KINGSWAY FINANCIAL SERVICES INC

(in thousands, except share data)

KINGSWAY FINANCIAL SERVICES INC.

Consolidated Statements of Operations

(in thousands, except per share data)

KINGSWAY FINANCIAL SERVICES INC.

Consolidated Statements of Comprehensive Loss

(in thousands)

(1) Net of income tax expense (benefit) of $0 for the three and nine months ended September 30, 2024 and September 30, 2023.

KINGSWAY FINANCIAL SERVICES INC.

Consolidated Statements of Shareholders' Equity

(in thousands, except share data)

KINGSWAY FINANCIAL SERVICES INC.

KINGSWAY FINANCIAL SERVICES INC.

Consolidated Statements of Cash Flows

(in thousands)

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) September 30, 2024

NOTE1 BUSINESS

Kingsway Financial Services Inc. (the "Company" or "Kingsway") was incorporated under the Business Corporations Act (Ontario) on* September 19, 1989.Effective December 31, 2018,*the Company changed its jurisdiction of incorporation from the province of Ontario, Canada, to the State of Delaware. Kingsway is a holding company with operating subsidiaries located in the United States. The Company owns or controls subsidiaries primarily in the extended warranty and business services industries.

NOTE2 BASIS OF PRESENTATION

The accompanying unaudited consolidated interim financial statements have been prepared in accordance with accounting principles generally accepted in the United States of America ("U.S. GAAP") for interim financial information and with the instructions to Form10-Q and Article10 of Regulation S-X. Accordingly, they donot include all of the information and notes required by U.S. GAAP for complete financial statements of the Company. In the opinion of management, all adjustments necessary for a fair presentation have been included and are of a normal recurring nature. Interim results arenot necessarily indicative of the results that* may*be expected for the year.

The accompanying unaudited consolidated interim financial statements and footnotes should be read in conjunction with the audited consolidated financial statements and footnotes included within our Annual Report on Form10-K ("2023 Annual Report") for the year ended* December 31, 2023*.

The unaudited consolidated interim financial statements include the accounts of the Company and its subsidiaries, as well as certain variable interest entities as further described in Note6, "Variable Interest Entities," to the consolidated financial statements in the2023 Annual Report. All material intercompany transactions and balances have been eliminated in consolidation.

The preparation of consolidated financial statements in accordance with U.S. GAAP requires management to make estimates and assumptions that affect the reported amounts and classifications of assets and liabilities, revenues and expenses, and the related disclosures of contingent assets and liabilities in the consolidated financial statements and accompanying notes. Actual results could differ from these estimates. Estimates and their underlying assumptions are reviewed on an ongoing basis. Changes in estimates are recorded in the accounting period in which they are determined.

The critical accounting estimates and assumptions in the accompanying unaudited consolidated interim financial statements include, but arenot limited to, revenue recognition; valuation of fixed maturities and equity investments; impairment assessment of investments; valuation of limited liability investment, at fair value; valuation of deferred income taxes; accounting for business combinations; contingent considerations; valuation and impairment assessment of intangible assets; goodwill recoverability; deferred contract costs; fair value assumptions for subordinated debt obligations; fair value assumptions for subsidiary stock-based compensation awards; and fair value assumptions for derivative financial instruments.

On* July 25, 2024,the Company completed the purchase of the 10% interest in IWSnot* previously owned by the Company. Therefore, as of* July 25,*2024, IWS became a wholly-owned subsidiary of the Company.

NOTE3 SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES

There have beenno material changes to our significant accounting policies as reported in our2023 Annual Report.

NOTE4 RECENTLY ISSUED ACCOUNTING STANDARDS

(a) Adoption of New Accounting Standards:

Effective* January 1, 2024,the Company adopted ASU2023*-02, Investments Equity Method and Joint Ventures (Topic323*): Accounting for Investments in Tax Credit Structures Using the Proportional Amortization Method.* These amendments allow reporting entities to elect to account for qualifying tax equity investments using the proportional amortization method, regardless of the program giving rise to the related income tax credits. The adoption of ASU2023-02 didnot have an impact on the Company's consolidated financial statements.

(b) Accounting StandardsNot Yet Adopted:

In* March 2023,the Financial Accounting Standards Board ("FASB") issued ASUNo.* 2023-09, Improvements to Income Tax Disclosures (“ASU2023-09”), which requires disaggregated information about a reporting entity’s effective tax rate reconciliation as well as information on income taxes paid. The standard is intended to benefit investors by providing more detailed income tax disclosures that would be useful in making capital allocation decisions. ASU2023-09 is effective for public companies with annual periods beginning after* December 15, 2024,*with early adoption permitted. The Company is currently evaluating the impact the adoption of this standard will have on its consolidated financial statements.

In* October 2023,the FASB issued ASU2023*-06, Disclosure Improvements: Codification Amendments in Response to the SEC’s Disclosure Update and Simplification Initiative issued in ** August 2018**("ASU2023-06"), which amends U.S. GAAP to reflect updates and simplifications to certain disclosure requirements referred to FASB by the SEC. The targeted amendments incorporate14 of the27 disclosures referred by the SEC into Codification. Some of the amendments represent clarifications to, or technical corrections of, the current requirements. ASU2023-06 could move certain disclosures from the nonfinancial portions of SEC filings to the financial statement notes. Each amendment in ASU2023-06 will only become effective if the SEC removes the related disclosure or presentation requirement from its existing regulation by* June 30, 2027.No amendments were effective at September 30, 2024*. The Company is currently evaluating the impact of the adoption of the new standard but doesnot expect a significant impact on its consolidated financial statements.

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) September 30, 2024

In* November 2023,the FASB issued ASUNo.* 2023-07, Improvements to Reportable Segment Disclosures(“ASU2023-07”), which improves reportable segment disclosure requirements, primarily through enhanced disclosures about significant segment expenses. In addition, the amendments enhance interim disclosure requirements, clarify circumstances in which an entity can disclose multiple segment measures of profit or loss, provide new segment disclosure requirements for entities with a single reportable segment, and contain other disclosure requirements. The purpose of the amendments is to enable investors to better understand an entity’s overall performance and assess potential future cash flows. ASU2023-07 is effective for public companies with annual periods beginning after* December 15, 2023,and interim periods within annual period beginning after December 15, 2024.Although the Company continues to evaluate the impact of adopting this new accounting standard, the amendments are disclosure-related and shouldnot* have a material impact on the Company's consolidated financial statements.

In* March 2024,the FASB issued ASU2024*-02, Codification Improvements - Amendments to Remove References to the Concepts Statements("ASU2024-02"). ASU2024-02 amends the Codification to remove references to various concepts statements and impacts a variety of topics in the Codification. The amendments apply to all reporting entities within the scope of the affected accounting guidance, but in most instances the references removed are extraneous andnot required to understand or apply the guidance. Generally, the amendments in ASU2024-02 arenot intended to result in significant accounting changes for most entities. ASU2024-02 is effective* January 1, 2025.The Company doesnot* expect ASU2024-02 to have a significant impact on its consolidated financial statements.

NOTE5 ACQUISITIONS AND DISCONTINUED OPERATIONS

Image Solutions, LLC

On* September 26, 2024,the Company acquired 100% of the outstanding membership interests of Image Solutions, LLC ("Image Solutions") for aggregate cash consideration of $20.4 million, less certain escrowed amounts for purposes of indemnification claims and working capital adjustments. Image Solutions, based in Fletcher, North Carolina, is an information technology managed services provider. As further discussed in Note20*, "Segmented Information," Image Solutions is included in the Kingsway Search Xcelerator segment. This acquisition was the Company’ssixth acquisition under its novel CEO Accelerator program and further expands the Company’s portfolio of businesses with recurring revenue and low capital intensity.

This acquisition was accounted for as a business combination using the acquisition method of accounting. The purchase price was provisionally allocated to the assets acquired and liabilities assumed based on their estimated fair values at the date of acquisition and are subject to adjustment during a measurement period subsequent to the acquisition date,not to exceedone year, as permitted under U.S. GAAP. The Company expects to complete its purchase price allocation within the nextsix months. These estimates, allocations and calculations are subject to change as we obtain further information; therefore, the final fair values of the assets acquired and liabilities assumed could change from the estimates included in these consolidated financial statements.

Refer to Note8,"Intangible Assets," for further disclosure of the intangible assets related to this acquisition. The goodwill of $6.1 million represents the premium paid over the fair value of the net tangible and intangible assets acquired, which the Company paid to grow its portfolio of companies and acquire an assembled workforce. The goodwill isnot deductible for tax purposes.

The following table summarizes the preliminary allocation of the Image Solutions purchase price and the estimated fair values of the assets acquired and liabilities assumed at the date of acquisition:

Since Image Solutions was acquired on* September 26, 2024,the consolidated statement of operations for thethree* andnine months ended* September 30, 2024* doesnot include any revenue, expenses or earnings of Image Solutions, as such items are insignificant. During thethree andnine months ended* September 30, 2024*, the Company incurred expenses related to the acquisition of Image Solutions of $0.4 million, which are included in general and administrative expenses in the consolidated statements of operations.

10

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) September 30, 2024

The following unaudited pro forma summary presents the Company's consolidated financial statements for thethree andnine months ended* September 30, 2024* and* September 30, 2023as if Image Solutions had been acquired on January 1, 2023.The pro forma summary is presented for illustrative purposes only and doesnot* purport to represent the results of our operations that would have actually occurred had the acquisition occurred as of the beginning of the period presented or project our results of operations as of any future date or for any future period, as applicable. The pro forma results primarily include purchase accounting adjustments related to the acquisition of Image Solutions, interest expense and the amortization of debt issuance costs and discounts associated with the related financing obtained in connection with the Image Solutions acquisition (see Note11, "Debt") and acquisition-related expenses.

Systems Products International, Inc.

On* September 7, 2023,the Company acquired 100% of the outstanding equity interests of Systems Products International, Inc. ("SPI") for aggregate cash consideration of $2.8 million, less certain escrowed amounts for purposes of indemnification claims and working capital adjustments. SPI, based in Miami, Florida, is a vertical market software company, created exclusively to serve the management needs of all types of shared-ownership properties. As further discussed in Note20*, "Segmented Information," SPI is included in the Kingsway Search Xcelerator segment. This acquisition was the Company’sfourth acquisition under its novel CEO Accelerator program and itsfirst in the vertical market software space and further expands the Company’s portfolio of businesses with recurring revenue and low capital intensity.

This acquisition was accounted for as a business combination using the acquisition method of accounting. The purchase price was provisionally allocated to the assets acquired and liabilities assumed based on their estimated fair values at the date of acquisition and are subject to adjustment during a measurement period subsequent to the acquisition date,not to exceedone year as permitted under U.S. GAAP. During thesecond quarter of2024, the Company finalized its fair value analysis of the assets acquired and liabilities assumed with the assistance of athird party.

The Company records measurement period adjustments in the period in which the adjustments occur. During thesecond quarter of2024, the Company recorded measurement period adjustments that increased goodwill by $0.3 million compared to the amount recorded at* December**31,* 2023. The measurement period adjustment primarily reflects changes in the estimated value of the contract asset of $0.3 million. The final fair values of the assets acquired and liabilities assumed as of* September 7, 2023,*were $3.7 million of assets and $1.2 million of liabilities, which included $1.4 million of contract asset and $1.7 million of intangible assets.

See Note4, "Acquisitions," to the consolidated financial statements in the2023 Annual Report for further details on the Company's acquisition of SPI.

Digital Diagnostics Imaging, Inc.

On* October 26, 2023,the Company acquired 100% of the outstanding equity interests of Digital Diagnostics Imaging, Inc. ("DDI") for aggregate cash consideration of approximately $11.0 million, less certain escrowed amounts for purposes of indemnification claims. The final purchase price was subject to a working capital true-up of less than $0.1 million that was settled during thesecond* quarter of2024. DDI, based in Wall, New Jersey, is a provider of fully managed outsourced cardiac telemetry services. As further discussed in Note20, "Segmented Information," DDI is included in the Kingsway Search Xcelerator segment. This acquisition was the Company’sfifth acquisition under its novel CEO Accelerator program and further expands the Company’s portfolio of businesses with recurring revenue and low capital intensity.

