KINGSWAY FINANCIAL SERVICES INC

(in thousands, except share data)

KINGSWAY FINANCIAL SERVICES INC.

Consolidated Statements of Operations

(in thousands, except per share data)

KINGSWAY FINANCIAL SERVICES INC.

Consolidated Statements of Comprehensive Loss

(in thousands)

(1) Net of income tax benefit of $0 for the three months ended March 31, 2026 and March 31, 2025.

KINGSWAY FINANCIAL SERVICES INC.

Consolidated Statements of Shareholders' Equity

(in thousands, except share data)

KINGSWAY FINANCIAL SERVICES INC.

Consolidated Statements of Cash Flows

(in thousands)

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) March 31, 2026

NOTE1 BUSINESS

Kingsway Financial Services Inc. (the "Company" or "Kingsway") is a Delaware holding company with operating subsidiaries located in the United States. Kingsway is the only publicly-traded US company employing the Search Fund model to acquire and build great businesses. The Company owns and operates a collection of high-qualityB2B andB2C services companies that are asset-light, growing, and that have recurring revenues. Kingsway seeks to compound long-term shareholder value on a per share basis via its decentralized management model, its talented team of operators, and its tax-advantaged corporate structure.

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 ("2025 Annual Report") for the year ended* December 31, 2025*.

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 the2025 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; valuation of contingent consideration; fair value assumptions for subordinated debt obligations; fair value assumptions for subsidiary stock-based compensation awards; and valuation of redeemable noncontrolling interest.

Certain prior year amounts have been reclassified to conform to current year presentation. At* March 31, 2026,the Company has presented a classified balance sheet. Accordingly, the consolidated balance sheet at December 31, 2025has been reclassified to present current assets and current liabilities separate from noncurrent assets and liabilities and to combine or further disaggregate certain balance sheet line items. In addition, the prior period consolidated statements of operations has been reclassified to combine certain income statement line items and to present a gross profit subtotal. Such reclassifications hadno* impact on previously reported net loss or total assets, liabilities, redeemable preferred stock, redeemable noncontrolling interest or shareholders' equity.

NOTE3 SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES

There have beenno material changes to our significant accounting policies as reported in our2025 Annual Report.

NOTE4 RECENTLY ISSUED ACCOUNTING STANDARDS

(a) Adoption of New Accounting Standards:

Effective* January 1, 2026,the Company adopted ASU2025*-05, Financial Instruments—Credit Losses (Topic326*): Measurement of Credit Losses for Accounts Receivable and Contract Assets* ("ASU2025-05"), which amends the guidance on measuring expected credit losses using a probabilistic method and provides a practical expedient for all entities that simplifies the estimation of expected credit losses for current trade accounts receivable and contract assets arising from revenue transactions. The adoption of ASU2025-05 didnot have an impact on the Company's consolidated financial statements.

(b) Accounting StandardsNot Yet Adopted:

In* October 2023,the Financial Accounting Standards Board ("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.

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 within the footnotes 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.

8

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) March 31, 2026

In* September 2025,the FASB issued ASU2025*-06, Intangibles—Goodwill and Other—Internal-Use Software (Subtopic350*-40): Targeted Improvements to the Accounting for Internal-Use Software*, to modernize the accounting guidance for the costs to develop software for internal use. ASU2025-06 applies to costs incurred to develop or obtain software for internal use and amends the existing standard that refers to various stages of a software development project to align better with current software development methods. Under ASU2025-06, entities will commence capitalizing eligible costs when (i) management has authorized and committed to funding the software project, and (ii) it is probable that the project will be completed and the software will be used to perform the function intended. ASU2025-06 is effective for public business entities for fiscal years beginning after* December 15, 2027,and interim periods within those fiscal years. Early adoption is permitted for any interim period. The Company 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.

In* December 2025,the FASB issued ASU2025*-11, Interim Reporting (Topic270*): Narrow-Scope Improvements* ("ASU2025-11"), which clarifies the scope and application of interim reporting requirements. The amendments enhance guidance on the form and content of interim financial statements, and consolidate required interim disclosures across the Codification, including a new disclosure principle requiring entities to describe events or changes since the last annual reporting period that have a material impact on interim results. ASU2025-11 is effective for interim periods within annual reporting periods beginning after* December 15, 2027.*The Company is currently evaluating the impact of this guidance on its interim consolidated financial statements.

In* December 2025,the FASB issued ASU2025*-12 Codification Improvements ("ASU2025-12"), which includes technical corrections, clarifications, and other minor amendments intended to improve the consistency and usability of the FASB Accounting Standards Codification. The amendments address a variety of topics and arenot intended to change existing accounting conclusions. ASU2025-12 is effective for annual periods beginning after* December 15, 2026,*and interim periods within those fiscal years. The Company is currently evaluating the impact of this guidance on its consolidated financial statements.

