KINGSWAY FINANCIAL SERVICES INC

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 (benefit) expense of $0 for the three and six months ended June 30, 2025 and June 30, 2024.

KINGSWAY FINANCIAL SERVICES INC.

Consolidated Statements of Shareholders' Equity

KINGSWAY FINANCIAL SERVICES INC.

Consolidated Statements of Shareholders' Equity

KINGSWAY FINANCIAL SERVICES INC.

Consolidated Statements of Cash Flows

(in thousands)

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) June 30, 2025

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 business services and extended warranty 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 ("2024 Annual Report") for the year ended* December 31, 2024*.

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 the2024 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 maturity investments; impairment assessment of investments; valuation of limited liability investment, at fair value; valuation of deferred income taxes; accounting for business combinations; valuation and impairment assessment of intangible assets; goodwill recoverability; fair value assumptions for subordinated debt obligations; and fair value assumptions for subsidiary stock-based compensation awards.

Certain prior year amounts have been reclassified to conform to current year presentation. Such reclassifications hadno impact on previously reported net loss or total assets, liabilities or shareholders' equity.

NOTE3 SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES

There have beenno material changes to our significant accounting policies as reported in our2024 Annual Report.

NOTE4 RECENTLY ISSUED ACCOUNTING STANDARDS

(a) Adoption of New Accounting Standards:

Effective* January 1, 2025,the Company adopted 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. The adoption of ASU2024-02 didnot have an impact on the Company's consolidated financial statements.

(b) Accounting StandardsNot Yet Adopted:

In* December**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 for annual periods beginning after* December 15, 2024,with early adoption permitted. The Company is currently evaluating the impact the adoption of this standard; however it is anticipated that the adoption will expand the Company's annual income tax disclosures included in our2025* Annual Report on Form10K.

In* October 2023,the FASB issued ASU2023*-06, Disclosure Improvements: Codification Amendments in Response to the SEC’s Disclosure Update and Simplification Initiative("ASU2023-06"), which amends the disclosure or presentation requirements related to various subtopics in the FASB Accounting Standards Codification. For SEC registrants, the effective date for each amendment will be the date on which the SEC’s removal of that related disclosure requirement from Regulation S-X or Regulation S-K becomes effective, with early adoption prohibited. The Company will monitor the removal of various requirements from the current regulations in order to determine when to adopt the related amendments, but doesnot anticipate the adoption of the new guidance will have a material impact on the Company’s consolidated financial statements. The Company will continue to evaluate the impact of this guidance on its consolidated financial statements.

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) June 30, 2025

In* November 2024,the FASB issued ASU2024*-03, Income Statement - Reporting Comprehensive Income - Expense Disaggregation Disclosures ("ASU2024-03"). ASU2024-03 requires new financial statement disclosures in tabular format, disaggregating information about prescribed categories underlying any relevant income statement expense caption. Qualitative disclosures about any remaining amounts in relevant expense line items must be provided. Separate disclosures of total selling expenses and an entity’s definition of those expenses are also required. ASU2024-03 is effective for public companies with annual periods beginning after* December 15, 2026,and interim periods within annual period beginning after December 15, 2027,*with early adoption permitted. The Company expects the adoption of the standard to result in additional disaggregation of expense captions within its footnote disclosures.

NOTE5 ACQUISITIONS AND DISCONTINUED OPERATIONS

M.L.C. Plumbing, LLC (d/b/a Bud's Plumbing)

On* March 14, 2025,the Company acquired 100% of the outstanding membership interests of M.L.C. Plumbing, LLC (d/b/a Bud's Plumbing Service, "Bud's Plumbing") for aggregate consideration consisting of cash and a seller note, of approximately $5.0 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 paid during thesecond* quarter of2025. Bud's Plumbing, based in Evansville, Indiana, is a provider of various plumbing installation, service and repair services to residential and commercial customers. As further discussed in Note19, "Segmented Information," Bud's Plumbing is included in the Kingsway Search Xcelerator segment. This acquisition was the Company’sseventh 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 nextthree 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 $0.9 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 purchase price of Bud's Plumbing:

The following table summarizes the preliminary allocation of the Bud's Plumbing purchase price and the estimated fair values of the assets acquired and liabilities assumed at the date of acquisition:

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) June 30, 2025

The preliminary fair value of the acquired service fee receivable of less than $0.1 million is equivalent to its gross contractual amount. The unaudited consolidated statements of operations include the earnings of Bud's Plumbing from the date of acquisition. From the date of acquisition through* June 30, 2025*, Bud's Plumbing earned revenue of $2.0 million and had net income of $0.2 million. During thethree andsix months ended* June 30, 2025*, the Company incurred expenses related to the acquisition of Bud's Plumbing of $0.4 million, which are included in general and administrative expenses in the unaudited consolidated statements of operations for thethree andsix months ended* June 30, 2025*. The proforma effects of the Bud’s Plumbing acquisition arenot material to the Company’s consolidated statements of operations for thethree andsix months ended* June 30, 2025* and* June 30, 2024*.

