# EDGAR Filing Document

**Accession Number:** 0001538186
**File Stem:** 0001104659-25-122413
**Filing Date:** 2025-12
**Character Count:** 20033
**Document Hash:** a8bfbfe3998b285fe3fe273ae7ca5d53
**Contains OCR:** False
**Source Format:** 

## Filing Content

## Filing Summary
**0001104659-25-122413.hdr.sgml**: 20251218

**ACCESSION NUMBER**: 0001104659-25-122413

**CONFORMED SUBMISSION TYPE**: SCHEDULE 13D/A

**PUBLIC DOCUMENT COUNT**: 1

**FILED AS OF DATE**: 20251218

**DATE AS OF CHANGE**: 20251218

**SUBJECT COMPANY**: 

**COMPANY DATA:**
- **COMPANY CONFORMED NAME:** KINGSWAY FINANCIAL SERVICES INC
- **CENTRAL INDEX KEY:** 0001072627
- **STANDARD INDUSTRIAL CLASSIFICATION:** FIRE, MARINE & CASUALTY INSURANCE [6331]
- **ORGANIZATION NAME:** 02 Finance
- **EIN:** 999999999
- **STATE OF INCORPORATION:** DE
- **FISCAL YEAR END:** 1231

**FILING VALUES:**
- **FORM TYPE:** SCHEDULE 13D/A
- **SEC ACT:** 1934 Act
- **SEC FILE NUMBER:** 005-78501
- **FILM NUMBER:** 251582018

**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
**FILED BY**: 

**COMPANY DATA:**
- **COMPANY CONFORMED NAME:** Hannon Gregory Paul
- **CENTRAL INDEX KEY:** 0001538186

**ORGANIZATION NAME:**

**FILING VALUES:**
- **FORM TYPE:** SCHEDULE 13D/A

**MAIL ADDRESS:**
- **STREET 1:** OAKMONT CAPITAL INC.
- **STREET 2:** 45 ST. CLAIR AVENUE WEST, SUITE 400
- **CITY:** TORONTO
- **STATE:** A6
- **ZIP:** M4V 1K9

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

## SCHEDULE 13D

### Under the Securities Exchange Act of 1934

**(Amendment No. 6)**

**KINGSWAY FINANCIAL SERVICES INC**

*(Name of Issuer)*

**Common Stock, $0.01 par value per share**

*(Title of Class of Securities)*

**496904202**

*(CUSIP Number)*

**Terence M. Kavanagh**<br>45 St. Clair Avenue West, Suite 400<br>Toronto A6 M4V 1K9<br>(416) 923-1477

*(Name, Address and Telephone Number of Person Authorized to Receive Notices and Communications)*

**12/17/2025**

*(Date of Event Which Requires Filing of this Statement)*

| **CUSIP No.** | **496904202** |

---

| | | | |
|:--|:--|:--|:--|
| 1 | Name of reporting person<br>**Oakmont Capital Inc.** | Name of reporting person<br>**Oakmont Capital Inc.** | |
| 2 | Check the appropriate box if a member of a Group (See Instructions)<br>[x] (a)<br>[ ] (b) | Check the appropriate box if a member of a Group (See Instructions)<br>[x] (a)<br>[ ] (b) | |
| 3 | SEC use only | SEC use only | |
| 4 | Source of funds (See Instructions)<br>**WC** | Source of funds (See Instructions)<br>**WC** | |
| 5 | Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)<br>[ ] | Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)<br>[ ] | |
| 6 | Citizenship or place of organization<br>**ONTARIO** | Citizenship or place of organization<br>**ONTARIO** | |
| Number of Shares<br>Beneficially Owned by<br>Each Reporting Person With: | 7 | Sole Voting Power<br>**2303619.00** |
| Number of Shares<br>Beneficially Owned by<br>Each Reporting Person With: | 8 | Shared Voting Power<br>**0.00** |
| Number of Shares<br>Beneficially Owned by<br>Each Reporting Person With: | 9 | Sole Dispositive Power<br>**2303619.00** |
| Number of Shares<br>Beneficially Owned by<br>Each Reporting Person With: | 10 | Shared Dispositive Power<br>**0.00** |
| 11 | Aggregate amount beneficially owned by each reporting person<br>**2386119.00** | Aggregate amount beneficially owned by each reporting person<br>**2386119.00** | |
| 12 | Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)<br>[ ] | Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)<br>[ ] | |
| 13 | Percent of class represented by amount in Row (11)<br>**8.24%** | Percent of class represented by amount in Row (11)<br>**8.24%** | |
| 14 | Type of Reporting Person (See Instructions)<br>**CO** | Type of Reporting Person (See Instructions)<br>**CO** | |

