KINGSWAY Corp

Index to the Consolidated Financial Statements of

Kingsway Financial Services Inc.

Opinions on the Consolidated Financial Statements and Internal Control Over Financial Reporting

We have audited the accompanying consolidated balance sheets of Kingsway Financial Services Inc. (the “Company”) as of December 31, 2024 and 2023; the related consolidated statements of operations, comprehensive loss, shareholders' equity, and cash flows for each of the years then ended; and the related notes and schedules (collectively referred to as the “financial statements”). We also have audited the Company's internal control over financial reporting as of December 31, 2024 based on criteria established in Internal Control - Integrated Framework (2013) issued by the Committee of Sponsoring Organizations of the Treadway Commission (the “COSO framework”).

In our opinion, the financial statements referred to above present fairly, in all material respects, the financial position of the Company as of December 31, 2024 and 2023 and the results of its operations and its cash flows for each of the years then ended in conformity with accounting principles generally accepted in the United States of America. Also, in our opinion, the Company maintained, in all material respects, effective internal control over financial reporting as of December 31, 2024, based on criteria established in the COSO framework.

Basis for Opinion

The Company's management is responsible for these financial statements; maintaining effective internal control over financial reporting; and its assessment of the effectiveness of internal control over financial reporting, included in the accompanying “Management's Report on Internal Control over Financial Reporting.” Our responsibility is to express an opinion on the Company’s financial statements and an opinion on the Company's internal control over financial reporting based on our audits. We are a public accounting firm registered with the Public Company Accounting Oversight Board (United States) (the “PCAOB”) and are required to be independent with respect to the Company in accordance with U.S. federal securities laws and the applicable rules and regulations of the Securities and Exchange Commission and the PCAOB.

We conducted our audits in accordance with the standards of the PCAOB. Those standards require that we plan and perform the audits to obtain reasonable assurance about whether the financial statements are free of material misstatement, whether due to error or fraud, and whether effective internal control over financial reporting was maintained in all material respects.

Our audits of the financial statements included performing procedures to assess the risks of material misstatement of the financial statements, whether due to error or fraud, and performing procedures that respond to those risks. Such procedures included examining, on a test basis, evidence regarding the amounts and disclosures in the financial statements. Our audits also included evaluating the accounting principles used and significant estimates made by management, as well as evaluating the overall presentation of the financial statements. Our audit of internal control over financial reporting included obtaining an understanding of internal control over financial reporting, assessing the risk that a material weakness exists, and testing and evaluating the design and operating effectiveness of internal control based on the assessed risk. Our audits also included performing such other procedures as we considered necessary in the circumstances. We believe that our audits provide a reasonable basis for our opinion.

Definition and Limitations of Internal Control Over Financial Reporting

A company's internal control over financial reporting is a process designed to provide reasonable assurance regarding the reliability of financial reporting and the preparation of financial statements for external purposes in accordance with generally accepted accounting principles. A company's internal control over financial reporting includes those policies and procedures that (1) pertain to the maintenance of records that, in reasonable detail, accurately and fairly reflect the transactions and dispositions of the assets of the company; (2) provide reasonable assurance that transactions are recorded as necessary to permit preparation of financial statements in accordance with generally accepted accounting principles and that receipts and expenditures of the company are being made only in accordance with authorizations of management and directors of the company; and (3) provide reasonable assurance regarding prevention or timely detection of unauthorized acquisition, use, or disposition of the Company's assets that could have a material effect on the financial statements.

Because of its inherent limitations, internal control over financial reporting may not prevent or detect misstatements. Also, projections of any evaluation of effectiveness to future periods are subject to the risk that controls may become inadequate because of changes in conditions or that the degree of compliance with the policies or procedures may deteriorate.

Critical Audit Matters

The critical audit matters communicated below are matters arising from the current period audit of the financial statements that were communicated or required to be communicated to the audit committee and that (1) relate to accounts or disclosures that are material to the financial statements and (2) involved our especially challenging, subjective, or complex judgments. The communication of critical audit matters does not alter in any way our opinion on the financial statements taken as a whole, and we are not, by communicating the critical audit matters below, providing a separate opinion on the critical audit matters or on the accounts or disclosures to which they relate.