**NOTE5 ACQUISITIONS **

During thethree months ended* March 31, 2025*, the Company incurred acquisition expenses related to business combinations of $0.4 million, which are included in selling, general and administrative expenses in the consolidated statements of operations.

The following acquisitions were accounted for as business combinations using the acquisition method of accounting. The purchase price for each acquisition 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. Unless noted otherwise, the purchase accounting for each acquisition is still open and is expected to be completed within theone year window. As such, the 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 goodwill recognized for each acquisition 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.

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 and working capital adjustments. 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.

During thethird quarter of2025, the Company finalized its fair value analysis of the assets acquired and liabilities assumed with the assistance of athird party.

The consolidated statements of operations include the earnings of Bud's Plumbing from the date of acquisition. From the date of acquisition through* March 31, 2025*, Bud's Plumbing earned revenue of $0.3 million and had net income of $0.1 million. The pro forma effects of the Bud's Plumbing acquisition werenot material to the Company's consolidated statements of operations for thethree months ended* March 31, 2025*.

The seller note was due to mature on* April 1, 2030;however, on August 7, 2025,*the seller note was repaid in full to the seller of Bud's Plumbing in exchange for shares of Kingsway common stock.

Roundhouse Electric & Equipment Co., Inc.

On* July**1,* 2025, the Company acquired 100% of the outstanding equity interests of Roundhouse Electric & Equipment Co., Inc. ("Roundhouse") for aggregate consideration consisting of cash and phantom equity awards to the selling stockholders, of approximately $23.5 million, less certain escrowed amounts for purposes of indemnification claims and working capital adjustments. During thefirst quarter of2026 and thefourth quarter of2025, funds that had been held in escrow for the purposes of indemnification claims of less than $0.1 million and $0.8 million, respectively, were released to the Company. The final purchase price was subject to a working capital true-up of less than $0.1 million that was paid to the Company during thefourth quarter of2025. Roundhouse, based in Odessa, Texas, is a provider of industrial-scale electric motor maintenance, repair, testing, and sales solutions primarily to midstream natural gas pipeline operators and utilities across the Permian Basin. As further discussed in Note21, "Segmented Information," Roundhouse is included in the Kingsway Search Xcelerator segment.

9

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) March 31, 2026

AAA Flexible Pipe Cleaning Corporation (d/b/a AAA Advanced Plumbing & Drain)

On* August 1, 2025,the Company (through its newly formed subsidiary, Advanced Plumbing & Drain LLC) acquired substantially all of the assets and certain specified liabilities of AAA Flexible Pipe Cleaning Corporation (d/b/a AAA Advanced Plumbing & Drain, "Advanced Plumbing") for aggregate consideration consisting of cash, a seller note and contingent consideration, of approximately $3.9 million, less certain escrowed amounts for purposes of indemnification claims and working capital adjustments. The final purchase price was subject to a working capital true-up of $0.1 million that was paid to the Company during thefirst* quarter of2026. 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 growth in adjusted EBITDA for Advanced Plumbing during thethree-year period following the acquisition date.

Efficient Plumbing, LLC (d/b/a Southside Plumbing)

On* August 14, 2025,the Company acquired 80% of the outstanding membership interests of Efficient Plumbing, LLC (d/b/a Southside Plumbing, "Southside Plumbing") for aggregate consideration consisting of cash, a seller note and contingent consideration, of approximately $4.7 million, less certain escrowed amounts for purposes of indemnification claims and working capital adjustments. The final purchase price was subject to a working capital true-up of less than $0.1 million that was paid to the Company during thefirst* quarter of2026. The Company will also pay additional contingent consideration, only to the extent earned, in an aggregate amount of up to $1.125 million, which is subject to certain conditions, including growth in adjusted EBITDA for Southside Plumbing during thethree-year period following the acquisition date. The 20% noncontrolling interest in Southside Plumbing is redeemable by the holder of the noncontrolling interest and includes a put option redemption feature that is outside of the Company’s control; therefore, the 20% interest is treated as redeemable noncontrolling interest and is presented outside of permanent equity in the consolidated balance sheets. See Note18, "Redeemable Noncontrolling Interest," for further discussion related to the redeemable noncontrolling interest.

Bud’s Plumbing (Evansville, IN), Advanced Plumbing (Cleveland, OH) and Southside Plumbing (Omaha, NE), provide various plumbing installation, service and repair services to residential and commercial customers. As further discussed in Note21, "Segmented Information," these companies are included in the Kingsway Search Xcelerator segment.