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 Note19*, "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 nextthree 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.

The Company records measurement period adjustments in the period in which the adjustments occur. During thesix months ended* June 30, 2025*, the Company recorded a measurement period adjustment that increased goodwill by $0.1 million compared to the amount recorded at* December 31, 2024*. The measurement period adjustment primarily reflects changes in the estimated fair value of inventory.

Refer to Note8,"Intangible Assets," for further disclosure of the intangible assets related to this acquisition. The goodwill of $6.6 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:

The preliminary fair value of the acquired service fee receivable of $0.6 million is equivalent to its gross contractual amount.

Leased Real Estate Segment

The Company’s 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.

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*.*

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) June 30, 2025

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 operating results and cash flows related to Leased Real Estate have been classified as discontinued operations in the unaudited consolidated interim financial statements for all periods presented.

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 Note21*, "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.

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 thesix months ended* June 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.

Summary financial information for Leased Real Estate included in income from discontinued operations, net of taxes in the unaudited consolidated statement of operations for thethree andsix months ended* June 30, 2024* is presented below:

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

Loss on disposal of discontinued operations, net of taxes, related to Leased Real Estate, in the unaudited consolidated statement of operations for thesix months ended* June 30, 2024* is comprised of $0.4 million 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* June 30, 2025* and* December 31, 2024* are summarized in the tables shown below:

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) June 30, 2025

The table below summarizes the Company's fixed maturities at* June 30, 2025* 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* June 30, 2025* and* December 31, 2024*. The tables segregate the holdings based on the period of time the investments have been continuously held in unrealized loss positions.

At* June 30, 2025* and* December 31, 2024*, there are approximately 139 and 191 individual available-for-sale investments, respectively, 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* June 30, 2025* and* December 31, 2024*. 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 is 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* June 30, 2025* and* December 31, 2024*.

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) June 30, 2025

The establishment of an impairment loss on an investment requires a number of judgments and estimates. Refer to the "Significant Accounting Policies and Critical Estimates" section of Management's Discussion and Analysis of Financial Condition included in the2024 Annual Report for further information regarding the Company's detailed analysis and factors considered in recording an impairment loss on an investment.

The Company didnot record any write-downs for impairment related to available-for-sale fixed maturity investments for thethree andsix months ended* June 30, 2025* and* June 30, 2024*.

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* June 30, 2025* and* December 31, 2024*, the carrying value of limited liability investments totaled $0.7 million. The Company recordedno impairments related to limited liability investments during thethree andsix months ended* June 30, 2025* and* June 30, 2024*. 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* June 30, 2025*, 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* June 30, 2025* and* December 31, 2024*, the carrying value of the Company's limited liability investment, at fair value was $3.0 million and $2.9 million, respectively. At* June 30, 2025*, the Company hadno unfunded commitments to fund limited liability investment, at fair value.

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* June 30, 2025* and* December 31, 2024*, the carrying value of the Company's investments in private companies totaled $0.6 million and $0.7 million, respectively. For thethree andsix months ended* June 30, 2025* and* June 30, 2024*, the Company didnot record any adjustments to the carrying value of its investments in private companies for observable price changes.

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 andsix months ended* June 30, 2025* and* June 30, 2024*.

Net investment income for thethree andsix months ended* June 30, 2025* and* June 30, 2024* is comprised as follows:

Net realized gains on investments for thethree andsix months ended* June 30, 2025* and* June 30, 2024* are comprised as follows:

Net loss on equity investments for thethree andsix months ended* June 30, 2025* and* June 30, 2024* is comprised as follows:

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) June 30, 2025

NOTE7 GOODWILL

The following table summarizes the goodwill activity for thesix months ended* June 30, 2025*:

As further discussed in Note5, "Acquisitions and Discontinued Operations," during thesix months ended* June 30, 2025*, the Company recorded goodwill of $0.9 million related to the acquisition of Bud's Plumbing on* March 14, 2025.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 nextthree* months. The estimates, allocations and calculations recorded at* June 30, 2025* 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 thesix months ended* June 30, 2025*, the Company recorded a measurement period adjustment, related to acquisition of Image Solutions, that increased goodwill by $0.1 million.

At each of* June 30, 2025* and* December 31, 2024*, accumulated goodwill impairment losses were $0.7 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. In evaluating the recoverability of goodwill, the Company estimates the fair value of its reporting units and compares it to the carrying value. 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 andsix months ended* June 30, 2025* and* June 30, 2024*.

NOTE8 INTANGIBLE ASSETS

Intangible assets at* June 30, 2025* and* December 31, 2024* are comprised as follows:

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) June 30, 2025

As further discussed in Note5, "Acquisitions and Discontinued Operations," during thefirst quarter of2025, the Company recorded $3.6 million of separately identifiable intangible assets, related to acquired customer relationships and trade name, as part of the acquisition of Bud’s Plumbing on* March 14, 2025.The customer relationships intangible asset of $0.5 million is being amortized oversix 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 $3.1 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 nextthree months. The estimates, allocations and calculations recorded at* June 30, 2025* 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.