Revenue Recognition - Extended Warranty Segment - Refer to Notes 2 and 14 to the Financial Statements

Critical Audit Matter Description

The Company's revenue from contracts with customers (ASC 606) includes extended warranty service fee and commission income, which is composed of multiple revenue streams, including vehicle service agreement fees, guaranteed asset protection commissions, maintenance support service fees, and warranty product commissions. Accordingly, the application of revenue recognition policies for the extended warranty segment requires the Company to exercise significant judgment in the following areas:

For these reasons, we identified revenue recognition for the extended warranty segment as a critical audit matter, as it involved especially subjective auditor judgment.

How the Critical Audit Matter was Addressed in the Audit

Addressing the matter involved performing procedures and evaluating audit evidence in connection with forming our overall opinion on the financial statements. These procedures included the following, among other procedures:

Indefinite-lived Intangible Asset Impairment Assessment - Certain Trade Name Intangible Assets in the Kingsway Search Xcelerator (KSX) Segment - Refer to Notes 2 and 9 to the Financial Statements

Critical Audit Matter Description

The Company’s indefinite-lived intangible assets consist of trade names with a balance of $16.2 million as of December 31, 2024, of which a portion relates to certain trade name intangibles in the KSX segment. Indefinite-lived intangible assets are tested annually for impairment at November 30, or between annual tests if the Company becomes aware of an event or a change in circumstances that would indicate the carrying value of an asset may be impaired. During 2024, management performed quantitative analyses for the impairment assessment of indefinite-lived intangible assets, which identified impairments. The impairment assessment requires the Company to exercise significant judgment in the following areas:

The principal considerations for our determination that performing procedures relating to impairment assessment of certain KSX segment trade name assets are a critical audit matter are (i) the significant judgment by management when developing the fair value estimate of those trade names; (ii) a high degree of auditor judgment, subjectivity, and effort in performing procedures and evaluating management’s significant assumptions related to projections of future revenue and the selection of discount and royalty rates; and (iii) the audit effort involved the use of professionals with specialized skill and knowledge.

How the Critical Audit Matter was Addressed in the Audit

Addressing the matter involved performing procedures and evaluating audit evidence in connection with forming our overall opinion on the financial statements. These procedures included the following, among other procedures:

/s/Plante & Moran, PLLC

We have served as the Company’s auditor since 2020.

Chicago, Illinois

March 17, 2025

(in thousands, except share data)

(in thousands, except per share data)

Consolidated Statements of Comprehensive Loss

(in thousands)

(1) Net of income tax benefit of $0 and $0 in 2024 and 2023, respectively

Consolidated Statements of Shareholders' Equity

(in thousands, except share data)

(in thousands)

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.

NOTE*2* SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES

The accompanying information in the2024 Annual Report has been prepared in accordance with accounting principles generally accepted in the United States of America ("U.S. GAAP").

The accompanying consolidated financial statements include the accounts of Kingsway and its majority owned and controlled subsidiaries. All significant intercompany accounts and transactions have been eliminated in consolidation.

In addition, the Company evaluates its relationships or investments for consolidation pursuant to authoritative accounting guidance related to the consolidation of a variable interest entity ("VIE") under the Variable Interest Model prescribed by the Financial Accounting Standards Board ("FASB").

The Company’s investments include certain investments, primarily in limited liability companies and limited partnerships in which the Company holds a variable interest. The Company evaluates these investments for the characteristics of a VIE. The Variable Interest Model identifies the characteristics of a VIE to include investments (1) lacking sufficient equity to finance activities without additional subordinated support or (2) in which the holders of equity at risk in the investments lack characteristics of a controlling financial interest, such as the power to direct activities that most significantly impact the legal entity’s economic performance; the obligation to absorb the legal entity’s expected losses; or the right to receive the expected residual returns of the legal entity. The equity investors as a group are considered to lack the power to direct activities that most significantly impact the legal entity’s economic performance when (1) the voting rights of some investors arenot proportional to their obligations to absorb the expected losses of the legal entity or their rights to receive the expected residual returns of the legal entity and (2) substantially all of the activities of the legal entity are conducted on behalf of an investor with disproportionately few voting rights. When evaluating whether an investment lacks characteristics of a controlling financial interest, the Company considers limited liability companies and limited partnerships to lack the power of a controlling financial interest if neither of the following exists: (1) a simple majority or lower threshold of partners or members with equity at risk are able to exercise substantive kick-out rights through voting interest over the general partner(s) or managing member(s) or (2) limited partners with equity at risk are able to exercise substantive participating rights over the general partner(s) or managing member(s).