Summary Information

The following table summarizes the purchase price for our acquisitions:

The estimated fair value of the Roundhouse seller phantom equity awards at the acquisition date of $3.3 million was determined based on the economic value of the phantom equity as of the acquisition date, which was derived from the fair value of Roundhouse, net of any debt, and is recorded in accrued expenses and other liabilities in the consolidated balance sheets. See Note22, "Fair Value of Financial Instruments," for further discussion related to the seller phantom equity awards.

The estimated fair value of the Advanced Plumbing and Southside Plumbing contingent consideration obligations at the respective acquisition dates of $0.8 million and $0.2 million, respectively, were determined using a Monte Carlo simulation based on forecasted future results, and are recorded in accrued expenses and other liabilities in the consolidated balance sheets. See Note22, "Fair Value of Financial Instruments," for further discussion related to contingent consideration.

10

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) March 31, 2026

The following table summarizes the allocation of the purchase price and the estimated fair values of the assets acquired and liabilities assumed for our acquisitions:

The fair value of the acquired service fee receivables in the table above are equivalent to their gross contractual amounts.

The fair value of the 20% redeemable noncontrolling interest in Southside Plumbing at the date of acquisition of $0.9 million was estimated by applying a market approach, utilizing a discount rate of 20%.

NOTE6 INVESTMENTS

Investments at* March 31, 2026* and* December 31, 2025* are comprised as follows:

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* March 31, 2026* and* December 31, 2025* are summarized in the tables shown below:

11

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) March 31, 2026

The table below summarizes the Company's fixed maturities at* March 31, 2026* 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* March 31, 2026* and* December 31, 2025*. The tables segregate the holdings based on the period of time the investments have been continuously held in unrealized loss positions.

At* March 31, 2026* and* December 31, 2025*, there are approximately 139 and 124 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* March 31, 2026* and* December 31, 2025*. 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* March 31, 2026* and* December 31, 2025*.

12

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) March 31, 2026

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 the2025 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 limited liability investments or investments in private companies for thethree months ended* March 31, 2026* and* March 31, 2025*.

At* March 31, 2026*, the Company hadno unfunded commitments related to limited liability investments or limited liability investment, at fair value.

For thethree months ended* March 31, 2026* and* March 31, 2025*, the Company didnot record any adjustments to the carrying value of its investments in private companies for observable price changes.

Interest and investment income, net reported in the consolidated statements of operations for thethree months ended* March 31, 2026* and* March 31, 2025* are comprised as follows:

Net investment income included in interest and investment income, net in the table above for thethree months ended* March 31, 2026* and* March 31, 2025* is comprised as follows:

Net realized gains (losses) on investments included in interest and investment income, net in the table above for thethree months ended* March 31, 2026* and* March 31, 2025* are comprised as follows:

Proceeds from sales of available-for-sale fixed maturities were zero for thethree months ended* March 31, 2026* and* March 31, 2025*.

13

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) March 31, 2026

NOTE7 GOODWILL

The following table summarizes the goodwill activity for thethree months ended* March 31, 2026*:

During thethree months ended* March 31, 2026*, the Company recorded goodwill of $0.7 million related to a small asset acquisition, that was accounted for as business combination.

At each of* March 31, 2026* and* December 31, 2025*, 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 months ended* March 31, 2026* and* March 31, 2025*.

NOTE8 INTANGIBLE ASSETS

Intangible assets at* March 31, 2026* and* December 31, 2025* are comprised as follows:

During thethree months ended* March 31, 2026*, the Company acquired intangible assets related to customer relationships of $0.9 million and trade name of $0.1 million, related to an acquisition.

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 $2.2 million and $1.7 million for thethree months ended* March 31, 2026* and* March 31, 2025*, 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.

14

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) March 31, 2026

At* March 31, 2026* and* March 31, 2025*, the Company determined that certain trade names should be further examined under a quantitative approach due to actual revenue coming in lower than previous projections. Based upon these assessments, the Company recorded impairment charges for thethree months ended* March 31, 2026* of $0.2 million related to the SNS trade name, and $0.1 million for thethree months ended* March 31, 2025* related to the Ravix trade name. The fair value of the SNS trade name of $2.0 million at* March 31, 2026* was 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* March 31, 2026* and* December 31, 2025* are comprised as follows:

Depreciation expense was $0.3 million and $0.1 million for thethree months ended* March 31, 2026* and* March 31, 2025*, respectively.

NOTE10 DEBT

Debt consists of the following instruments at* March 31, 2026* and* December 31, 2025*:

All of the KSX and Extended Warranty indebtedness arises from individual, stand-alone credit agreements with the applicable Company subsidiary.None of such indebtedness is guaranteed by the Company or any other subsidiary or affiliate of the Company other than the borrower entity and its direct subsidiary, if any, and there areno cross-collateral, cross-default or similar provisions in the credit agreements.

