KINGSWAY Corp (KWY)

Data as of Sep 30, 2026, from SEC Form 4 filings.

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Latest KWY insider trades

Joshua Horowitz - Director
Open-market purchase$25K

About KINGSWAY Corp (KWY)

Kingsway Corp is a U.S.-based company employing the Search Fund model to acquire and build great businesses. The company owns and operates a collection of B2B and B2C services companies that are asset-light, growing, profitable, and that have recurring revenues. It seeks to compound long-term shareholder value on a per share basis via its decentralized management model, its talented team of operators, and its tax-advantaged corporate structure.

Headquarters: CHICAGO, IL
Employees: 607
Listed: 1998
Exchange: XNYS
Sector: Financials

https://www.kingsway-financial.com SEC filings for KWY on EDGAR

KWY Form 4 activity by transaction type, last 90 days

Form 4 transaction type	Transactions	Shares	Total value
Open-market purchase	17	15,198	$147K
Open-market sale	3	100,000	$1.00M

KWY insider transactions (Form 4)

111 Form 4 filings on record, the earliest from Oct 1, 2024, newest first. Filing history page 1 of 3.

Date	Insider	Transaction	Security	Shares	Price	Value
Sep 28, 2026	Joshua Horowitz - Director	Open-market purchase	Common Stock	2,717	$9.28^{footnote F3}	$25K
Sep 30, 2026	Joshua Horowitz - Director	Open-market purchase	Common Stock	858	$9.23	$8K
Footnote F3 (price): The price reported represents a weighted average price. These shares were purchased in multiple transactions at prices ranging from $9.255 to $9.28 per share. The Reporting Person undertakes to provide to the Company, any security holder of the Company, or the staff of the… Full note on SEC EDGAR
Sep 30, 2026	John Taylor Maloney Fitzgerald - Officer	Open-market purchase	Common Stock	269^{footnote F1}	$9.30	$3K
Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR
Sep 30, 2026	Kent A. Hansen - Officer	Open-market purchase	Common Stock	169^{footnote F1}	$9.30	$2K
Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR
Sep 15, 2026	Kent A. Hansen - Officer	Open-market purchase	Common Stock	159^{footnote F1}	$9.82	$2K
Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR
Sep 15, 2026	John Taylor Maloney Fitzgerald - Officer	Open-market purchase	Common Stock	254^{footnote F1}	$9.82	$2K
Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR
Aug 31, 2026	Kent A. Hansen - Officer	Open-market purchase	Common Stock	149^{footnote F1}	$10.45	$2K
Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR
Aug 31, 2026	John Taylor Maloney Fitzgerald - Officer	Open-market purchase	Common Stock	239^{footnote F1}	$10.45	$2K
Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR
Aug 18, 2026	Joshua Horowitz - Director	Open-market purchase	Common Stock	1,300	$9.75	$13K
Aug 19, 2026	Joshua Horowitz - Director	Open-market purchase	Common Stock	7,034	$9.84^{footnote F3}	$69K
Aug 20, 2026	Joshua Horowitz - Director	Open-market purchase	Common Stock	769	$9.89	$8K
Footnote F3 (price): The price reported represents a weighted average price. These shares were purchased in multiple transactions at prices ranging from $9.82 to $9.86 per share. The Reporting Person undertakes to provide to the Company, any security holder of the Company, or the staff of the… Full note on SEC EDGAR
Aug 17, 2026	John Taylor Maloney Fitzgerald - Officer	Open-market purchase	Common Stock	254^{footnote F1}	$9.87	$3K
Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR
Aug 17, 2026	Kent A. Hansen - Officer	Open-market purchase	Common Stock	158^{footnote F1}	$9.87	$2K
Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR
Aug 13, 2026	Joseph Stilwell - Director	Open-market sale	Common Stock	32,982	$10.00	$330K
Aug 13, 2026	Joseph Stilwell - Director	Open-market sale	Common Stock	26,168	$10.00	$262K
Aug 13, 2026	Joseph Stilwell - Director	Open-market sale	Common Stock	40,850	$10.00	$409K
Jul 30, 2026	Kent A. Hansen - Officer	Open-market purchase	Common Stock	174^{footnote F1}	$8.98	$2K
Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR
Jul 30, 2026	John Taylor Maloney Fitzgerald - Officer	Open-market purchase	Common Stock	278^{footnote F1}	$8.98	$2K
Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR