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 5 to 15 years. Amortization of intangible assets was $1.7 million and $1.5 million for thethree months ended* June 30, 2025* and* June 30, 2024*, respectively ($3.4 million and $2.9 million for thesix months ended* June 30, 2025* and* June 30, 2024*, respectively).

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 each quarter end of thefirst andsecond quarters of2025 and2024, 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 andsix months ended* June 30, 2025* of $0.1 million and $0.2 million, respectively, related to the Ravix indefinite-lived trade name, and $0.7 million and $1.2 million for thethree andsix months ended* June 30, 2024*, respectively, related to the SNS and CSuite indefinite-lived trade names. The fair value of the Ravix, SNS and CSuite 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.

NOTE9 PROPERTY AND EQUIPMENT

Property and equipment at* June 30, 2025* and* December 31, 2024* are comprised as follows:

For thethree months ended* June 30, 2025* and* June 30, 2024*, depreciation expense related to medical equipment and certain computer hardware of $0.1 million andzero, respectively ( $0.1 million andzero for thesix months ended* June 30, 2025* and* June 30, 2024*, respectively), is included in cost of services sold in the unaudited consolidated statements of operations. For thethree months ended* June 30, 2025* and* June 30, 2024*, depreciation expense on all other property and equipment of $0.1 million and $0.2 million, respectively ( $0.2 million and $0.4 million for thesix months ended* June 30, 2025* and* June 30, 2024*, respectively), is included in general and administrative expenses in the unaudited consolidated statements of operations.

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) June 30, 2025

NOTE10 DEBT

Debt consists of the following instruments at* June 30, 2025* and* December 31, 2024*:

Subordinated debt mentioned above consists of the following trust preferred debt instrument at* June 30, 2025* and* December 31, 2024*:

The contractual maturities of the Company's principal debt balances as of* June 30, 2025* were as follows:

(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 required monthly payments of principal and interest.

The2021 Ravix Loan had an annual interest rate equal to the greater of the Prime Rate plus 0.5%, or 3.75% and the term loan was due to mature on* October**1,* 2027, prior to thefourth amendment of the2021 Ravix Loan on* February 7, 2025 (see further discussion below). 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 sheet at* December 31, 2024*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* Ravix Revolver"). The2022 Ravix Loan required monthly payments of principal and interest. The2022 Ravix Loan was due to mature on* November 16, 2028and had an annual interest rate equal to the Prime Rate plus 0.75%, prior to thefourth* amendment of the2021 Ravix Loan on* February 7, 2025 (*see further discussion below).

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 sheet at* December 31, 2024* 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.

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) June 30, 2025

The2022 Ravix Loan and the2021 Ravix Loan werenot deemed to be substantially different; therefore, the2022 Ravix Loan was 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, Ravix LLC and CSuite 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 Ravix 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 was accounted for as a modification of the original2021 Ravix Loan.

On* October 4, 2024,Ravix, Ravix LLC and CSuite entered into athird* amendment to the2021 Ravix Loan to extend the maturity date of the2022 Ravix Revolver to* February 13, 2025.*

On* February 7, 2025,Ravix, Ravix LLC and CSuite entered into afourth* amendment to the2021 Ravix Loan that provides for: (1) a new2025 term loan in the principal amount of $9.1 million, with a maturity date of* February 7, 2031 (the"2025* Ravix Loan"); and (2) extending the maturity date of the2022 Ravix Revolver to* February 7, 2027.In connection with thefourth* amendment, Ravix used a portion of the proceeds from the2025 Ravix Loan to repay the following outstanding principal balances under the2021 and2022 Ravix Loans: (1) $2.2 million related to the2021 Ravix term loan; and (2) $4.2 million related to the2022 Ravix term loan. The2025 Ravix Loan and2022 Ravix Revolver have an annual interest rate equal to the Prime Rate plus 0.5%. At* June 30, 2025*, the interest rate was 8.00%.

The Company also recorded as a discount to the carrying value of the2025 Ravix Loan issuance costs of less than $0.1 million specifically related to the2025 Ravix Loan. The2025 Ravix Loan is carried in the consolidated balance sheet at* June 30, 2025* 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.

The2025 Ravix Loan and the2021 and2022 Ravix Loans werenot deemed to be substantially different as a result of thefourth amendment; therefore, the2025 Ravix Loan is accounted for as a modification of thesecond amended2021 Ravix Loan. The unamortized debt discount and issuance costs from the2021 and2022 Ravix Loans at the modification date of $0.1 million were recorded as loss on extinguishment of debt during thesix months ended* June 30, 2025* since the original debt related the2021 Ravix Loan and2022 Ravix Loan were fully repaid as part of the modification.

The fair values of the2021 Ravix Loan,2022 Ravix Loan,2022 Ravix Revolver and2025 Ravix Loan disclosed in the table above are 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, as amended, is secured by certain of the equity interests and assets of Ravix and CSuite.