Term loans are carried in the consolidated balance sheets at their amortized cost, which reflects the monthly or quarterly pay-down of principal, as well as amortization of any debt discount and issuance costs using the effective interest rate method.

15

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) March 31, 2026

The various bank loans contain 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 the respective bank loan agreements that, among other things, restrict the respective borrower’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.

The contractual maturities of the Company's principal debt balances as of* March 31, 2026* were as follows:

(a) Bank loans - KSX:

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. The term loan was due to mature on October**1,* 2027 prior to thefourth amendment of the tern loan on* February 7, 2025 (*see further discussion below).

The Ravix term loan has a carrying value of $8.6 million and $8.3 million as of* March 31, 2026* and* December 31, 2025*, respectively. The Ravix revolver has a carrying value of $0.5 million at* March 31, 2026* and* December 31, 2025*.

Since origination, the Ravix term loan and revolver have been amended as follows:

As a result of thefourth amendment, the Ravix term loan and revolver have an annual interest rate equal to the Prime Rate plus 0.5%. At* March 31, 2026*, the interest rate was 7.25%.

The various amendments to the term loan and revolver werenot deemed to be substantially different than prior to the amendment; therefore, the amendments were accounted for as modifications. The unamortized debt discount and issuance costs from the original Ravix term loan at the* February 7, 2025modification date of $0.1 million were recorded as loss on extinguishment of debt and are included in non-operating other revenue, net in the consolidated statement of operations forthree* months ended* March 31, 2025*, since the original and supplemental term loans were fully repaid as part of the modification.

The Ravix term loan, as amended, is secured by certain of the equity interests and assets of Ravix and CSuite.

SNS

The SNS term loan has a carrying value of $2.4 million and $2.5 million as of* March 31, 2026* and* December 31, 2025*, respectively. The SNS revolver has a carrying value of $1.0 million as of* March 31, 2026* and* December 31, 2025*.

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 March 31, 2026*, the interest rate was 7.25%. The revolver matures on* June 2, 2026and the term loan matures on November 18, 2028.As of December 31, 2025*, the SNS revolver is fully drawn.

16

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) March 31, 2026

The SNS Loan is secured by certain of the equity interests and assets of SNS.

Beginning* March 31, 2024through March 31, 2026*, SNS was in default under the SNS Loan due to debt covenant violations related to the leverage and fixed charge ratios (measured quarterly). In* February 2026,SNS and the lender amended the credit agreement to (1) extend the SNS revolver maturity date to be June 2, 2026;and (2) suspend monthly principal payments beginning February 2026through May 2026,with the next principal payment resuming in June 2026.The Company has entered into an amendment to the SNS Loan that waives the events of default for the fiscal quarter ended March 31, 2026*. 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

The DDI term loan has a carrying value of $4.0 million and $4.2 million as of* March 31, 2026* and* December 31, 2025*, respectively. The DDI revolver has a carrying value of $0.3 million and $0.2 million as of* March 31, 2026* and* December 31, 2025*, respectively.

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 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 March 31, 2026*, the interest rate was 7.25%. The DDI revolver matures on* November 1, 2026and the term loan matures on October 26, 2029.During thethree* months ended* March 31, 2026*, DDI borrowed $0.2 million under the DDI revolver.

The DDI Loan is secured by certain of the equity interests and assets of DDI.

Beginning* September 30, 2025through March 31, 2026*, DDI was in default under the DDI Loan due to a debt covenant violation related to the fixed charge ratio (measured quarterly). The Company has entered into an amendment to the DDI Loan that waives the event of default for the fiscal quarter ended* March 31, 2026*. 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 DDI Loan immediately due and payable, exercise their rights with respect to collateral securing the obligation, and/or exercise any other rights and remedies available.

Image Solutions

The Image Solutions term loan has a carrying value of $6.5 million and $6.7 million as of* March 31, 2026* and* December 31, 2025*, respectively. At* March 31, 2026* and* December 31, 2025*, the balance of the revolver waszero.

As part of the acquisition of Image Solutions, LLC ("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 March 31, 2026*, the interest rate was 7.25%. The revolver matures on* September 26, 2026and the term loan matures on September 26, 2030.*

The Image Solutions Loan is secured by certain of the equity interests and assets of Image Solutions.

Roundhouse

The Roundhouse term loan has a carrying value of $9.9 million and $10.3 million as of* March 31, 2026* and* December 31, 2025*, respectively. At* March 31, 2026* and* December 31, 2025*, the balance of the revolver waszero.