If the characteristics of a VIE are met, the Company evaluates whether it meets the primary beneficiary criteria. The primary beneficiary is considered to be the entity holding a variable interest that has the power to direct activities that most significantly impact the economic performance of the VIE; the obligation to absorb losses of the VIE; or the right to receive benefits from the VIE that could potentially be significant to the VIE. In instances where the Company is considered to be the primary beneficiary, the Company consolidates the VIE. When the Company isnot considered to be the primary beneficiary of the VIE, the VIE isnot consolidated and the Company uses the equity method to account for the investment. Under this method, the carrying value is generally the Company’s share of the net asset value of the unconsolidated entity, and changes in the Company’s share of the net asset value are recorded in net investment income.

Subsidiaries

The Company's consolidated financial statements include the assets, liabilities, shareholders' equity, revenues, expenses and cash flows of the holding company and its subsidiaries and have been prepared in accordance with U.S. GAAP. A subsidiary is an entity controlled, directly or indirectly, through ownership of more than50% of the outstanding voting rights, or where the Company has the power to govern the financial and operating policies so as to obtain benefits from its activities. Assessment of control is based on the substance of the relationship between the Company and the entity and includes consideration of both existing voting rights and, if applicable, potential voting rights that are currently exercisable and convertible. The operating results of subsidiaries that have been disposed are included up to the date control ceased, and any difference between the fair value of the consideration received and the carrying value of a subsidiary that has been disposed is recognized in the consolidated statements of operations. All intercompany balances and transactions are eliminated in full.

44

The consolidated financial statements are prepared as of* December 31, 2024* based on individual company financial statements at the same date, or in the case of certain limited liability companies that are consolidated, on athree-month lag basis. Accounting policies of subsidiaries have been aligned where necessary to ensure consistency with those of Kingsway.

The Company's subsidiary, Argo Holdings Fund I, LLC ("Argo Holdings"), meets the definition of an investment company and follows the accounting and reporting guidance in Financial Accounting Standards Codification Topic946, Financial Services-Investment Companies.

Noncontrolling interests

The Company has noncontrolling interests attributable to certain of its subsidiaries. A noncontrolling interest arises where the Company owns less than100% of the voting rights and economic interests in a subsidiary. A noncontrolling interest is initially recognized at the proportionate share of the identifiable net assets of the subsidiary at the acquisition date and is subsequently adjusted for the noncontrolling interest's share of the acquiree's net income (loss) and changes in capital. The effects of transactions with noncontrolling interests are recorded in shareholders' equity where there isno change of control.

On* July 25, 2024,the Company completed the purchase of the 10% interest in its subsidiary, IWS Acquisition Corporation ("IWS"),not previously owned by the Company. Therefore, as of July 25,*2024, IWS became a wholly-owned subsidiary of the Company.

During thethird quarter of2024, the Company's subsidiary, CMC Industries Inc. ("CMC") and its subsidiaries Texas Rail Terminal LLC and TRT Leaseco, LLC ("TRT"), were legally dissolved. As a result, the remaining equity related to CMC and its subsidiaries that was included in noncontrolling interests in consolidated subsidiaries is now included in accumulated deficit in the consolidated balance sheet at* December 31, 2024*.

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 classification 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 consolidated 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.

The Company evaluates acquisitions in accordance with Accounting Standards Codification ("ASC")805, Business Combinations("ASC805"), to determine if a transaction represents an acquisition of a business or an acquisition of assets. The results of acquired subsidiaries are included in the consolidated statements of operations from the date of acquisition.