This acquisition was accounted for as a business combination using the acquisition method of accounting. The purchase price was provisionally allocated to the assets acquired and liabilities assumed based on their estimated fair values at the date of acquisition and are subject to adjustment during a measurement period subsequent to the acquisition date,not to exceedone year as permitted under U.S. GAAP. During thesecond quarter of2024, the Company finalized its fair value analysis of the assets acquired and liabilities assumed with the assistance of athird party.

The Company records measurement period adjustments in the period in which the adjustments occur. During thesecond quarter of2024, the Company recorded a measurement period adjustment that increased goodwill by $0.2 million compared to the amount recorded at* December* 31, 2023. The measurement period adjustments primarily relate to a decrease in the estimated fair value of property and equipment of $0.4 million, partially offset by an increase to the customer relationships intangible asset of $0.2 million. The final fair values of the assets acquired and liabilities assumed as of* October 26, 2023,*were $8.5 million of assets and $2.5 million of liabilities, which included $0.8 million of property and equipment and $7.0 million of intangible assets.

See Note4, "Acquisitions," to the consolidated financial statements in the2023 Annual Report for further details on the Company's acquisition of DDI.

Leased Real Estate Segment

The Company’s former subsidiaries, VA Lafayette, LLC ("VA Lafayette") and CMC Industries Inc. ("CMC"), which included CMC’s subsidiaries Texas Rail Terminal LLC and TRT Leaseco, LLC ("TRT"), comprised the Company's entire Leased Real Estate segment prior to thefourth quarter of2022. Each of CMC, through indirect wholly owned subsidiary, TRT, and VA Lafayette own a single asset, which is real estate property. On* December 29, 2022,TRT sold its assets and at December 31, 2022,*VA Lafayette was classified as held for sale.

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) September 30, 2024

In accordance with ASUNo. 2014-08, Reporting of Discontinued Operations and Disclosures of Disposals of Components of an Entity, a disposal is categorized as a discontinued operation if the disposal group is a component of an entity or group of components that meets the held for sale criteria, is disposed of by sale, or is disposed of other than by sale, and represents a strategic shift that has or will have a major effect on an entity’s operations and financial results*.*

Leased Real Estate was a component of Kingsway since its operations and cash flows could be clearly distinguished, both operationally and for financial reporting purposes, from the rest of the reporting entity. A component of an entity* mayconsist of multiple disposal groups and doesnot* need to be disposed of in a single transaction. The disposal of the Leased Real Estate segment represents a strategic shift that will have a major effect on the Company's operations and financial results, as the disposal of the Leased Real Estate assets was in excess of20% of the entity's total assets. As a result, the assets, liabilities, operating results and cash flows related to Leased Real Estate have been classified as discontinued operations in the consolidated financial statements for all periods presented.

During thethird quarter of2024, CMC and its subsidiaries were legally dissolved. As a result, the remaining equity related to CMC and its subsidiaries that was included in noncontrolling interests in consolidated subsidiaries is now included in accumulated deficit in the consolidated balance sheet at* September 30, 2024*.

VA Lafayette

During thefourth quarter of2022, the Company began executing a plan to sell its subsidiary, VA Lafayette. VA Lafayette owns the LA Real Property, that is subject to a long-term lease and the LA Mortgage. During thesecond quarter of2024, the Company entered into a letter of intent for the sale of VA Lafayette. On* August 16, 2024,the Company completed the sale of VA Lafayette to an entity associated with a current holder of the Company's Class B Preferred Stock (the sale occurred prior to negotiations regarding the issuance of the Class B Preferred Stock). Refer to Note22*, "Related Parties," for further disclosure. The purchase price paid by the purchaser at the closing consisted of $1.3 million in cash plus the assumption of the unpaid principal balance as of the closing of the LA Mortgage of approximately $11.8 million, netting cash proceeds of $1.1 million to Kingsway after expenses.

During thethree months ended* September 30, 2024*, the Company recognized a loss on disposal of $0.2 million, which is included in loss on disposal of discontinued operations, net of taxes in the consolidated statements of operations for thethree andnine months ended* September 30, 2024*. As part of recognizing the business as held for sale, the Company was required to measure VA Lafayette at the lower of its carrying amount or fair value less cost to sell. As a result of this analysis, during thefirst quarter of2024, the Company recognized an estimated non-cash, loss on disposal of $0.4 million, which is included in loss on disposal of discontinued operations, net of taxes in the consolidated statements of operations for thenine months ended* September 30, 2024*. The loss is a result of adjusting the net carrying value of VA Lafayette to be equal to the estimated selling price and was determined by comparing the expected cash consideration received for the sale of VA Lafayette with the net assets of VA Lafayette.

As discussed above, VA Lafayette was part of the Leased Real Estate disposal group. In conjunction with the sale of the CMC Real Property on* December 29, 2022,the sale of the Leased Real Estate's assets represents a strategic shift that will have a major effect on the Company's operations and financial results. As a result, VA Lafayette has been classified as a discontinued operation and the results of its operations are reported separately for all periods presented. The assets and liabilities of VA Lafayette are presented as held for sale in the consolidated balance sheet at December 31, 2023*.

Summary financial information for Leased Real Estate included in income from discontinued operations, net of taxes in the unaudited consolidated statements of operations for thethree andnine months ended* September 30, 2024* and* September 30, 2023* is presented below:

For thethree andnine months ended* September 30, 2024*, and* September 30, 2023*, all of the pre-tax income from discontinued operations disclosed in the table above is attributable to the controlling interest.

The carrying amounts of the major classes of assets and liabilities of Leased Real Estate presented as held for sale at* December 31, 2023* are as follows:

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) September 30, 2024

Loss on disposal of discontinued operations, net of taxes, related to Leased Real Estate, in the unaudited consolidated statement of operations for thethree andnine months ended* September 30, 2024* is comprised of $0.2 million and $0.6 million, respectively, of loss on disposal of discontinued operations before income tax benefit and income tax benefit of zero.

NOTE6 INVESTMENTS

The amortized cost, gross unrealized gains and losses included in accumulated other comprehensive loss, and estimated fair value of the Company's available-for-sale investments at* September 30, 2024* and* December 31, 2023* are summarized in the tables shown below:

The table below summarizes the Company's fixed maturities at* September 30, 2024* by contractual maturity periods. Actual results* maydiffer as issuers may*have the right to call or prepay obligations, with or without penalties, prior to the contractual maturity of these obligations.

The following tables highlight the aggregate unrealized loss position, by security type, of available-for-sale investments in unrealized loss positions whereno credit loss allowance had been established as of* September 30, 2024* and* December 31, 2023*. The tables segregate the holdings based on the period of time the investments have been continuously held in unrealized loss positions.

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) September 30, 2024

At* September 30, 2024* and* December 31, 2023*, there are approximately 155 and 181 individual available-for-sale investments that were in unrealized loss positions, for which an allowance for credit losses hasnot been recorded. The Company didnot have the intent to sell these investments, and it wasnot more likely thannot that the Company would be required to sell these investments before recovery of its amortized cost. The Company evaluated these investments for credit losses at* September 30, 2024* and* December 31, 2023*. The Company considers many factors in evaluating whether the unrealized losses were credit related including, butnot limited to, the extent to which the fair value has been less than amortized cost, conditions related to the security, industry, or geographic area, payment structure of the investment and the likelihood of the issuer’s ability to make contractual cashflows, defaults or other collectability concerns related to the issuer, changes in the ratings assigned by a rating agency, and other credit enhancements that affect the investment’s expected performance. The Company determined that the unrealized losses on the fixed maturity investments were due to non-credit related factors at* September 30, 2024* and* December 31, 2023*.

The Company didnot record any write-downs for impairment related to available-for-sale fixed maturity investments for thethree andnine months ended* September 30, 2024* and* September 30, 2023*.

The Company doesnot have any exposure to subprime mortgage-backed investments.

Limited liability investments include investments in limited liability companies and limited partnerships. The Company's interests in these investments arenot deemed minor and, therefore, are accounted for under the equity method of accounting. The most recently available financial statements are used in applying the equity method. The difference between the end of the reporting period of the limited liability entities and that of the Company isno more thanthree months. As of* September 30, 2024* and* December 31, 2023*, the carrying value of limited liability investments totaled $0.7 million and $0.8 million, respectively. The Company recordedno impairments related to limited liability investments during thethree andnine months ended* September 30, 2024* ($0.1 million during thethree andnine months ended * September 30, 2023*), which are included in impairment losses on investments in the consolidated statements of operations. Income or loss from limited liability investments is recognized based on the Company's share of the earnings of the limited liability entities and is included in net investment income in the consolidated statements of operations. At* September 30, 2024*, the Company hadno unfunded commitments related to limited liability investments.

Limited liability investment, at fair value represents the underlying investments of the Company’s consolidated entity Argo Holdings Fund I, LLC ("Argo Holdings"). As of* September 30, 2024* and* December 31, 2023*, the carrying value of the Company's limited liability investment, at fair value was $2.7 million and $3.5 million, respectively. At* September 30, 2024*, the Company hadno unfunded commitments to fund limited liability investments, at fair value.

Prior to thesecond quarter of2023, the Company's limited liability investments, at fair value included the underlying investments of the Company's consolidated entity, Net Lease Investment Grade Portfolio LLC ("Net Lease"). The Company consolidated the financial statements of Net Lease on athree-month lag. Net Lease owned investments in limited liability companies that held investment properties. During thefourth quarter of2022, one of Net Lease's limited liability companies refinanced their existing debt. Debt proceeds of $5.2 million were distributed to Net Lease, which decreased Net Lease's investment in the limited liability company, which the Company recorded during thefirst quarter of2023. During thefirst quarter of2023, Net Lease sold its final investment property for $15.8 million. Net Lease received net proceeds of $8.1 million after the repayment of debt at the limited liability company and transaction expenses. Given thethree-month reporting lag discussed above, the Company recorded this transaction in itssecond quarter2023 financial statements. As a result of the sale and subsequent distribution of the net proceeds, the carrying value of Net Lease's investments in limited liability companies waszero at* June 30, 2023.*

Investments in private companies consist of convertible preferred stocks and notes in privately owned companies and investments in limited liability companies in which the Company’s interests are deemed minor. The Company's investments in private companies donot have readily determinable fair values. The Company has elected to record investments in private companies at cost, adjusted for observable price changes and impairments. As of* September 30, 2024* and* December 31, 2023*, the carrying value of the Company's investments in private companies totaled $0.7 million and $0.9 million, respectively. For thethree andnine months ended* September 30, 2024*, the Company didnot record any adjustments to the carrying value of its investments in private companies for observable price changes (adjustment of $0.1 million for thethree andnine months ended * September 30, 2023* to increase the fair value of certain investments in private companies for observable price changes, which is included in net change in unrealized gain on private company investments in the consolidated statements of operations).

The Company performs a quarterly impairment analysis of its investments in private companies. As a result of the analysis performed, the Company didnot record any impairments related to investments in private companies for thethree andnine months ended* September 30, 2024* and* September 30, 2023*.

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) September 30, 2024

Net investment income for thethree andnine months ended* September 30, 2024* and* September 30, 2023* is comprised as follows:

Net realized gains on investments for thethree andnine months ended* September 30, 2024* and* September 30, 2023* are comprised as follows:

Net gain (loss) on equity investments for thethree andnine months ended* September 30, 2024* and* September 30, 2023* is comprised as follows:

Prior to thesecond quarter of2023, the Company held 400,000 warrants in Limbach Holdings, Inc. ("Limbach"). During thefirst quarter of2023, the underlying common stock price of Limbach increased, resulting in an increase in the fair value of the warrants held at* March 31, 2023.During thesecond* quarter of2023, the Company completed a cashless exercise of its Limbach warrants and received 110,036 shares of Limbach common stock. During thethird quarter of2023, the Company sold all of its Limbach common shares. The Company recorded total gains related to Limbach of $3.3 million during thenine months ended* September 30, 2023.*

NOTE7 GOODWILL

The following table summarizes the goodwill activity for thenine months ended* September 30, 2024*:

As further discussed in Note5, "Acquisitions and Discontinued Operations," during thethird quarter of2024 the Company recorded goodwill of $6.1 million related to the acquisition of Image Solutions on* September 26, 2024.The goodwill related to this acquisition is provisional and subject to adjustment during the measurement period. The Company expects to complete its purchase price allocation within the nextsix* months. The estimates, allocations and calculations recorded at* September 30, 2024* are subject to change as we obtain further information; therefore, the final fair values of the assets acquired and liabilities assumed* may**not* agree with the estimates included in these consolidated financial statements.