The2021 Ravix Loan, as amended (including by the2025 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, as amended 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"), which 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 (the "SNS 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 June 30, 2025*, the interest rate was 8.00%. The SNS Revolver matures on* August 2, 2025and the term loan matures on November 18, 2028.On July 22, 2025,the SNS Loan was amended to extend the maturity date on the SNS Revolver to November 2, 2025.During thefourth* quarter of2024, the Company borrowed $0.5 million under the SNS Revolver. During thesix months ended* June 30, 2025*, the Company borrowed an additional $0.3 million under the SNS Revolver.

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 sheets 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 plus 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 each quarter end beginning* March 31, 2024through June 30, 2025*, 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* June 30, 2025*. 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 Digital Diagnostics Inc. ("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 (the "DDI 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 June 30, 2025*, the interest rate was 8.00%. Monthly principal payments on the term loan began on* December 15, 2024.The DDI Revolver matures on November 1, 2025and the term loan matures on October 26, 2029.During thesix* months ended* June 30, 2025*, the Company borrowed $0.1 million and and made principal repayments of less than $0.1 million under the DDI Revolver.

18

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) June 30, 2025

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 sheets 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 June 30, 2025*, the interest rate was 8.00%. The revolver matures on* September 26, 2026and the term loan matures on September 26, 2030.At June 30, 2025* and* December 31, 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 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. 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 had an annual interest rate equal to the Secured Overnight Financing Rate ("SOFR"), having a floor of 0.75%, plus spreads ranging from 2.62% to 3.12%. 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 KWH DDTL. Proceeds from certain assets dispositions, as defined, maybe required to be used to repay outstanding draws under the KWH 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 (as defined below).

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. The2024 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* June 30, 2025*, the interest rate was 7.44%.

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 was 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 thesecond quarter of2024 since the original debt was fully repaid as part of the modification.

During thethird andfourth quarters of2024, $6.0 million was borrowed under the KWH DDTL and $1.0 million was drawn on the KWH Revolver. As of* December 31, 2024and June 30, 2025*, both the KWH DDTL and the KWH Revolver are fully drawn.

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. The2024 KWH Loan is 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 the2024 KWH Loan,2024 KWH DDTL and KWH Revolver disclosed in the table above are 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. The2020 KWH Loan, as amended is secured by certain of the equity interests and assets of KWH and its subsidiaries.

19

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) June 30, 2025

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.

SPI

On* June 15, 2025,the Company's subsidiaries, Systems Products International Inc. ("SPI") and Vertical Market Solutions LLC, together established a $0.3 million revolver with a bank (the "SPI Revolver"). The SPI Revolver has an annual interest rate equal to the Prime Rate. The SPI Revolver matures on July 15, 2026.At June 30, 2025*, the balance of the SPI Revolver waszero.

(b) Note payable:

As part of the acquisition of Bud's Plumbing on* March 14, 2025,Bud's Plumbing became a wholly owned subsidiary of Kingsway Plumbing Holdco LLC ("KPH LLC"), and together they borrowed from the seller of Bud's Plumbing a principal amount of $1.25 million in the form of a promissory note, to partially finance the acquisition of Bud's Plumbing (the "KPH Note"). The KPH Note, which is recorded as note payable in the consolidated balance sheet at June 30, 2025*, was recorded at its estimated fair value of $1.1 million, which included the unpaid principal amount of $1.3 million as of the date of acquisition less a discount of $0.2 million. The KPH Note requires monthly payments of principal and interest and has an annual fixed interest rate of 6.00%. The KPH Note matures on* April 1, 2030.*

(c) Subordinated debt:

On* May 22, 2003,a subsidiary trust of the Company issued $15.0 million of 30-year capital securities tothird*-parties in a private transaction. 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 debenture bears interest at the rate of CME Term SOFR, plus a spread of 4.20%. The Company has the right to call these securities at par value any time afterfive years from its issuance until its maturity.

The subordinated debt, or TruPs, is carried in the consolidated balance sheets at fair value. See Note20, "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 (loss) income.

Of the $0.5 million increase in fair value of the Company's subordinated debt between* December 31, 2024* and* June 30, 2025*, $0.5 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 gain on change in fair value of debt in the Company's unaudited consolidated statement of operations.

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.

NOTE11 LEASES

(a) Lessee 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 andsix months ended* June 30, 2025* and* June 30, 2024* were as follows:

The annual maturities of lease liabilities as of* June 30, 2025* were as follows:

20

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) June 30, 2025

The weighted-average remaining lease term for our operating leases was 4.99 years as of* June 30, 2025*. The weighted-average discount rate of our operating leases was 6.24% as of* June 30, 2025*. Cash paid for amounts included in the measurement of lease liabilities was $0.4 million and $0.3 million for thesix months ended* June 30, 2025* and* June 30, 2024*, respectively.