---

**Comment for Reporting Person:** In reference to Rows 11 and 13 above, see Item 5 herein.

| **CUSIP No.** | **496904202** |

---

| | | | |
|:--|:--|:--|:--|
| 1 | Name of reporting person<br>**E.J.K. Holdings Inc.** | Name of reporting person<br>**E.J.K. Holdings Inc.** | |
| 2 | Check the appropriate box if a member of a Group (See Instructions)<br>[x] (a)<br>[ ] (b) | Check the appropriate box if a member of a Group (See Instructions)<br>[x] (a)<br>[ ] (b) | |
| 3 | SEC use only | SEC use only | |
| 4 | Source of funds (See Instructions)<br>**WC** | Source of funds (See Instructions)<br>**WC** | |
| 5 | Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)<br>[ ] | Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)<br>[ ] | |
| 6 | Citizenship or place of organization<br>**ONTARIO** | Citizenship or place of organization<br>**ONTARIO** | |
| Number of Shares<br>Beneficially Owned by<br>Each Reporting Person With: | 7 | Sole Voting Power<br>**0.00** |
| Number of Shares<br>Beneficially Owned by<br>Each Reporting Person With: | 8 | Shared Voting Power<br>**2303619.00** |
| Number of Shares<br>Beneficially Owned by<br>Each Reporting Person With: | 9 | Sole Dispositive Power<br>**0.00** |
| Number of Shares<br>Beneficially Owned by<br>Each Reporting Person With: | 10 | Shared Dispositive Power<br>**2303619.00** |
| 11 | Aggregate amount beneficially owned by each reporting person<br>**2386119.00** | Aggregate amount beneficially owned by each reporting person<br>**2386119.00** | |
| 12 | Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)<br>[ ] | Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)<br>[ ] | |
| 13 | Percent of class represented by amount in Row (11)<br>**8.24%** | Percent of class represented by amount in Row (11)<br>**8.24%** | |
| 14 | Type of Reporting Person (See Instructions)<br>**CO** | Type of Reporting Person (See Instructions)<br>**CO** | |

---

**Comment for Reporting Person:** In reference to Rows 11 and 13 above, see Item 5 herein.

| **CUSIP No.** | **496904202** |

---

| | | | |
|:--|:--|:--|:--|
| 1 | Name of reporting person<br>**1272562 Ontario Inc** | Name of reporting person<br>**1272562 Ontario Inc** | |
| 2 | Check the appropriate box if a member of a Group (See Instructions)<br>[x] (a)<br>[ ] (b) | Check the appropriate box if a member of a Group (See Instructions)<br>[x] (a)<br>[ ] (b) | |
| 3 | SEC use only | SEC use only | |
| 4 | Source of funds (See Instructions)<br>**WC** | Source of funds (See Instructions)<br>**WC** | |
| 5 | Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)<br>[ ] | Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)<br>[ ] | |
| 6 | Citizenship or place of organization<br>**ONTARIO** | Citizenship or place of organization<br>**ONTARIO** | |
| Number of Shares<br>Beneficially Owned by<br>Each Reporting Person With: | 7 | Sole Voting Power<br>**0.00** |
| Number of Shares<br>Beneficially Owned by<br>Each Reporting Person With: | 8 | Shared Voting Power<br>**2303619.00** |
| Number of Shares<br>Beneficially Owned by<br>Each Reporting Person With: | 9 | Sole Dispositive Power<br>**0.00** |
| Number of Shares<br>Beneficially Owned by<br>Each Reporting Person With: | 10 | Shared Dispositive Power<br>**2303619.00** |
| 11 | Aggregate amount beneficially owned by each reporting person<br>**2386119.00** | Aggregate amount beneficially owned by each reporting person<br>**2386119.00** | |
| 12 | Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)<br>[ ] | Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)<br>[ ] | |
| 13 | Percent of class represented by amount in Row (11)<br>**8.24%** | Percent of class represented by amount in Row (11)<br>**8.24%** | |
| 14 | Type of Reporting Person (See Instructions)<br>**CO** | Type of Reporting Person (See Instructions)<br>**CO** | |