As further discussed in Note5, "Acquisitions and Discontinued Operations," during thesecond quarter of2024, the Company recorded measurement period adjustments, related to acquisitions of SPI and DDI, that increased goodwill by $0.4 million.

Goodwill is assessed for impairment annually as of* November 30,or more frequently if events or circumstances indicate that the carrying value may**not* be recoverable. Although the Company believes its estimates of fair value are reasonable, actual financial results could differ from those estimates due to the inherent uncertainty involved in making such estimates. Changes in assumptions concerning future financial results or other underlying assumptions could have a significant impact on either the fair value of the reporting units, the amount of the goodwill impairment charge, or both. No goodwill impairment charges were recorded during thethree andnine months ended* September 30, 2024* and* September 30, 2023*.

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) September 30, 2024

NOTE8 INTANGIBLE ASSETS

Intangible assets at* September 30, 2024* and* December 31, 2023* are comprised as follows:

As further discussed in Note5, "Acquisitions and Discontinued Operations," during thethird quarter of2024, the Company recorded $12.6 million of separately identifiable intangible assets, related to acquired customer relationships and trade name, as part of the acquisition of Image Solutions on* September 26, 2024.The customer relationships intangible asset of $11.1 million is being amortized over thirteen years, based on the pattern in which the economic benefits of the intangible asset is expected to be consumed. The trade name intangible asset of $1.5 million is deemed to have indefinite useful life and isnot* amortized. The intangible assets related to this acquisition are provisional and subject to adjustment during the measurement period. The Company expects to complete its purchase price allocation within the nextsix months. The estimates, allocations and calculations recorded at* September 30, 2024* are subject to change as we obtain further information; therefore, the final fair values of the assets acquired and liabilities assumed* may**not* agree with the estimates included in these consolidated financial statements

As further discussed in Note5, "Acquisitions and Discontinued Operations," during thesecond quarter of2024, the Company recorded a measurement period adjustment related to acquisition of DDI that increased the customer relationships intangible asset by $0.2 million.

The Company's intangible assets with definite useful lives are amortized either based on the patterns in which the economic benefits of the intangible assets are expected to be consumed or using the straight-line method over their estimated useful lives, which range from 7 to 15 years. Amortization of intangible assets was $1.4 million for thethree months ended* September 30, 2024* and* September 30, 2023* ($4.3 million for thenine months ended* September 30, 2024* and* September 30, 2023*).

The trade names intangible assets have indefinite useful lives and arenot amortized. Indefinite-lived intangible assets are assessed for impairment annually as of* November 30,or more frequently if events or circumstances indicate that the carrying value may**not* be recoverable. The Company* mayperform its impairment test for any indefinite-lived intangible asset through a qualitative assessment or elect to proceed directly to a quantitative impairment test, however, the Company may*resume a qualitative assessment in any subsequent period if facts and circumstances permit.

At* March 31, 2024,** June 30, 2024and September 30, 2024*, the Company determined that certain trade names should be further examined under a quantitative approach due to actual revenue coming in lower than previous projections. Based upon these assessments, the Company recorded impairment charges for thethree months ended* September 30, 2024* of $0.6 million related to the CSuite and Ravix indefinite-lived trade names, and $1.8 million for thenine months ended* September 30, 2024*, related to the SNS, CSuite and Ravix indefinite-lived trade names. The fair value of the SNS, CSuite and Ravix trade names were estimated using the relief-from-royalty method. The significant unobservable inputs used in the relief-from-royalty method, which are level3 inputs, include a royalty rate and discount rate. The reduction in value is primarily due to higher discount rates and a reduction in projected revenue. Future impairments* maybe recorded if discount rates increase further, or if actual revenue falls short of current projections. The valuation of these assets isnot* dependent on the underlying profit or loss generated by the respective business. Therefore, even if a change in revenue doesnot have a significant impact on operating results, it could significantly impact the fair value of the trade name. No impairment charges were recorded during thethree andnine months ended* September 30, 2023*.

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) September 30, 2024

NOTE9 PROPERTY AND EQUIPMENT

Property and equipment at* September 30, 2024* and* December 31, 2023* are comprised as follows:

For thethree months ended* September 30, 2024* and* September 30, 2023*, depreciation expense related to medical equipment of $0.1 million andzero, respectively ( $0.1 million andzero for thenine months ended* September 30, 2024* and* September 30, 2023*, respectively), is included in cost of services sold in the unaudited consolidated statements of operations. For thethree months ended* September 30, 2024* and* September 30, 2023*, depreciation expense on all other property and equipment of $0.1 million and $0.1 million, respectively ( $0.4 million and $0.2 million for thenine months ended* September 30, 2024* and* September 30, 2023*, respectively), is included in general and administrative expenses in the unaudited consolidated statements of operations.

As discussed in Note5, " Acquisitions and Discontinued Operations," during thesecond quarter of2024, the Company recorded a measurement period adjustment related to acquisition of DDI that decreased property and equipment, specifically medical equipment, by $0.4 million.

NOTE10 DERIVATIVES

On* April 1, 2021,the Company entered into an interest rate swap agreement with CIBC Bank USA to convert the variable London interbank offered interest rate forthree*-month U.S. dollar deposits ("LIBOR") interest rate on a portion of its2020 KWH Loan (as defined below in Note11, "Debt,") to a fixed interest rate of 1.18%. On* September 15, 2022,the interest rate swap agreement was amended to convert from a variable Secured Overnight Financing Rate ("SOFR") to a fixed interest rate of 1.103%. The interest rate swap had an initial notional amount of $11.9 million. On February**29,* 2024, the interest rate swap matured and the Company didnot enter into any additional interest rate swap agreement upon its expiration.

The purpose of this interest rate swap, which wasnot designated as a cash flow hedge, was to reduce the Company's exposure to variability in cash flows from interest payments attributable to fluctuations in the variable interest rate associated with the2020 KWH Loan. The Company hadnot elected hedge accounting for the interest rate swap. The interest rate swap was recorded in theconsolidated balance sheets at fair value with changes in fair value recorded ininterest expense in the consolidated statements of operations.

On* August 2, 2022,the Company entered into an agreement with a holder offour* of the trust preferred debt instruments ("TruPs") that gave the Company the option to repurchase up to 100% of the holder’s principal and deferred interest for a purchase price equal to 63.75% of the outstanding principal and deferred interest (* "AugustOption"). Originally, the agreement called for a repurchase at 63%, which escalated to 63.75% once the September 26, 2022agreement (described below) was signed. The Company agreed that any repurchase made would be forno* less than 50% of the TruPs held by the holder.

Until the earlier of (i) the date that allfour of the preferred debt instruments have been repurchased and (ii) thenine month anniversary of the agreement (* "MayTermination Date"), all interest on thefour* preferred debt instruments continued to accrue. However, with respect to TruPs that were repurchased prior to the* MayTermination Date, the amount of interest accrued during the term of the agreement was treated as an offset and reduced the repurchase price for such TruPs. The Company hadno* obligation to pay any such accrued interest with respect to any of the TruPs that were repurchased prior to the* May*Termination Date.

The Company paid approximately $2.0 million to the holder for this option and the Company had until the* May*Termination Date to execute the repurchases. Given the Company repurchased an amount equal to or greater than $30.0 million, the $2.0 million paid was applied to the repurchases.

17

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) September 30, 2024

On* September 20, 2022,the Company entered into an additional agreement with the same party to the August 2, 2022agreement that gave the Company the option to repurchase up to 100% of the holder’s principal and deferred interest for 63.75% of the outstanding principal and deferred interest relating to a portion of afifth* TruPs held (* "September 20Option"). The September 20, 2022agreement was subject to the same terms and conditions as the August 2, 2022agreement andno* additional consideration was paid.

On* September 26, 2022,the Company entered into an agreement with a holder of a portion ofone* of the TruPs that gave the Company the option to repurchase up to 100% of the holder’s principal and deferred interest for a purchase price equal to 63% of the outstanding principal and deferred interest (* "September 26*Option").

Until the earlier of (i) the date that all of the preferred debt instrument has been repurchased and (ii) the* MayTermination Date, all interest on the preferred debt instrument continued to accrue. However, with respect to TruPs that were repurchased prior to the MayTermination Date, the amount of interest accrued during the term of the agreement was treated as an offset and reduce the repurchase price for such TruPs. The Company hadno* obligation to pay any such accrued interest with respect to the TruPs that were repurchased prior to the* May*Termination Date.

The Company paid approximately $0.3 million to the holder for this option and the Company had until the* May*Termination Date to execute the repurchase. Given the Company repurchased the TruPs, the $0.3 million paid was applied to the repurchases.

In* February 2023,the Company entered into amendments to the repurchase agreements described above that gave the Company an additional discount on the total repurchase price if the Company effected a 100% repurchase on or before March 15, 2023.On March 2, 2023,the Company gave notice to the holders of its intent to exercise its options to repurchase 100% of the principal. On March 22, 2023,the Company completed the repurchases. See Note11*, "Debt," for further discussion.

The* AugustOption, September 20Option and September 26Options (collectively "the TruPs Options") are derivative contracts. The Company's accounting policies donot* apply hedge accounting treatment to derivative instruments. The TruPs options were recorded in the consolidated balance sheet at fair value with changes in fair value recorded in the unaudited consolidated statements of operations. See Note21, "Fair Value of Financial Instruments," for further discussion.

During thenine months ended* September 30, 2023*, the Company recognized a loss on change in fair value of the TruPs Options contracts of $1.4 million, which is included in loss on change in fair value of derivative asset option contracts in the unaudited consolidated statement of operations and as an adjustment to calculate cash flows provided by (used in) operating activities in the unaudited consolidated statement of cash flows. Cash payments of $56.5 million were made to repurchase the TruPs during thenine months ended* September 30, 2023* with respect to the TruPs Options contracts.

NOTE11 DEBT

Debt consists of the following instruments at* September 30, 2024* and* December 31, 2023*:

Subordinated debt mentioned above consists of the following trust preferred debt instrument at* September 30, 2024* and* December 31, 2023*:

(a) Bank loans:

Ravix

As part of the acquisition of Ravix Group, Inc. ("Ravix") on* October 1, 2021,Ravix became a wholly owned subsidiary of Ravix Acquisition LLC ("Ravix LLC"), and together they borrowed from a bank a principal amount of $6.0 million in the form of a term loan, and established a $1.0 million revolver to finance the acquisition of Ravix (together, the"2021* Ravix Loan"). The2021 Ravix Loan requires monthly payments of principal and interest.

18

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) September 30, 2024

The2021 Ravix Loan has an annual interest rate equal to the greater of the Prime Rate plus 0.5%, or 3.75%. At* September 30, 2024*, the interest rate was 8.50%. The term loan matures on* October**1,* 2027. The Company also recorded as a discount to the carrying value of the2021 Ravix Loan issuance costs of $0.2 million specifically related to the2021 Ravix Loan. The2021 Ravix Loan is carried in the consolidated balance sheets at its unpaid principal balance.

Subsequent to the acquisition of CSuite Financial Partners, LLC ("CSuite") on* November 1, 2022,CSuite became a wholly owned subsidiary of Ravix LLC. As a result of the acquisition of CSuite, on November 16, 2022,the2021* Ravix Loan was amended to: (1) include CSuite as a borrower; (2) borrow an additional principal amount of $6.0 million in the form of a supplemental term loan (the*"2022* Ravix Loan"); and (3) amend the maturity date and interest rate of the $1.0 million revolver (the*"2022* Revolver"). The2022 Ravix Loan requires monthly payments of principal and interest. The2022 Ravix Loan matures on* November 16, 2028and has an annual interest rate equal to the Prime Rate plus 0.75%. At September 30, 2024*, the interest rate was 8.75%. The2022 Revolver matures on* November 16, 2024and has an annual interest rate equal to the Prime Rate plus 0.50%. At September 30, 2024*, the interest rate was 8.50%.

The Company also recorded as a discount to the carrying value of the2022 Ravix Loan issuance costs of $0.1 million specifically related to the2022 Ravix Loan. The2022 Ravix Loan is carried in the consolidated balance sheets at its amortized cost, which reflects the monthly pay-down of principal as well as the amortization of the debt discount and issuance costs using the effective interest rate method.

