stockholders may obtain a copy of these documents (when they are filed and become available) free of charge at the SEC’s website at www.sec.gov. The Company will also provide a copy of these materials without charge on its website at https://ir.bowheadspecialty.com/.

Participants in the Solicitation

The Company, its executive officers and certain members of its Board may be deemed to be participants in the solicitation of proxies from the Company’s stockholders in connection with the transaction. Information regarding the Company’s directors and executive officers, including a description of their direct interests, by security holdings or otherwise, is contained in the Company’s annual proxy statement filed with the SEC on March 16, 2026. A more complete description will be available in the proxy statement on Schedule 14A to be filed regarding the transaction. You may obtain copies of these documents as described in the preceding paragraph filed with, or furnished to, the SEC free of charge. All such documents, when filed or furnished, are available free of charge at the SEC’s website (www.sec.gov) or by directing a request to the investor relations department of the Company.

4

Item 9.01.    Financial Statements and Exhibits.

(d) Exhibits.

Exhibit No.						Description
2.1*^						Agreement and Plan of Merger, dated as of August 2, 2026, by and among Bowhead Specialty Holdings Inc., American Family Mutual Insurance Company, S.I. and Trident Superior Inc.
99.1**						Press release of Bowhead Specialty Holdings Inc., dated August 3, 2026
99.2**						Press release of Bowhead Specialty Holdings Inc., dated August 3, 2026
104*						Cover Page Interactive Data File - the cover page XBRL tags are embedded within the Inline XBRL document

*Filed herewith.

^Schedules have been omitted pursuant to Item 601(b)(2) of Regulation S-K. The Company agrees to furnish supplementally a copy of any omitted schedule to the SEC upon request; provided, however, that the Company may request confidential treatment pursuant to Rule 24b-2 of the Exchange Act for any schedules or exhibits so furnished.

**Furnished herewith.

5

SIGNATURES

Pursuant to the requirements of the Securities Exchange Act of 1934, the registrant has duly caused this report to be signed on its behalf by the undersigned hereunto duly authorized.

Dated: August 3, 2026

			By:			/s/ H. Matthew Crusey
			Name:			H. Matthew Crusey
			Title:			General Counsel and Secretary

Bowhead Specialty Holdings Inc. Reports Second Quarter 2026 Results and Cancels Earnings Conference Call Following Announcement of Merger Agreement with American Family

NEW YORK, New York. (BusinessWire) – August 3, 2026 – Following the issuance of a news release earlier today announcing that Bowhead Specialty Holdings Inc. (“Bowhead”, the “Company” or “us”) (NYSE: BOW), has entered into a definitive merger agreement under which American Family will acquire Bowhead, the Company today announced financial results for the second quarter ended June 30, 2026(1) and cancelled the previously scheduled conference call to discuss its second quarter ended June 30, 2026 financial results.

Second Quarter 2026 Highlights

•Gross written premiums increased 28.2% to $297.9 million.

•Net income of $16.1 million, or $0.48 per diluted share.

•Adjusted net income(2) of $16.1 million, or $0.48 per diluted share(2).

•Return on equity of 13.8% and adjusted return on equity(2) of 13.8%.

•Book value per share $14.39 and diluted book value per share of $14.12.

Bowhead Chief Executive Officer, Stephen Sills, commented, “Since Bowhead's founding, we have benefited from a strong and trusting relationship with American Family, whose support and partnership have enabled us to build the company we are today. Over the years, they have developed a deep understanding of our business, our culture, and the underwriting discipline that defines Bowhead. I believe this transaction delivers compelling value to our stockholders while bringing together two organizations that share a long history, aligned values, and a commitment to disciplined underwriting and long-term success. I am proud of what the Bowhead team has accomplished, and I believe this combination recognizes the strength of the Bowhead franchise while continuing to enhance our ability to create value for our insureds, distribution partners and employees. I look forward to joining American Family and continuing to lead the Bowhead franchise.”

Mr. Sills continued, “Turning to our second quarter results, Bowhead once again delivered a strong quarter highlighted by consistent strong top and bottom line growth. Gross written premiums in the second quarter grew over 28% year-over-year, while adjusted net income grew over 26%, and diluted adjusted earnings per share grew just under 30%.”

