UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 _________________________ FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For Quarterly Period Ended March 31, 2021 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from _____ to _____ Commission File Number: 001-15204 Kingsway Financial Services Inc. (Exact name of registrant as specified in its charter) ...

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K x ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2020 OR o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from _____ to _____ Commission File Number 001-15204 Kingsway Financial Services Inc. (Exact name of registrant as specified in its charter) Delaware 85-1792291 (State or other ju ...

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 _________________________ FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For Quarterly Period Ended September 30, 2020 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from _____ to _____ Commission File Number: 001-15204 Kingsway Financial Services Inc. (Exact name of registrant as specified in its char ...

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 _________________________ FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For Quarterly Period Ended June 30, 2020 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from _____ to _____ Commission File Number: 001-15204 Kingsway Financial Services Inc. (Exact name of registrant as specified in its charter) ...

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Kingsway Financial Services Inc. Washington, D.C. 20549 _________________________ FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For Quarterly Period Ended March 31, 2020 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from _____ to _____ Commission File Number: 001-15204 (Exact name of registrant as specified in its charter) ...

Acquisition and Business Expansion - Kingsway Financial Services Inc. acquired Geminus Holding Company, Inc. for a cash consideration of $8.4 million, which includes $7.7 million in cash and a $0.7 million installment payable[22] - Kingsway secured $10.0 million in acquisition financing for the Geminus acquisition, with $1.3 million available for general corporate purposes after transaction expenses[23] - On March 1, 2019, the Company acquired Geminus for $8.4 million, enhancing its portfolio in the vehicle service agreement business[438] - The acquisition of Geminus resulted in recognized goodwill of $7.4 million and identifiable intangible assets of $5.7 million[441] - From the acquisition date to December 31, 2019, Geminus generated revenue of $9.9 million and net income of $0.6 million[441] Revenue and Financial Performance - Total revenues increased to $59,948,000 in 2019, up from $52,078,000 in 2018, representing a growth of 15.5%[347] - Service fee and commission income rose to $46,111,000, compared to $38,286,000 in the previous year, marking an increase of 20.5%[347] - The Company reported revenues of $61.9 million for the year ended December 31, 2019, compared to $63.7 million in 2018[444] - The Company recognized a loss from continuing operations attributable to common shareholders of $6.5 million for 2019, an improvement from a loss of $25.9 million in 2018[444] Operational Efficiency and Loss Management - Operating loss narrowed to $(1,409,000) in 2019 from $(2,293,000) in 2018, showing improvement in operational efficiency[347] - Net loss attributable to common shareholders decreased to $(6,905,000) in 2019, down from $(30,721,000) in 2018, reflecting a reduction of 77.5%[347] - Comprehensive loss attributable to common shareholders was $(11,307,000) in 2019, compared to $(25,976,000) in 2018, indicating a significant improvement[350] - The Company incurred a loss on disposal of discontinued operations amounting to $1.5 million for the year ended December 31, 2019[446] - Loss on disposal of discontinued operations for 2019 was $1,544,000, an improvement from a loss of $7,136,000 in 2018[450] Investment and Financial Management - The Company manages its investments to support liabilities, preserve capital, and maximize after-tax returns, with a focus on high-quality fixed maturities[54] - The Company actively reviews its investment portfolio to manage exposure to interest rate fluctuations and maximize total after-tax returns[315] - The Company manages equity price risk through diversification and asset allocation techniques, indicating a proactive approach to risk management[321] - The Investment Committee oversees key investment policies, ensuring they are subject to annual review and approval, which supports effective governance[323] - The Company assesses its investment in investee for potential impairment at each reporting date[386] Customer Base and Market Position - No single customer accounts for 10% or more of the Company's consolidated revenues, indicating a diversified customer base[40] - IWS focuses exclusively on the automotive finance market, providing vehicle service agreements and related products, differentiating itself from competitors who take a generalist approach[41] - Trinity claims to provide superior customer service and warranty solutions for a wider range of equipment compared to its competitors[42] - PWSC differentiates its insured warranty product through its relationship with an A+ rated global insurance carrier and over 20 years of experience in new home warranty administration[43] Financial Health and Compliance - As of December 31, 2019, surplus as regards to policyholders reported by Amigo exceeded the 200% threshold, indicating strong financial health[60] - The Company is in compliance with state regulations regarding vehicle service agreements and warranty products, ensuring adherence to legal requirements[63] - The company’s financial statements for the year ended December 31, 2019, were audited and presented fairly in all material respects, confirming compliance with accounting principles[330] Assets and Liabilities - Total assets increased to $399,623,000 in 2019, up from $378,240,000 in 2018, a growth of 5.5%[345] - Total liabilities rose to $378,850,000 in 2019, compared to $348,182,000 in 2018, an increase of 8.8%[345] - Goodwill increased to $82,104,000 in 2019 from $74,659,000 in 2018, reflecting a growth of 9.8%[347] - Cash and cash equivalents decreased to $13,478,000 in 2019 from $14,619,000 in 2018, a decline of 7.8%[345] - Accumulated deficit increased to $(388,082,000) in 2019 from $(382,196,000) in 2018, indicating a worsening of 1.0%[347] Cash Flow and Operating Activities - Cash used in operating activities for continuing operations was $759 thousand in 2019, compared to $2,765 thousand in 2018, reflecting a decrease of about 72.6%[355] - Total cash provided by investing activities for continuing operations was a net outflow of $6,466 thousand in 2019, contrasting with a net inflow of $18,071 thousand in 2018[355] - Cash provided by financing activities from continuing operations was $1,308 million, a decrease from $(4,090) million in the prior period[356] - Cash and cash equivalents and restricted cash at the end of the period were $25,661 million, down from $31,578 million at the beginning of the period[356] Risk Management - Credit risk arises from positions in short-term investments, corporate debt instruments, and government bonds, highlighting areas of potential financial exposure[322] - The Company records a right of use asset and lease liability for all leases exceeding twelve months, effective January 1, 2019[405] - The Company has options to increase liquidity, including selling passive investments and issuing debt or equity securities[424]

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 _________________________ FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For Quarterly Period Ended September 30, 2019 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from _____ to _____ Commission File Number: 001-15204 Kingsway Financial Services Inc. (Exact name of registrant as specified in its char ...

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 _________________________ FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For Quarterly Period Ended June 30, 2019 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from _____ to _____ Commission File Number: 001-15204 Kingsway Financial Services Inc. (Exact name of registrant as specified in its charter) ...

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 _________________________ FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For Quarterly Period Ended March 31, 2019 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from _____ to _____ Commission File Number: 001-15204 Kingsway Financial Services Inc. (Exact name of registrant as specified in its charter) ...

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K x ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2018 OR o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Transition Period from _____ to _____ Commission File Number 001-15204 Kingsway Financial Services Inc. (Exact name of registrant as specified in its charter) Delaware 98-0475673 (State or other ju ...