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KWY

KINGSWAY Corp

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Tapewire entity
5976
SEC CIK
0001072627
Parsed reports
890

Last 12 months

Inside the activity.

50 purchase rows · 14 sale rows

Disclosed non-derivative P/S rows, by transaction month. Includes amendments and private transactions.
Monthly counts
MonthPurchasesSales
Nov 202540
Dec 202548
Jan 202620
Feb 202660
Mar 202640
Apr 202630
May 202663
Jun 202640
Jul 202640
Aug 202673
Sep 202660
Oct 202600

Latest available

Insider transactions

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Purchases/sales include open-market and private transactions. Plan disclosure applies to the filing; individual rows may differ. “Not disclosed” is not “unplanned.”

The cutoff filters transaction history only. Company summaries and owner relationships show the latest available disclosures. Parser corrections can improve historical records.

Transaction dateOwner / reported roleActivity / securityShares / unitsReported priceReported valueDetails
November 19, 2021 Filed Nov 22, 2021 21:23 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 1,269 $5.50 $6,979.50
Disclosure

SEC source: 0001104659-21-142512 · tm2133710-1_4.xml · nonDerivative · entry 6

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 580,684

F2 · kind: This Form 4 reports the following acquisitions on November 18, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,696 shares at $5.50 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,269 shares at $5.50 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 2,035 shares at $5.50 USD per share; and on November 19, 2021: (a) SAI acquired 6,696 shares at $5.50 USD per share, (b) SAF acquired 1,269 shares at $5.50 USD per share, and (c) SVP VII acquired 2,035 shares at $5.50 USD per share.

F4 · ownership.nature: These are shares owned directly by SAF and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAF. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
November 18, 2021 Filed Nov 22, 2021 21:23 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 2,035 $5.50 $11,192.50
Disclosure

SEC source: 0001104659-21-142512 · tm2133710-1_4.xml · nonDerivative · entry 5

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 838,066

F2 · kind: This Form 4 reports the following acquisitions on November 18, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,696 shares at $5.50 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,269 shares at $5.50 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 2,035 shares at $5.50 USD per share; and on November 19, 2021: (a) SAI acquired 6,696 shares at $5.50 USD per share, (b) SAF acquired 1,269 shares at $5.50 USD per share, and (c) SVP VII acquired 2,035 shares at $5.50 USD per share.

F6 · ownership.nature: These are shares owned directly by SVP VII and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SVP VII. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
November 18, 2021 Filed Nov 22, 2021 21:23 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 6,696 $5.50 $36,828.00
Disclosure

SEC source: 0001104659-21-142512 · tm2133710-1_4.xml · nonDerivative · entry 4

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 4,588,977

F2 · kind: This Form 4 reports the following acquisitions on November 18, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,696 shares at $5.50 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,269 shares at $5.50 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 2,035 shares at $5.50 USD per share; and on November 19, 2021: (a) SAI acquired 6,696 shares at $5.50 USD per share, (b) SAF acquired 1,269 shares at $5.50 USD per share, and (c) SVP VII acquired 2,035 shares at $5.50 USD per share.

F5 · ownership.nature: These are shares owned directly by SAI and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAI. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
November 18, 2021 Filed Nov 22, 2021 21:23 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 1,269 $5.50 $6,979.50
Disclosure

SEC source: 0001104659-21-142512 · tm2133710-1_4.xml · nonDerivative · entry 3

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 579,415

F2 · kind: This Form 4 reports the following acquisitions on November 18, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,696 shares at $5.50 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,269 shares at $5.50 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 2,035 shares at $5.50 USD per share; and on November 19, 2021: (a) SAI acquired 6,696 shares at $5.50 USD per share, (b) SAF acquired 1,269 shares at $5.50 USD per share, and (c) SVP VII acquired 2,035 shares at $5.50 USD per share.

F4 · ownership.nature: These are shares owned directly by SAF and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAF. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
November 15, 2021 Filed Nov 16, 2021 21:04 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 1,777 $5.40 $9,595.80
Disclosure

SEC source: 0001104659-21-139926 · tm2133166-1_4seq1.xml · nonDerivative · entry 8

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 836,031

F2 · kind: This Form 4 reports the following acquisitions on November 12, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,104 shares at $5.40 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,157 shares at $5.40 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,854 shares at $5.40 USD per share; and on November 15, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 5,848 shares at $5.40 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,108 shares at $5.40 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,777 shares at $5.40 USD per share.

