On May 24, 2024 (the ? Third Amendment Effective Date?), certain subsidiaries (the ? Loan Parties?) of Kingsway Financial Services Inc. (the ?

Company?) entered into an amendment (the ? Third Amendment?) to the Loan and Security Agreement, dated as of December 1, 2020 (as amended, the ? Loan Agreement?), with CIBC Bank USA as lender (?

Lender?). As further described on Current Reports filed on Form 8-K by the Company with the Securities and Exchange Commission (the ? SEC?) on December 2, 2020 (the ?

Original 8-K?) and March 1, 2023, the Loan Agreement provides for certain lending facilities including a Term Loan, Delayed Draw Term Loan and Revolving Note. The Third Amendment provides for a new term loan in the principal amount of $15,000,000 (the ? 2024 Term Loan?), the proceeds of which were used in part to repay the outstanding balance of the existing Term Loan, Delayed Draw Term Loan and Revolving Note.

The Third Amendment also provides for a new delayed draw term loan in a principal amount of up to $6,000,000 (the ? 2024 Delayed Draw Term Loan?). All or any portion, subject to a $2,000,000 minimum amount, of the 2024 Delayed Draw Term Loan may be requested by the Loan Parties at any time in up to three advances until the second anniversary of the Third Amendment Effective Date.

Until such date, in addition to other fees payable pursuant to the Loan Agreement, the Loan Parties agree to pay Lender a non-use fee based on the average daily undrawn 2024 Delayed Draw Term Loan commitment. In connection with the Third Amendment, the Loan Parties also paid to Lender a commitment fee equal to $96,559.11. The principal amount of the 2024 Term Loan and each 2024 Delayed Draw Term Loan shall be repaid in quarterly installments and, together with the Revolving Note, will mature on May 24, 2029.

The Third Amendment also modifies certain financial covenants in the Loan Agreement. Pursuant to the terms of the Third Amendment (i) the maximum permissible Fixed Charge Coverage Ratio (as defined in the Third Amendment) was reduced to 1.20 to 1.00 and (ii) the maximum permissible Senior Cash Flow Leverage Ratio (as defined in the Loan Agreement) was amended for certain periods.