As part of the acquisition of Roundhouse on* July 1, 2025,Roundhouse became a wholly owned subsidiary of Longhorns Acquisition LLC ("Longhorns LLC"), and together they borrowed from a bank a principal amount of $11.0 million in the form of a term loan, and established a $0.5 million revolver to finance the acquisition of Roundhouse (together, the "Roundhouse Loan"). The Roundhouse term loan requires monthly payments of principal and interest and has an annual interest rate equal to the greater of theone*-month term Secured Overnight Financing Rate ("SOFR") plus 3.3%, or 5.0%. At* March 31, 2026*, the interest rate was 7.38%. The Roundhouse term loan and revolver mature on* July 1, 2035.*

The Roundhouse Loan is secured by certain of the equity interests and assets of Roundhouse.

Kingsway Plumbing Holdco LLC ("KPH")

The KPH term loan has a carrying value of $3.6 million as of* March 31, 2026* and* December 31, 2025*. The KPH revolver has a carrying value of $0.4 million as of* March 31, 2026* and* December 31, 2025*.

In2025, the Company formed KPH, whose subsidiaries include Bud's Plumbing, Advanced Plumbing and Southside Plumbing. As part of the acquisition of Southside Plumbing on* August 14, 2025,KPH and its subsidiaries borrowed from a bank a principal amount of $3.75 million in the form of a term loan, and established a $0.5 million revolver (together, the "KPH Loan"). The KPH term loan requires monthly payments of interest and has an annual fixed interest rate of 7.5%. Monthly principal payments on the KPH term loan begin September 14, 2026.The term loan matures on August 14, 2032.The KPH revolver requires monthly payments of interest and has an annual interest rate equal to the greater of the Prime Rate plus 0.75%, or 7.5%. The KPH revolver matures on August 14, 2026.*

The KPH Loan is secured by certain of the equity interests and assets of KPH.

17

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) March 31, 2026

(b) Bank loans - Extended Warranty:

Kingsway Warranty Holdings LLC ("KWH")

The KWH term loan has a carrying value of $10.2 million and $10.8 million as of* March 31, 2026* and* December 31, 2025*, respectively. The KWH delayed draw term loan ("DDTL") has a carrying value of $4.4 million and $4.7 million as of* March 31, 2026* and* December 31, 2025*, respectively. The KWH revolver has a carrying value of $3.0 million and $2.0 million as of* March 31, 2026* and* December 31, 2025*, respectively.

In2019, the Company formed KWH, whose original subsidiaries included 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 KWH term loan and revolver had an annual interest rate equal to SOFR, having a floor of 0.75%, plus spreads ranging from 2.62% to 3.12%, and was to mature on* December 1, 2025.*

Since origination, the KWH term loan and revolver have been amended as follows:

The amendments werenot deemed to be substantially different than prior to the amendments; therefore, the amendments were accounted for as a modification.

The term loan and revolver, as amended, are secured by certain of the equity interests and assets of KWH and its subsidiaries.

(c) Notes payable - KSX:

On* July 1, 2025Roundhouse established a $0.75 million non-revolving equipment line of credit with a bank. On March 4, 2026,Roundhouse borrowed $0.4 million under the equipment line of credit. The Roundhouse equipment loan matures on March 1, 2033,*requires monthly payments of principal and interest and has an annual fixed interest rate of 7.0%.

The following seller notes were entered into during2026 and2025 in connection with various acquisitions which were used to partially finance the respective acquisitions:

(d) Subordinated debt:

On* May 22, 2003,a subsidiary trust of the Company, Kingsway DE Statutory Trust III, 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.

18

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) March 31, 2026

The subordinated debt, or TruPs, is carried in the consolidated balance sheets at fair value. See Note22, "Fair Value of Financial Instruments," for further discussion of the subordinated debt. The portion of the change in fair value of subordinated debt related to the instrument-specific credit risk is recognized in other comprehensive income.

The change in fair value of the Company’s subordinated debt is recorded in the consolidated financial statements for thethree months ended* March 31, 2026* and* March 31, 2025* are as follows:

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.

The following table summarizes the operating lease amounts included in the Company's consolidated balance sheets as of* March 31, 2026* and* December 31, 2025*:

Operating lease costs, variable lease costs and short-term lease costs included in selling, general and administrative expenses for thethree months ended* March 31, 2026* and* March 31, 2025* were as follows:

The annual maturities of lease liabilities as of* March 31, 2026* were as follows:

19

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) March 31, 2026

The weighted-average remaining lease term for our operating leases was 7.31 years and 7.47 years as of* March 31, 2026* and* December 31, 2025*, respectively. The weighted-average discount rate of our operating leases was 6.87% and 6.86% as of* March 31, 2026* and* December 31, 2025*, respectively. Cash paid for amounts included in the measurement of lease liabilities was $0.4 million and $0.2 million for thethree months ended* March 31, 2026* and* March 31, 2025*, 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 revenue, and cost of services, respectively, upon delivery and installation of the equipment to the customer. For thethree months ended* March 31, 2026* and* March 31, 2025*, total revenue recognized from sales-type leases was $0.6 million and $0.3 million, respectively.

