KINGSWAY FINANCIAL SERVICES INC

S-11 kfs20250822_s1.htm FORM S-1

As filed with the U.S. Securities and Exchange Commission on August 26, 2025 Registration No. 333-

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

FORM S-1

REGISTRATION STATEMENT

UNDER

THE SECURITIES ACT OF 1933

Kingsway Financial Services Inc.

(Exact name of registrant as specified in its charter)

10 S. Riverside Plaza, Suite 1520

Chicago, IL 60606

(312) 766-2138

(Address, including zip code, and telephone number,

including area code, of registrant’s principal executive offices)

John T. Fitzgerald

President and Chief Executive Officer

10 S. Riverside Plaza, Suite 1520

Chicago, IL 60606

(312) 766-2138

(Name, address, including zip code, and telephone number, including area code, of agent for service)

Copies to:

Daniel P. Raglan

Cadwalader, Wickersham & Taft LLP

200 Liberty Street

New York, NY 10281

(212) 504-6790

Approximate date of commencement of proposed sale to the public: From time to time after the effective date of this registration statement.

If any of the securities being registered on this Form are to be offered on a delayed or continuous basis pursuant to Rule 415 under the Securities Act of 1933 check the following box: ☒

If this Form is filed to register additional securities for an offering pursuant to Rule 462(b) under the Securities Act, please check the following box and list the Securities Act registration statement number of the earlier effective registration statement for the same offering. ☐

If this Form is a post-effective amendment filed pursuant to Rule 462(c) under the Securities Act, check the following box and list the Securities Act registration statement number of the earlier effective registration statement for the same offering. ☐

If this Form is a post-effective amendment filed pursuant to Rule 462(d) under the Securities Act, check the following box and list the Securities Act registration statement number of the earlier effective registration statement for the same offering. ☐

Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, smaller reporting company, or an emerging growth company. See the definitions of “large accelerated filer,” “accelerated filer,” “smaller reporting company,” and “emerging growth company” in Rule 12b-2 of the Exchange Act.

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 7(a)(2)(B) of the Securities Act. □

The registrant hereby amends this registration statement on such date or dates as may be necessary to delay its effective date until the registrant shall file a further amendment which specifically states that this registration statement shall thereafter become effective in accordance with section 8(a) of the Securities Act of 1933 or until the registration statement shall become effective on such date as the Commission acting pursuant to said section 8(a), may determine.

The information in this prospectus is not complete and may be changed. The Selling Stockholders may not sell these securities until the registration statement filed with the Securities and Exchange Commission is effective. This prospectus is not an offer to sell these securities and is not soliciting an offer to buy these securities in any state where the offer or sale is not permitted.

SUBJECT TO COMPLETION, DATED AUGUST 26, 2025

Preliminary Prospectus

Kingsway Financial Services Inc.

Up to 1,419,001 Shares of Common Stock

This prospectus relates to the resale by the selling stockholders named herein or their permitted transferees (the “Selling Stockholders”) of up to 1,419,001 shares of our common stock, par value $0.01 per share (the “common stock”), including up to (i) 1,336,264 shares of our common stock to certain accredited investor purchasers (the “PIPE Selling Stockholders”) pursuant to the 2025 Private Placement (as defined below) and (ii) 82,737 shares of our common stock to Mark L. Corn (the “Bud’s Selling Stockholder”) pursuant to the Letter Agreement (as defined below). We are registering the shares for resale pursuant to such stockholders’ registration rights under the 2025 Private Placement or Letter Agreement, as applicable. For additional information, see “Prospectus Summary-Private Placements“ beginning on page 1 of this prospectus.

Subject to any applicable contractual restrictions, the Selling Stockholders may offer, sell or distribute all or a portion of their shares of our common stock publicly or through private transactions at prevailing market prices or at negotiated prices. For additional information, see “Plan of Distribution” beginning on page 20 of this prospectus. The Selling Stockholders may sell some, all or none of the shares being offered for resale in this offering.

We are not selling any shares of our common stock under this prospectus and will not receive any of the proceeds from the sale of the shares of our common stock owned by the Selling Stockholders. For additional information, see “Use of Proceeds“ beginning on page 11 of this prospectus and “Selling Stockholders“ beginning on page 12 of this prospectus.

We will bear all costs, expenses and fees in connection with the registration of these shares of our common stock. The Selling Stockholders will bear all commissions and discounts, if any, attributable to their sale of shares of our common stock. We have agreed to reimburse the PIPE Selling Stockholders for up to $35,000 of their expenses in the aggregate, including expenses incurred in connection with negotiation and execution of the securities purchase agreement and the registration of these shares.

We are a “smaller reporting company” for purposes of federal securities laws and are subject to reduced public company reporting requirements. Accordingly, the information in this prospectus may not be comparable to information provided by companies that are not smaller reporting companies.

Our common stock is listed on the New York Stock Exchange under the symbol “KFS.” On August 25, 2025, the last reported sale price of our common stock was $14.01.

INVESTING IN OUR SECURITIES INVOLVES RISKS. SEE“RISK FACTORS“** BEGINNING ON PAGE 10 OF THIS PROSPECTUS AND IN ANY PROSPECTUS SUPPLEMENT OR SIMILAR SECTION CONTAINED IN THE DOCUMENTS INCORPORATED BY REFERENCE INTO THIS PROSPECTUS.**

Neither the Securities and Exchange Commission nor any state securities commission has approved or disapproved of these securities or determined if this prospectus is truthful or complete. Any representation to the contrary is a criminal offense.

Prospectus dated _______, 2025