# EDGAR Filing Document

**Accession Number:** 0001072627
**File Stem:** 0001127602-23-011195
**Filing Date:** 2023-3
**Character Count:** 9475
**Document Hash:** c03067785d06555e01ff5fcb00d54a03
**Contains OCR:** False
**Source Format:** 

## Filing Content

## Filing Summary
**0001127602-23-011195.hdr.sgml**: 20230323

**ACCESSION NUMBER**: 0001127602-23-011195

**CONFORMED SUBMISSION TYPE**: 4

**PUBLIC DOCUMENT COUNT**: 2

**CONFORMED PERIOD OF REPORT**: 20230321

**FILED AS OF DATE**: 20230323

**DATE AS OF CHANGE**: 20230323

**REPORTING-OWNER**: 

**OWNER DATA:**
- **COMPANY CONFORMED NAME:** LEVINE DOUGLAS
- **CENTRAL INDEX KEY:** 0001164694

**FILING VALUES:**
- **FORM TYPE:** 4
- **SEC ACT:** 1934 Act
- **SEC FILE NUMBER:** 001-15204
- **FILM NUMBER:** 23756781

**MAIL ADDRESS:**
- **STREET 1:** 2602 NW 5TH AVENUE
- **CITY:** MIAMI
- **STATE:** FL
- **ZIP:** 33127
**ISSUER**: 

**COMPANY DATA:**
- **COMPANY CONFORMED NAME:** KINGSWAY FINANCIAL SERVICES INC
- **CENTRAL INDEX KEY:** 0001072627
- **STANDARD INDUSTRIAL CLASSIFICATION:** FIRE, MARINE & CASUALTY INSURANCE [6331]
- **IRS NUMBER:** 999999999
- **STATE OF INCORPORATION:** DE
- **FISCAL YEAR END:** 1231

**BUSINESS ADDRESS:**
- **STREET 1:** 10 S. RIVERSIDE PLAZA
- **STREET 2:** SUITE 1520
- **CITY:** CHICAGO
- **STATE:** IL
- **ZIP:** 60606
- **BUSINESS PHONE:** (312) 766-2144

**MAIL ADDRESS:**
- **STREET 1:** 10 S. RIVERSIDE PLAZA
- **STREET 2:** SUITE 1520
- **CITY:** CHICAGO
- **STATE:** IL
- **ZIP:** 60606

## Ex-24

```

POWER OF ATTORNEY

Know all by these presents that the undersigned hereby constitutes
and appoints each of
Kent Hansen, Debra Rouse, Ninette Lewis Voiles and Kelly
Marketti, signing singly,
 as the undersigned?s true and lawful attorney-in-fact to:

(1) execute for and on behalf of the undersigned all reports
to be filed by the
undersigned pursuant to Section 16  of the Securities
Exchange Act of 1934, as
amended (the ?Exchange Act?), and the rules promulgated
thereunder
 (including Forms 3, 4, and 5 and any successor forms)
(the ?Section 16 Reports?)
 with respect to the equity
 securities of Kingsway Financial Services Inc.
 (the ?Company?);

(2) 	do and perform any and all acts for and on behalf of the
undersigned that may be necessary or desirable
 to complete and execute any such Section 16 Report, complete
and execute any amendment or amendments thereto,
 and file such report with the United States Securities and Exchange
 Commission and any stock exchange or similar
authority; and

(3) 	take any other action of any type whatsoever in
connection with the foregoing that, in the opinion of
 such attorney-in-fact, may be of benefit to, in the best
interest of, or legally required by, the undersigned,
 it being understood that the documents executed by such attorney
-in-fact on behalf of the undersigned pursuant
 to this Power of Attorney shall be in such form and shall
contain such terms and conditions as such a
ttorney-in-fact may approve in such attorney-in-fact?s discretion.

      The powers granted above may be exercised by each such
 attorney-in-fact on behalf of the undersigned,
 individually, and on behalf of the undersigned in the
undersigned?s individual capacity and in any fiduciary
 or representative capacity in which the undersigned may be acting.
	The undersigned hereby grants to each such
attorney-in-fact full power and authority to do and perform
 any and every act and thing whatsoever requisite, necessary,
 or proper to be done in the exercise of any of the
 rights and powers herein granted, as fully to all intents
and purposes as the undersigned might or could do if
 personally present, with full power of substitution or
revocation, hereby ratifying and confirming all that such
 attorney-in-fact, or such attorney-in-fact?s substitute
or substitutes, shall lawfully do or cause to be done by
 virtue of this Power of Attorney and the rights and powers
 herein granted.  The undersigned acknowledges that
 the foregoing attorneys-in-fact, in serving in such capacity
 at the request of the undersigned, are not assuming
, nor is the Company assuming, any of the undersigned?s
responsibilities to comply with Section 16 of the Exchange Act.

	This Power of Attorney shall be effective as of the date
set forth below and shall continue in full force
 and effect until the undersigned is no longer required to file
 Section 16 Reports with respect to the equity
 securities of the Company, unless earlier revoked by the
undersigned in a signed writing delivered to the foregoing
 attorneys-in-fact. This Power of Attorney amends, modifies
and replaces in its entirety any and all prior powers of
 attorney given by the undersigned with respect to the equity
 securities of the Company.
IN WITNESS WHEREOF, the undersigned has caused this Power of
 Attorney to be executed as of this 15th day of June 2021.

Signature: /S/ Doug Levine
Name:           Doug Levine

	2