F6 · ownership.nature: These are shares owned directly by SVP VII and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SVP VII. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
November 15, 2021 Filed Nov 16, 2021 21:04 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 5,848 $5.40 $31,579.20
Disclosure

SEC source: 0001104659-21-139926 · tm2133166-1_4seq1.xml · nonDerivative · entry 7

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 4,582,281

F2 · kind: This Form 4 reports the following acquisitions on November 12, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,104 shares at $5.40 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,157 shares at $5.40 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,854 shares at $5.40 USD per share; and on November 15, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 5,848 shares at $5.40 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,108 shares at $5.40 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,777 shares at $5.40 USD per share.

F5 · ownership.nature: These are shares owned directly by SAI and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAI. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
November 15, 2021 Filed Nov 16, 2021 21:04 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 1,108 $5.40 $5,983.20
Disclosure

SEC source: 0001104659-21-139926 · tm2133166-1_4seq1.xml · nonDerivative · entry 6

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 578,146

F2 · kind: This Form 4 reports the following acquisitions on November 12, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,104 shares at $5.40 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,157 shares at $5.40 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,854 shares at $5.40 USD per share; and on November 15, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 5,848 shares at $5.40 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,108 shares at $5.40 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,777 shares at $5.40 USD per share.

F4 · ownership.nature: These are shares owned directly by SAF and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAF. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
November 15, 2021 Filed Nov 16, 2021 21:03 UTC
Fitzgerald John Taylor MaloneyDirector · President and CEO
PurchaseCommon Stock 379 $5.49 $2,080.71
Disclosure

SEC source: 0001127602-21-029303 · form4.xml · nonDerivative · entry 1

Fitzgerald John Taylor Maloney · CIK 0001584349 · Director · President and CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,915,852

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 regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution.? The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc.? The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker

F2 · balance_after: Includes 500,000 shares of restricted stock issued on September 5, 2018 and 700,000 shares of restricted stock granted on March 31, 2021.

Read SEC document
November 15, 2021 Filed Nov 16, 2021 21:02 UTC
Hansen Kent ACFO & EVP
PurchaseCommon Stock 273 $5.49 $1,498.77
Disclosure

SEC source: 0001127602-21-029302 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 60,895

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 regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution.? The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc.? The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker

F2 · balance_after: Includes 40,000 shares of restricted stock granted on February 26, 2021.

Read SEC document
November 12, 2021 Filed Nov 16, 2021 21:04 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 1,854 $5.40 $10,011.60
Disclosure

SEC source: 0001104659-21-139926 · tm2133166-1_4seq1.xml · nonDerivative · entry 5

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 834,254

F2 · kind: This Form 4 reports the following acquisitions on November 12, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,104 shares at $5.40 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,157 shares at $5.40 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,854 shares at $5.40 USD per share; and on November 15, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 5,848 shares at $5.40 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,108 shares at $5.40 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,777 shares at $5.40 USD per share.

F6 · ownership.nature: These are shares owned directly by SVP VII and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SVP VII. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
November 12, 2021 Filed Nov 16, 2021 21:04 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 6,104 $5.40 $32,961.60
Disclosure

SEC source: 0001104659-21-139926 · tm2133166-1_4seq1.xml · nonDerivative · entry 4

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 4,576,433

F2 · kind: This Form 4 reports the following acquisitions on November 12, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,104 shares at $5.40 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,157 shares at $5.40 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,854 shares at $5.40 USD per share; and on November 15, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 5,848 shares at $5.40 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,108 shares at $5.40 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,777 shares at $5.40 USD per share.

F5 · ownership.nature: These are shares owned directly by SAI and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAI. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
November 12, 2021 Filed Nov 16, 2021 21:04 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 1,157 $5.40 $6,247.80
Disclosure

SEC source: 0001104659-21-139926 · tm2133166-1_4seq1.xml · nonDerivative · entry 3

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 577,038

F2 · kind: This Form 4 reports the following acquisitions on November 12, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,104 shares at $5.40 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,157 shares at $5.40 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,854 shares at $5.40 USD per share; and on November 15, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 5,848 shares at $5.40 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,108 shares at $5.40 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,777 shares at $5.40 USD per share.