Underwriting Results

The 28.2% increase in gross written premiums to $297.9 million in the second quarter of 2026 was driven by our increasing renewal book, new business and continued growth in our platform across all divisions:

•Our Casualty division led the growth with a 32.5% increase to $199.8 million;

•Professional Liability increased 0.6% to $55.1 million;

•Healthcare Liability increased 23.9% to $29.1 million;

•Baleen Specialty increased 311.1% to $13.9 million.

Our loss ratio of 67.3% for the second quarter of 2026 increased 1.1 points compared to 66.2% in the same period of 2025 due to an increase in our current accident year loss ratio. The higher current accident year loss ratio was driven by lower ceded loss activity under our excess of loss treaties, and to a lesser extent, changes in our portfolio mix.

As communicated in the past, the development in our prior accident year losses were driven by expected loss ratios applied to net additional premiums that were billed and fully earned in the quarter, but associated with policies from prior accident years. Once again, these amounts were not based on actual losses settling for more than reserved, and did not represent an increase in estimated reserves on unresolved claims.

Our expense ratio was 28.6% for the three months ended June 30, 2026, reflecting a decrease of 2.0 points compared to 30.6% for the same period in 2025. This decrease in our expense ratio was primarily driven by the 3.4 point decrease in our operating expense ratio and a 0.3 point increase in other insurance-related income, which contributed to the lowering of our expense ratio. These improvements were partially offset by the 1.7 point increase in our net acquisition costs ratio.

The decrease in our operating expense ratio was due to the continued scaling of our business, where net earned premiums grew at a higher rate than our expenses, as well as the prudent management of our expenses, including estimates of deferrable costs.

The increase in our net acquisition costs ratio was driven by the increase in earned broker commissions due to changes in our portfolio mix and higher commission rates, an increase in the ceding fee we pay to American Family and deferred employment related underwriting costs, partially offset by an increase in earned ceding commissions from our ceded reinsurance treaties.

Investment Results

Net investment income increased 37.6% in the quarter to $18.8 million, driven by a higher balance of investments. Our investment portfolio had a book yield of 4.7% and a new money rate of 4.9% as of June 30, 2026.

The weighted average effective duration of our investment portfolio, which included cash equivalents, was 3.3 years and had an average rating of “AA-” as of June 30, 2026.

__________________

(1)Comparisons in this release are made to June 30, 2025 financial results unless otherwise noted.

(2)Non-GAAP financial measure. See “Reconciliation of Non-GAAP Financial Measures” for a reconciliation of the non-GAAP financial measures to their most directly comparable U.S. GAAP measures.

Summary of Operating Results

The following table summarizes the Company’s results of operations for the three and six months ended June 30, 2026 and 2025:

			Three Months Ended June 30,																		Six Months Ended June 30,
			2026						2025						% Change						2026						2025						% Change
			($ in thousands, except percentages and per share data)
Gross written premiums			$	297,894					$	232,361					28.2		%				$	514,635					$	407,209					26.4		%
Ceded written premiums			(116,869)						(83,508)						39.9		%				(193,268)						(141,587)						36.5		%
Net written premiums			$	181,025					$	148,853					21.6		%				$	321,367					$	265,622					21.0		%
Revenues
Net earned premiums			$	143,953					$	119,137					20.8		%				$	280,762					$	228,954					22.6		%
Net investment income			18,820						13,677						37.6		%				36,847						26,236						40.4		%
Net realized investment losses			(11)						(11)						—		%				(32)						(15)						113.3		%
Other insurance-related income			1,095						460						138.0		%				1,974						805						145.2		%
Total revenues			163,857						133,263						23.0		%				319,551						255,980						24.8		%
Expenses
Net losses and loss adjustment expenses			96,945						78,900						22.9		%				188,427						152,327						23.7		%
Net acquisition costs			15,820						11,038						43.3		%				29,713						20,834						42.6		%
Operating expenses			26,384						25,849						2.1		%				52,187						49,785						4.8		%
Non-operating expenses			—						437						(100.0)		%				—						548						(100.0)		%
Warrant expense			783						783						—		%				1,558						1,558						—		%
Interest expense and financing fees			3,266						261						1151.3		%				6,429						508						1165.6		%
Foreign exchange (gains) losses			(2)						79						(102.5)		%				6						33						(81.8)		%
Total expenses			143,196						117,347						22.0		%				278,320						225,593						23.4		%
Income before income taxes			20,661						15,916						29.8		%				41,231						30,387						35.7		%
Income tax expense			(4,523)						(3,574)						26.6		%				(9,083)						(6,620)						37.2		%
Net income			$	16,138					$	12,342					30.8		%				$	32,148					$	23,767					35.3		%
Key Operating and Financial Metrics:
Adjusted net income(1)			$	16,145					$	12,758					26.5		%				$	32,178					$	24,238					32.8		%
Loss ratio			67.3		%				66.2		%										67.1		%				66.5		%
Expense ratio			28.6		%				30.6		%										28.5		%				30.4		%
Combined ratio			95.9		%				96.8		%										95.6		%				96.9		%
Return on equity(2)			13.8		%				12.4		%										13.9		%				12.2		%
Adjusted return on equity(1)(2)			13.8		%				12.8		%										13.9		%				12.5		%
Diluted earnings per share			$	0.48					$	0.36					33.3		%				$	0.96					$	0.70					37.1		%
Diluted adjusted earnings per share(1)			$	0.48					$	0.37					29.7		%				$	0.96					$	0.72					33.3		%