---

**Comment for Reporting Person:** In reference to Rows 11 and 13 above, see Item 5 herein.

| **CUSIP No.** | **496904202** |

---

| | | | |
|:--|:--|:--|:--|
| 1 | Name of reporting person<br>**Terence M. Kavanagh** | Name of reporting person<br>**Terence M. Kavanagh** | |
| 2 | Check the appropriate box if a member of a Group (See Instructions)<br>[x] (a)<br>[ ] (b) | Check the appropriate box if a member of a Group (See Instructions)<br>[x] (a)<br>[ ] (b) | |
| 3 | SEC use only | SEC use only | |
| 4 | Source of funds (See Instructions)<br>**PF** | Source of funds (See Instructions)<br>**PF** | |
| 5 | Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)<br>[ ] | Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)<br>[ ] | |
| 6 | Citizenship or place of organization<br>**ISRAEL** | Citizenship or place of organization<br>**ISRAEL** | |
| Number of Shares<br>Beneficially Owned by<br>Each Reporting Person With: | 7 | Sole Voting Power<br>**34750.00** |
| Number of Shares<br>Beneficially Owned by<br>Each Reporting Person With: | 8 | Shared Voting Power<br>**2303619.00** |
| Number of Shares<br>Beneficially Owned by<br>Each Reporting Person With: | 9 | Sole Dispositive Power<br>**34750.00** |
| Number of Shares<br>Beneficially Owned by<br>Each Reporting Person With: | 10 | Shared Dispositive Power<br>**2303619.00** |
| 11 | Aggregate amount beneficially owned by each reporting person<br>**2386119.00** | Aggregate amount beneficially owned by each reporting person<br>**2386119.00** | |
| 12 | Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)<br>[x] | Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)<br>[x] | |
| 13 | Percent of class represented by amount in Row (11)<br>**8.24%** | Percent of class represented by amount in Row (11)<br>**8.24%** | |
| 14 | Type of Reporting Person (See Instructions)<br>**IN** | Type of Reporting Person (See Instructions)<br>**IN** | |

---

**Comment for Reporting Person:** In reference to Rows 11, 12 and 13 above, see Item 5 herein.

| **CUSIP No.** | **496904202** |

---

| | | | |
|:--|:--|:--|:--|
| 1 | Name of reporting person<br>**Gregory P. Hannon** | Name of reporting person<br>**Gregory P. Hannon** | |
| 2 | Check the appropriate box if a member of a Group (See Instructions)<br>[x] (a)<br>[ ] (b) | Check the appropriate box if a member of a Group (See Instructions)<br>[x] (a)<br>[ ] (b) | |
| 3 | SEC use only | SEC use only | |
| 4 | Source of funds (See Instructions)<br>**PF** | Source of funds (See Instructions)<br>**PF** | |
| 5 | Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)<br>[ ] | Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)<br>[ ] | |
| 6 | Citizenship or place of organization<br>**ISRAEL** | Citizenship or place of organization<br>**ISRAEL** | |
| Number of Shares<br>Beneficially Owned by<br>Each Reporting Person With: | 7 | Sole Voting Power<br>**34000.00** |
| Number of Shares<br>Beneficially Owned by<br>Each Reporting Person With: | 8 | Shared Voting Power<br>**2317369.00** |
| Number of Shares<br>Beneficially Owned by<br>Each Reporting Person With: | 9 | Sole Dispositive Power<br>**34000.00** |
| Number of Shares<br>Beneficially Owned by<br>Each Reporting Person With: | 10 | Shared Dispositive Power<br>**2317369.00** |
| 11 | Aggregate amount beneficially owned by each reporting person<br>**2386119.00** | Aggregate amount beneficially owned by each reporting person<br>**2386119.00** | |
| 12 | Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)<br>[ ] | Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)<br>[ ] | |
| 13 | Percent of class represented by amount in Row (11)<br>**8.24%** | Percent of class represented by amount in Row (11)<br>**8.24%** | |
| 14 | Type of Reporting Person (See Instructions)<br>**IN** | Type of Reporting Person (See Instructions)<br>**IN** | |