The2022 Ravix Loan and the2021 Ravix Loan werenot deemed to be substantially different; therefore, the2022 Ravix Loan is accounted for as a modification of the2021 Ravix Loan and a new effective interest rate was determined based on the carrying amount of the2021 Ravix Loan. The issuance costs related to the2022 Ravix Loan, along with the existing unamortized issuance costs from the2021 Ravix Loan, are being amortized over the remaining term of the2022 Ravix Loan using the effective interest rate.

On* July 23, 2024,Ravix and Ravix LLC entered into asecond* amendment to the2021 Ravix Loan that provides for: (1) a principal prepayment of the2021 Ravix term loan of $1.5 million, partially financed by borrowing $0.5 million under the2022 Revolver and the remainder to be paid with available cash; and (2) amending the loan amortization payment schedule to provide for equal monthly payments through the loan maturity date. The2021 Ravix Loan wasnot deemed to be substantially different as a result of thesecond amendment; therefore, the amended2021 Ravix Loan is accounted for as a modification of the original2021 Ravix Loan.

The fair values of the2021 Ravix Loan,2022 Ravix Loan and2022 Revolver disclosed in the table above is derived from quoted market prices of B and BB minus rated industrial bonds with similar maturities and is categorized within Level2 of the fair value hierarchy. The2021 Ravix Loan and the2022 Ravix Loan are secured by certain of the equity interests and assets of Ravix and CSuite.

The2021 Ravix Loan and the2022 Ravix Loan contains a number of covenants, including, butnot limited to, a leverage ratio and a fixed charge ratio, all of which are as defined in and calculated pursuant to the2021 Ravix Loan and2022 Ravix Loan that, among other things, restrict Ravix and CSuite’s ability to incur additional indebtedness, create liens, make dividends and distributions, engage in mergers, acquisitions and consolidations, make certain payments and investments and dispose of certain assets.

SNS

As part of the asset acquisition of Secure Nursing Service, Inc. on* November 18, 2022,the Company formed Secure Nursing Service LLC ("SNS"), who became a wholly owned subsidiary of Pegasus Acquirer Holdings LLC ("Pegasus LLC"), and together they borrowed from a bank a principal amount of $6.5 million in the form of a term loan, and established a $1.0 million revolver to finance the acquisition of SNS (together, the "SNS Loan"). The SNS Loan has an annual interest rate equal to the greater of the Prime Rate plus 0.5%, or 5.00%. At September 30, 2024*, the interest rate was 8.50%. Monthly principal payments on the term loan began on* November 15, 2023.The revolver matures on May 2, 2025and the term loan matures on November 18, 2028.At September 30, 2024* and* December 31, 2023*, the balance of the revolver waszero.

The Company also recorded as a discount to the carrying value of the SNS Loan issuance costs of $0.1 million specifically related to the SNS Loan. The SNS Loan is carried in the consolidated balance sheet at its amortized cost, which reflects principal payments as well as the amortization of the debt discount and issuance costs using the effective interest rate method. The fair value of the SNS Loan disclosed in the table above is derived from quoted market prices of B and BB minus rated industrial bonds with similar maturities and is categorized within Level2 of the fair value hierarchy. The SNS Loan is secured by certain of the equity interests and assets of SNS.

The SNS Loan contains a number of covenants, including, butnot limited to, a leverage ratio and a fixed charge ratio and limits on annual capital expenditures, all of which are as defined in and calculated pursuant to the SNS Loan that, among other things, restrict SNS’s ability to incur additional indebtedness, create liens, make dividends and distributions, engage in mergers, acquisitions and consolidations, make certain payments and investments and dispose of certain assets. At* September 30,** June 30,and March 31, 2024,SNS was in default under the SNS Loan due to debt covenant violations related to the leverage and fixed charge ratios. The Company has entered into an amendment to the SNS Loan that waives the events of default for the fiscal quarter ended September 30, 2024*. As of the report date, there is some uncertainty as to whether the Company will be in compliance with the covenants in future periods, and ifnot, when the Company will be able to cure any potential violations. A default* may*permit the lender to declare the amounts owed under the SNS Loan immediately due and payable, exercise their rights with respect to collateral securing the obligation, and/or exercise any other rights and remedies available.

DDI

As part of the acquisition of DDI on* October 26, 2023,DDI became a wholly owned subsidiary of DDI Acquisition, LLC ("DDI LLC"), and together they borrowed from a bank a principal amount of $5.6 million in the form of a term loan, and established a $0.4 million revolver to finance the acquisition of DDI (together, the "DDI Loan"). The DDI Loan has an annual interest rate equal to the greater of the Prime Rate plus 0.5%, or 5.00%. At September 30, 2024*, the interest rate was 8.50%. Monthly principal payments on the term loan begin on* December 15, 2024.The revolver matured on September 1, 2024and the term loan matures on October 26, 2029.At December 31, 2023*, the balance of the revolver waszero.

19

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) September 30, 2024

The Company also recorded as a discount to the carrying value of the DDI Loan issuance costs of $0.1 million specifically related to the DDI Loan. The DDI Loan is carried in the consolidated balance sheet at its amortized cost, which reflects the amortization of the debt discount and issuance costs using the effective interest rate method. The fair value of the DDI Loan disclosed in the table above is derived from quoted market prices of B and BB minus rated industrial bonds with similar maturities and is categorized within Level2 of the fair value hierarchy. The DDI Loan is secured by certain of the equity interests and assets of DDI.

The DDI Loan contains a number of covenants, including, butnot limited to, a senior leverage ratio and a fixed charge ratio and limits on annual capital expenditures, all of which are as defined in and calculated pursuant to the DDI Loan that, among other things, restrict DDI’s ability to incur additional indebtedness, create liens, make dividends and distributions, engage in mergers, acquisitions and consolidations, make certain payments and investments and dispose of certain assets.

Image Solutions

As part of the acquisition of Image Solutions on* September 26, 2024,Image Solutions became a wholly owned subsidiary of Steel Bridge Acquisition, LLC ("SB LLC"), and together they borrowed from a bank a principal amount of $7.75 million in the form of a term loan, and established a $0.5 million revolver to finance the acquisition of Image Solutions (together, the "Image Solutions Loan"). The Image Solutions Loan requires monthly payments of principal and interest and has an annual interest rate equal to the greater of the Prime Rate plus 0.5%, or 7.25%. At September 30, 2024*, the interest rate was 8.50%. The revolver matures on* September 26, 2026and the term loan matures on September 26, 2030.At September 30, 2024*, the balance of the revolver waszero.

The Company also recorded as a discount to the carrying value of the Image Solutions Loan issuance costs of $0.2 million specifically related to the Image Solutions Loan. The Image Solutions Loan is carried in the consolidated balance sheet at its amortized cost, which reflects the monthly pay-down of principal as well as the amortization of the debt discount and issuance costs using the effective interest rate method. The fair value of the Image Solutions Loan disclosed in the table above is derived from quoted market prices of BB plus rated industrial bonds with similar maturities and is categorized within Level2 of the fair value hierarchy. The Image Solutions Loan is secured by certain of the equity interests and assets of Image Solutions.

The Image Solutions Loan contains a number of covenants, including, butnot limited to, a senior leverage ratio and a fixed charge ratio, all of which are as defined in and calculated pursuant to the Image Solutions Loan that, among other things, restrict Image Solutions’ ability to incur additional indebtedness, create liens, make dividends and distributions, engage in mergers, acquisitions and consolidations, make certain payments and investments and dispose of certain assets.

KWH

In2019, the Company formed Kingsway Warranty Holdings LLC ("KWH"), whose subsidiaries include IWS Acquisition Corporation ("IWS"), Geminus Holdings Company, Inc. ("Geminus") and Trinity Warranty Solutions LLC ("Trinity"). As part of the acquisition of PWI Holdings, Inc. ("PWI") on* December 1, 2020,PWI became a wholly owned subsidiary of KWH, which borrowed a principal amount of $25.7 million from a bank, consisting of a $24.7 million term loan and a $1.0 million revolving credit facility (the"2020* KWH Loan"). The proceeds from the2020 KWH Loan were used to partially fund the acquisition of PWI and to fully repay the prior outstanding loan at KWH, which occurred on* December 1, 2020.The2020* KWH Loan has an annual interest rate equal to SOFR, having a floor of 0.75%, plus spreads ranging from 2.62% to 3.12%. At* September 30, 2024*, the interest rate was 7.73%. The2020 KWH Loan was to mature on* December 1, 2025,prior to entering into thethird* amendment to the KWH Loan further discussed below. The Company also recorded as a discount to the carrying value of the2020 KWH Loan issuance costs of $0.4 million specifically related to the2020 KWH Loan.

On* February 28, 2023,KWH entered into asecond* amendment to the2020 KWH Loan (the “KWH DDTL”) that provides for an additional delayed draw term loan in the principal amount of up to $10.0 million, with a maturity date of* December 1, 2025.All or any portion of the KWH DDTL, subject to a $2.0 million minimum draw amount, could be requested at any time through February 27, 2024.The proceeds are evidenced by an intercompany loan and guarantee between KAI and KWH. The principal amount shall be repaid in quarterly installments in an amount equal to 3.75% of the original amount of the drawn DDTL. Proceeds from certain assets dispositions, as defined, maybe required to be used to repay outstanding draws under the DDTL. The KWH DDTL also increases the senior cash flow leverage ratio maximum permissible for certain periods. During thefirst* quarter of2024, the Company borrowed $3.5 million under the KWH DDTL and $0.5 million under the KWH Revolver.

On* May 24, 2024,KWH entered into athird* amendment to the2020 KWH Loan that provides for: (1) a new2024 term loan in the principal amount of $15.0 million, with a maturity date of* May 24, 2029 (the“2024* KWH Loan”); and (2) a new2024 delayed draw term loan in a principal amount of up to $6.0 million, with a maturity date of* May 24, 2029 (the“2024* KWH DDTL”). All or any portion of the2024 KWH DDTL, subject to a $2.0 million minimum draw amount, could be requested at any time in up tothree advances through* May 24, 2026.In connection with thethird* amendment, KWH used the proceeds from the2024 KWH Loan to repay the following outstanding balances under the2020 KWH Loan: (1) $9.6 million related to the original2020 term loan; (2) $1.0 million related to the revolver; and (3) $3.1 million related to the KWH DDTL.

KWH continues to have access to a $1.0 million revolving credit facility (“KWH Revolver”) under the2020 KWH Loan.

The2020 KWH Loan and the2024 KWH Loan werenot deemed to be substantially different; therefore, the2024 KWH Loan is accounted for as a modification of the2020 KHW Loan. The unamortized debt discount and issuance costs from the2020 KWH Loan at the modification date of $0.2 million were recorded as loss on extinguishment of debt during thenine months ended* September 30, 2024* since the original debt was fully repaid as part of the modification.

During thethird quarter of2024, $5.5 million was borrowed under the2024 KWH DDTL and $1.0 million was drawn on the KWH Revolver.

20

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) September 30, 2024

The Company also recorded as a discount to the carrying value of the2024 KWH Loan issuance costs of $0.1 million specifically related to the2024 KWH Loan. The2020 KWH Loan and2024 KWH Loan are carried in the consolidated balance sheets at amortized cost, which reflects the quarterly pay-down of principal as well as the amortization of the debt discount and issuance costs using the effective interest rate method. The fair values of the2020 KWH Loan,2024 KWH Loan,2024 KWH DDTL and KWH Revolver disclosed in the table above are derived from quoted market prices of BB and BB minus rated industrial bonds (2020 KWH Loan) and B and BB minus rated industrial bonds (2024 KWH Loan) with similar maturities and is categorized within Level2 of the fair value hierarchy. The2020 KWH Loan is secured by certain of the equity interests and assets of KWH and its subsidiaries.

The2024 KWH Loan contains a number of covenants, including, butnot limited to, a leverage ratio, a fixed charge ratio and limits on annual capital expenditures, all of which are as defined in and calculated pursuant to the2024 KWH Loan that, among other things, restrict KWH’s ability to incur additional indebtedness, create liens, make dividends and distributions, engage in mergers, acquisitions and consolidations, make certain payments and investments and dispose of certain assets.