Jul 15, 2026	Kent A. Hansen - Officer	Open-market purchase	Common Stock	161^{footnote F1}	$9.76	$2K
Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR
Jul 15, 2026	John Taylor Maloney Fitzgerald - Officer	Open-market purchase	Common Stock	256^{footnote F1}	$9.76	$2K
Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR
Jun 30, 2026	Kent A. Hansen - Officer	Open-market purchase	Common Stock	149^{footnote F1}	$10.45	$2K
Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR
Jun 30, 2026	John Taylor Maloney Fitzgerald - Officer	Open-market purchase	Common Stock	239^{footnote F1}	$10.45	$2K
Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR
Jun 15, 2026	John Taylor Maloney Fitzgerald - Officer	Tax withholding / forfeiture	Common Stock	30,233^{footnote F1}	$10.12	$306K
Footnote F1 (shares): Reflects shares of the Issuer's common stock surrendered by the Reporting Person to satisfy tax withholding obligations upon the vesting of shares granted under a restricted stock agreement.
Jun 15, 2026	Kent A. Hansen - Officer	Open-market purchase	Common Stock	150^{footnote F1}	$10.43	$2K
Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR
Jun 15, 2026	John Taylor Maloney Fitzgerald - Officer	Open-market purchase	Common Stock	240^{footnote F1}	$10.43	$3K
Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR
May 29, 2026	Kent A. Hansen - Officer	Open-market purchase	Common Stock	156^{footnote F1}	$10.03	$2K
Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR
May 29, 2026	John Taylor Maloney Fitzgerald - Officer	Open-market purchase	Common Stock	250^{footnote F1}	$10.03	$3K
Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR
May 28, 2026	Joshua Horowitz - Director	Open-market purchase	Common Stock	700	$9.95	$7K
May 29, 2026	Joshua Horowitz - Director	Open-market purchase	Common Stock	3,800	$9.91^{footnote F3}	$38K
Footnote F3 (price): The price reported represents a weighted average price. These shares were purchased in multiple transactions at prices ranging from $9.80 to $9.95 per share. The Reporting Person undertakes to provide to the Company, any security holder of the Company, or the staff of the… Full note on SEC EDGAR
May 27, 2026	John Taylor Maloney Fitzgerald - Officer	Gift	Common Stock	6,257^{footnote F1}	$9.99	$63K
Footnote F1 (shares): Charitable gift.
May 21, 2026	John Taylor Maloney Fitzgerald - Officer	Open-market sale	Common Stock	5,000	$10.14	$51K
May 19, 2026	John Taylor Maloney Fitzgerald - Officer	Open-market sale	Common Stock	5,000	$10.30	$52K
May 20, 2026	John Taylor Maloney Fitzgerald - Officer	Open-market sale	Common Stock	5,000	$10.43	$52K
May 18, 2026	Adam Jonathan Patinkin - Director	Grant or award	Nonqualified Stock Option	200,000	$0.00	-
May 18, 2026	Adam Jonathan Patinkin - Director	Grant or award	Nonqualified Stock Option	200,000	$0.00	-
May 15, 2026	John Taylor Maloney Fitzgerald - Officer	Open-market purchase	Common Stock	230^{footnote F1}	$10.85	$2K
Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR
May 15, 2026	Kent A. Hansen - Officer	Open-market purchase	Common Stock	144^{footnote F1}	$10.85	$2K
Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR
Apr 30, 2026	Kent A. Hansen - Officer	Open-market purchase	Common Stock	143^{footnote F1}	$10.93	$2K
Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR

Recent KWY Form 8-K filings

Read KWY company news

Aug 6, 2026Item 2.02, 9.01

Read the filing on SEC EDGAR

May 21, 2026Item 5.07

Read the filing on SEC EDGAR

May 19, 2026Item 5.03, 7.01, 8.01, 9.01

Read the filing on SEC EDGAR

May 11, 2026Item 1.01, 7.01, 9.01

Recent KWY Form 144 notices of proposed sale

An insider files Form 144 before selling restricted or control stock. It announces a planned sale. If the sale goes ahead, it shows up later on a Form 4.

Filed	Filer	Relationship	Shares	Market value	Notice
May 21, 2026	-	-	-	-	View on EDGAR
May 20, 2026	-	-	-	-

KWY insider trading FAQ

What is the latest insider trade for KWY?

KINGSWAY Corp (KWY) had 15 insider filings in the last 90 days, with the most recent on 2026-09-30. The full record for KWY runs to 111 Form 4 filings, the earliest from 2024-10-01. InsiderAlpha adds new Form 4, Form 144 and 8-K filings as they arrive from SEC EDGAR.