__________________

NM - Percentage change is not meaningful.

(1)Non-GAAP financial measure. See “Reconciliation of Non-GAAP Financial Measures” for a reconciliation of the non-GAAP financial measures to their most directly comparable U.S. GAAP measures.

(2)For the three and six months ended June 30, 2026 and 2025, net income and adjusted net income are annualized to arrive at return on equity and adjusted return on equity.

Condensed Consolidated Balance Sheets

			June 30, 2026						December 31, 2025
			($ in thousands, except share data)
Assets
Investments
Fixed maturity securities, available for sale, at fair value (amortized cost of $1,593,861 and $1,364,228, respectively)			$	1,585,217					$	1,371,006
Total investments			1,585,217						1,371,006
Cash and cash equivalents			141,748						193,545
Restricted cash and cash equivalents			23,073						40,225
Accrued investment income			13,686						10,958
Premium balances receivable			122,370						84,415
Reinsurance recoverable, net			466,205						399,676
Prepaid reinsurance premiums			227,048						191,821
Deferred policy acquisition costs			45,491						35,284
Property and equipment, net			11,951						10,636
Income taxes receivable			4,307						3,073
Deferred tax assets, net			29,574						22,476
Other assets			10,622						8,261
Total assets			$	2,681,292					$	2,371,376
Liabilities
Reserve for losses and loss adjustment expenses			$	1,318,644					1,129,936
Unearned premiums			628,266						552,594
Reinsurance balances payable			85,577						65,778
Debt			146,573						146,447
Income taxes payable			314						314
Accrued expenses			11,604						19,047
Other liabilities			16,375						7,986
Total liabilities			2,207,353						1,922,102
Commitments and contingencies (Note 13)
Mezzanine equity
Performance stock units			1,578						1,008
Stockholders' equity
Common stock			329						328
($0.01 par value; 400,000,000 shares authorized, 32,943,005 and 32,783,451 shares issued and outstanding at June 30, 2026 and December 31, 2025, respectively)
Additional paid-in capital			330,017						325,889
Accumulated other comprehensive gain (loss)			(6,828)						5,354
Retained earnings			148,843						116,695
Total stockholders' equity			472,361						448,266
Total mezzanine equity and stockholders' equity			473,939						449,274
Total liabilities, mezzanine equity and stockholders' equity			$	2,681,292					$	2,371,376

Gross Written Premiums

The following tables present gross written premiums by underwriting division for the three and six months ended June 30, 2026 and 2025:

			Three Months Ended June 30,
			2026						% of Total						2025						% of Total						$ Change						% Change
			($ in thousands, except percentages)
Casualty			$	199,764					67.0		%				$	150,720					64.9		%				$	49,044					32.5		%
Professional Liability			55,085						18.5		%				54,752						23.5		%				333						0.6		%
Healthcare Liability			29,133						9.8		%				23,505						10.1		%				5,628						23.9		%
Baleen Specialty			13,912						4.7		%				3,384						1.5		%				10,528						311.1		%
Gross written premiums			$	297,894					100.0		%				$	232,361					100.0		%				$	65,533					28.2		%