F4 · ownership.nature: These are shares owned directly by SAF and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAF. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
October 29, 2021 Filed Nov 2, 2021 20:47 UTC
Fitzgerald John Taylor MaloneyDirector · President and CEO
PurchaseCommon Stock 373 $5.57 $2,077.61
Disclosure

SEC source: 0001127602-21-028119 · form4.xml · nonDerivative · entry 1

Fitzgerald John Taylor Maloney · CIK 0001584349 · Director · President and CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,915,473

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 regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution.? The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc.? The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker

F2 · balance_after: Includes 500,000 shares of restricted stock issued on September 5, 2018 and 700,000 shares of restricted stock granted on March 31, 2021.

Read SEC document
October 29, 2021 Filed Nov 2, 2021 20:46 UTC
Hansen Kent ACFO & EVP
PurchaseCommon Stock 269 $5.57 $1,498.33
Disclosure

SEC source: 0001127602-21-028116 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 60,622

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 regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution.? The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc.? The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker

F2 · balance_after: Includes 40,000 shares of restricted stock granted on February 26, 2021.

Read SEC document
October 15, 2021 Filed Oct 18, 2021 21:00 UTC
Fitzgerald John Taylor MaloneyDirector · President and CEO
PurchaseCommon Stock 369 $5.64 $2,081.16
Disclosure

SEC source: 0001127602-21-027209 · form4.xml · nonDerivative · entry 1

Fitzgerald John Taylor Maloney · CIK 0001584349 · Director · President and CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,915,100

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 regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution.? The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc.? The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker

F2 · balance_after: Includes 500,000 shares of restricted stock issued on September 5, 2018 and 700,000 shares of restricted stock granted on March 31, 2021.

Read SEC document
October 15, 2021 Filed Oct 18, 2021 21:00 UTC
Hansen Kent ACFO & EVP
PurchaseCommon Stock 265 $5.64 $1,494.60
Disclosure

SEC source: 0001127602-21-027207 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 60,353

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 regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution.? The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc.? The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker

F2 · balance_after: Includes 40,000 shares of restricted stock granted on February 26, 2021.

Read SEC document
October 01, 2021 Filed Oct 4, 2021 20:36 UTC
Hansen Kent ACFO & EVP
PurchaseCommon Stock 277 $5.41 $1,498.57
Disclosure

SEC source: 0001127602-21-026450 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 60,088

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 regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution.? The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc.? The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker

F2 · balance_after: Includes 40,000 shares of restricted stock granted on February 26, 2021.

Read SEC document
October 01, 2021 Filed Oct 4, 2021 20:34 UTC
Fitzgerald John Taylor MaloneyDirector · President and CEO
PurchaseCommon Stock 384 $5.41 $2,077.44
Disclosure

SEC source: 0001127602-21-026449 · form4.xml · nonDerivative · entry 1

Fitzgerald John Taylor Maloney · CIK 0001584349 · Director · President and CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,914,731

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 regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution.? The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc.? The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker

F2 · balance_after: Includes 500,000 shares of restricted stock issued on September 5, 2018 and 700,000 shares of restricted stock granted on March 31, 2021.

Read SEC document
September 23, 2021 Filed Sep 24, 2021 20:37 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 4,345 $5.27 $22,917.70
Disclosure

SEC source: 0001104659-21-119328 · tm2128456-1_4.xml · nonDerivative · entry 8

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 832,400

F2 · kind: This Form 4 reports the following acquisitions on September 22, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 13,739 shares at $5.25 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 2,064 shares at $5.25 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 3,324 shares at $5.25 USD per share; and on September 23, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 17,957 shares at $5.2745 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 2,698 shares at $5.2745 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 4,345 shares at $5.2745 USD per share.

