Kingsway to Host 2021 Investor Day on Wednesday, October 6, 2021

Presentation to be Held In-Person at the New York Stock Exchange as well as Virtually

(NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”) today announced that the Company will host an Investor Day on Wednesday, October 6, 2021.

Management will discuss a range of topics covering all aspects of the Company’s operations, long-term growth strategy, and financial structure. Prepared presentations will begin at 10:00 a.m. (Eastern Time) followed by a Q&A session.

Event Location / Details The event will take place at the New York Stock Exchange, contingent on health and safety guidelines associated with the COVID-19 pandemic, and will also be available virtually.

Interested Parties Individuals interested in attending or registering for the event can contact Adam Prior at The Equity Group Inc. at [e-mail] or by calling [phone].

Investor Day Presentation A live webcast, including video, audio and presentation slides, will be accessible on www.kingsway-financial.com at the time of the meeting. Those who attend virtually will also have the opportunity to participate in the question-and-answer session following the presentation.

About the Company

Kingsway is a holding company that owns or controls subsidiaries primarily in the extended warranty, asset management and real estate industries. The common shares of Kingsway are listed on the New York Stock Exchange under the trading symbol “KFS.”

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.

View source version on businesswire.com: https://www.businesswire.com/news/home/20210907005872/en/

Investor Relations Contact Adam Prior [phone] [e-mail]