An acquisition of a business represents a business combination. The acquisition method of accounting is used to account for a business combination. The cost of an acquired business is measured as the fair value of the assets received, equity instruments issued and liabilities incurred or assumed at the date of exchange. Identifiable assets acquired and liabilities and contingent liabilities assumed in a business combination are measured initially at their fair values at the acquisition date, irrespective of the extent of any noncontrolling interest. The excess of the cost of an acquired business over the fair value of the Company's share of the identifiable net assets acquired is recorded as goodwill. If the cost of acquired business is less than the fair value of the net assets of the subsidiary acquired, the difference is recognized in the consolidated statements of operations. Noncontrolling interests in the net assets of consolidated entities are reported separately in shareholders' equity and initially measured at fair value. Acquisition costs related to a business combination are expensed as incurred.

45

When an acquisition doesnot meet the definition of a business combination either because: (i) substantially all of the fair value of the gross assets acquired is concentrated in a single identifiable asset, or group of similar identified assets, or (ii) the acquired entity doesnot have an input and a substantive process that together significantly contribute to the ability to create outputs, the Company accounts for the acquisition as an asset acquisition. In an asset acquisition, goodwill isnot recognized. Any excess of the total purchase price plus transaction costs over the fair value of the net assets acquired is allocated on a relative fair value basis to the identifiable net assets at the acquisition date.

Investments in fixed maturities are classified as available-for-sale and reported at fair value. Unrealized gains and losses are included in accumulated other comprehensive loss, net of tax.

Equity investments include common stocks and are reported at fair value. Changes in fair value of equity investments are reco gnized in net (loss) income.

Limited liability investments include investments in limited liability companies and limited partnerships in which the Company's interests 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. 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.

Limited liability investment, at fair value is accounted for at fair value with changes in fair value included in gain on change in fair value of limited liability investments, at fair value. The difference between the end of the reporting period of the limited liability investment, at fair value and that of the Company isno more thanthree months.

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. These investments donot have readily determinable fair values and, therefore, are reported at cost, adjusted for observable price changes and impairments. Changes in carrying value are included in net change in unrealized gain on private company investments.

Other investments include collateral loans and are reported at their unpaid principal balance, net of an allowance for credit losses, which approximates fair value.

Short-term investments, which consist of investments with original maturities betweenthree months andone year, are reported at cost, which approximates fair value.

Realized gains and losses on sales, determined on afirst-infirst-out basis, are included in net realized gains.

Dividends and interest income are included in net investment income. Investment income is recorded as it accrues.

The Company accounts for all financial instruments using trade date accounting.

The Company conducts a quarterly review to identify and evaluate investments that show objective indications of possible impairment. Impairment is charged to the consolidated statements of operations if the fair value of an instrument falls below its cost or amortized cost.

When an available-for-sale fixed maturity investment is impaired, it is evaluated to determine whether there is an intent to sell the investment before recovery of amortized cost or whether a credit loss exists.

For fixed maturity investments that the Company intends to sell or for which it is more likely thannot that the Company will be required to sell before an anticipated recovery of value, the full amount of the impairment is recognized as an impairment loss in the consolidated statements of operations. The investment’s amortized cost is written down to its fair value and isnot adjusted for any subsequent recoveries.

For fixed maturity investments that the Company doesnot intend to sell or for which it is more likely thannot that the Company willnot be required to sell before an anticipated recovery of value, the Company evaluates whether a decline in fair value below the amortized cost basis has occurred from a credit loss or other non-credit related factors.

Considerations in the credit loss assessment include (1) extent to which the fair value has been less than amortized cost, (2) conditions related to the investment, an industry, or a geographic area, (3) payment structure of the investment and the likelihood of the issuer's ability to make contractual cash flows, (4) defaults or other collectability concerns related to the issuer, (5) changes in the ratings assigned by a rating agency and (6) other credit enhancements that affect the investment’s expected performance.

46

If a credit loss exists, an allowance is established, which is equal to the difference between the present value of cash flows expected to be collected and the amortized cost basis. The expected allowance for credit losses is limited by the amount that the fair value is less than the amortized cost basis and is adjusted in subsequent periods for any additional expected credit losses or subsequent recoveries. Changes in the allowance are reported as impairment losses in the consolidated statements of operations. The amortized cost basis of the investment isnot adjusted for the expected allowance for credit loss. The impairment related to other non-credit related factors is reported in other comprehensive (loss) income.

The Company reports accrued investment income separately for available-for-sale fixed maturity investments and has made a policy election tonot measure an allowance for credit losses on accrued investment income. Accrued investment income is written off against net investment income at the time the issuer of the bond defaults or is expected to default on interest payments.