---

**Comment for Reporting Person:** In reference to Rows 11 and 13 above, see Item 5 herein.

**Item 1. Security and Issuer**

**(a) Title of Class of Securities:**
Common Stock, $0.01 par value per share

**(b) Name of Issuer:**
KINGSWAY FINANCIAL SERVICES INC

**(c) Address of Issuer's Principal Executive Offices:**
10 S. RIVERSIDE PLAZA, SUITE 1520, CHICAGO, IL, 60606

This Amendment No. 6 to Schedule 13D (this "Amendment") amends the Statement on Schedule 13D filed on March 5, 2009, as previously amended on December 12, 2012, September 13, 2013, September 20, 2013, March 21, 2019 and April 9, 2025 (the "Schedule 13D") by Oakmont Capital Inc., an Ontario corporation ("Oakmont"), E.J.K. Holdings Inc., an Ontario corporation ("EJK"), 1272562 Ontario Inc., an Ontario corporation ("1272562"), and Gregory P. Hannon and Terence M. Kavanagh, each of whom is a citizen of Canada (collectively, the "Reporting Persons"). Capitalized terms used herein not otherwise defined shall have the meaning ascribed to them in the Schedule 13D. All references to common stock in this Amendment have been adjusted for the rights offering which expired on September 6, 2013 (the "Rights Offering").

**Item 4. Purpose of Transaction**

Item 4 of this Schedule 13D is hereby supplemented as follows:

On December 17, 2025, the option agreement described in Item 6 of this Amendment No. 6 was exercised.  Pursuant to such option agreement, Oakmont sold 500,000 Shares to DCP Special (as hereafter defined) at a price of US$8.25 per Share.

Except as disclosed in Item 6 of this Amendment No. 6, the Reporting Persons have no current plans or proposals which relate to or would result in any of the events described in Items (a) through (j) of the instructions to Item 4 of Schedule 13D. The information set forth in Item 6 of this Amendment No. 6 is incorporated herein by reference.

**Item 5. Interest in Securities of the Issuer**

**(a)**
(a) Item 5(a) and 5(b) of the Schedule 13D is hereby amended, restated and replaced in its entirety by the following:

As of the close of business on December 17, 2025, the Reporting Persons may be deemed to beneficially own, in the aggregate, 2,386,119 Shares, representing approximately 8.24% of the Issuer's outstanding Shares (based upon the 28,956,152 Shares stated to be outstanding as of November 6, 2025 in the Issuer's Form 10-Q dated November 6, 2025 for the quarter ended September 30, 2025 plus 315,789 Shares issuable upon exercise of the Reporting Persons' Series B Warrants and conversion of the Report Persons' Class C Preferred Shares).

Oakmont has sole voting power and sole dispositive power with respect to the 2,303,619 Shares that it owns directly. Oakmont may be deemed to be a beneficial owner of the balance of the 2,386,119 Shares beneficially owned by the Group, by virtue of its participation in the Group.

EJK has shared voting power and shared dispositive power with respect to the 2,303,619 Shares owned directly by Oakmont, by virtue of EJK's ownership of 50% of the outstanding voting stock of Oakmont and its right to nominate one of the two members of the Board of Directors of Oakmont. EJK may be deemed to be a beneficial owner of the balance of the 2,386,119 Shares beneficially owned by the Group, by virtue of its participation in the Group.

1272562 has shared voting power and shared dispositive power with respect to the 2,303,619 Shares owned directly by Oakmont, by virtue of its ownership of 50% of the outstanding voting stock of Oakmont and its right to nominate one of the two members of the Board of Directors of Oakmont. 1272562 may be deemed to be a beneficial owner of the balance of the 2,386,119 Shares beneficially owned by the Group, by virtue of its participation in the Group.