F6 · ownership.nature: These are shares owned directly by SVP VII and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SVP VII. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
September 23, 2021 Filed Sep 24, 2021 20:37 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 17,957 $5.27 $94,714.20
Disclosure

SEC source: 0001104659-21-119328 · tm2128456-1_4.xml · nonDerivative · entry 7

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 4,570,329

F2 · kind: This Form 4 reports the following acquisitions on September 22, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 13,739 shares at $5.25 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 2,064 shares at $5.25 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 3,324 shares at $5.25 USD per share; and on September 23, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 17,957 shares at $5.2745 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 2,698 shares at $5.2745 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 4,345 shares at $5.2745 USD per share.

F5 · ownership.nature: These are shares owned directly by SAI and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAI. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
September 23, 2021 Filed Sep 24, 2021 20:37 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 2,698 $5.27 $14,230.60
Disclosure

SEC source: 0001104659-21-119328 · tm2128456-1_4.xml · nonDerivative · entry 6

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 575,881

F2 · kind: This Form 4 reports the following acquisitions on September 22, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 13,739 shares at $5.25 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 2,064 shares at $5.25 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 3,324 shares at $5.25 USD per share; and on September 23, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 17,957 shares at $5.2745 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 2,698 shares at $5.2745 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 4,345 shares at $5.2745 USD per share.

F4 · ownership.nature: These are shares owned directly by SAF and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAF. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
September 22, 2021 Filed Sep 24, 2021 20:37 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 3,324 $5.25 $17,451.00
Disclosure

SEC source: 0001104659-21-119328 · tm2128456-1_4.xml · nonDerivative · entry 5

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 828,055

F2 · kind: This Form 4 reports the following acquisitions on September 22, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 13,739 shares at $5.25 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 2,064 shares at $5.25 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 3,324 shares at $5.25 USD per share; and on September 23, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 17,957 shares at $5.2745 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 2,698 shares at $5.2745 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 4,345 shares at $5.2745 USD per share.

F6 · ownership.nature: These are shares owned directly by SVP VII and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SVP VII. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
September 22, 2021 Filed Sep 24, 2021 20:37 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 13,739 $5.25 $72,129.75
Disclosure

SEC source: 0001104659-21-119328 · tm2128456-1_4.xml · nonDerivative · entry 4

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 4,552,372

F2 · kind: This Form 4 reports the following acquisitions on September 22, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 13,739 shares at $5.25 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 2,064 shares at $5.25 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 3,324 shares at $5.25 USD per share; and on September 23, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 17,957 shares at $5.2745 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 2,698 shares at $5.2745 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 4,345 shares at $5.2745 USD per share.

F5 · ownership.nature: These are shares owned directly by SAI and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAI. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
September 22, 2021 Filed Sep 24, 2021 20:37 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 2,064 $5.25 $10,836.00
Disclosure

SEC source: 0001104659-21-119328 · tm2128456-1_4.xml · nonDerivative · entry 3

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 573,183

F2 · kind: This Form 4 reports the following acquisitions on September 22, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 13,739 shares at $5.25 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 2,064 shares at $5.25 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 3,324 shares at $5.25 USD per share; and on September 23, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 17,957 shares at $5.2745 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 2,698 shares at $5.2745 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 4,345 shares at $5.2745 USD per share.

F4 · ownership.nature: These are shares owned directly by SAF and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAF. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
September 17, 2021 Filed Sep 20, 2021 20:01 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 3,476 $5.25 $18,249.00
Disclosure

SEC source: 0001104659-21-117324 · tm2128051-1_4seq1.xml · nonDerivative · entry 8

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 824,731

F2 · kind: This Form 4 reports the following acquisitions on September 16, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 7,180 shares at $5.35 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,080 shares at $5.35 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,740 shares at $5.35 USD per share; and on September 17, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 14,365 shares at $5.25 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 2,159 shares at $5.25 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 3,476 shares at $5.25 USD per share

F6 · ownership.nature: These are shares owned directly by SVP VII and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SVP VII. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
September 17, 2021 Filed Sep 20, 2021 20:01 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 14,365 $5.25 $75,416.25
Disclosure

SEC source: 0001104659-21-117324 · tm2128051-1_4seq1.xml · nonDerivative · entry 7

