CHICAGO, IL / ACCESS Newswire / May 5, 2026 / (NYSE: KFS) Kingsway Financial Services Inc. ("Kingsway" or the "Company"), the only publicly-traded US company employing the Search Fund model to acquire and build great businesses, today announced speakers for its Investor Day on Monday, May 18, 2026, at the New York Stock Exchange.

In addition to JT Fitzgerald, Kingsway's President and CEO, and Kent Hansen, Kingsway's Executive Vice President and Chief Financial Officer, the program will feature:

• Miles Mamon, CEO of Roundhouse Electric & Equipment Co., Inc.

• Davide Zanchi, CEO of Image Solutions LLC

"The theme of this year's Investor Day is 'From Theory to Action', as we provide deep dives into how Kingsway supports its Operator CEO's in translating the Search Fund model and the Kingsway Business System into tangible, real world business success," said Mr. Fitzgerald. "Miles and Davide are wonderful examples of Kingsway's strategy in action, and I am confident the investor community will enjoy hearing their stories at our 2026 Investor Day."

At the Investor Day, members of the Kingsway management team will discuss the Company's operations, long-term growth strategy, and financial structure. Prepared presentations will begin at 9:30 am ET, running until approximately midday.

Investor Day Details

The Company's Investor Day will be held on Monday, May 18, at the New York Stock Exchange. In-person attendance is by RSVP only. The event will also be streamed live on the Investors section of the Company's website: https://kingsway-financial.com/investor-day/.

To attend in person, please RSVP by emailing James@HaydenIR.com.

About the Company

Kingsway Financial Services Inc. (NYSE: KFS) is the only publicly-traded US company employing the Search Fund model to acquire and build great businesses.

Kingsway owns and operates a collection of high-quality B2B and B2C services companies that are asset-light, growing, profitable, and that have recurring revenues. Kingsway seeks to compound long-term shareholder value on a per share basis via its decentralized management model, its talented team of operators, and its tax-advantaged corporate structure.

Additional Information

Additional information about Kingsway, including a copy of its Annual Reports can be accessed on the EDGAR section of the U.S. Securities and Exchange Commission's website at www.sec.gov, on the Canadian Securities Administrators' website at www.sedar.com, or through the Company's website at www.kingsway-financial.com.

For Investor Inquiries:
Hayden IR
James Carbonara
(646) 755-7412
james@haydenir.com

For Company Inquiries:
Kingsway Financial Services Inc.
Kent Hansen, CFO
(312) 766-2163
khansen@kingsway-financial.com

SOURCE: Kingsway Financial Services, Inc.