Cash and cash equivalents include cash and investments with original maturities ofno more thanthree months when purchased that are readily convertible into cash.

Restricted cash represents certain cash and cash equivalent balances restricted as to withdrawal or use. The Company's restricted cash is comprised primarily of cash held for the payment of vehicle service agreement claims under the terms of certain contractual agreements, funds held in escrow, statutory deposits and amounts pledged tothird-parties as deposits or to collateralize liabilities.

Service fee receivable includes balances due and uncollected from customers. Service fee receivable is reported net of an estimated allowance for credit losses. The Company recognizes credit losses based on a forward-looking current expected credit losses. The Company estimates expected credit losses based upon its assessment of various factors, including historical collection experience, the age of service fee receivable balances, credit quality of its customers, current economic conditions, management’s experience, reasonable and supportable forecasts of future economic conditions, and other factors that* may*affect its ability to collect from customers. Expected credit losses are recorded as general and administrative expenses in the consolidated statements of operations. Amounts are written off against the allowance when determined to be uncollectible. Write-offs are applied as a reduction to the allowance for credit losses and any recoveries of previous write-offs are netted against bad debt expense in the period recovered.

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 are recorded in commissions and cost of services sold, respectively, in the consolidated statements of operations. Changes in estimates, if any, are recorded in the accounting period in which they are determined.

Property and equipment are reported in the consolidated financial statements at cost. Depreciation of property and equipment has been provided using the straight-line method over the estimated useful lives of such assets. Repairs and maintenance are recognized in operations during the period incurred. The Company estimates useful life to bethree toten years for leasehold improvements; three toseven years for furniture and equipment; three toseven years for computer hardware; five years for medical equipment; andfive years for vehicles.

Inventory, which is included in other assets in the consolidated balance sheet, consists of printer and computer equipment, parts, supplies and software with a total value of $0.7 million at* December 31, 2024*. The Company didnot have inventory prior to the acquisition of Image Solutions, LLC on* September 26, 2024.Inventory is stated at the lower of cost or net realizable value and includes the product cost, inbound freight and warehousing costs, where applicable, and is maintained on thefirst*-in,first-out method. The Company regularly reviews inventory quantities on hand, future purchase commitments with suppliers and the estimated utility of inventory. An assessment is made periodically to determine what slow-moving inventory items, if any, should be deemed obsolete and written down to their estimated net realizable value.

When the Company acquires a subsidiary or other business where it exerts significant influence, the fair value of the net tangible and intangible assets acquired is determined and compared to the amount paid for the subsidiary or business acquired. Any excess of the amount paid over the fair value of those net assets is considered to be goodwill.

47

Goodwill is tested 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. Any excess of a reporting unit's carrying value over its fair value is recognized as an impairment loss in the consolidated statements of operations in the period in which the impairment is determined.

When the Company acquires a subsidiary or other business where it exerts significant influence or acquires certain assets, intangible assets* maybe acquired, which are recorded at their fair value at the time of the acquisition. An intangible asset with a definite useful life is amortized in the consolidated statements of operations over its estimated useful life. The Company writes down the value of an intangible asset with a definite useful life when the undiscounted cash flows arenot* expected to allow for full recovery of the carrying value.

Intangible assets with indefinite useful lives arenot subject to amortization and are tested for impairment annually as of* November 30,or more frequently if events or circumstances indicate that the carrying value may**not* be recoverable, to ensure that fair values are greater than or equal to carrying values. Any excess of carrying value over fair value is charged to the consolidated statements of operations in the period in which the impairment is determined. 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.

Derivative financial instruments included an interest rate swap contact and the trust preferred debt repurchase options. The Company measures derivative financial instruments at fair value. The fair value of derivative financial instruments is required to be revalued each reporting period, with corresponding changes in fair value recorded in the consolidated statements of operations. Realized gains or losses are recognized upon settlement of the contracts. Refer to Note11, "Derivatives," for further information.