NOTE12 OTHER ASSETS AND OTHER LIABILITIES

Other current assets includes accrued investment income, inventory, other receivables and the current portion of deferred contract costs, prepaid expenses and contract asset. Other receivables are recorded net of an allowance of $0.1 million at* March 31, 2026* and* December 31, 2025*.

Other assets includes other investments, lease right of use asset and the noncurrent potion of prepaid expenses and contract asset.

Accrued expenses and other current liabilities includes the following:

Other liabilities, noncurrent includes contingent and phantom liabilities and the noncurrent portion of the lease liability.

NOTE13 REVENUE FROM CONTRACTS WITH CUSTOMERS

Revenue from contracts with customers relates to the Kingsway Search Xcelerator and Extended Warranty segments and includes: business services consulting revenue, healthcare services revenue, software license and support revenue, motor sales and repair service revenue, skilled trades repair and service revenue, vehicle service agreement fees, maintenance support service fees and warranty product commissions, based on terms of various agreements with consumers, businesses and credit unions. Customers either pay in full when consulting, healthcare, software license and support, motor sales and skilled trades services are billed, or at the inception of a warranty contract or commission product sale, 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 months ended* March 31, 2026* and* March 31, 2025*:

20

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) March 31, 2026

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 6.65% to 10.90% 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 revenue includes the revenue from providing outsourced finance and human resources consulting services and information technology managed services. The Company invoices for business services revenue based on contracted rates. Revenue is earned over time as services are provided to the customer.

Healthcare services revenue includes revenue from providing healthcare professional staffing services and outsourced cardiac telemetry services for general acute care, 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 to the customer.

Software license and support revenue includes 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.

Motor sales and repair service revenue include the service fees collected from the sale of new electric motors, in-shop repair and refurbishment of customer-owned electric motors, transformers, switchgear, ancillary parts, and on-site services for customers, including preventative maintenance, infrared scans, VLF cable testing, and vibration analysis for various types of electrical equipment. Motor sales and repair service revenue is earned as motors are delivered to the customer or as repair services are provided to the customer.

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

The Company's revenue recognition policies are further described in Note2(q), "Summary of Significant Accounting Policies - Revenue recognition," to the consolidated financial statements in the2025 Annual Report.

Service fee receivables

Receivables from contracts with customers are reported as service fee receivable, net in the consolidated balance sheets and at* March 31, 2026* and* December 31, 2025* were $16.4 million and $13.8 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* March 31, 2026* and* December 31, 2025* of $1.3 million and $1.1 million, respectively. During thethree months ended* March 31, 2026* and* March 31, 2025*, the Company recorded an increase to its allowance for credit losses of $0.2 million and less than $0.1 million, 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 for each of thethree months ended* March 31, 2026* and* March 31, 2025*.

21

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) March 31, 2026

Contract asset

Contract asset is included in the Company's consolidated balance sheets as of* March 31, 2026* and* December 31, 2025* as follows:

The Company records a contract asset when revenue is recognized prior to billing the customer. Upon billing, which typically occurs over athree tofive year installment period, the value of the contract asset is reversed and service fee receivable is recorded. Changes in the contract asset for thethree months ended* March 31, 2026* were as follows:

The contract asset is reported net of an estimated allowance for credit losses ofzero at* March 31, 2026* and* December 31, 2025*. Contract assets that are deemed to be uncollectible are written off against the allowance for credit losses when identified. During each of thethree months ended* March 31, 2026* and* March 31, 2025*, the Company recorded write-offs to the contract asset for amounts that were deemed to be uncollectible ofzero.

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 thethree months ended* March 31, 2026* were as follows:

Approximately $12.7 million and $13.1 million of revenues from contracts with customers recognized during thethree months ended* March 31, 2026* and* March 31, 2025* was included in deferred service fees as of* December 31, 2025* and* December 31, 2024*, respectively.

Remaining performance obligations

The Company expects to recognize withinone year as revenue approximately 48.2% of theoutstanding performance obligations as of* March 31, 2026*. 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 cost of services in the unaudited consolidated statements of operations. No impairment charges related to deferred contract costs were recorded during thethree months ended* March 31, 2026* and* March 31, 2025*.