(b) Subordinated debt:

Between* December 4, 2002and December 16, 2003,six subsidiary trusts of the Company issued $90.5 million of 30-year capital securities tothird-parties in separate private transactions. In each instance, a corresponding floating rate junior subordinated deferrable interest debenture was then issued by KAI to the trust in exchange for the proceeds from the private sale. The floating rate debentures bore interest at the rate of LIBOR, plus spreads ranging from 3.85% to 4.20%. Effective July 3, 2023,the index used for determining the interest rate for the floating rate debentures was converted from LIBOR to CME Term SOFR. The Company has the right to call each of these securities at par value any time afterfive* years from their issuance until their maturity.

The subordinated debt, or TruPs, is carried in the consolidated balance sheets at fair value. See Note21, "Fair Value of Financial Instruments," for further discussion of the subordinated debt. The portion of the change in fair value of subordinated debt related to the instrument-specific credit risk is recognized in other comprehensive income (loss).

Of the $0.1 million increase in fair value of the Company's subordinated debt between* December 31, 2023* and* September 30, 2024*, less than $0.1 million is reported as increase in fair value of debt attributable to instrument-specific credit risk in the Company's unaudited consolidated statements of comprehensive loss and less than $0.1 million is reported as loss on change in fair value of debt in the Company's unaudited consolidated statement of operations.

In* February 2023,the Company entered into amendments to the trust preferred option repurchase agreements described in Note10*, "Derivatives," that would give the Company an additional discount on the total repurchase price of the TruPs if the Company effected a100% repurchase on or before* March 15, 2023.On March 2, 2023,the Company gave notice to the holders offive* of its TruPs that it intended to exercise its options to repurchase100% of the principal. On* March 22, 2023,the Company completed the repurchases of thefive* TruPs using available funds from working capital to fund the repurchases. The total amount paid for thefive TruPs was $56.5 million, which included a credit for the $2.3 million that the Company previously paid at the time of entering into the trust preferred option repurchase agreements. As a result, the Company repurchased $75.5 million of TruPs principal and $23.0 million of deferred interest payable. The Company recognized a gain of $31.6 million, which is included in gain on extinguishment of debt in the unaudited consolidated statement of operations for thenine months ended* September 30, 2023*. At* September 30, 2024*, the Company has $15.0 million of principal outstanding related to the remaining trust preferred debt instrument.

The unaudited consolidated statements of comprehensive loss for thenine months ended* September 30, 2023* includes a reclassification adjustment of $27.2 million from accumulated other comprehensive income to gain on extinguishment of debt related to the instrument-specific credit risk related to the repurchased TruPs.

During thethird quarter of2018, the Company gave notice to its Trust Preferred trustees of its intention to exercise its voluntary right to defer interest payments for up to20 quarters, pursuant to the contractual terms of its outstanding Trust Preferred indentures, which permit interest deferral. This action didnot constitute a default under the Company's Trust Preferred indentures or any of its other debt indentures. In order to execute the TruPs repurchases described above, on* March 13, 2023,the Company paid $5.0 million to the remaining Trust Preferred trustee to be used by the trustee to pay the interest which the Company had been deferring since thethird* quarter of2018.

The agreement governing the remaining subordinated debt contains a number of covenants that, among other things, restrict the Company’s ability to incur additional indebtedness, make dividends and distributions, and make certain payments in respect of the Company’s outstanding securities.

NOTE12 LEASES

The Company has operating leases for office space that include fixed base rent payments, as well as variable rent payments to reimburse the landlord for operating expenses and taxes. The Company’s variable lease payments donot depend on a published index or rate, and therefore, are expensed as incurred. The Company includes only fixed payments for lease components in the measurement of the right-of-use asset and lease liability. There areno residual value guarantees.

Operating lease costs, variable lease costs and short-term lease costs included in general and administrative expenses for thethree andnine months ended* September 30, 2024* and* September 30, 2023* were as follows:

21

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) September 30, 2024

The annual maturities of lease liabilities as of* September 30, 2024* were as follows:

The weighted-average remaining lease term for our operating leases was 3.34 years as of* September 30, 2024*. The weighted-average discount rate of our operating leases was 5.86% as of* September 30, 2024*. Cash paid for amounts included in the measurement of lease liabilities was $0.4 million and $0.3 million for thenine months ended* September 30, 2024* and* September 30, 2023*, respectively.

NOTE13 REVENUE FROM CONTRACTS WITH CUSTOMERS

Revenue from contracts with customers relates to the Extended Warranty and Kingsway Search Xcelerator segments and includes: vehicle service agreement fees, guaranteed asset protection products ("GAP") commissions, maintenance support service fees, warranty product commissions, business services consulting revenue, healthcare services revenue and software license and support revenue. Revenue is based on terms of various agreements with credit unions, consumers and businesses. Customers either pay in full at the inception of a warranty contract or commission product sale, or when consulting, healthcare and software license and support services are billed, or on terms subject to the Company’s customary credit reviews.

The following table disaggregates revenues from contracts with customers by revenue type for thethree andnine months ended* September 30, 2024* and* September 30, 2023*:

Vehicle service agreement fees include the fees collected to cover the costs of future automobile mechanical breakdown claims and the associated administration of those claims. Vehicle service agreement fees are earned over the duration of the vehicle service agreement contracts as the single performance obligation is satisfied. Vehicle service agreement fees are initially recorded as deferred service fees with revenues recognized over the term of the contract based on the proportion of expected claims to total overall claims to be incurred over the life of the contract. The Company believes this reasonably represents the transfer of services to the vehicle service contract holder over the warranty term. The Company compares the remaining deferred service fees balance to the estimated amount of expected future claims under the vehicle service agreement contracts and records an additional accrual if the deferred service fees balance is less than expected future claims costs.

In certain jurisdictions the Company is required to refund to a customer a pro-rata share of the vehicle service agreement fees if a customer cancels the agreement prior to the end of the term. Depending on the jurisdiction, the Company* may*be entitled to deduct from the refund a cancellation fee and/or amounts for claims incurred prior to cancellation. While refunds vary depending on the term and type of product offered, historically refunds have averaged 5.8% to 11.7% of the original amount of the vehicle service agreement fee. Revenues recorded by the Company are net of variable consideration related to refunds and the associated refund liability is included in accrued expenses and other liabilities. The Company estimates refunds based on the actual historical refund rates by warranty type taking into consideration current observable refund trends in estimating the expected amount of future customer refunds to be paid at each reporting period.

Maintenance support service fees include the service fees collected to administer equipment breakdown and maintenance support services and are earned as services are rendered.

Warranty product commissions include the commissions from the sale of warranty contracts for certain new and used heating, ventilation, air conditioning ("HVAC"), standby generator, commercial LED lighting and commercial refrigeration equipment. The Company acts as an agent on behalf of thethird-party insurance companies that underwrite and guaranty these warranty contracts. The Company doesnot guaranty the performance underlying the warranty contracts it sells. Warranty product commissions are earned at the time of the warranty product sales.

Business services consulting fees include the revenue from providing outsourced finance and human resources consulting services. The Company invoices for business services revenue based on contracted rates. Revenue is earned as services are provided.

Healthcare services fees include revenue from providing healthcare professional staffing services and outsourced cardiac telemetry services for long-term acute care and inpatient rehabilitation hospitals. The Company invoices for healthcare services revenue based on contracted rates. Revenue is earned as services are provided.

22

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) September 30, 2024

Software license and support fees include revenue from the sale or rental of software products created exclusively to serve the management needs of all types of shared-ownership properties. Software licenses are on-premise at customer locations and considered fully functional when made available and delivered to the customer. As the customer can use and benefit from the license on its own, software licenses represent distinct performance obligations. Revenue is recognized upfront at the point in time when control is transferred, which is defined as the point in time when the customer can use and benefit from the license. The Company's software licenses are sold as term licenses, and the contracts include software support services, which are accounted for as separate performance obligations. Software support revenue is recognized ratably over the contract period as services are rendered. For certain SPI contracts, the transaction price of the software license is billed in installments, typically over athree tofive year period. The Company allocates a portion of the consideration received from these arrangements to a financing component when it determines that a significant financing component exists. The financing component is subsequently recognized as interest income separate from software license and support fee revenue over the term of the arrangement with the customer. Pursuant to practical expedients afforded under ASC606, the Company doesnot recognize a financing component for software license sales that have a term ofone year or less.

The Company's revenue recognition policies are further described in Note2(p), "Summary of Significant Accounting Policies - Revenue recognition," to the consolidated financial statements in the2023 Annual Report.

Service fee receivables

Receivables from contracts with customers are reported as service fee receivable, net in the consolidated balance sheets and at* September 30, 2024* and* December 31, 2023* were $10.0 million and $10.1 million, respectively. The decrease in receivables from contracts with customers is primarily due to the timing difference between the Company's satisfaction of performance obligations and customer payments, partially offset by an increase related to Image Solutions receivables which were acquired om* September 26, 2024.*

Service fee receivable is reported net of an estimated allowance for credit losses. During each of thethree months ended* September 30, 2024* and* September 30, 2023*, the Company recorded an increase to its allowance for credit losses of $0.1 million ($0.2 million for each of thenine months ended* September 30, 2024* and* September 30, 2023*, respectively). Service fee receivables that are deemed to be uncollectible are written off against the allowance for credit losses when identified. The Company recorded write-offs of service fee receivables that were deemed to be uncollectible ofzero and less than $0.1 million during thethree months ended* September 30, 2024* and* September 30, 2023*, respectively ($0.1 million and less than $0.1 million for thenine months ended* September 30, 2024* and* September 30, 2023*, respectively).

Contract asset

The Company records a contract asset when revenue is recognized prior to billing the customer. Upon billing, which typically occurs over athree tofive year installment period, the value of the contract asset is reversed and service fee receivable is recorded. The Company hadno contract asset prior to the acquisition of SPI on* September 7, 2023.The contract asset is included in other assets in the consolidated balance sheets, and at September 30, 2024* and* December 31, 2023* was $1.7 million. During thenine months ended* September 30, 2024*, the Company recorded additions to the contract asset of $0.8 million, reduced the contract asset by $0.4 million as a result of billings to customers and recorded a measurement period adjustment to decrease the contract asset related by $0.3 million (the latter as discussed in Note5, "Acquisitions and Discontinued Operations").

The contract asset is reported net of an estimated allowance for credit losses. During thethree andnine months ended* September 30, 2024*, the Company recorded an increase to its allowance for credit losses of $0.2 million. Contract assets that are deemed to be uncollectible are written off against the allowance for credit losses when identified. The Company recorded write-offs to the contract asset for amounts that were deemed to be uncollectible ofzero and less than $0.1 million during thethree andnine months ended* September 30, 2024*.

Deferred service fees

The Company records deferred service fees resulting from contracts with customers when payment is received in advance of satisfying the performance obligations. Changes in deferred service fees for thenine months ended* September 30, 2024* were as follows:

The increase in deferred service fees between* December 31, 2023* and* September 30, 2024* is primarily due to additions to deferred service fees in excess of deferred service fees recognized during thenine months ended* September 30, 2024*.

Approximately $35.3 million and $32.9 million of service fee and commission revenue recognized during thenine months ended* September 30, 2024* and* September 30, 2023* was included in deferred service fees as of* December 31, 2023* and* December 31, 2022*, respectively.

Remaining performance obligations

The Company expects to recognize withinone year as service fee and commission revenue approximately 47.0% of theoutstanding performance obligations as of* September 30, 2024*. The balance relates primarily to vehicle service agreement fees.

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) September 30, 2024

Deferred contract costs

Deferred contract costs represent the deferral of incremental costs to obtain or fulfill a contract with a customer. Incremental costs to obtain a contract with a customer primarily include sales commissions. The Company capitalizes costs incurred to fulfill a contract if the costs are identifiable, generate or enhance resources used to satisfy future performance obligations and are expected to be recovered. Costs to fulfill a contract include labor costs for set-up activities directly related to the acquisition of vehicle service agreements. Contract costs are deferred and amortized over the expected customer relationship period consistent with the pattern in which the related revenues are earned. Amortization of incremental costs to obtain a contract and costs to fulfill a contract with a customer are recorded in commissions in the unaudited consolidated statements of operations. No impairment charges related to deferred contract costs were recorded during thethree andnine months ended* September 30, 2024* and* September 30, 2023*.