```

### UNITED STATES SECURITIES AND EXCHANGE COMMISSION
**Washington, D.C. 20549**

## FORM 4

### STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

[ ] Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

[ ] Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

---

| | | |
|:---|:---|:---|
| **1. Name and Address of Reporting Person**<sup>*</sup><br>LEVINE DOUGLAS<br><sub>(Last) (First) (Middle)</sub><br>2602 NW 5TH AVENUE<br><sub>(Street)</sub><br>MIAMI, FL 33127<br><sub>(City) (State) (Zip)</sub> | **3. Date of Earliest Transaction (Month/Day/Year)**<br>2023-03-21 | **5. Relationship of Reporting Person(s) to Issuer**<br>(Check all applicable)<br>[X] Director [ ] 10% Owner<br>[ ] Officer (give title below) [ ] Other (specify below)<br>_ _ |
| **2. Issuer Name and Ticker or Trading Symbol**<br>KINGSWAY FINANCIAL SERVICES INC [ KFS ] | **4. If Amendment, Date of Original Filed (Month/Day/Year)**<br>  | **6. Individual or Joint/Group Filing (Check Applicable Line)**<br>[X] Form filed by One Reporting Person<br>[ ] Form filed by More than One Reporting Person |

---

## Table I - Non-Derivative Securities

---

|  |  |  |  |  |  |  |  |  |  |  |
| --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- |
| 1. Title of Security | 2. Transaction Date | 2A. Deemed Execution Date | 3. Transaction Code (V) | 3. Transaction Code (V) | 4. Securities Acquired (A) or Disposed of (D) | 4. Securities Acquired (A) or Disposed of (D) | 4. Securities Acquired (A) or Disposed of (D) | 5. Amount of Securities Beneficially Owned | 6. Ownership Form | 7. Nature of Indirect Beneficial Ownership |
| 1. Title of Security | 2. Transaction Date | 2A. Deemed Execution Date | Code | V | Amount | (A) or (D) | Price | 5. Amount of Securities Beneficially Owned | 6. Ownership Form | 7. Nature of Indirect Beneficial Ownership |
| Common Stock | 2023-03-21 |  | C |  | 166187 | A | 0<sup>(1)</sup> | 1157671 | D |  |
| Common Stock |  |  |  |  |  |  |  | 90200 | I | By family member |
| Common Stock |  |  |  |  |  |  |  | 189102 | I | By Trust |

---

## Table II - Derivative Securities

---

|  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |
| --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- | --- |
| 1. Title of Derivative Security | 2. Conversion or Exercise Price | 3. Transaction Date | 3A. Deemed Execution Date | 4. Transaction Code (V) | 4. Transaction Code (V) | 5. Number of Derivative Securities Acquired (A) or Disposed of (D) | 5. Number of Derivative Securities Acquired (A) or Disposed of (D) | 6. Date Exercisable and Expiration Date | 6. Date Exercisable and Expiration Date | 7. Title and Amount of Underlying Securities | 7. Title and Amount of Underlying Securities | 8. Price of Derivative Security | 9. Number of Derivative Securities Beneficially Owned | 10. Ownership Form | 11. Nature of Indirect Beneficial Ownership |
| 1. Title of Derivative Security | 2. Conversion or Exercise Price | 3. Transaction Date | 3A. Deemed Execution Date | Code | V | (A) | (D) | Date Exercisable | Expiration Date | Title | Amount or Number of Shares | 8. Price of Derivative Security | 9. Number of Derivative Securities Beneficially Owned | 10. Ownership Form | 11. Nature of Indirect Beneficial Ownership |
| Class A convertible preferred share, series 1 | 0<sup>(1)</sup> | 2023-03-21 |  | C |  |  | 26590 | 2022-01-01 | 2023-03-22 | Common Stock | 166187.5<sup>(1)</sup> | $0 | 0 | D |  |

---

### Footnotes:

(1) The Class A Preferred Stock ("Preferred Stock") was convertible at a rate of one (1) share of Preferred Stock for six and 25/100th shares of Common Stock: Oakmont Capital Inc. converted 13,143 shares of Preferred Stock into 82,144 shares of Common Stock (rounded down).

**Signature:** /s/ Debra Rouse, attorney-in-fact for Douglas Levine  
**Date:** 2023-03-23

### Remarks:

Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.

* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).

** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).

Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.

**Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.**