The deferred contract costs balances and related amortization expense for thethree months ended* March 31, 2026* and* March 31, 2025* are comprised as follows:

22

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) March 31, 2026

NOTE14 INCOME TAXES

Income tax benefit for thethree months ended* March 31, 2026* and* March 31, 2025* varies from the amount that would result by applying the applicable U.S. federal corporate income tax rate of 21% to loss before income tax benefit. The following table summarizes the differences:

The Company maintains a valuation allowance for its gross deferred tax assets at* March 31, 2026* and* December 31, 2025*. 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 valuation allowance on its* March 31, 2026* and* December 31, 2025* 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 $3.0 million and $3.2 million at* March 31, 2026* and* December 31, 2025*, respectively, that consists of:

As of* March 31, 2026* and* December 31, 2025*, the Company hadno unrecognized tax benefits. The Company classifies interest and penalty accruals, if any, related to unrecognized tax benefits as income tax benefit. The Company recorded income tax expense ofzero related to interest and penalty accruals for thethree months ended* March 31, 2026* and* March 31, 2025*.

NOTE15 LOSS PER SHARE

The following table sets forth the reconciliation of numerators and denominators for the basic and diluted loss pershare computation for thethree months ended* March 31, 2026* and* March 31, 2025*:

23

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) March 31, 2026

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.

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:

NOTE16 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. No new share-based awards were granted during the three months ended* March 31, 2026*.

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 and $0.4 millionfor thethree months ended* March 31, 2026* and* March 31, 2025*, respectively.

NOTE17 REDEEMABLE PREFERRED STOCK

At* March 31, 2026*, the Company hadthree series of redeemable preferred stock ("Preferred Stock") outstanding. 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. For each series of the Preferred Stock outstanding, the holder has the option to convert each share of Preferred Stock into 2.6316 common shares at any time; however, ifnot converted, they are required to be redeemed on certain dates. As such, the Preferred Stock is presented in temporary or mezzanine equity on the consolidated balance sheets.

The following table summarizes the Company's redeemable preferred stock outstanding at* March 31, 2026* and* December 31, 2025*:

The Class B Preferred Stock ranks senior to the Company's common shares. The Class C and Class D Preferred Stock rankspari passuwith the Company’s Class B Preferred Stock and senior to the Company's common shares.

The holders of each series of 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 each series of Preferred Stock are entitled to receive fixed, cumulative, preferential cash dividends at a rate of 8% per share of Preferred Stock per year, payable in equal quarterly installments if declared by the Board of Directors of the Company. Dividends on outstanding shares of each series of Preferred Stock will accrue from day to day commencing on the date of issuance of each such share of Preferred Stock. The cash dividend rate will increase to 18% per share of 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 Preferred Stocknot previously converted into common shares, and which remain outstanding on the conversion date, for the price of $25.00 per share of 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 each series of 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 Preferred Stock submitted for redemption.

24

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) March 31, 2026

Declared dividends to be paid to the holders of the Company's Preferred Stock for thethree months ended* March 31, 2026* and* March 31, 2025* are as follows:

Accrued dividend included in accrued expenses and other current liabilities in the consolidated balance sheets, are $0.3 million at* March 31, 2026* and* December 31, 2025*.

Cash dividends paid during thethree months ended* March 31, 2026* and* March 31, 2025* were $0.3 million and $0.2 million, respectively.

Note18 Redeemable Noncontrolling Interest

Redeemable noncontrolling interest represents a 20% noncontrolling ownership in Southside Plumbing, which was acquired on* August 14, 2025*. Redeemable noncontrolling interest is presented outside of permanent equity in the consolidated balance sheets as it is redeemable by the holder of the noncontrolling interest and the redemption is outside the control of the Company. Shares are redeemable at their fair value on thefifth anniversary of the acquisition of Southside Plumbing. The redeemable noncontrolling interest was initially recorded at fair value at the date of issuance. The Company records the carrying amount of the redeemable noncontrolling interest at the greater of (i) the initial carrying amount, increased or decreased for the noncontrolling interest’s share of net income or loss and its share of other comprehensive income or loss, and dividends or (ii) the redemption value. For interests that are redeemable in the future, the Company recognizes changes in the redemption value immediately as they occur, with an offsetting entry to additional paid-in capital. The redemption amount is estimated based on the fair value of the subsidiary, determined using discounted cash flow methods, which represents a level3 fair value measurement.

Changes in the Company's redeemable noncontrolling interest for thethree months ended* March 31, 2026* were as follows:

NOTE19 Shareholders' Equity

On* March 21, 2023,the Company's Board of Directors approved a security repurchase program under which the Company was 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* months ended* March 31, 2025*, the Company repurchased 42,900 shares of common stock for an aggregate purchase price of $0.3 million, including fees and commissions. The repurchased common stock will be held as treasury stock at cost and has been removed from common shares outstanding at* March 31, 2026* and* December 31, 2025.*

NOTE20 ACCUMULATED OTHER COMPREHENSIVE INCOME (LOSS)

The tables below detail the change in the balance of each component of accumulated other comprehensive income (loss), net oftax, for thethree months ended* March 31, 2026* and* March 31, 2025*, as relates to shareholders' equity attributable to common shareholders on the consolidated balance sheets.