			Six Months Ended June 30,
			2026						% of Total						2025						% of Total						$ Change						% Change
			($ in thousands, except percentages)
Casualty			$	347,032					67.4		%				$	273,034					67.1		%				$	73,998					27.1		%
Professional Liability			82,746						16.1		%				80,752						19.8		%				1,994						2.5		%
Healthcare Liability			59,578						11.6		%				47,293						11.6		%				12,285						26.0		%
Baleen Specialty			25,279						4.9		%				6,130						1.5		%				19,149						312.4		%
Gross written premiums			$	514,635					100.0		%				$	407,209					100.0		%				$	107,426					26.4		%

The following tables present gross written premiums by underwriting model(1) for the three and six months ended June 30, 2026 and 2025:

			Three Months Ended June 30,
			2026						% of Total						2025						% of Total						$ Change						% Change
			($ in thousands, except percentages)
Craft			$	279,190					93.7		%				$	228,875					98.5		%				$	50,315					22.0		%
Digital
Baleen Specialty			13,912						4.7		%				3,384						1.5		%				10,528						311.1		%
Express			4,792						1.6		%				102						—		%				4,690						4598.0		%
Digital			18,704						6.3		%				3,486						1.5		%				15,218						436.5		%
Gross written premiums			$	297,894					100.0		%				$	232,361					100.0		%				$	65,533					28.2		%

			Six Months Ended June 30,
			2026						% of Total						2025						% of Total						$ Change						% Change
			($ in thousands, except percentages)
Craft			$	481,106					93.5		%				$	400,977					98.5		%				$	80,129					20.0		%
Digital
Baleen Specialty			25,279						4.9		%				6,130						1.5		%				19,149						312.4		%
Express			8,250						1.6		%				102						—		%				8,148						7988.2		%
Digital			33,529						6.5		%				6,232						1.5		%				27,297						438.0		%
Gross written premiums			$	514,635					100.0		%				$	407,209					100.0		%				$	107,426					26.4		%

__________________

NM - Percentage change is not meaningful.

(1)Our products are delivered through two complementary underwriting models designed to support sustainable and profitable growth across market cycles: a “craft” model for large, complex, higher-severity risks, and a “digital” model, which includes Baleen Specialty and other small-business offerings (“express”), for smaller, simpler, scalable business.

Loss Ratio

The following tables summarize current and prior accident year loss ratios for the three and six months ended June 30, 2026 and 2025:

			Three Months Ended June 30,
			2026												2025
			Net Losses and Loss Adjustment Expenses						% of Net Earned Premiums						Net Losses and Loss Adjustment Expenses						% of Net Earned Premiums
			($ in thousands, except percentages)
Current accident year			$	96,792					67.2		%				$	78,785					66.1		%
Prior accident year(1)			153						0.1		%				115						0.1		%
Total			$	96,945					67.3		%				$	78,900					66.2		%

			Six Months Ended June 30,
			2026												2025
			Net Losses and Loss Adjustment Expenses						% of Net Earned Premiums						Net Losses and Loss Adjustment Expenses						% of Net Earned Premiums
			($ in thousands, except percentages)
Current accident year			$	187,672					66.8		%				$	151,768					66.3		%
Prior accident year(1)			755						0.3		%				559						0.2		%
Total			$	188,427					67.1		%				$	152,327					66.5		%

__________________

(1)The existence of our prior accident year losses for the three and six months ended June 30, 2026 and 2025 were driven by expected loss ratios applied to net additional premiums billed and fully earned in the period, but associated with policies from prior accident years. These amounts were not based on actual losses settling for more than reserved, and did not represent an increase in estimated reserves on unresolved claims.

Expense Ratio

The following tables summarize the components of our expense ratio for the three and six months ended June 30, 2026 and 2025:

			Three Months Ended June 30,
			2026												2025
			Expenses						% of Net Earned Premiums						Expenses						% of Net Earned Premiums
			($ in thousands, except percentages)
Net acquisition costs			$	15,820					11.0		%				$	11,038					9.3		%
Operating expenses			26,384						18.3		%				25,849						21.7		%
Less: Other insurance related-income			(1,095)						(0.7)		%				(460)						(0.4)		%
Total			$	41,109					28.6		%				$	36,427					30.6		%