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 4,538,633

F2 · kind: This Form 4 reports the following acquisitions on September 16, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 7,180 shares at $5.35 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,080 shares at $5.35 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,740 shares at $5.35 USD per share; and on September 17, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 14,365 shares at $5.25 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 2,159 shares at $5.25 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 3,476 shares at $5.25 USD per share

F5 · ownership.nature: These are shares owned directly by SAI and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAI. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
September 17, 2021 Filed Sep 20, 2021 20:01 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 2,159 $5.25 $11,334.75
Disclosure

SEC source: 0001104659-21-117324 · tm2128051-1_4seq1.xml · nonDerivative · entry 6

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 571,119

F2 · kind: This Form 4 reports the following acquisitions on September 16, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 7,180 shares at $5.35 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,080 shares at $5.35 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,740 shares at $5.35 USD per share; and on September 17, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 14,365 shares at $5.25 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 2,159 shares at $5.25 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 3,476 shares at $5.25 USD per share

F4 · ownership.nature: These are shares owned directly by SAF and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAF. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
September 16, 2021 Filed Sep 16, 2021 21:32 UTC
Fitzgerald John Taylor MaloneyDirector · President and CEO
PurchaseCommon Stock 383 $5.43 $2,079.69
Disclosure

SEC source: 0001127602-21-025420 · form4.xml · nonDerivative · entry 1

Fitzgerald John Taylor Maloney · CIK 0001584349 · Director · President and CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,914,347

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 regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution.? The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc.? The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker

F2 · balance_after: Includes 500,000 shares of restricted stock issued on September 5, 2018 and 700,000 shares of restricted stock granted on March 31, 2021.

Read SEC document
September 16, 2021 Filed Sep 16, 2021 21:28 UTC
Hansen Kent ACFO & EVP
PurchaseCommon Stock 276 $5.43 $1,498.68
Disclosure

SEC source: 0001127602-21-025419 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 59,811

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 regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution.? The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc.? The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker

F2 · balance_after: Includes 40,000 shares of restricted stock granted on February 26, 2021.

Read SEC document
September 16, 2021 Filed Sep 20, 2021 20:01 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 1,740 $5.35 $9,309.00
Disclosure

SEC source: 0001104659-21-117324 · tm2128051-1_4seq1.xml · nonDerivative · entry 5

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 821,255

F2 · kind: This Form 4 reports the following acquisitions on September 16, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 7,180 shares at $5.35 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,080 shares at $5.35 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,740 shares at $5.35 USD per share; and on September 17, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 14,365 shares at $5.25 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 2,159 shares at $5.25 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 3,476 shares at $5.25 USD per share

F6 · ownership.nature: These are shares owned directly by SVP VII and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SVP VII. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
September 16, 2021 Filed Sep 20, 2021 20:01 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 7,180 $5.35 $38,413.00
Disclosure

SEC source: 0001104659-21-117324 · tm2128051-1_4seq1.xml · nonDerivative · entry 4

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 4,524,268

F2 · kind: This Form 4 reports the following acquisitions on September 16, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 7,180 shares at $5.35 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,080 shares at $5.35 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,740 shares at $5.35 USD per share; and on September 17, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 14,365 shares at $5.25 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 2,159 shares at $5.25 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 3,476 shares at $5.25 USD per share

F5 · ownership.nature: These are shares owned directly by SAI and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAI. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
September 16, 2021 Filed Sep 20, 2021 20:01 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 1,080 $5.35 $5,778.00
Disclosure

SEC source: 0001104659-21-117324 · tm2128051-1_4seq1.xml · nonDerivative · entry 3

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 568,960

F2 · kind: This Form 4 reports the following acquisitions on September 16, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 7,180 shares at $5.35 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,080 shares at $5.35 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,740 shares at $5.35 USD per share; and on September 17, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 14,365 shares at $5.25 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 2,159 shares at $5.25 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 3,476 shares at $5.25 USD per share

F4 · ownership.nature: These are shares owned directly by SAF and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAF. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
September 13, 2021 Filed Sep 15, 2021 20:11 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 1,464 $5.35 $7,832.40
Disclosure

SEC source: 0001104659-21-115932 · tm2127698-1_4.xml · nonDerivative · entry 5

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 819,515

F2 · kind: This Form 4 reports the following acquisitions on September 13, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,048 shares at $5.35 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 909 shares at $5.35 USD per share, (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,464 shares at $5.35 USD per share, and (d) Stilwell Associates, L.P. ("Associates") acquired 579 shares at $5.35 USD per share.