The deferred contract costs balances and related amortization expense for thethree months ended* September 30, 2024* and* September 30, 2023* are comprised as follows:

The deferred contract costs balances and related amortization expense for thenine months ended* September 30, 2024* and* September 30, 2023* are comprised as follows:

NOTE14 INCOME TAXES

Income tax expense (benefit) for thethree andnine months ended* September 30, 2024* and* September 30, 2023* varies from the amount that would result by applying the applicable U.S. federal corporate income tax rate of 21% to (loss) income from continuing operations before income tax expense(benefit). The following table summarizes the differences:

The Company maintains a valuation allowance for its gross deferred tax assets at* September 30, 2024* and* December 31, 2023*. The Company's operations have generated substantial operating losses in prior years. These losses can be available to reduce income taxes that might otherwise be incurred on future taxable income; however, it is uncertain whether the Company will generate the taxable income necessary to utilize these losses or other reversing temporary differences. This uncertainty has caused management to place a full valuation allowance on its* September 30, 2024* and* December 31, 2023* net deferred tax asset, excluding the deferred income tax liability amounts set forth in the paragraph below which were determined tonot reverse and offset existing deferred tax assets.

The Company carries net deferred income tax liabilities of*$4.7* million and $5.0 million at* September 30, 2024* and* December 31, 2023*, respectively, that consists of:

As of* September 30, 2024* and* December 31, 2023*, the Company carried a liability for unrecognized tax benefits of zero. The Company classifies interest and penalty accruals, if any, related to unrecognized tax benefits as income tax expense. The Company recorded income tax expense ofzero related to interest and penalty accruals for thethree andnine months ended* September 30, 2024* and* September 30, 2023*.

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) September 30, 2024

NOTE15 (LOSS) EARNINGS PER SHARE

The following table sets forth the reconciliation of numerators and denominators for the basic and diluted (loss)earnings pershare computation for thethree andnine months ended* September 30, 2024* and* September 30, 2023*:

Basic (loss) earnings per share excludes dilution and is computed by dividing (loss) income attributable to common shareholders by the weighted-average number of common shares outstanding for the period. Diluted (loss) earnings per share is calculated using weighted-average diluted shares. Weighted-average diluted shares is calculated by adding the effect of potentially dilutive securities to weighted-average common shares outstanding. Potentially dilutive securities are excluded from the diluted (loss) earnings per share computation in loss periods and when the applicable exercise price is greater than the market price on the period end date as their effect would be anti-dilutive.

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) September 30, 2024

The following weighted-average potentially dilutive securities arenot included in thedilut ed (loss) earnings per share calculations above because they would have had an antidilutive effect on the (loss) earnings per share:

NOTE16 STOCK-BASED COMPENSATION

(a) Restricted Stock Awards of the Company

Under the2013 Equity Incentive Plan, the Company granted 500,000 restricted common stock awards to an officer on* September 5, 2018 (the"2018* Restricted Stock Award"). The2018 Restricted Stock Award fully vested on* March 28, 2024.The2018* Restricted Stock Award was amortized on a straight-line basis over the requisite service period. The grant-date fair value of the2018 Restricted Stock Award was determined using the closing price of Kingsway common stock on the date of grant. Total unamortized compensation expense related to unvested2018 Restricted Stock Award at* September 30, 2024* waszero.

Under the2020 Equity Incentive Plan, the Company has granted restricted common stock awards to certain officers of the Company (the*"2020* Plan Restricted Stock Awards"). The2020 Plan Restricted Stock Awards vest according to a graded vesting schedule and shall become fully vested subject to the officers' continued employment through the applicable vesting dates. The2020 Plan Restricted Stock Awards are amortized on a straight-line basis over the requisite service periods. The grant-date fair values of the2020 Plan Restricted Stock Awards were determined using the closing price of Kingsway common stock on the date of grant. During thenine months ended* September 30, 2024*,100,000 shares of the2020 Plan Restricted Stock Awards became fully vested. Total unamortized compensation expense related to unvested2020 Plan Restricted Stock Awards at* September 30, 2024* was$2.0 million.

The following table summarizes the activity related to unvested2020 Plan Restricted Stock Awards and2018 Restricted Stock Award (collectively "Restricted Stock Awards") for thenine months ended* September 30, 2024*:

The unvested balance at* September 30, 2024* in the table above is comprised of 448,964 shares of the2020 Restricted Stock Awards andzero shares of the2018 Restricted Stock Award.

Stock-based compensation expense related to the Restricted Stock Awards was $0.2 million for each of thethree months ended* September 30, 2024* and* September 30, 2023* ($0.6 million and $0.7 million for thenine months ended* September 30, 2024* and* September 30, 2023*, respectively).

(b) Restricted Common Unit Awards of Ravix

Ravix LLC granted 199,000 restricted Class B common unit awards to an officer of Ravix pursuant to an agreement dated* October 1, 2021 (**"2021* Ravix RUA"). The2021 Ravix RUA vests based on service and the achievement of criteria based on the internal rate of return ("IRR") of Ravix.

The grant-date fair value of the2021 Ravix RUA was estimated using the Black-Scholes option pricing model, using the following assumptions: expected term offour years, expected volatility of 75%, expected dividend yield of zero, and risk-free interest rate of 0.93%.

On* October 1, 2021,83,333 units, representingone* half of the service condition for the2021 Ravix RUA, became fully vested. The remainder of the service condition vests according to a graded vesting schedule and shall become fully vested subject to the officer's continued employment through the applicable vesting dates.

On* November 1, 2022,the Company modified the inputs related to the IRR portion of the2021* Ravix RUA to be based on the combined internal rate of return of Ravix and CSuite. The modified portion of the awards was probable of vesting both immediately before and after the modification. As a result, the fair value of the award that is subject to the IRR was measured at the modification date and compared to the fair value of the modified portion of the award immediately prior to the modification, with the difference resulting in incremental compensation expense of less than $0.1 million. The incremental fair value was estimated using the Monte Carlo simulation model, using the following assumptions at the modification date: expected term of 2.92 years, expected volatility of 72% and risk-free interest rate of 4.44%; and the following assumptions prior to the modification: expected term of 2.92 years, expected volatility of 58% and risk-free interest rate of 4.44%.

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) September 30, 2024

During thenine months ended* September 30, 2024*,15,625 units of the2021 Ravix RUA became fully vested. At* September 30, 2024* and* December 31, 2023*, there were 54,903 and 70,528 unvested units, respectively, of the2021 Ravix RUA with a weighted-average grant date fair value of $3.08 per Class B common unit. Total unamortized compensation expense related to unvested2021 Ravix RUA at* September 30, 2024* was $0.1 million.

Stock-based compensation expense related to the2021 Ravix RUA was less than $0.1 millionfor each of thethreemonths ended* September 30, 2024* and* September 30, 2023* ($0.1 million for each of thenine months ended* September 30, 2024* and* September 30, 2023*, respectively).

(c) Restricted Common Unit Awards of SNS

Pegasus LLC granted 75,000 restricted Class B common unit awards to an officer of SNS pursuant to an agreement dated* November 18, 2022 (*"SNS RUA"). The SNS RUA vests based on service and the achievement of criteria based on the IRR of SNS.

The grant-date fair value of the SNS RUA was estimated using the Monte Carlo simulation model, using the following assumptions: expected term offour years, expected volatility of 85% and risk-free interest rate of 4.09%.

On* November 18, 2022,25,000 units, representingone* half of the service condition for the SNS RUA, became fully vested. The remainder of the service condition vests according to a graded vesting schedule and shall become fully vested subject to the officer's continued employment through the applicable vesting dates.

During thenine months ended* September 30, 2024*,4,688 units of the SNS RUA vested. At* September 30, 2024* and* December 31, 2023*, there were 38,542 and 43,229 unvested units, respectively, of the SNS RUA with a weighted-average grant date fair value of $5.74 and $5.84 per Class B common unit, respectively. Total unamortized compensation expense related to unvested SNS RUA at* September 30, 2024* was $0.2 million.

Stock-based compensation expense related to the SNS RUA was less than $0.1 million for each of thethreemonths ended* September 30, 2024* and* September 30, 2023* ($0.1 millionfor each of thenine months ended* September 30, 2024* and* September 30, 2023*).

(d) Restricted Common Unit Awards of SPI

Vertical Market Solutions LLC, a subsidiary of the Company, granted 199,000 restricted Class B common unit awards to an officer of SPI pursuant to an agreement dated* September 7, 2023 (*"SPI RUA"). The SPI RUA vests based on service and the achievement of criteria based on the IRR of SPI.

The grant-date fair value of the SPI RUA was estimated using the Monte Carlo simulation model, using the following assumptions: expected term offive years, expected volatility of 59% and risk-free interest rate of 4.29%.

On* September 7, 2023,83,333 units, representingone* half of the service condition for the SPI RUA, became fully vested. The remainder of the service condition vests according to a graded vesting schedule and shall become fully vested subject to the officer's continued employment through the applicable vesting dates.

During thenine months ended* September 30, 2024*,20,833 units of the SPI RUA vested. At* September 30, 2024* and* December 31, 2023*, there were 94,833 and 115,667 unvested units, respectively, of the SPI RUA with a weighted-average grant date fair value of $1.09 and $1.11 per Class B common unit, respectively. Total unamortized compensation expense related to unvested SPI RUA at* September 30, 2024* was $0.1 million.

Stock-based compensation expense related to the SPI RUA was less than $0.1 million and$0.1 million for thethree months ended* September 30, 2024* and* September 30, 2023*, respectively(less than $0.1 millionand $0.1 million for thenine months ended* September 30, 2024* and* September 30, 2023*, respectively).

(e) Restricted Common Unit Awards of DDI

DDI LLC granted 199,000 restricted Class B common unit awards to an officer of DDI pursuant to an agreement dated* October 26, 2023 (*"DDI RUA"). The DDI RUA vests based on service and the achievement of criteria based on the IRR of DDI.

The grant-date fair value of the DDI RUA was estimated using the Monte Carlo simulation model, using the following assumptions: expected term offive years, expected volatility of 57% and risk-free interest rate of 4.68%.

On* October 26, 2023,83,333 units, representingone* half of the service condition for the DDI RUA, became fully vested. The remainder of the service condition vests according to a graded vesting schedule and shall become fully vested subject to the officer's continued employment through the applicable vesting dates.

During thenine months ended* September 30, 2024*, no units of the DDI RUA vested. At* September 30, 2024* and* December 31, 2023*, there were 115,667 unvested units of the DDI RUA with a weighted-average grant date fair value of $4.16 per Class B common unit. Total unamortized compensation expense related to unvested DDI RUA at* September 30, 2024* was $0.4 million.

Stock-based compensation expense related to the DDI RUA was less than$0.1 million andzero for thethree months ended* September 30, 2024* and* September 30, 2023*, respectively($0.1 millionand zero for thenine months ended* September 30, 2024* and* September 30, 2023*, respectively).

27

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) September 30, 2024

(f) Restricted Common Unit Awards of Image Solutions

SB LLC granted 199,000 restricted Class B common unit awards to an officer of Image Solutions pursuant to an agreement dated* September 26, 2024 (*"IS RUA"). The IS RUA vests based on service and the achievement of criteria based on the IRR of Image Solutions.

The grant-date fair value of the IS RUA was estimated using the Monte Carlo simulation model, using the following assumptions: expected term offive years, expected volatility of 51% and risk-free interest rate of 3.72%.

On* September 26, 2024,* 83,333 units, representingone half of the service condition for the IS RUA, became fully vested. The remainder of the service condition vests according to a graded vesting schedule and shall become fully vested subject to the officer's continued employment through the applicable vesting dates.

At* September 30, 2024*, there were 115,667 unvested units of the IS RUA with a weighted-average grant date fair value of $6.12 per Class B common unit. Total unamortized compensation expense related to unvested IS RUA at* September 30, 2024* was $0.7 million.

Stock-based compensation expense related to the IS RUA was $0.6 million for each of thethree months andnine months ended* September 30, 2024*.

(g) Stock Options

Under the2020 Equity Incentive Plan, the Company granted 265,000 stock options awards to certain employees of the Company during thesecond quarter of2024 (the "Stock Options"). The Stock Options vest and become exercisable ratably over afive-year period and expireten years after the date of grant. The Stock Options are amortized on a straight-line basis over the exercise period.