			Six Months Ended June 30,
			2026												2025
			Expenses						% of Net Earned Premiums						Expenses						% of Net Earned Premiums
			($ in thousands, except percentages)
Net acquisition costs			$	29,713					10.6		%				$	20,834					9.1		%
Operating expenses			52,187						18.6		%				49,785						21.7		%
Less: Other insurance-related income			(1,974)						(0.7)		%				(805)						(0.4)		%
Total			$	79,926					28.5		%				$	69,814					30.4		%

Net Investment Income

The following table summarizes the sources of net investment income for the three and six months ended June 30, 2026 and 2025:

			Three Months Ended June 30,												Six Months Ended June 30,
			2026						2025						2026						2025
			($ in thousands)
U.S. government and government agency			$	642					$	1,633					$	1,381					$	3,478
State and municipal			1,727						876						3,101						1,564
Commercial mortgage-backed securities			2,116						1,267						4,231						2,447
Residential mortgage-backed securities			4,326						3,129						8,581						5,668
Asset-backed securities			2,329						1,569						4,392						3,052
Corporate			6,825						4,244						12,965						7,496
Short-term investments			25						86						46						214
Cash and cash equivalents			1,206						1,154						2,890						2,859
Gross investment income			19,196						13,958						37,587						26,778
Investment expenses			(376)						(281)						(740)						(542)
Net investment income			$	18,820					$	13,677					$	36,847					$	26,236

Reconciliation of Non-GAAP Financial Measures

This earnings release contains certain financial measures that are not presented in accordance with generally

accepted accounting principles in the United States (“U.S. GAAP”). We use these non-GAAP financial measures

when planning, monitoring and evaluating our performance. Management believes that each of the non-GAAP

financial measures described below provides useful insight into our underlying business performance.

•Adjusted net income is defined as net income excluding the impact of net realized investment losses, non-operating expenses, loss on extinguishment of credit facility, foreign exchange (gains) losses, and certain strategic initiatives. Adjusted net income excludes the impact of certain items that may not be indicative of underlying business trends, operating results, or future outlook, net of tax impact. We calculate the tax impact only on adjustments that would be included in calculating our income tax expense using the estimated tax rate at which we received a deduction for these adjustments.

•Adjusted return on equity is defined as adjusted net income as a percentage of average beginning and ending mezzanine equity and stockholders’ equity.

•Diluted adjusted earnings per share is defined as adjusted net income divided by the weighted average common shares outstanding for the period, reflecting the dilution that may occur if equity based awards are converted into common stock equivalents as calculated using the treasury stock method.

You should not rely on these non-GAAP financial measures as a substitute for any U.S. GAAP financial measure.

While we believe that these non-GAAP financial measures are useful in evaluating our business, this information

should be considered supplemental in nature and not as a replacement for or superior to the comparable U.S. GAAP

measures. In addition, other companies, including companies in our industry, may calculate such measures

differently, which reduces their usefulness as comparative measures.

Adjusted net income

Adjusted net income for the three and six months ended June 30, 2026 and 2025 reconciles to net income as follows:

			Three Months Ended June 30,
			2026												2025
			Before income taxes						After income taxes						Before income taxes						After income taxes
			($ in thousands)
Income as reported			$	20,661					$	16,138					$	15,916					$	12,342
Adjustments:
Net realized investment losses			11						11						11						11
Non-operating expenses			—						—						437						437
Foreign exchange (gains) losses			(2)						(2)						79						79
Tax impact			—						(2)						—						(111)
Adjusted net income			$	20,670					$	16,145					$	16,443					$	12,758

			Six Months Ended June 30,
			2026												2025
			Before income taxes						After income taxes						Before income taxes						After income taxes
			($ in thousands)
Income as reported			$	41,231					$	32,148					$	30,387					$	23,767
Adjustments:
Net realized investment losses			32						32						15						15
Non-operating expenses			—						—						548						548
Foreign exchange losses			6						6						33						33
Tax impact			—						(8)						—						(125)
Adjusted net income			$	41,269					$	32,178					$	30,983					$	24,238

Adjusted return on equity

Adjusted return on equity for the three and six months ended June 30, 2026 and 2025 reconciles to return on equity as follows:

			Three Months Ended June 30,												Six Months Ended June 30,
			2026						2025						2026						2025
			($ in thousands, except percentages)
Numerator: Adjusted net income(1)			$	64,579					$	51,031					$	64,356					$	48,477
Denominator: Average mezzanine equity and stockholders' equity			466,550						399,588						461,607						389,127
Adjusted return on equity			13.8		%				12.8		%				13.9		%				12.5		%

_______________

(1)For the three and six months ended June 30, 2026 and 2025, net income and adjusted net income are annualized to arrive at return on equity and adjusted return on equity.