F6 · ownership.nature: These are shares owned directly by SVP VII and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SVP VII. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
September 13, 2021 Filed Sep 15, 2021 20:11 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 6,048 $5.35 $32,356.80
Disclosure

SEC source: 0001104659-21-115932 · tm2127698-1_4.xml · nonDerivative · entry 4

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 4,517,088

F2 · kind: This Form 4 reports the following acquisitions on September 13, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,048 shares at $5.35 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 909 shares at $5.35 USD per share, (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,464 shares at $5.35 USD per share, and (d) Stilwell Associates, L.P. ("Associates") acquired 579 shares at $5.35 USD per share.

F5 · ownership.nature: These are shares owned directly by SAI and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAI. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
September 13, 2021 Filed Sep 15, 2021 20:11 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 909 $5.35 $4,863.15
Disclosure

SEC source: 0001104659-21-115932 · tm2127698-1_4.xml · nonDerivative · entry 3

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 567,880

F2 · kind: This Form 4 reports the following acquisitions on September 13, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,048 shares at $5.35 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 909 shares at $5.35 USD per share, (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,464 shares at $5.35 USD per share, and (d) Stilwell Associates, L.P. ("Associates") acquired 579 shares at $5.35 USD per share.

F4 · ownership.nature: These are shares owned directly by SAF and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAF. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
September 13, 2021 Filed Sep 15, 2021 20:11 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 579 $5.35 $3,097.65
Disclosure

SEC source: 0001104659-21-115932 · tm2127698-1_4.xml · nonDerivative · entry 2

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 939,242

F2 · kind: This Form 4 reports the following acquisitions on September 13, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,048 shares at $5.35 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 909 shares at $5.35 USD per share, (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,464 shares at $5.35 USD per share, and (d) Stilwell Associates, L.P. ("Associates") acquired 579 shares at $5.35 USD per share.

F3 · ownership.nature: These are shares owned directly by Associates and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Stilwell Value LLC ("Value"), which is the general partner of Associates. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
September 08, 2021 Filed Sep 10, 2021 20:06 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 1,626 $5.35 $8,699.10
Disclosure

SEC source: 0001104659-21-114660 · tm2127371-1_4.xml · nonDerivative · entry 5

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 818,051

F2 · kind: This Form 4 reports the following acquisitions on September 8, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,720 shares at $5.35 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,010 shares at $5.35 USD per share, (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,626 shares at $5.35 USD per share, and (d) Stilwell Associates, L.P. ("Associates") acquired 644 shares at $5.35 USD per share.

F6 · ownership.nature: These are shares owned directly by SVP VII and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SVP VII. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
September 08, 2021 Filed Sep 10, 2021 20:06 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 6,720 $5.35 $35,952.00
Disclosure

SEC source: 0001104659-21-114660 · tm2127371-1_4.xml · nonDerivative · entry 4

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 4,511,040

F2 · kind: This Form 4 reports the following acquisitions on September 8, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,720 shares at $5.35 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,010 shares at $5.35 USD per share, (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,626 shares at $5.35 USD per share, and (d) Stilwell Associates, L.P. ("Associates") acquired 644 shares at $5.35 USD per share.

F5 · ownership.nature: These are shares owned directly by SAI and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAI. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
September 08, 2021 Filed Sep 10, 2021 20:06 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 1,010 $5.35 $5,403.50
Disclosure

SEC source: 0001104659-21-114660 · tm2127371-1_4.xml · nonDerivative · entry 3

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 566,971

F2 · kind: This Form 4 reports the following acquisitions on September 8, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,720 shares at $5.35 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,010 shares at $5.35 USD per share, (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,626 shares at $5.35 USD per share, and (d) Stilwell Associates, L.P. ("Associates") acquired 644 shares at $5.35 USD per share.