The Company entered into a pay fixed, receive variable interest rate swap contract to reduce its exposure to changes in interest rates. The interest rate swap contract was included in other assets in the consolidated balance sheet at* December 31, 2023.The Company hadnot* elected hedge accounting for the interest rate swap, therefore changes in fair value were recorded in current period earnings and included in interest expense in the consolidated statements of operations. On* February**29,* 2024, the interest rate swap matured and the Company didnot enter into any additional interest rate swap agreement upon its expiration.

During thethird quarter of2022, the Company entered intothree trust preferred debt repurchase option agreements. Changes in fair value were included in loss on change in fair value of derivative asset option contracts in the consolidated statement of operations. The Company exercised the repurchase options during thefirst quarter of2023.

Bank loans are reported in the consolidated balance sheets at par value adjusted for unamortized discount or premium and unamortized issuance costs. Discounts, premiums, and costs directly related to the issuance of debt are capitalized and amortized through the maturity date of the debt using the effective interest rate method and are recorded in interest expense in the consolidated statements of operations. Gains and losses on the extinguishment of debt are recorded in (loss) gain on extinguishment of debt.

The Company's subordinated debt is measured and reported at fair value. 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 portion of the change in fair value of subordinated debt related to the instrument-specific credit risk is recognized inother comprehensive income (loss).

The consideration for certain of the Company's acquisitions include future payments to 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 at the date of acquisition and are included in accrued expenses and other liabilities in the consolidated balance sheets. 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. These fair value measurements are based on significant inputsnot observable in the market. Changes in assumptions could have an impact on the payout of contingent consideration liabilities. Changes in fair value are reported in the consolidated statements of operations as non-operating other revenue (expense).

The Company follows the asset and liability method of accounting for income taxes, whereby deferred income tax assets and liabilities are recognized for (i) the differences between the financial statement carrying amount of existing assets and liabilities and their respective tax bases and (ii) loss and tax credit carryforwards. Deferred income tax assets and liabilities are measured using enacted tax rates expected to apply to taxable income in the years in which those temporary differences are expected to be recovered or settled. The effect on deferred tax assets and liabilities of a change in tax rates is recognized in income in the period that includes the date of enactment. Future tax benefits are recognized to the extent that realization of such benefits is more likely thannot and a valuation allowance is established for any portion of a deferred tax asset that management believes willnot be realized. Current federal income taxes are charged or credited to operations based upon amounts estimated to be payable or recoverable as a result of taxable operations for the current year. The Company accounts for uncertain tax positions in accordance with the income tax accounting guidance. The Company recognizes interest and penalties, if any, related to unrecognized tax benefits in income tax expense (benefit).

48

The Company records a right of use asset and lease liability for all leases in which the estimated term exceedstwelve months. The Company treats contracts as a lease when the contract: (1) conveys the right to use a physically distinct property or equipment asset for a period of time in exchange for consideration, (2) the Company directs the use of the asset and (3) the Company obtains substantially all the economic benefits of the asset. Right-of-use assets and lease liabilities are measured and recognized based on the present value of the future minimum lease payments over the lease term at the commencement date. As the Company’s leases are office leases, the Company is unable to determine an implicit rate; therefore, the Company uses its incremental borrowing rate based on the information available at the lease commencement date in determining the present value of future payments for those leases. The Company includes options to extend or terminate the lease in the measurement of the right-of-use asset and lease liability when it is reasonably certain that such options will be exercised. Lease expense for minimum lease payments is recognized on a straight-line basis over the lease term.

The Company determines lease classification at the commencement date. Leasesnot classified as sales-type (lessor) or financing leases (lessor and lessee) are classified as operating leases. The primary accounting criteria the Company uses that results in operating lease classification are: (a) the lease doesnot transfer ownership of the underlying asset to the lessee by the end of the lease term, (b) the lease doesnot grant the lessee a purchase option that the lessee is reasonably certain to exercise, (c) using aseventy-five percent or more threshold in addition to other qualitative factors, the lease term isnot for a major part of the remaining economic life of the underlying asset and, (d) using aninety percent or more threshold in addition to other qualitative factors, the present value of the sum of the lease payments and residual value guarantee from the lessee, if any, doesnot equal or substantially exceed the fair value of the underlying asset.

As an accounting policy, the Company has electednot to apply the recognition requirements in ASC842 to short-term leases (generally those with terms oftwelve months or less). Instead, the Company recognizes the lease payments as expense on a straight-line basis over the lease term and any variable lease payments in the period in which the obligation for those payments is incurred.