Diluted adjusted earnings per share

Diluted adjusted earnings per share for the three and six months ended June 30, 2026 and 2025 reconciles to diluted earnings per share as follows:

			Three Months Ended June 30,												Six Months Ended June 30,
			2026						2025						2026						2025
			($ in thousands, except share and per share data)
Numerator: Adjusted net income			$	16,145					$	12,758					$	32,178					$	24,238
Denominator: Diluted weighted average shares outstanding			33,557,875						34,045,961						33,456,675						33,885,414
Diluted adjusted earnings per share			$	0.48					$	0.37					$	0.96					$	0.72

Subsequent Event

On August 3, 2026, the Company and American Family announced that they have entered into a definitive agreement under which American Family has agreed to acquire all of the issued and outstanding shares of common stock of Bowhead that it does not currently own for $34.00 per share in cash, without interest, for a total transaction value of approximately $1.2 billion.

Conference Call Cancelled

As previously announced, given the transaction with American Family announced earlier today, the Company will not be hosting a conference call to discuss its results for the second quarter ended June 30, 2026, which was originally scheduled for 8:30 a.m. Eastern Time on Tuesday, August 4, 2026.

About Bowhead

Bowhead 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. Our products are delivered through two complementary underwriting models designed to support sustainable and profitable growth across market cycles: a “craft” model for large, complex, higher-severity risks, and a “digital” model, which includes Baleen Specialty and other small-business offerings (“express”), for smaller, simpler, and scalable business.

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

Statements in this press release, and any related oral statements, contain forward-looking statements within the meaning of the Private Securities Litigation Reform Act of 1995. 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 or the converse of such 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 press release and include statements regarding intentions, beliefs or current expectations concerning, among other things, the transaction, regulatory approvals, and the timing of the transaction, the industries in which Bowhead operates, and other statements relating to Bowhead’s future performance.

The transaction is subject to risks and uncertainties, including: that Bowhead and American Family may be unable to complete the transaction because, among other reasons, conditions to the closing of the transaction may not be satisfied or waived; uncertainty as to the timing of completion of the transaction; the inability to complete the transaction due to the failure to obtain the Bowhead stockholder approvals for the transaction or the failure to satisfy other conditions to completion of the transaction, including that a governmental entity may prohibit, delay or refuse to grant approval for the consummation of the transaction; interloper risk; the occurrence of any event, change or other circumstances that could give rise to the termination of the merger agreement; risks related to disruption of management’s attention from Bowhead’s ongoing business operations due to the transaction; the effect of the announcement of the transaction on Bowhead’s relationships with its insureds, operating results and business generally; and the outcome of any legal proceedings to the extent initiated against Bowhead, American Family or others following the announcement of the transaction, as well as Bowhead’s and American Family management’s response to any of the aforementioned factors.

A more fulsome discussion of the risks related to the transaction will be included in Bowhead’s proxy statement for the transaction. For a discussion of factors that could cause actual results to differ materially from those contemplated by forward-looking statements, see the section captioned “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 Securities and Exchange Commission (“SEC”). Should one or more of these risks or uncertainties materialize, or should underlying assumptions prove incorrect, actual results may vary materially from those indicated or anticipated by such forward-looking statements. While the list of factors presented here is, and the list of factors presented in the proxy statement will be, considered representative, no such list should be considered to be a complete statement of all potential risks and uncertainties. Unlisted factors may present significant additional obstacles to the realization of forward-looking statements.

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 SEC, Bowhead does 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 Bowhead are expressly qualified by these cautionary statements.

The information contained on or connected to any websites referenced in this communication is not incorporated by reference into this communication.