F4 · ownership.nature: These are shares owned directly by SAF and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAF. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
September 08, 2021 Filed Sep 10, 2021 20:06 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 644 $5.35 $3,445.40
Disclosure

SEC source: 0001104659-21-114660 · tm2127371-1_4.xml · nonDerivative · entry 2

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 938,663

F2 · kind: This Form 4 reports the following acquisitions on September 8, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 6,720 shares at $5.35 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,010 shares at $5.35 USD per share, (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,626 shares at $5.35 USD per share, and (d) Stilwell Associates, L.P. ("Associates") acquired 644 shares at $5.35 USD per share.

F3 · ownership.nature: These are shares owned directly by Associates and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Stilwell Value LLC ("Value"), which is the general partner of Associates. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
September 05, 2021 Filed Sep 8, 2021 20:09 UTC
Fitzgerald John Taylor MaloneyDirector · President and CEO
Tax withholdingCommon Stock 29,300 $5.60 $164,080.00
Disclosure

SEC source: 0001127602-21-025004 · form4.xml · nonDerivative · entry 1

Fitzgerald John Taylor Maloney · CIK 0001584349 · Director · President and CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,913,964

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.

F2 · balance_after: Includes 500,000 shares of restricted stock issued on September 5, 2018 and 700,000 shares of restricted stock granted on March 31, 2021.

Read SEC document
August 30, 2021 Filed Aug 31, 2021 20:27 UTC
Hansen Kent ACFO & EVP
PurchaseCommon Stock 267 $5.61 $1,497.87
Disclosure

SEC source: 0001127602-21-024585 · form4.xml · nonDerivative · entry 1

Hansen Kent A · CIK 0001686017 · CFO & EVP

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 59,535

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 regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution.? The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc.? The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker

F2 · balance_after: Includes 40,000 shares of restricted stock granted on February 26, 2021.

Read SEC document
August 30, 2021 Filed Aug 31, 2021 20:26 UTC
Fitzgerald John Taylor MaloneyDirector · President and CEO
PurchaseCommon Stock 371 $5.61 $2,081.31
Disclosure

SEC source: 0001127602-21-024584 · form4.xml · nonDerivative · entry 1

Fitzgerald John Taylor Maloney · CIK 0001584349 · Director · President and CEO

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,943,264

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 regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution.? The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc.? The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker

F2 · balance_after: Includes 500,000 shares of restricted stock issued on September 5, 2018 and 800,000 shares of restricted stock granted on March 31, 2021.

Read SEC document
August 26, 2021 Filed Aug 30, 2021 20:02 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 810 $5.35 $4,333.50
Disclosure

SEC source: 0001104659-21-110981 · tm2126550-2_4seq1.xml · nonDerivative · entry 4

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 816,425

F2 · kind: This Form 4 reports the following acquisitions on August 26, 2021: (a) Stilwell Activist Fund, L.P. ("SAF") acquired 500 shares at $5.35 USD per share (b) Stilwell Activist Investments, L.P. ("SAI") acquired 3,690 shares at $5.35 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 810 shares at $5.35 USD per share.

F5 · ownership.nature: These are shares owned directly by SVP VII and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SVP VII. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
August 26, 2021 Filed Aug 30, 2021 20:02 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 3,690 $5.35 $19,741.50
Disclosure

SEC source: 0001104659-21-110981 · tm2126550-2_4seq1.xml · nonDerivative · entry 3

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 4,504,320

F2 · kind: This Form 4 reports the following acquisitions on August 26, 2021: (a) Stilwell Activist Fund, L.P. ("SAF") acquired 500 shares at $5.35 USD per share (b) Stilwell Activist Investments, L.P. ("SAI") acquired 3,690 shares at $5.35 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 810 shares at $5.35 USD per share.

F4 · ownership.nature: These are shares owned directly by SAI and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAI. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
August 26, 2021 Filed Aug 30, 2021 20:02 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 500 $5.35 $2,675.00
Disclosure

SEC source: 0001104659-21-110981 · tm2126550-2_4seq1.xml · nonDerivative · entry 2

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 565,961

F2 · kind: This Form 4 reports the following acquisitions on August 26, 2021: (a) Stilwell Activist Fund, L.P. ("SAF") acquired 500 shares at $5.35 USD per share (b) Stilwell Activist Investments, L.P. ("SAI") acquired 3,690 shares at $5.35 USD per share, and (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 810 shares at $5.35 USD per share.