(b) Lessor leases:

The Company enters into contracts withthird-parties to lease equipment to its customers. In certain of these contracts, the Company has the option to purchase the equipment back from suchthird-party at the end of the lease term with the end customer. In these cases, the Company determined that these contracts represent a lease, and the Company is a lessor under these contracts. The sum of the lease payments received by the Company exceed the cost of the equipment. Therefore, these leases are determined to be sales-type leases. The Company receives the full lease payment for the equipment upfront when the equipment is delivered to the customer and installation is complete. Therefore the Company doesnot record a receivable or interest income related to these leases. The Company recognizes all revenue and costs associated with the sales-type lease within service fee and commission revenue, and cost of services sold, respectively, upon delivery and installation of the equipment to the customer. For thethree months ended* June 30, 2025* and* June 30, 2024*, total revenue recognized from sales-type leases was $0.4 million andzero, respectively ($0.7 million andzero for thesix months ended* June 30, 2025* and* June 30, 2024*, respectively).

NOTE12 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, software license and support revenue and skilled trades repair and service 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, skilled trades, 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 andsix months ended* June 30, 2025* and* June 30, 2024*:

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 5.91% to 12.00% 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 and information technology ("IT") managed services. The Company invoices for business services revenue based on contracted rates. Revenue is earned over time as services are provided.

21

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) June 30, 2025

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 over time as services are provided.

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.

Skilled trades repair and service revenue include the service fees collected to administer plumbing repairs and maintenance support services and are earned as services are rendered.

The Company's revenue recognition policies are further described in Note2(r), "Summary of Significant Accounting Policies - Revenue recognition," to the consolidated financial statements in the2024 Annual Report.

Service fee receivables

Receivables from contracts with customers are reported as service fee receivable, net in the consolidated balance sheets and at* June 30, 2025* and* December 31, 2024* were $10.9 million and $9.4 million, respectively. The increase in receivables from contracts with customers is primarily due to the timing difference between the Company's satisfaction of performance obligations and customer payments.

Service fee receivable is reported net of an estimated allowance for credit losses at* June 30, 2025* and* December 31, 2024* of $0.8 million and $0.6 million, respectively. During thethree months ended* June 30, 2025* and* June 30, 2024*, the Company recorded an increase to its allowance for credit losses of $0.1 million and less than $0.1 million, respectively ($0.1 million and $0.1 million for thesix months ended* June 30, 2025* and* June 30, 2024*, 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 of less than $0.1 million during each of thethree months ended* June 30, 2025* and* June 30, 2024*, respectively (less than $0.1 million and $0.1 million for thesix months ended* June 30, 2025* and* June 30, 2024*, respectively).

Contract asset

The Company records a contract asset, which is included in other assets in the consolidated balance sheets, 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. Changes in the contract asset for thesix months ended* June 30, 2025* were as follows:

The contract asset is reported net of an estimated allowance for credit losses ofzero at* June 30, 2025* and* December 31, 2024*. During thethree months ended* June 30, 2025* and* June 30, 2024*, the Company recorded an increase to the contract asset allowance for credit losses ofzero and less than $0.1 million, respectively (zero and less than $0.1 million for thesix months ended* June 30, 2025* and* June 30, 2024*, respectively). Contract assets that are deemed to be uncollectible are written off against the allowance for credit losses when identified. During each of thethree andsix months ended* June 30, 2025* and* June 30, 2024*, the Company recorded write-offs to the contract asset for amounts that were deemed to be uncollectible of less than $0.1 million.

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 thesix months ended* June 30, 2025* were as follows:

22

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) June 30, 2025

The increase in deferred service fees between* December 31, 2024* and* June 30, 2025* is primarily due to additions to deferred service fees in excess of deferred service fees recognized during thesix months ended* June 30, 2025*.

Approximately $24.9 million and $24.5 million of service fee and commission revenue recognized during thesix months ended* June 30, 2025* and* June 30, 2024* was included in deferred service fees as of* December 31, 2024* and* December 31, 2023*, respectively.

Remaining performance obligations

The Company expects to recognize withinone year as service fee and commission revenue approximately 46.8% of theoutstanding performance obligations as of* June 30, 2025*. The balance relates primarily to vehicle service agreement fees.

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 and cost of services sold, respectively, in the unaudited consolidated statements of operations. No impairment charges related to deferred contract costs were recorded during thethree andsix months ended* June 30, 2025* and* June 30, 2024*.

The deferred contract costs balances and related amortization expense for thethree months ended* June 30, 2025* and* June 30, 2024* are comprised as follows:

The deferred contract costs balances and related amortization expense for thesix months ended* June 30, 2025* and* June 30, 2024* are comprised as follows:

NOTE13 INCOME TAXES

Income tax (benefit) expense for thethree andsix months ended* June 30, 2025* and* June 30, 2024* varies from the amount that would result by applying the applicable U.S. federal corporate income tax rate of 21% to loss from continuing operations before income tax (benefit)expense. The following table summarizes the differences:

23

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) June 30, 2025

The Company maintains a valuation allowance for its gross deferred tax assets at* June 30, 2025* and* December 31, 2024*. 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* June 30, 2025* and* December 31, 2024* 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 $3.8 million and $4.4 million at* June 30, 2025* and* December 31, 2024*, respectively, that consists of:

As of* June 30, 2025* and* December 31, 2024*, 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 andsix months ended* June 30, 2025* and* June 30, 2024*.