25

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) March 31, 2026

NOTE21 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: Kingsway Search Xcelerator and Extended Warranty.

Kingsway Search Xcelerator Segment

Kingsway Search Xcelerator includes the Company's subsidiaries CSuite, Ravix, SNS, SPI, DDI, Image Solutions, Roundhouse, Bud's Plumbing, Advanced Plumbing and Southside Plumbing (collectively, "KSX").

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, fractional and interim staffing of senior finance professionals, CFO mentoring, board advisory services, and executive search services for permanent placements for its clients throughout the United States.

Ravix provides outsourced financial services and human resources consulting to its clients on a fractional basis for both projects with definitive endpoints and ongoing engagements of indeterminate length 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 globally.

DDI provides outsourced24 hours a day and7 days per week ("24/7") cardiac telemetry services for general acute care, long-term acute care and inpatient rehabilitation hospitals. Outsourcing cardiac monitoring allows 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.

Roundhouse provides industrial-scale electric motor solutions, including field maintenance, in-shop repair, testing, and new motor sales primarily to midstream natural gas pipeline operators and utilities across the Permian Basin.

Kingsway Skilled Trades ("KST") includes Bud's Plumbing, Advanced Plumbing and Southside Plumbing. KST 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 (Bud's Plumbing), Cleveland, Ohio (Advanced Plumbing) and Omaha, Nebraska (Southside Plumbing).

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 subsidiary, The Penn Warranty Corporation ("Penn"). Penn distributes these products in 46 states via independent used car dealerships and franchised car dealerships.

PWI markets, sells and administers vehicle service agreements to used car buyers in 47 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.

26

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) March 31, 2026

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.

Revenues and Operating Income by Reportable Segment

Revenues by reportable segment reconciled to consolidated revenues for thethree months ended* March 31, 2026* and* March 31, 2025* 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 current U.S. conflict with Iran, the degree and pace of inflation and interest rate changes* mayhave impacts on our business and 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 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.

Total segment operating income reconciled to the consolidated net lossfor thethree months ended* March 31, 2026* and* March 31, 2025* is as follows:

27

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) March 31, 2026

NOTE22 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, contingent consideration and seller phantom equity awards 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.

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.

28

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) March 31, 2026

Contingent consideration - The consideration for the Company's acquisitions of Advanced Plumbing and Southside Plumbing 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 other liabilities, noncurrent 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. The contingent consideration liabilities are categorized in Level3 of the fair value hierarchy.

Seller phantom equity awards -In connection with the acquisition of Roundhouse, the Company granted phantom equity awards to the former owners. The seller phantom equity awards are measured and reported at fair value and are included in other liabilities, noncurrent in the consolidated balance sheets. The seller phantom equity awards liability is measured and reported at fair value at the date of grant and is revalued each reporting period. Changes in the fair value of the seller phantom equity awards can result from changes toone or multiple inputs, including adjustments to the discount rates or changes in Roundhouse performance. Any changes in fair value are reported in the consolidated statements of operations. The seller phantom equity awards liability is 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* March 31, 2026* and* December 31, 2025* are as follows.

29

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) March 31, 2026

The following table provides a reconciliation of the fair value of recurring Level3 fair value measurements for thethree months ended* March 31, 2026* and* March 31, 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* March 31, 2026*:

30

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) March 31, 2026

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, 2025*:

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.

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 months ended* March 31, 2026* and* March 31, 2025*.

Assets and LiabilitiesNot Carried at Fair Value

The carrying amounts reported in the consolidated balance sheets approximate fair values for cash and cash equivalents, restricted cash, short-term investments and certain other assets and other liabilities because of their short-term nature. The fair values of the Company's bank loans, which are reported as debt in the consolidated balance sheets, are derived from quoted market prices of industrial bonds with similar maturities and are categorized within Level2 of the fair value hierarchy. The estimated fair value of bank loans was $56.3 million and $57.3 million as of* March 31, 2026* and* December 31, 2025*, respectively.

NOTE23 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 March 31, 2026* and* December 31, 2025*, 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 thethree months ended* March 31, 2026* and the year ended* December 31, 2025*.

Preferred Stock Private Placements

As further described in Note17, " Redeemable Preferred Stock,":

Common Stock Private Placement

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.

31

KINGSWAY FINANCIAL SERVICES INC. Notes to Consolidated Financial Statements (Unaudited) March 31, 2026

NOTE24 COMMITMENTS AND CONTINGENCIES

(a) Collateral pledged and restricted cash:

The Company has restricted cash of $7.8 million and $8.0 million at* March 31, 2026* and* December 31, 2025*, respectively. Included in restricted cash are:

KINGSWAY FINANCIAL SERVICES INC.