How many insiders are buying KWY stock?

17 insider purchases of KWY were filed in the last 90 days, totaling $147K.

How many insiders are selling KWY stock?

3 insider sales of KWY were filed in the last 90 days, totaling $1.00M.

Where can I see KWY SEC filings (Form 4, 10-K, 10-Q, 8-K)?

This page collects KWY Form 4 insider transactions, Form 144 sale notices and 8-K filings in one place. Annual 10-K and quarterly 10-Q reports live on the company's SEC EDGAR page.

More Financials companies with insider activity

Recent insider filings

The EDGAR links open each original Form 4, so you can check any number on this page against the filing it came from.

Sep 30, 2026 - Joshua Horowitz view on EDGAR
Sep 30, 2026 - John Taylor Maloney Fitzgerald view on EDGAR
Sep 30, 2026 - Kent A. Hansen view on EDGAR
Sep 16, 2026 - Kent A. Hansen view on EDGAR
Sep 16, 2026 - John Taylor Maloney Fitzgerald view on EDGAR
Sep 1, 2026 - Kent A. Hansen view on EDGAR
Sep 1, 2026 - John Taylor Maloney Fitzgerald view on EDGAR
Aug 20, 2026 - Joshua Horowitz view on EDGAR
Aug 18, 2026 - John Taylor Maloney Fitzgerald view on EDGAR

Related companies with recent insider activity

Learn more

Insider selling: signal or noise?: Why most insider sales are routine, and the few patterns worth a second look.
Form 144 vs Form 4: A Form 144 announces a planned sale; the Form 4 reports it after it happens.
Insider activity in Financials: Where KWY's peers are being bought and sold.
Every recent Form 4: The market-wide feed, updated as filings arrive from SEC EDGAR.

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Form 4 transaction type

Transactions

Total value

Open-market purchase

15,198

$147K

Open-market sale

100,000

$1.00M

Date

Insider

Transaction

Security

Price

Value

Sep 28, 2026

Joshua Horowitz - Director

Open-market purchase

Common Stock

2,717

$9.28^{footnote F3}

$25K

Sep 30, 2026

Joshua Horowitz - Director

Open-market purchase

Common Stock

858

$9.23

$8K

Footnote F3 (price): The price reported represents a weighted average price. These shares were purchased in multiple transactions at prices ranging from $9.255 to $9.28 per share. The Reporting Person undertakes to provide to the Company, any security holder of the Company, or the staff of the… Full note on SEC EDGAR

Sep 30, 2026

John Taylor Maloney Fitzgerald - Officer

Open-market purchase

Common Stock

269^{footnote F1}

$9.30

$3K

Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR

Sep 30, 2026

Kent A. Hansen - Officer

Open-market purchase

Common Stock

169^{footnote F1}

$9.30

$2K

Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR

Sep 15, 2026

Kent A. Hansen - Officer

Open-market purchase

Common Stock

159^{footnote F1}

$9.82

$2K

Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR

Sep 15, 2026

John Taylor Maloney Fitzgerald - Officer

Open-market purchase

Common Stock

254^{footnote F1}

$9.82

$2K

Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR

Aug 31, 2026

Kent A. Hansen - Officer

Open-market purchase

Common Stock

149^{footnote F1}

$10.45

$2K

Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR

Aug 31, 2026

John Taylor Maloney Fitzgerald - Officer

Open-market purchase

Common Stock

239^{footnote F1}

$10.45

$2K

Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR

Aug 18, 2026

Joshua Horowitz - Director

Open-market purchase

Common Stock

1,300

$9.75

$13K

Aug 19, 2026

Joshua Horowitz - Director

Open-market purchase

Common Stock

7,034

$9.84^{footnote F3}

$69K

Aug 20, 2026

Joshua Horowitz - Director

Open-market purchase

Common Stock

769

$9.89

$8K

Footnote F3 (price): The price reported represents a weighted average price. These shares were purchased in multiple transactions at prices ranging from $9.82 to $9.86 per share. The Reporting Person undertakes to provide to the Company, any security holder of the Company, or the staff of the… Full note on SEC EDGAR