The following table summarizes the stock option activity during thenine months ended* September 30, 2024*:

The aggregate intrinsic value of stock options outstanding and exercisable is the difference between the* September 30, 2024* market price for the Company's common shares and the exercise price of the options, multiplied by the number of options where the* September 30, 2024* market price exceeds the exercise price.

Stock-based compensation expense related to the Stock Options was less than$0.1 million and $0.1 million for thethree andnine months ended* September 30, 2024*, respectively. Total unamortized compensation expense related to unvested Stock Options at* September 30, 2024* was $0.9 million.

The Company uses the Black-Scholes option pricing model to estimate the fair value of each option on the date of grant. The fair value of grants and the related assumptions used in the Black-Scholes pricing model for options granted during thenine months ended* September 30, 2024* were as follows:

The risk-free rate was determined based on U.S. treasury yields that most closely approximated the option’s expected term. The dividend yield was determined based on the Company's dividend paying history. The expected volatility was calculated based on the weekly closing price of the Company's common stock over the expected life of the options. The expected term was determined by estimating a cost of equity for the Company to determine time to when the option would be at-the-money, and then adding that amount to the average time to vest.

NOTE17 REDEEMABLE CLASS B PREFERRED STOCK

Following approval by the Company's Board of Directors, on* September 24, 2024,the Company closed on a private placement for aggregate proceeds totaling $8.3 million, resulting from the sale and issuance of 330,000 shares of a new series of Class B Preferred Stock, par value $0.01 per share ("Class B Preferred Stock") for a purchase price of $25.00 per share. The Class B Preferred Stock ranks senior to the Company's common shares. There were 330,000 shares of Class B Preferred Stock outstanding at September 30, 2024*.

Each share of Class B Preferred Stock is convertible into 2.6316 common shares at any time at the option of the holder prior to* September 24, 2031.Subject to certain adjustments set forth in the certificate of designations for the Class B Preferred Stock, a copy of which is attached hereto as Exhibit3.1* and incorporated by reference, the maximum number of common shares issuable upon conversion of the Class B Preferred Stock is 868,421 common shares.

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) September 30, 2024

The holders of Class B Preferred Stock willnot be entitled to receive notice of or to attend any meeting of the shareholders of the Company and willnot be entitled to vote at any such meeting. The holders of the Class B Preferred Stock are entitled to receive fixed, cumulative, preferential cash dividends at a rate of 8% per share of Class B Preferred Stock per year, payable in equal quarterly installments if declared by the Board of Directors of the Company. Dividends on outstanding shares of Class B Preferred Stock will accrue from day to day commencing on the date of issuance of each such share of Class B Preferred Stock. The cash dividend rate will increase to 18% per share of Class B Preferred Stock if the dividend isnot paid and accumulates for a period greater thantwo consecutive quarters from the date of the most recent dividend payment. The Company will redeem any Class B Preferred Stocknot previously converted into common shares, and which remain outstanding on* September 24, 2031,for the price of $25.00 per share of Class B Preferred Stock, plus accrued but unpaid dividends thereon, whether ornot* declared, up to and including the date specified for redemption.

The Company shall have the option to redeem 25% of the Class B Preferred Stock it has issued following a sale of assets representing more than 15% of the Company’s consolidated revenues in the prior12 month period at a price equal to the amount that would yield a total internal rate of return of 15% on the subscription price paid to the Company for the purchase of shares of Class B Preferred Stock submitted for redemption.

At* September 30, 2024*, accrued dividends declared of less than $0.1 million were included in accrued expenses and other liabilities in the consolidated balance sheet. The redemption amount of the Class B Preferred Stock was $8.3 million at* September 30, 2024*.

In accordance with FASB ASC Topic480-10-S99-3A, SEC Staff Announcement: Classification and Measurement of Redeemable Securities, redemption featuresnot solely within the control of the issuer are required to be presented outside of permanent equity on the consolidated balance sheets. As described above, the holder has the option to convert the Class B Preferred Stock at any time; however, ifnot converted, they are required to be redeemed on* September 24, 2031.*As such, the Class B Preferred Stock is presented in temporary or mezzanine equity on the consolidated balance sheets.

NOTE18 Shareholders' Equity

The Company previously had redeemable Class A Preferred Shares outstanding. During thenine months ended* September 30, 2023*,149,733 Class A Preferred Shares were converted into 935,831 common shares. As a result, during thenine months ended* September 30, 2023*, $6.1 million was reclassified from redeemable Class A preferred stock to additional paid-in capital on the consolidated balance sheet. There areno Class A Preferred Shares outstanding at* September 30, 2024* and* December 31, 2023*.

On* March 21, 2023,the Company's Board of Directors approved a security repurchase program under which the Company is authorized to repurchase up to $10.0 million of its currently issued and outstanding securities through March 22,2024. On March 22, 2024,the Company entered into aone* year extension of its existing share repurchase program. As amended, the share repurchase program will now expire on* March 21, 2025.The timing and amount of any repurchases are determined based on market and economic conditions, share price and other factors, and the program maybe terminated, modified or suspended at any time at the Company's discretion. During thethree* andnine months ended* September 30, 2024*, the Company repurchased 194,300 and 312,850 shares, respectively, of common stock for an aggregate purchase price of approximately $1.5 million and $2.5 million, respectively, including fees and commissions. During thethree andnine months ended* September 30, 2023*, the Company repurchased, in the aggregate,628,587 and 1,193,557 shares, respectively, of common stock and warrants to purchase common stock for an aggregate purchase price of approximately $2.8 million and $4.8 million, respectively, including fees and commissions. The repurchased common stock will be held as treasury stock at cost and has been removed from common shares outstanding as of* September 30, 2024*.

The Company previously had warrants outstanding that expired on* September 15, 2023.Prior to the expiration thereof, the warrants were recorded in shareholders' equity and entitled each subscriber to purchaseone common share of Kingsway at an exercise price of $5.00 for each warrant. During thethree* andnine months ended* September 30, 2023*, warrants to purchase 2,019,720 and 3,331,661 shares of common stock, respectively, were exercised, resulting in cash proceeds of $10.1 million and $16.7 million, respectively. Any warrants that werenot exercised prior to the expiration date became null and void on the expiration date.

NOTE19 ACCUMULATED OTHER COMPREHENSIVE LOSS

The tables below detail the change in the balance of each component of accumulated other comprehensive loss, net oftax, for thethree andnine months ended* September 30, 2024* and* September 30, 2023* as relates to shareholders' equity attributable to common shareholders on the consolidated balance sheets.

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) September 30, 2024

30

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) September 30, 2024

It should be noted that the unaudited consolidated statements ofcomprehensive loss present the components of other comprehensive income (loss), net of tax, only for thethree andnine months ended* September 30, 2024* and* September 30, 2023* and inclusive of the components attributable to noncontrolling interests in consolidated subsidiaries.

Components of accumulated other comprehensive loss were reclassified to the following lines of the unaudited consolidated statements of operations for thethree andnine months ended* September 30, 2024* and* September 30, 2023*:

As further discussed in Note11, "Debt,"during thefirst quarter of2023, the Company completed the repurchases offive TruPs. The unaudited consolidated statements of comprehe nsive loss for thenine months ended* September 30, 2023* includes a reclassification adjustment of $27.2 million from accumulated other comprehensive income to gain on extinguishment of debt related to the instrument-specific credit risk portion of the repurchased TruPs.

NOTE20 SEGMENTED INFORMATION

The Company reports segment information based on the "management" approach. The management approach designates the internal reporting used by management for making decisions and assessing performance as a source of the Company’s reportable operating segments. The Company conducts its business through the followingtwo reportable segments: Extended Warranty and Kingsway Search Xcelerator.

Extended Warranty Segment

Extended Warranty includes the following subsidiaries of the Company: IWS, Geminus, PWI and Trinity (collectively, "Extended Warranty").

IWS is a licensed motor vehicle service agreement company and is a provider of after-market vehicle protection services distributed by credit unionsin 25 states and the District of Columbia to their members, with customers in allfifty states.

Geminus primarily sells vehicle service agreements to used car buyers across the United States, through its subsidiaries, Penn and Prime. Penn and Prime distribute these products in 47 and 34 states, respectively, via independent used car dealerships and franchised car dealerships.

PWI markets, sells and administers vehicle service agreements to used car buyers in allfifty states via independent used car and franchise network of approved automobile and motorcycle dealer partners. PWI’s business model is supported by an internal sales and operations team and partners with American Auto Shield inthree states with a "white label" agreement. PWI also sells and administers a GAP product, under the Penn name, in states where Penn is approved.

Trinity sells HVAC, standby generator, commercial LED lighting and commercial refrigeration warranty products and provides equipment breakdown and maintenance support services to companies across the United States. As a seller of warranty products, Trinity markets and administers product warranty contracts for certain new and used products in the HVAC, standby generator, commercial LED lighting and commercial refrigeration industries throughout the United States. Trinity acts as an agent on behalf of thethird-party insurance companies that underwrite and guaranty these warranty contracts. Trinity doesnot guaranty the performance underlying the warranty contracts it sells. As a provider of equipment breakdown and maintenance support services, Trinity acts as a single point of contact to its clients for both certain equipment breakdowns and scheduled maintenance of equipment. Trinity will provide such repair and breakdown services by contracting with certain HVAC providers.

Kingsway Search Xcelerator Segment

Kingsway Search Xcelerator includes the Company's subsidiaries CSuite, Ravix, SNS, SPI, DDI and Image Solutions.

CSuite is a professional services firm that provides experienced chief financial officer and other finance professionals to its clients through a variety of flexible offerings. These offerings include project and interim staffing engagements, and contingent search services for permanent placements for its clients throughout the United States.

Ravix provides outsourced financial services and human resources consulting for short or long duration engagements for customers throughout the United States.

SNS provides healthcare staffing services to acute healthcare facilities on a contract or per diem basis in the United States, primarily in California.

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) September 30, 2024

SPI provides software products created exclusively to serve the management needs of all types of shared-ownership properties throughout the United States, Europe, Asia, Mexico and the Caribbean.

DDI provides outsourced24 hours a day and7 days per week ("24/7") cardiac telemetry services for long-term acute care ("LTAC") and inpatient rehabilitation hospitals. Outsourcing cardiac monitoring is intended to allow hospitals to eliminate personnel callouts and human resources issues, remove distractions from onsite operations, and free up facility staff to assist directly with patient care. DDI has been operating for over10 years and currently has a presence in 39 states.

Image Solutions provides comprehensive information technology managed services, including equipment sales, service, and helpdesk support to customers primarily in North Carolina, Kansas, Georgia, Kentucky and Tennessee. Since Image Solutions was acquired on* September 26, 2024,the consolidated statement of operations for thethree* andnine months ended* September 30, 2024*, doesnot include any revenue, expenses or earnings of Image Solutions, as such items are insignificant.

Revenues and Operating Income by Reportable Segment

Results for the Company's reportable segments are based on the Company's internal financial reporting systems and are consistent with those followed in the preparation of the unaudited consolidated interim financial statements. The following tables provide financial data used by management. Segment assets arenot allocated for management use and, therefore, arenot included in the segment disclosures below.

Revenues by reportable segment reconciled to consolidated revenues for thethree andnine months ended* September 30, 2024* and* September 30, 2023* were:

The operating income by reportable segment in the following table is before income taxes and includes revenues and direct segment costs. Total segment operating income reconciled to the consolidated (loss) income from continuing operations for thethree andnine months ended* September 30, 2024* and* September 30, 2023* were:

NOTE21 FAIR VALUE OF FINANCIAL INSTRUMENTS

Fair value is the price that would be received upon sale of an asset or paid to transfer a liability in an orderly transaction between market participants at the measurement date. Fair value is best evidenced by quoted bid or ask price, as appropriate, in an active market. Where bid or ask prices arenot available, such as in an illiquid or inactive market, the closing price of the most recent transaction of that instrument subject to appropriate adjustments as required is used. Where quoted market prices arenot available, the quoted prices of similar financial instruments or valuation models with observable market-based inputs are used to estimate the fair value. These valuation models* mayuse multiple observable market inputs, including observable interest rates, foreign-exchange rates, index levels, credit spreads, equity prices, counterparty credit quality, corresponding market volatility levels and option volatilities. Minimal management judgment is required for fair values calculated using quoted market prices or observable market inputs for models. Greater subjectivity is required when making valuation adjustments for financial instruments in inactive markets or when using models where observable parameters donot* exist. Also, the calculation of estimated fair value is based on market conditions at a specific point in time and* may**not* be reflective of future fair values. For the Company's financial instruments carried at cost or amortized cost, the book value isnot adjusted to reflect increases or decreases in fair value due to market fluctuations, including those due to interest rate changes, as it is the Company's intention to hold them until there is a recovery of fair value, which* may*be to maturity.