Rental expense for operating leases is recognized on a straight-line basis over the lease term, net of any applicable lease incentive amortization.

The Company accounts for its redeemable preferred stock in accordance with the guidance in Accounting Standards Codification (“ASC”) Topic480, Distinguishing Liabilities from Equity. The Company measures its redeemable preferred stock at its current redemption value plus dividendsnot currently declared or paid but which will be payable upon redemption. Redeemable preferred stock with redemption featuresnot solely within the control of the issuer are presented in temporary or mezzanine equity in the consolidated balance sheets.

Service fee and commission revenue and contract balances

Service fee and commission revenue represents vehicle service agreement fees, guaranteed asset protection products ("GAP") commissions, maintenance support service fees, warranty product commissions, business services consulting revenue, healthcare services revenue and software license and support revenue based on terms of various agreements with credit unions, consumers and businesses. Customers either pay in full at the inception of a warranty contract or commission product sale, or when consulting, healthcare and software license and support services are billed, or on terms subject to the Company’s customary credit reviews.

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* maybe 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 averaged5.83%* to12.00% 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 revenue includes 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 to the customer.

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

49

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. The Company recognizes the portion of the transaction price allocated to the software license on a residual basis. The residual basis is used to allocate revenue when the contract arrangement includes a software license and has at leastone performance obligation for which the stand-alone selling price ("SASP") is observable, such as the software support services. The residual method is used as the selling price for software licenses in circumstances when the transaction price is highly variable and the SASP isnot discernable from past transactions or other observable evidence. The Company evaluates the residual approach estimate compared to all available observable data in order to conclude the estimate is representative of its SASP. Software support revenue is recognized ratably over the contract period as services are rendered. The SASP of software support is consistent with the stand-alone pricing of subsequent software support renewals. 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.

Contract balances

The timing of revenue recognition* maydiffer from the timing of billing and cash receipts from customers. A contract asset is established for revenue that is recognized prior to billing the customer and is included in other assets in the consolidated balance sheets. 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. When payment is made prior to satisfaction of performance obligations, a contract liability is established which is recorded as deferred service fees in the consolidated balance sheets. If the satisfaction of the performance obligation occurs over time, the contract liability is reversed over the contract term, as the services are provided to the customer. If the satisfaction of the performance obligation is at a point in time, the contract liability reverses upon delivery to the customer.

The Company uses the fair-value method of accounting for stock-based compensation awards granted to employees. Expense is recognized on a straight-line basis over the requisite service period during which awards are expected to vest, with a corresponding increase to either additional paid-in capital for equity-classified awards or to a liability for liability-classified awards. Liability-classified awards, included in accrued expenses and other liabilities in the consolidated balance sheets, are measured and reported at fair value on the date of grant and are remeasured each reporting period. Compensation expense related to the change in fair value for liability-classified awards is reported in the consolidated statements of operations as general and administrative expenses. For awards with a graded vesting schedule, expense is recognized on a straight-line basis over the requisite service period for each separately vesting portion of the award. For awards subject to a performance condition, expense is recognized when the performance condition has been satisfied or is probable of being satisfied. For awards subject to a market condition, compensation expense is recognized on a straight-line basis regardless of whether the market condition is satisfied, provided that the requisite service has been provided. Forfeitures are recognized in the period that the award is forfeited.

The fair values of the Company's investments in fixed maturities and equity investments, limited liability investment, at fair value, subordinated debt, derivative financial instruments and contingent considerationare estimated using a fair value hierarchy to categorize the inputs it uses in valuation techniques. Fair values for other investments approximate their unpaid principal balance. 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.