F3 · ownership.nature: These are shares owned directly by SAF and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAF. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
August 20, 2021 Filed Aug 24, 2021 20:02 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 1,852 $5.27 $9,760.04
Disclosure

SEC source: 0001104659-21-108944 · tm2125791-1_4seq1.xml · nonDerivative · entry 5

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 815,615

F2 · kind: This Form 4 reports the following acquisitions on August 20, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 7,669 shares at $5.27 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,153 shares at $5.27 USD per share, (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,852 shares at $5.27 USD per share, and (d) Stilwell Associates, L.P. ("Associates") acquired 751 shares at $5.27 USD per share.

F6 · ownership.nature: These are shares owned directly by SVP VII and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SVP VII. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
August 20, 2021 Filed Aug 24, 2021 20:02 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 7,669 $5.27 $40,415.63
Disclosure

SEC source: 0001104659-21-108944 · tm2125791-1_4seq1.xml · nonDerivative · entry 4

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 4,500,630

F2 · kind: This Form 4 reports the following acquisitions on August 20, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 7,669 shares at $5.27 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,153 shares at $5.27 USD per share, (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,852 shares at $5.27 USD per share, and (d) Stilwell Associates, L.P. ("Associates") acquired 751 shares at $5.27 USD per share.

F5 · ownership.nature: These are shares owned directly by SAI and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAI. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
August 20, 2021 Filed Aug 24, 2021 20:02 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 1,153 $5.27 $6,076.31
Disclosure

SEC source: 0001104659-21-108944 · tm2125791-1_4seq1.xml · nonDerivative · entry 3

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 565,461

F2 · kind: This Form 4 reports the following acquisitions on August 20, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 7,669 shares at $5.27 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,153 shares at $5.27 USD per share, (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,852 shares at $5.27 USD per share, and (d) Stilwell Associates, L.P. ("Associates") acquired 751 shares at $5.27 USD per share.

F4 · ownership.nature: These are shares owned directly by SAF and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Value, which is the general partner of SAF. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

Read SEC document
August 20, 2021 Filed Aug 24, 2021 20:02 UTC
Stilwell JosephDirector · 10% owner
PurchaseCommon Stock 751 $5.27 $3,957.77
Disclosure

SEC source: 0001104659-21-108944 · tm2125791-1_4seq1.xml · nonDerivative · entry 2

STILWELL JOSEPH · CIK 0001113303 · Director · 10% owner

Stilwell Value LLC · CIK 0001397076 · 10% owner

STILWELL ASSOCIATES L P · CIK 0000913960 · 10% owner

Stilwell Activist Fund, L.P. · CIK 0001564452 · 10% owner

Stilwell Activist Investments, L.P. · CIK 0001573720 · 10% owner

Stilwell Value Partners VII, L.P. · CIK 0001555931 · 10% owner

Joint disclosure: these amounts are not allocated separately to each reporting owner.

10b5-1 filing: Not disclosed

Ownership: Indirect · See footnote

Disclosed balance after: 938,019

F2 · kind: This Form 4 reports the following acquisitions on August 20, 2021: (a) Stilwell Activist Investments, L.P. ("SAI") acquired 7,669 shares at $5.27 USD per share, (b) Stilwell Activist Fund, L.P. ("SAF") acquired 1,153 shares at $5.27 USD per share, (c) Stilwell Value Partners VII, L.P. ("SVP VII") acquired 1,852 shares at $5.27 USD per share, and (d) Stilwell Associates, L.P. ("Associates") acquired 751 shares at $5.27 USD per share.

F3 · ownership.nature: These are shares owned directly by Associates and indirectly by Joseph Stilwell in his capacity as the managing member and owner of Stilwell Value LLC ("Value"), which is the general partner of Associates. Joseph Stilwell disclaims beneficial ownership of all shares reported as owned indirectly except to the extent of his pecuniary interest therein.

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Value uses the disclosed total when available, otherwise shares × reported transaction price. It is not an estimate of exercise cash cost or investment performance.