On* July 4, 2025,the “Big Beautiful Bill” P.L.119-21 was signed into law. This legislation includes changes to U.S. federal tax law, which maybe subject to further clarification and the issuance of interpretive guidance. We are assessing the legislation and its effect on our consolidated financial statements, which we expect to begin reflecting in thethree*-month period ended* September 30, 2025.*

NOTE14 LOSS PER SHARE

The following table sets forth the reconciliation of numerators and denominators for the basic and diluted loss pershare computation for thethree andsix months ended* June 30, 2025* and* June 30, 2024*:

Basic loss per share excludes dilution and is computed by dividing loss attributable to common shareholders by the weighted-average number of common shares outstanding for the period. Diluted loss 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 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.

24

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) June 30, 2025

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

NOTE15 STOCK-BASED COMPENSATION

The Company recognizes stock-based compensation expense for all share-based awards made to employees, including restricted stock awards, restricted common unit awards and employee stock options based on estimated fair values.

During thefirst quarter of2025, KPH LLC, a subsidiary of the Company, granted 199,000 restricted Class B common unit awards to an officer of Bud's Plumbing pursuant to an agreement dated* March 14, 2025 ("KPH RUA"). The KPH RUA vests based on service and the achievement of criteria based on the IRR of Bud's Plumbing. The KPH RUA has a weighted-average grant date fair value of $0.85 per Class B common unit. The grant-date fair value of the KPH RUA was estimated using the Monte Carlo simulation model, using the following assumptions: expected term offive years, expected volatility of 34% and risk-free interest rate of 4.26%. On March 14, 2025,83,333 units, representingone* half of the service condition for the KPH 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.

Total stock-based compensation expense related to all of the Company's restricted stock awards, restricted common unit awards and employee stock optionswas $0.3 million for each of thethree months ended* June 30, 2025* and* June 30, 2024* ($0.8 million and $0.6 million for thesix months ended* June 30, 2025* and* June 30, 2024*, respectively).

NOTE16 REDEEMABLE PREFERRED STOCK

(a) 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 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 June 30, 2025* and* December 31, 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, the maximum number of common shares issuable upon conversion of the Class B Preferred Stock is 868,421 common shares.

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* June 30, 2025* and* December 31, 2024*, accrued dividends declared of $0.2 million and $0.2 million, respectively, were included in accrued expenses and other liabilities in the consolidated balance sheets. The redemption amount of the Class B Preferred Stock was $8.3 million at* June 30, 2025* and* December 31, 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.

(b) Class C Preferred Stock

In* February 2025,the Company closed on a private placement for aggregate proceeds totaling $6.0 million, resulting from the sale and issuance of 240,000 shares of a new series of Class C Preferred Stock, par value $0.01 per share ("Class C Preferred Stock") for a purchase price of $25.00 per share. The Class C Preferred Stock rankspari passuwith the Company’s Class B Preferred Stock and senior to the Company's common shares. There were 240,000 shares of Class C Preferred Stock outstanding at June 30, 2025*.

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) June 30, 2025

Each share of Class C Preferred Stock is convertible into 2.6316 common shares at any time at the option of the holder prior to* February 12, 2032.*Subject to certain adjustments set forth in the certificate of designations for the Class C Preferred Stock, the maximum number of common shares issuable upon conversion of the Class C Preferred Stock is 631,579 common shares.

The holders of Class C 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 C Preferred Stock are entitled to receive fixed, cumulative, preferential cash dividends at a rate of 8% per share of Class C 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 C Preferred Stock will accrue from day to day commencing on the date of issuance of each such share of Class C Preferred Stock. The cash dividend rate will increase to 18% per share of Class C 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 C Preferred Stocknot previously converted into common shares, and which remain outstanding on* February 12, 2032,for the price of $25.00 per share of Class C 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 C 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 C Preferred Stock submitted for redemption.

At* June 30, 2025*, accrued dividends declared of $0.1 million were included in accrued expenses and other liabilities in the consolidated balance sheet. The redemption amount of the Class C Preferred Stock was $6.0 million at* June 30, 2025*.

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 C Preferred Stock at any time; however, ifnot converted, they are required to be redeemed on* February 12, 2032.*As such, the Class C Preferred Stock is presented in temporary or mezzanine equity on the consolidated balance sheet.

(c) Class D Preferred Stock

On* May 8, 2025,the Company closed on a private placement for aggregate proceeds totaling $2.0 million, resulting from the sale and issuance of 80,000 shares of a new series of Class D Preferred Stock, par value $0.01 per share ("Class D Preferred Stock") for a purchase price of $25.00 per share. The Class D Preferred Stock rankspari passu* with the Company’s Class B and Class C Preferred Stock and senior to the Company's common shares. There were 80,000 shares of Class D Preferred Stock outstanding at* June 30, 2025*.