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) September 30, 2024

The Company employs a fair value hierarchy to categorize the inputs it uses in valuation techniques to measure the fair value. The following fair value hierarchy is used in selecting inputs, with the highest priority given to Level1:

The Company classifies its investments in fixed maturities as available-for-sale and reports these investments at fair value. The Company's equity investments, limited liability investment, at fair value, subordinated debt, derivative contracts (interest rate swap and trust preferred debt repurchase options) and contingent consideration are measured and reported at fair value.

Fixed maturities - Fair values of fixed maturities for whichno active market exists are derived from quoted market prices of similar instruments or otherthird-party evidence. All classes of the Company’s fixed maturities, primarily consisting of investments in US. Treasury bills and government bonds; obligations of states, municipalities and political subdivisions; mortgage-backed securities; and corporate securities, are classified as Level2. Level2 is applied to valuations based upon quoted prices for similar assets in active markets; quoted prices for identical or similar assets in markets that are inactive; or valuations based on models where the significant inputs are observable or can be corroborated by observable market data.

The Company engages athird-party vendor who utilizesthird-party pricing sources and primarily employs a market approach to determine the fair values of our fixed maturities. The market approach includes primarily obtaining prices from independentthird-party pricing services as well as, to a lesser extent, quotes from broker-dealers. Ourthird-party vendor also monitors market indicators, as well as industry and economic events, to ensure pricing is appropriate. All classes of our fixed maturities are valued using this technique. The Company has obtained an understanding of ourthird-party vendor’s valuation methodologies and inputs. Fair values obtained from ourthird-party vendor arenot adjusted by the Company.

The following is a description of the significant inputs, by asset class, used by thethird-party pricing services to determine the fair values of our fixed maturities included in Level2:

Equity investments - Fair values of equity investments reflect quoted market values based on latest bid prices, where active markets exist, or models based on significant market observable inputs, whereno active markets exist.

Limited liability investment, at fair value - Limited liability investment, at fair value, include the underlying investments of Argo Holdings. Argo Holdings makes investments in limited liability companies and limited partnerships that hold investments in search funds and private operating companies.

The fair value of Argo Holdings' limited liability investments that hold investments in search funds is based on the initial investment in the search funds. The fair value of Argo Holdings' limited liability investments that hold investments in private operating companies is valued using a market approach including valuation multiples applied to corresponding performance metrics, such as earnings before interest, tax, depreciation and amortization; revenue; or net earnings. The selected valuation multiples were estimated using multiples provided by the investees and review of those multiples in light of investor updates, performance reports, financial statements and other relevant information. These investments are categorized in Level3 of the fair value hierarchy.

Subordinated debt - The fair value of the subordinated debt is calculated using a model based on significant market observable inputs and inputs developed by athird party. These inputs include credit spread assumptions developed by athird party and market observable swap rates. The subordinated debt is categorized in Level2 of the fair value hierarchy.

Derivative contract - interest rate swap - As described in Note10, "Derivatives," the Company entered into an interest rate swap agreement effective* April 1, 2021to convert the variable interest rate on a portion of the2020* KWH Loan to a fixed interest rate. On* February**29,* 2024, the interest rate swap matured and the Company didnot enter into any additional interest rate swap agreement upon its expiration. The interest rate swap contract was measured and reported at fair value and is included in other receivables in the consolidated balance sheet at* December 31, 2023*. The fair value of the interest rate swap contract was estimated using inputs which the Company obtained from the counterparty and was determined using a discounted cash flow analysis on the expected cash flows of the derivative. The discounted cash flow valuation technique reflected the contractual term of the derivative contract, including the period to maturity, and used observable market based inputs, including quoted mid-market prices orthird-party consensus pricing, interest rate curves and implied volatilities. The interest rate swap contract is categorized in Level2 of the fair value hierarchy.

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) September 30, 2024

Derivative contracts - trust preferred debt repurchase options - As described in Note10, "Derivatives," the Company entered into three TruPs Options contracts during thethird quarter of2022. During thefirst quarter of2023, the Company executed the TruPs Options contracts. The TruPs Options contracts were measured and reported at fair value. The fair value of the TruPs Options contracts was estimated using the binomial lattice model. Key inputs in the valuation included credit spread assumptions, interest rate volatility, debt coupon interest rate and time to maturity. The TruPs Options contracts arecategorized in Level3 of the fair value hierarchy.

Contingent consideration -The consideration for the Company's acquisitions of Ravix and CSuite includes future payments to the former owners that are contingent upon the achievement of certain targets over future reporting periods. Liabilities for contingent consideration are measured and reported at fair value and are included in accrued expenses and other liabilities in the consolidated balance sheets. Contingent consideration liabilities are revalued each reporting period. Changes in the fair value of contingent consideration liabilities can result from changes toone or multiple inputs, including adjustments to the discount rates or changes in the assumed achievement or timing of any targets. Any changes in fair value are reported in the consolidated statements of operations as non-operating other expense. The contingent consideration liabilities are categorized in Level3 of the fair value hierarchy.

Assets and Liabilities Measured at Fair Value on a Recurring Basis

The balances of the Company's financial assets and liabilities measured at fair value on a recurring basis by level within the fair value hierarchy as of* September 30, 2024* and* December 31, 2023* are as follows.

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) September 30, 2024

The following table provides a reconciliation of the fair value of recurring Level3 fair value measurements for thethree andnine months ended* September 30, 2024* and* September 30, 2023*:

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) September 30, 2024

The following table summarizes the valuation techniques and significant unobservable inputs utilized in determining fair values for the Company's financial assets and liabilities that are categorized as Level3 at* September 30, 2024*:

The following table summarizes the valuation techniques and significant unobservable inputs utilized in determining fair values for the Company's financial assets and liabilities that are categorized as Level3 at* December 31, 2023*:

Assets and Liabilities Measured at Fair Value on a Nonrecurring Basis

Certain assets and liabilities are measured at fair value on a nonrecurring basis, including assets that are adjusted for observable price changes or written down to fair value as a result of an impairment. For thethree andnine months ended* September 30, 2024*, the Company didnot record any adjustments to the fair value of its investments in private companies for observable price changes. For thethree andnine months ended* September 30, 2023*, the Company recorded adjustments to increase the fair value of certain investments in private companies for observable price changes of $0.1 million, which are included in net change in unrealized gain on private company investments in the unaudited consolidated statements of operations. The Company didnot record any impairments related to investments in private companies for thethree and nine months ended* September 30, 2024* and* September 30, 2023*. To determine the fair value of investments in these private companies, the Company considered rounds of financing andthird-party transactions, discounted cash flow analyses and market-based information, including comparable transactions, trading multiples and changes in market outlook, among other factors. The Company has classified the fair value measurements of these investments in private companies as Level3 because they involve significant unobservable inputs.

Indefinite-lived intangible assets are recorded at carrying value, and, if impaired, are adjusted to fair value using Level3 inputs. Refer to Note8, "Intangible Assets" for further information regarding the process of determining the fair value of indefinite-lived intangible assets and the impairment charges recorded for thethree andnine months ended* September 30, 2024*.

As further discussed in Note5, "Acquisitions and Discontinued Operations," the Company acquired Image Solutions on* September 26, 2024and provisionally allocated the purchase price to the assets acquired and liabilities assumed. The fair values of intangible assets associated with the acquisition of Image Solutions were determined to be Level3* under the fair value hierarchy.

The following table summarizes the valuation techniques and significant unobservable inputs utilized in determining fair values for these Level3 measurements:

NOTE22 RELATED PARTIES

Related party transactions, including services provided to or received by the Company's subsidiaries, are measured in part by the amount of consideration paid or received as established and agreed by the parties. Except where disclosed elsewhere in these unaudited consolidated interim financial statements, the following is a summary of related party relationships and transactions.

Argo Management Group, LLC

The Company acquired Argo Management Group, LLC ("Argo Management") in* April 2016.Argo Management's primary business is to act as Managing Member of Argo Holdings. At September 30, 2024* and* December 31, 2023*, each of the Company, John T. Fitzgerald ("Fitzgerald"), the Company's Chief Executive Officer and President, and certain of Fitzgerald’s immediate family members owns equity interests in Argo Holdings, all of which interests were acquired prior to the Company’s acquisition of Argo Management. Subject to certain limitations, Argo Holdings' governing documents require all individuals and entities owning an equity interest in Argo Holdings to fund upon request his/her/its pro rata share of any funding requirements of Argo Holdings up to an aggregate maximum amount equal to his/her/its total capital commitment (each request for funds being referred to as a "Capital Call"). Argo Holdings madeno Capital Calls during thenine months ended* September 30, 2024* and the year ended* December 31, 2023*.

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) September 30, 2024

Private Placement

As further described in Note17, " Redeemable Class B Preferred Stock," on* September 24, 2024,*the Company closed on a private placement for aggregate proceeds totaling $8.3 million, resulting from the sale and issuance of 330,000 shares of Class B Preferred Stock. The Company's Chief Executive Officer and President, certain members of the Company's Board of Directors and members of the KSX Advisory Board invested a total of $5.0 million in the private placement transaction.

VA Lafayette

On* August 16 2024,the Company closed on the sale of 100% of the membership interests in VA Lafayette to athird*-party, who subsequently invested in the Company's private placement transaction that closed on* September 24, 2024and is a current holder of the Company’s Class B Preferred Stock (refer to Note5*, "Acquisitions and Discontinued Operations," for further detail of the sale of VA Lafayette and Note17, "Redeemable Class B Preferred Stock," for further detail of the private placement). The Company determined the sale was an arms-length transaction based upon the purchase price paid compared to the pricing of similarthird-party transactions, and given the fact that the terms of the sale were negotiated before the private placement was contemplated.

NOTE23 COMMITMENTS AND CONTINGENCIES

(a) Legal proceedings:

In* May 2016,Aegis Security Insurance Company ("Aegis") filed a complaint for breach of contract and declaratory relief against the Company in the Eastern District of Pennsylvania alleging, among other things, that the Company breached a contractual obligation to indemnify Aegis for certain customs bond losses incurred by Aegis under the indemnity and hold harmless agreements provided by the Company to Aegis for certain customs bonds reinsured by Lincoln General Insurance Company ("Lincoln General") during the period of time that Lincoln General was a subsidiary of the Company. Lincoln General was placed into liquidation in November 2015and Aegis subsequently invoked its rights to indemnity under the indemnity and hold harmless agreements. Effective January 20, 2020,Aegis and the Company entered into a Settlement Agreement with respect to such litigation pursuant to which the Company agreed to pay Aegis aone*-time settlement amount of $0.9 million, and to reimburse Aegis for 60% of future losses that Aegis* maysustain in connection with such customs bonds, up to a maximum reimbursement amount of $4.8 million. From2020* through2023, the Company made reimbursement payments to Aegis totaling $1.5 million in connection with the Settlement Agreement. During thethree months ended* September 30, 2024* and* September 30, 2023*, the Company made reimbursement payments to Aegis of $0.2 million and $0.1 million, respectively ($0.2 million for each of thenine months ended* September 30, 2024* and* September 30, 2023*), in connection with the Settlement Agreement, which is included in general and administrative expenses in the unaudited consolidated statement of operations for thethree andnine months ended* September 30, 2024* and* September 30, 2023*. The remaining maximum reimbursement amount is $3.1 million as of* September 30, 2024*. The ultimate amount incurred under these agreements wasnot reasonably determinable at* September 30, 2024*, andno liability has been recorded in the unaudited consolidated interim financial statements at* September 30, 2024*.

(b) Collateral pledged and restricted cash:

Short-term investments with an estimated fair value of $0.2 million at* September 30, 2024* and* December 31, 2023*, were on deposit with state regulatory authorities.

The Company also has restricted cash of $8.6 million and $8.4 million at* September 30, 2024* and* December 31, 2023*, respectively. Included in restricted cash are:

KINGSWAY FINANCIAL SERVICES INC.