Investor Relations Contact:

Shirley Yap, Head of Investor Relations

investorrelations@bowheadspecialty.com

American Family to Acquire Bowhead Specialty in $1.2 Billion Transaction Bowhead Stockholders to Receive $34.00 per Share in Cash, Representing 11% Premium to Bowhead’s Closing Share Price on July 31, 2026 New York, New York, August 3, 2026 – Bowhead Specialty Holdings Inc. (NYSE: BOW) (“Bowhead”) today announced that it has entered into a definitive agreement pursuant to which American Family Mutual Insurance Company, S.I. (together with its affiliates, “American Family”) has agreed to acquire all of the issued and outstanding shares of common stock of Bowhead that it does not currently own in an all-cash transaction that values Bowhead at approximately $1.2 billion. Under the terms of the transaction, each Bowhead stockholder will receive $34.00 per share in cash, representing an 11% premium to Bowhead’s closing share price on July 31, 2026. Bowhead Chairman of the Board, Matthew Botein, commented, “This transaction recognizes the strength of the Bowhead franchise and reinforces the strategic partnership with American Family. It also represents the natural evolution of a longstanding relationship between both companies, built on shared values, underwriting discipline, and a commitment to delivering long-term value for policyholders and other stakeholders. On behalf of the Board of Directors, I want to express our sincere gratitude to the management team and employees whose vision, dedication, and hard work have built Bowhead into the exceptional company it is today. We believe this transaction creates a strong foundation for the future while preserving the values, culture and disciplined approach to underwriting that have been central to the success of both organizations.” Bowhead Chief Executive Officer and President, Stephen Sills, commented, “Since Bowhead's founding, we have benefited from a strong and trusting relationship with American Family, whose support and partnership have enabled us to build the company we are today. Over the years, they have developed a deep understanding of our business, our culture, and the underwriting discipline that defines Bowhead. I believe this transaction delivers compelling value to our stockholders while bringing together two organizations that share a long history, aligned values and a commitment to disciplined underwriting and long-term success. I am proud of what the Bowhead team has accomplished, and I believe this combination recognizes the strength of the Bowhead franchise while continuing to enhance our ability to create value for our insureds, distribution partners and employees. I look forward to joining American Family and continuing to lead the Bowhead franchise.” “We’re pleased to welcome Bowhead’s talented team and commercial specialty capabilities to American Family,” said Bill Westrate, Chair and Chief Executive Officer of American Family. “American Family’s relationship with Bowhead has continued to grow since its founding investment in 2020. As a minority stockholder and strategic partner, American Family has seen firsthand the strength of its business model, disciplined execution, and strong market position. American Family has great confidence in Bowhead’s leadership, employees and culture, and it looks forward to supporting the next phase of Bowhead’s growth. Together, we are well positioned to advance our shared long-term objectives while preserving the qualities that have made Bowhead a leader in its market. Bowhead’s capabilities complement American Family’s strategy to diversify its commercial portfolio, broaden product offerings, enhance capital efficiency and drive sustainable profitable growth.” Transaction Details Bowhead’s board of directors approved the transaction with American Family. The transaction is targeted to close prior to the end of 2026, subject to customary closing conditions, including receipt of required regulatory approvals and approvals of Bowhead’s stockholders. American Family will fund the purchase through cash and other liquid investments on hand. The transaction is not subject to any financing conditions or contingency. Upon completion of the transaction, Bowhead will operate as a standalone entity within the American Family platform. Stephen Sills will continue as Chief Executive Officer and President of Bowhead, and the Bowhead name and brand will remain the same. Ardea Partners LP is serving as exclusive financial advisor and Skadden, Arps, Slate, Meagher & Flom LLP is serving as legal advisor to Bowhead. Exhibit 99.2