Each share of Class D Preferred Stock is convertible into 2.6316 common shares at any time at the option of the holder prior to* May 7, 2032.*Subject to certain adjustments set forth in the certificate of designations for the Class D Preferred Stock, the maximum number of common shares issuable upon conversion of the Class D Preferred Stock is 210,526 common shares.

The holders of Class D 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 D Preferred Stock are entitled to receive fixed, cumulative, preferential cash dividends at a rate of 8% per share of Class D 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 D Preferred Stock will accrue from day to day commencing on the date of issuance of each such share of Class D Preferred Stock. The cash dividend rate will increase to 18% per share of Class D 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 D Preferred Stocknot previously converted into common shares, and which remain outstanding on* May 7, 2032,for the price of $25.00 per share of Class D 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 D 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 D Preferred Stock submitted for redemption.

At* June 30, 2025*, 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 D Preferred Stock was $2.0 million at* June 30, 2025*.

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 D Preferred Stock at any time; however, ifnot converted, they are required to be redeemed on* May 7, 2032.*As such, the Class D Preferred Stock is presented in temporary or mezzanine equity on the consolidated balance sheet.

NOTE17 Shareholders' Equity

On* June 24, 2025,the Company entered into a Stock Purchase Agreement (the “Purchase Agreement”) with certainthird*-parties. Pursuant to the Purchase Agreement, the Company sold an aggregate of 1,336,264 shares of its Common Stock, par value $0.01 per share for aggregate gross proceeds of $15.7 million. The purchase price for each share of Common Stock was $11.75 per share. Net proceeds to the Company were $15.6 million after deducting offering expenses.

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) June 30, 2025

During thethree andsix months ended* June 30, 2025*, the Company declared dividends to be paid to the holders of (i) its Class B Preferred Stock of $0.2 million and $0.3 million, respectively, (ii) its Class C Preferred Stock of $0.1 million and $0.2 million, respectively, and (iii) its Class D Preferred Stock of less than $0.1 million, with respect to the Class D Preferred Stock for the partial quarter period commencing on the date such shares were issued and ending* June 30, 2025.Cash dividends paid during thethree* andsix months ended* June 30, 2025* were $0.2 million and $0.4 million, respectively.

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 expired on* March 21, 2025;however, in January 2025the Company fully utilized the authorized amount. The timing and amount of any repurchases were determined based on market and economic conditions, share price and other factors, and the program could have been be terminated, modified or suspended at any time at the Company's discretion. During thethree* andsix months ended* June 30, 2025*, the Company repurchased zero and 42,900 shares, respectively, of common stock for an aggregate purchase price ofzero and $0.3 million, respectively (110,550 and 118,550 shares, respectively, of common stock for an aggregate purchase price of $0.9 million and $1.0 million, respectively during thethree andsix months ended* June 30, 2024*, 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* June 30, 2025*.

NOTE18 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 andsix months ended* June 30, 2025* and* June 30, 2024* 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) June 30, 2025

For thethree andsix months ended* June 30, 2024*, the unaudited consolidated statements ofcomp rehensive loss present the components of other comprehensive income (loss), net of tax, 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 andsix months ended* June 30, 2025* and* June 30, 2024*:

NOTE19 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's chief operating decision maker is its President and Chief Executive Officer. 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 28 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 46 and 35 states, respectively, via independent used car dealerships and franchised car dealerships. Penn also sells and administers a GAP product, in states where Penn is approved.

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.

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) June 30, 2025

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 ("KSX")

KSX includes the Company's subsidiaries CSuite, Ravix, SNS, SPI, DDI, Image Solutions and Bud's Plumbing.

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.

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

DDI provides outsourced24 hours a day and7 days per week cardiac telemetry services for long-term acute care 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 currently has a presence in 42 states and Puerto Rico.

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.

Bud's Plumbing provides a comprehensive range of plumbing services, including emergency repairs, drain cleaning, water heater installations, and water treatment solutions to residential and commercial customers, primarily in Evansville, Indiana.

Revenues and Operating Income by Reportable Segment

Revenues by reportable segment reconciled to consolidated revenues for thethree andsix months ended* June 30, 2025* and* June 30, 2024* were:

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 Company uses operating income as the measure of profit or loss for our segments. The Company's chief operating decision maker uses segment operating income to allocate resources in the annual budget and forecasting process and considers actual versus plan variances in assessing the performance of each segment. The chief operating decision maker also uses segment operating income as an input to the overall compensation measures for segment management under the Company's incentive compensation plans. From time to time we* mayreport the impact of certain events, gains, losses or other charges related to our segments outside of segment operating income. Segment assets arenot* regularly reviewed by the Company's chief operating decision maker and, therefore, arenot included in the segment disclosures below.

Among other items, the degree and pace of inflation and interest rate changes* mayhave impacts on our business and the recently announced tariffs or retaliatory responses to such tariffs may*impact the Company’s operating income. The potential impact of current macroeconomic uncertainties on the Company’s financial condition, results of operations, and cash flows is subject to change and continues to depend on the extent and duration of these uncertainties.

The operating income (loss) by reportable segment in the following table is before income taxes and includes revenues and direct segment costs. The significant expense categories and amounts by segment align with the segment level information that is regularly provided to the chief operating decision maker.