Aug 17, 2026

John Taylor Maloney Fitzgerald - Officer

Open-market purchase

Common Stock

254^{footnote F1}

$9.87

$3K

Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR

Aug 17, 2026

Kent A. Hansen - Officer

Open-market purchase

Common Stock

158^{footnote F1}

$9.87

$2K

Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR

Aug 13, 2026

Joseph Stilwell - Director

Open-market sale

Common Stock

32,982

$10.00

$330K

Aug 13, 2026

Joseph Stilwell - Director

Open-market sale

Common Stock

26,168

$10.00

$262K

Aug 13, 2026

Joseph Stilwell - Director

Open-market sale

Common Stock

40,850

$10.00

$409K

Jul 30, 2026

Kent A. Hansen - Officer

Open-market purchase

Common Stock

174^{footnote F1}

$8.98

$2K

Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR

Jul 30, 2026

John Taylor Maloney Fitzgerald - Officer

Open-market purchase

Common Stock

278^{footnote F1}

$8.98

$2K

Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR

Jul 15, 2026

Kent A. Hansen - Officer

Open-market purchase

Common Stock

161^{footnote F1}

$9.76

$2K

Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR

Jul 15, 2026

John Taylor Maloney Fitzgerald - Officer

Open-market purchase

Common Stock

256^{footnote F1}

$9.76

$2K

Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR

Jun 30, 2026

Kent A. Hansen - Officer

Open-market purchase

Common Stock

149^{footnote F1}

$10.45

$2K

Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR

Jun 30, 2026

John Taylor Maloney Fitzgerald - Officer

Open-market purchase

Common Stock

239^{footnote F1}

$10.45

$2K

Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR

Jun 15, 2026

John Taylor Maloney Fitzgerald - Officer

Tax withholding / forfeiture

Common Stock

30,233^{footnote F1}

$10.12

$306K

Footnote F1 (shares): Reflects shares of the Issuer's common stock surrendered by the Reporting Person to satisfy tax withholding obligations upon the vesting of shares granted under a restricted stock agreement.

Jun 15, 2026

Kent A. Hansen - Officer

Open-market purchase

Common Stock

150^{footnote F1}

$10.43

$2K

Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR

Jun 15, 2026

John Taylor Maloney Fitzgerald - Officer

Open-market purchase

Common Stock

240^{footnote F1}

$10.43

$3K

Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR

May 29, 2026

Kent A. Hansen - Officer

Open-market purchase

Common Stock

156^{footnote F1}

$10.03

$2K

Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR

May 29, 2026

John Taylor Maloney Fitzgerald - Officer

Open-market purchase

Common Stock

250^{footnote F1}

$10.03

$3K

Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR

May 28, 2026

Joshua Horowitz - Director

Open-market purchase

Common Stock

700

$9.95

$7K

May 29, 2026

Joshua Horowitz - Director

Open-market purchase

Common Stock

3,800

$9.91^{footnote F3}

$38K

Footnote F3 (price): The price reported represents a weighted average price. These shares were purchased in multiple transactions at prices ranging from $9.80 to $9.95 per share. The Reporting Person undertakes to provide to the Company, any security holder of the Company, or the staff of the… Full note on SEC EDGAR

May 27, 2026

John Taylor Maloney Fitzgerald - Officer

Gift

Common Stock

6,257^{footnote F1}

$9.99

$63K

Footnote F1 (shares): Charitable gift.

May 21, 2026

John Taylor Maloney Fitzgerald - Officer

Open-market sale

Common Stock

5,000

$10.14

$51K

May 19, 2026

John Taylor Maloney Fitzgerald - Officer

Open-market sale

Common Stock

5,000

$10.30

$52K

May 20, 2026

John Taylor Maloney Fitzgerald - Officer

Open-market sale

Common Stock

5,000

$10.43

$52K

May 18, 2026

Adam Jonathan Patinkin - Director

Grant or award

Nonqualified Stock Option

200,000

$0.00

May 18, 2026

Adam Jonathan Patinkin - Director

Grant or award

Nonqualified Stock Option

200,000

$0.00

May 15, 2026

John Taylor Maloney Fitzgerald - Officer

Open-market purchase

Common Stock

230^{footnote F1}

$10.85

$2K

Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR

May 15, 2026

Kent A. Hansen - Officer

Open-market purchase

Common Stock

144^{footnote F1}

$10.85

$2K

Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR

Apr 30, 2026

Kent A. Hansen - Officer

Open-market purchase

Common Stock

143^{footnote F1}

$10.93

$2K

Footnote F1 (shares): The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each… Full note on SEC EDGAR

Filed

Filer

Relationship

Market value

Notice

May 21, 2026

View on EDGAR

May 20, 2026