KFS Form 144: Insider files to sell 5,000 shares

KFS files a Form 144 reporting a proposed resale of 5,000 shares of Common stock.

Rhea-AI Filing Summary

KFS files a Form 144 reporting a proposed resale of 5,000 shares of Common stock. The notice lists 05/20/2026 and shows a prior sale of 5,000 shares on 05/19/2026 by John T. Fitzgerald. The filing also lists shares acquired as compensation via stock option exercises on 06/13/2016 (3,706 shares) and 06/10/2016 (1,294 shares).

Insights

Securities Compliance Specialist

Rule 144 notice for an insider resale of 5,000 shares; procedural disclosure.

The filing lists an intended resale of 5,000 shares of Common stock with a filing date noted as 05/20/2026. It also documents a prior sale of 5,000 shares on 05/19/2026 by John T. Fitzgerald, suggesting recent disposition activity.

Timing and cash‑flow treatment are set out as part of the notice; the filing references option-derived shares acquired on 06/13/2016 and 06/10/2016. Subsequent SEC or broker statements would clarify settlement and proceeds details.

Key Figures

Noticed resale: 5,000 shares Prior sale: 5,000 shares Reported dollar figure: 51255.43 +3 more

6 metrics

Noticed resale 5,000 shares intended resale listed on 05/20/2026

Prior sale 5,000 shares sold on 05/19/2026 by John T. Fitzgerald

Reported dollar figure 51255.43 numeric amount adjacent to 05/19/2026 sale entry in the excerpt

Shares acquired (option) 1 3,706 shares acquired as compensation via stock options on 06/13/2016

Shares acquired (option) 2 1,294 shares acquired as compensation via stock options on 06/10/2016

Listed share figure (context) 28,946,664 numeric field appearing alongside date <date>05/20/2026</date> (context only)

Key Terms

Rule 144, cashless exercise, same-day sale

3 terms

Rule 144 regulatory

"Filing type is 144; the form is a Rule 144 resale notice"

Rule 144 is a U.S. securities regulation that sets conditions under which restricted or insider-held shares can be legally resold to the public, such as required holding periods, availability of public information, limits on how much can be sold at once, and certain filing requirements. For investors it matters because it determines when previously locked-up shares can enter the market — like a release valve that can increase supply, affect share price, and signal insider intent.

cashless exercise financial

"Acquired as compensation -- Stock Options; Compensation -- Cashless exercise / same-day sale"

A cashless exercise is a way for an option holder to convert stock options into actual shares without paying the purchase price in cash; instead they immediately give up a portion of the newly issued shares to cover the cost and any withholding taxes. Investors care because this process increases the number of shares available and can slightly dilute existing holdings, while also signaling how insiders or employees are realizing compensation without needing cash — similar to paying for a purchase by handing over part of what you just bought.

same-day sale market

"Compensation -- Cashless exercise / same-day sale (listed for option acquisitions)"

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

What does the KFS Form 144 disclose about the sale?

It discloses an intended resale of 5,000 shares of Common stock by an affiliate. The notice lists 05/20/2026 and records a prior sale of 5,000 shares on 05/19/2026 by John T. Fitzgerald, per the filing.

Who is the seller named in the KFS Form 144?

The filing names John T. Fitzgerald as the seller associated with the disclosed transactions. The form lists a sale dated 05/19/2026 and the intended resale entry dated 05/20/2026.

Does the Form 144 show how the shares were acquired?

Yes. The filing lists shares acquired as compensation through stock option exercises on 06/13/2016 (3,706 shares) and 06/10/2016 (1,294 shares). These acquisition dates are stated in the notice.

What proceeds or dollar amounts are shown in the KFS filing?

The filing includes a numeric amount of 51255.43 adjacent to a 5,000-share sale entry. The value is presented in the form but the filing excerpt does not attach an explicit label explaining the figure in full detail.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Accepted by SEC EDGAR 05/20/2026 - 06:29 PM EDT Learn about SEC filing dates

Form 144 Filer Information	UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 144 NOTICE OF PROPOSED SALE OF SECURITIES PURSUANT TO RULE 144 UNDER THE SECURITIES ACT OF 1933
FORM 144

144: Filer Information

Filer CIK	0001584349
Filer CCC	XXXXXXXX
Is this a LIVE or TEST Filing?	LIVE TEST
Submission Contact Information
Name
Phone
E-Mail Address

144: Issuer Information

Name of Issuer	KINGSWAY FINANCIAL SERVICES INC.
SEC File Number	001-15204
Address of Issuer	10 S. Riverside Plaza Suite 1520 Chicago ILLINOIS 60606
Phone	1-312-766-2138
Name of Person for Whose Account the Securities are To Be Sold	John T. Fitzgerald
See the definition of "person" in paragraph (a) of Rule 144. Information is to be given not only as to the person for whose account the securities are to be sold but also as to all other persons included in that definition. In addition, information shall be given as to sales by all persons whose sales are required by paragraph (e) of Rule 144 to be aggregated with sales for the account of the person filing this notice.
Relationship to Issuer	Officer

144: Securities Information

Title of the Class of Securities To Be Sold	Name and Address of the Broker	Number of Shares or Other Units To Be Sold	Aggregate Market Value	Number of Shares or Other Units Outstanding	Approximate Date of Sale	Name the Securities Exchange
Common	Goldman Sachs & Co. LLC 200 West Street New York NY 10282	5000	51200	28946664	05/20/2026	NYSE

Furnish the following information with respect to the acquisition of the securities to be sold and with respect to the payment of all or any part of the purchase price or other consideration therefor:

144: Securities To Be Sold

Title of the Class	Date you Acquired	Nature of Acquisition Transaction	Name of Person from Whom Acquired	Is this a Gift?	Date Donor Acquired	Amount of Securities Acquired	Date of Payment	Nature of Payment *
Common	06/13/2016	Acquired as compensation -- Stock Options	Issuer			3706	06/13/2016	Compensation -- Cashless exercise / same-day sale
Common	06/10/2016	Acquired as compensation -- Stock Options	Issuer			1294	06/10/2016	Compensation -- Cashless exercise / same-day sale

* If the securities were purchased and full payment therefor was not made in cash at the time of purchase, explain in the table or in a note thereto the nature of the consideration given. If the consideration consisted of any note or other obligation, or if payment was made in installments describe the arrangement and state when the note or other obligation was discharged in full or the last installment paid.

Furnish the following information as to all securities of the issuer sold during the past 3 months by the person for whose account the securities are to be sold.

144: Securities Sold During The Past 3 Months

Name and Address of Seller	Title of Securities Sold	Date of Sale	Amount of Securities Sold	Gross Proceeds
John T. Fitzgerald 10 S. Riverside Plaza Suite 1520 Chicago IL 60606	Common	05/19/2026	5000	51255.43

144: Remarks and Signature

Remarks
Date of Notice	05/20/2026
ATTENTION:
The person for whose account the securities to which this notice relates are to be sold hereby represents by signing this notice that he does not know any material adverse information in regard to the current and prospective operations of the Issuer of the securities to be sold which has not been publicly disclosed. If such person has adopted a written trading plan or given trading instructions to satisfy Rule 10b5-1 under the Exchange Act, by signing the form and indicating the date that the plan was adopted or the instruction given, that person makes such representation as of the plan adoption or instruction date.
Signature	Goldman Sachs & Co. LLC on behalf of John T. Fitzgerald
ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)