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) June 30, 2025

Total segment operating income reconciled to the consolidated loss from continuing operationsfor thethree months ended* June 30, 2025* and* June 30, 2024* is as follows:

Total segment operating income reconciled to the consolidated loss from continuing operationsfor thefor thesix months ended* June 30, 2025* and* June 30, 2024* is as follows:

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) June 30, 2025

NOTE20 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.

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 limited liability investment, at fair value, subordinated debt 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:

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 private operating companies.

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.

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) June 30, 2025

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.

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 revenue, net. 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* June 30, 2025* and* December 31, 2024* are as follows.

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) June 30, 2025

The following table provides a reconciliation of the fair value of recurring Level3 fair value measurements for thethree andsix months ended* June 30, 2025* and* June 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* June 30, 2025*:

33

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) June 30, 2025

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, 2024*:

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 andsix months ended* June 30, 2025* and* June 30, 2024*, the Company didnot record any adjustments to the fair value of its investments in private companies for observable price changes. The Company didnot record any impairments related to investments in private companies for thethree and six months ended* June 30, 2025* and* June 30, 2024*. 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 andsix months ended* June 30, 2025* and* June 30, 2024*.

As further discussed in Note5, "Acquisitions and Discontinued Operations," the Company acquired Bud's Plumbing on* March 14, 2025and provisionally allocated the purchase price to the assets acquired and liabilities assumed. The fair values of intangible assets associated with the acquisition of Bud's Plumbing 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:

NOTE21 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 June 30, 2025* and* December 31, 2024*, 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 thesix months ended* June 30, 2025* and the year ended* December 31, 2024*.

Preferred Stock Private Placements

As further described in Note16, " Redeemable Preferred Stock,":

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KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) June 30, 2025

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 Note16, "Redeemable 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.

Seller Note Payable

As part of the acquisition of Bud's Plumbing on* March 14, 2025,the Company entered into a $1.25 million promissory note, which is recorded as note payable in the consolidated balance sheet the ("KPH Note"), with the seller of Bud's Plumbing to partially finance the acquisition of Bud's Plumbing. The seller is a current employee of Bud's Plumbing. The KPH Note matures on April 1, 2030,*requires monthly payments of principal and interest and has an annual fixed interest rate of 6.00%.

Common Stock Private Placement

As further described in Note17, "Shareholders' Equity", on* June 24, 2025,the Company entered into a Purchase Agreement with certainthird*-parties for aggregate gross proceeds of $15.7 million, resulting from the sale of 1,336,264 shares of its Common Stock in a private placement transaction. Blue Riband Fund LP invested $3.0 million in the Common Stock private placement transaction. Mirabella Financial Services LLP acts as the Investment Manager for Blue Riband Fund LP and is a shareholder known by the Company to be a beneficial owner of more than 5% of the Company’s outstanding common shares.

NOTE22 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 (the "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* through2024, the Company made reimbursement payments to Aegis totaling $1.7 million in connection with the Settlement Agreement. During thethree months ended* June 30, 2025* and* June 30, 2024*, the Company made reimbursement payments to Aegis of $0.6 million and less than $0.1 million, respectively ($0.8 million and less than $0.1 million for thethree andsix months ended* June 30, 2025* and* June 30, 2024*, respectively), in connection with the Settlement Agreement, which is included in general and administrative expenses in the unaudited consolidated statements of operations for thethree andsix months ended* June 30, 2025* and* June 30, 2024*.

The Company's obligation to make reimbursement payments to Aegis terminated on* June 30, 2025.*

(b) Collateral pledged and restricted cash:

Short-term investments with an estimated fair value of $0.2 million at* June 30, 2025* and* December 31, 2024*, were on deposit with state regulatory authorities.

The Company also has restricted cash of $7.4 million and $7.6 million at* June 30, 2025* and* December 31, 2024*, respectively. Included in restricted cash are:

NOTE23 SUBSEQUENT EVENTS

On* July 1, 2025,the Company acquired Roundhouse Electric & Equipment Co., Inc. ("Roundhouse"), a leading provider of industrial-scale electric motor maintenance, repair, testing, and sales solutions, for a purchase price of $22.4 million, plus transaction expenses and a working capital adjustment. The transaction closed on July 1, 2025,*and was funded with $10.3 million in cash on hand and $11.0 million from a senior credit facility.

On* August 1, 2025,the Company acquired 100% of the outstanding equity interests of AAA Flexible Pipe Cleaning Corp. (“Advanced Plumbing and Drain”), a provider of commercial and residential plumbing services for $2.8 million, plus transaction expenses and a working capital adjustment, in cash and a $0.5 million seller note. The Company will also pay additional contingent consideration, only to the extent earned, in an aggregate amount of up to $1.5 million, which is subject to certain conditions, including the successful achievement of certain financial metrics for Advanced Plumbing and Drain during thetwo*-year period following the acquisition date.

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KINGSWAY FINANCIAL SERVICES INC.