Mr. Kavanagh has sole voting power and sole dispositive power with respect to 34,750 Shares owned through a self-directed Retirement Savings Plan. Mr. Kavanagh has shared voting power and shared dispositive power with respect to the 2,303,619 Shares owned directly by Oakmont, by virtue of Mr. Kavanagh's ownership of all the outstanding voting stock of EJK, and EJK's ownership of 50% of the outstanding voting stock of Oakmont and its right to nominate one of the two members of the Board of Directors of Oakmont. Mr. Kavanagh may be deemed to be a beneficial owner of the balance of the 2,386,119 Shares beneficially owned by the Group, by virtue of his participation in the Group.

Mr. Kavanagh's sister owns directly and through a registered retirement savings account 13,500 Shares as to which Mr. Kavanagh disclaims beneficial ownership.

Mr. Hannon has sole voting power and sole dispositive power with respect to the following 34,000 Shares:

(i) the 29,500 Shares owned directly by him or through a self-directed Retirement Savings Plan; and
(ii) the 4,500 Shares owned directly by two trusts for Mr. Hannon's children; Mr. Hannon is the sole trustee of each such trust.

Mr. Hannon has shared voting power and shared dispositive power with respect to the following 2,317,369 Shares:

(i) the 2,303,619 Shares owned directly by Oakmont, by virtue of his ownership of all of the capital stock of 1272562, and 1272562's ownership of 50% of the outstanding voting stock of Oakmont and its right to nominate one of the two members of the Board of Directors of Oakmont; and
(ii) the 13,750 Shares owned directly by Mr. Hannon's spouse.

Mr. Hannon may be deemed to be a beneficial owner of the balance of the 2,386,119 Shares beneficially owned by the Group, by virtue of his participation in the Group.

**(b)**
The information set forth in Item 5(a) of this Amendment No. 6 is incorporated herein by reference.

**(c)**
The information set forth in Item 4 of this Amendment No. 6 is incorporated herein by reference.

**Item 6. Contracts, Arrangements, Understandings or Relationships With Respect to Securities of the Issuer.**

Item 6 of the Schedule 13D is hereby amended, restated and replaced in its entirety by the following:

On December 17, 2025, David Capital Partners Special Situation Fund, LP ("DCP Special") exercised in full the option agreement with Oakmont filed as Exhibit 99.1 to Amendment No. 5 to the 13D. Pursuant to such option agreement, Oakmont sold 500,000 Shares to DCP Special at a price of US$8.25 per Share.

### SIGNATURE

After reasonable inquiry and to the best of my knowledge and belief, I certify that the information set forth in this statement is true, complete and correct.

**Reporting Person:** Oakmont Capital Inc.

**Signature:** /s/ Terence M. Kavanagh

**Name/Title:** Terence M. Kavanagh, President

**Date:** 12/17/2025

After reasonable inquiry and to the best of my knowledge and belief, I certify that the information set forth in this statement is true, complete and correct.

**Reporting Person:** E.J.K. Holdings Inc.

**Signature:** /s/ Terence M. Kavanagh

**Name/Title:** Terence M. Kavanagh, President

**Date:** 12/17/2025

After reasonable inquiry and to the best of my knowledge and belief, I certify that the information set forth in this statement is true, complete and correct.

**Reporting Person:** 1272562 Ontario Inc

**Signature:** /s/ Gregory P. Hannon

**Name/Title:** Gregory P. Hannon, President

**Date:** 12/17/2025

After reasonable inquiry and to the best of my knowledge and belief, I certify that the information set forth in this statement is true, complete and correct.

**Reporting Person:** Terence M. Kavanagh

**Signature:** /s/ Terence M. Kavanagh

**Name/Title:** Terence M. Kavanagh

**Date:** 12/17/2025

After reasonable inquiry and to the best of my knowledge and belief, I certify that the information set forth in this statement is true, complete and correct.

**Reporting Person:** Gregory P. Hannon

**Signature:** /s/ Gregory P. Hannon

**Name/Title:** Gregory P. Hannon

**Date:** 12/17/2025