Second Quarter 2026 Results Bowhead’s second quarter 2026 results will be issued on August 3, 2026. In light of the announcement of the transaction, Bowhead will not host an earnings conference call, which was originally scheduled for 8:30 a.m. Eastern Time on Tuesday, August 4, 2026. Bowhead’s second quarter 2026 results will be available on its investor relations website at https://ir.bowheadspecialty.com. About Bowhead Bowhead 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. Our products are delivered through two complementary underwriting models designed to support sustainable and profitable growth across market cycles: a “craft” model for large, complex, higher-severity risks, and a “digital” model, which includes Baleen Specialty and other small-business offerings (“express”), for smaller, simpler, and scalable business. 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 Statements in this press release, and any related oral statements, contain forward-looking statements within the meaning of the Private Securities Litigation Reform Act of 1995. 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 or the converse of such 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 press release and include statements regarding intentions, beliefs or current expectations concerning, among other things, the transaction, regulatory approvals, and the timing of the transaction, the industries in which Bowhead operates, and other statements relating to Bowhead’s future performance. The transaction is subject to risks and uncertainties, including: that Bowhead and American Family may be unable to complete the transaction because, among other reasons, conditions to the closing of the transaction may not be satisfied or waived; uncertainty as to the timing of completion of the transaction; the inability to complete the transaction due to the failure to obtain the Bowhead stockholder approvals for the transaction or the failure to satisfy other conditions to completion of the transaction, including that a governmental entity may prohibit, delay or refuse to grant approval for the consummation of the transaction; interloper risk; the occurrence of any event, change or other circumstances that could give rise to the termination of the merger agreement; risks related to disruption of management’s attention from Bowhead’s ongoing business operations due to the transaction; the effect of the announcement of the transaction on Bowhead’s relationships with its insureds, operating results and business generally; and the outcome of any legal proceedings to the extent initiated against Bowhead, American Family or others following the announcement of the transaction, as well as Bowhead’s and American Family management’s response to any of the aforementioned factors. A more fulsome discussion of the risks related to the transaction will be included in Bowhead’s proxy statement for the transaction. For a discussion of factors that could cause actual results to differ materially from those contemplated by forward-looking statements, see the section captioned “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 Securities and Exchange Commission (“SEC”). Should one or more of these risks or uncertainties materialize, or should underlying assumptions prove incorrect, actual results may vary materially from those indicated or anticipated by such forward-looking statements. While the list of factors presented here is, and the list of factors presented in the proxy statement will be, considered representative, no such list should be considered to be

a complete statement of all potential risks and uncertainties. Unlisted factors may present significant additional obstacles to the realization of forward-looking statements. 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 SEC, Bowhead does 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 Bowhead are expressly qualified by these cautionary statements. The information contained on or connected to any websites referenced in this press release is not incorporated by reference into this press release. Additional Information and Where to Find It In connection with the transaction, Bowhead will file with the SEC a proxy statement on Schedule 14A, the definitive version of which will be sent or provided to Bowhead’s stockholders. Bowhead and affiliates of Bowhead intend to jointly file a transaction statement on Schedule 13E-3 (the “Schedule 13E-3”). Bowhead may also file or furnish other documents with the SEC regarding the transaction. This material is not a substitute for the proxy statement, the Schedule 13E-3 or any other document that Bowhead may file with, or furnish to, the SEC. INVESTORS IN AND STOCKHOLDERS OF BOWHEAD ARE URGED TO READ THE PROXY STATEMENT, THE SCHEDULE 13E-3 AND ANY OTHER RELEVANT DOCUMENTS THAT ARE FILED OR FURNISHED OR WILL BE FILED WITH OR WILL BE FURNISHED TO THE SEC, AS WELL AS ANY AMENDMENTS OR SUPPLEMENTS TO THESE DOCUMENTS, CAREFULLY AND IN THEIR ENTIRETY (IF AND WHEN THEY BECOME AVAILABLE) BECAUSE THEY CONTAIN OR WILL CONTAIN IMPORTANT INFORMATION ABOUT THE TRANSACTION AND RELATED MATTERS. Investors and stockholders may obtain a copy of these documents (when they are filed and become available) free of charge at the SEC’s website at www.sec.gov. Bowhead will also provide a copy of these materials without charge on its website at https://ir.bowheadspecialty.com/. Participants in the Solicitation Bowhead, its executive officers and certain members of its board of directors may be deemed to be participants in the solicitation of proxies from Bowhead’s stockholders in connection with the transaction. Information regarding Bowhead’s directors and executive officers, including a description of their direct interests, by security holdings or otherwise, is contained in Bowhead’s annual proxy statement filed with the SEC on March 16, 2026. A more complete description will be available in the proxy statement on Schedule 14A to be filed regarding the transaction. You may obtain copies of these documents as described in the preceding paragraph filed with, or furnished to, the SEC free of charge. All such documents, when filed or furnished, are available free of charge at the SEC’s website (www.sec.gov) or by directing a request to the investor relations department of Bowhead. Bowhead Investor Relations Contact: Shirley Yap, Head of Investor Relations investorrelations@bowheadspecialty.com

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