NOTE3 RECENTLY ISSUED ACCOUNTING STANDARDS

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

50

In* November 2023,the FASB issued ASUNo.* 2023-07, Improvements to Reportable Segment Disclosures(“ASU2023-07”), which improves reportable segment disclosure requirements, primarily through enhanced disclosures about significant segment expenses. In addition, the amendments enhance interim disclosure requirements, clarify circumstances in which an entity can disclose multiple segment measures of profit or loss, provide new segment disclosure requirements for entities with a single reportable segment, and contain other disclosure requirements. The purpose of the amendments is to enable investors to better understand an entity’s overall performance and assess potential future cash flows. ASU2023-07 is effective for public companies with annual periods beginning after* December 15, 2023,and interim periods within annual period beginning after December 15, 2024.The Company adopted ASU2023*-07 on a retrospective basis for the year ended* December 31, 2024,which resulted in additional disclosures in our segment footnote, primarily related to significant segment expenses that are regularly provided to the chief operating decision maker and included within our reported measure of segment profit or loss. Refer to Note22*, "Segmented Information." for these additional disclosures.

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 with annual periods beginning after* December 15, 2024,*with early adoption permitted. The Company is currently evaluating the impact the adoption of this standard will have on its consolidated financial statements.

In* October 2023,the FASB issued ASU2023*-06, Disclosure Improvements: Codification Amendments in Response to the SEC’s Disclosure Update and Simplification Initiative* ("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* March 2024,the FASB issued ASU2024*-02, Codification Improvements - Amendments to Remove References to the Concepts Statements ("ASU2024-02"). ASU2024-02 amends the Codification to remove references to various concepts statements and impacts a variety of topics in the Codification. The amendments apply to all reporting entities within the scope of the affected accounting guidance, but in most instances the references removed are extraneous andnot required to understand or apply the guidance. Generally, the amendments in ASU2024-02 arenot intended to result in significant accounting changes for most entities. ASU2024-02 is effective* January 1, 2025.The Company doesnot* expect ASU2024-02 to have a significant impact on its consolidated financial statements.

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.

NOTE4 ACQUISITIONS

During the years ended* December 31, 2024and December 31, 2023*, the Company incurred acquisition expenses related to business combinationsof$0.5 million and$0.7 million, respectively, which are included in general and administrative expenses in the consolidated statements of operations.

51

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 Note22*, "Segmented Information," Image Solutions is included in the Kingsway Search Xcelerator segment. This acquisition was the Company’ssixth acquisition under its novel CEO Accelerator program and further expands the Company’s portfolio of businesses with recurring revenue and low capital intensity.

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

Refer to Note9, "Intangible Assets," for further disclosure of the intangible assets related to this acquisition. The goodwill of $6.5 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. The consolidated statements of operations include the earnings of Image Solutions from the date of acquisition. From the date of acquisition through* December 31, 2024*, Image Solutions earned revenue of $2.5 million and had a net loss of $0.1 million.

Systems Products International, Inc.

On* September 7, 2023,the Company acquired 100% of the outstanding equity interests of Systems Products International, Inc. ("SPI") for aggregate cash consideration of $2.8 million, less certain escrowed amounts for purposes of indemnification claims and working capital adjustments. SPI, based in Miami, Florida, is a vertical market software company, created exclusively to serve the management needs of all types of shared-ownership properties. As further discussed in Note22*, "Segmented Information," SPI is included in the Kingsway Search Xcelerator segment. This acquisition was the Company’sfourth acquisition under its novel CEO Accelerator program and itsfirst in the vertical market software space and further expands the Company’s portfolio of businesses with recurring revenue and low capital intensity.

52

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

The Company records measurement period adjustments in the period in which the adjustments occur. During thesecond quarter of2024, the Company recorded measurement period adjustments that increased goodwill by $0.3 million compared to the amount recorded at* December**31,* 2023. The measurement period adjustment primarily reflects changes in the estimated value of the contract asset of $0.3 million.

Refer to Note9, "Intangible Assets," for further disclosure of the intangible assets related to this acquisition. The final goodwill recorded of$0.4 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 allocation of the SPI purchase price and the estimated fair values of the assets acquired and liabilities assumed at the date of acquisition:

The consolidated statements of operations include the earnings of SPI from the date of acquisition. From the date of acquisition through* December 31, 2023*, SPI earned revenue of $0.8 million and had a net income of$0.4 million.

Digital Diagnostics Imaging, Inc.

On* October 26, 2023,the Company acquired 100% of the outstanding equity interests of Digital Diagnostics Imaging, Inc. ("DDI") for aggregate cash consideration of approximately $11.0 million, less certain escrowed amounts for purposes of indemnification claims. The final purchase price was subject to a working capital true-up of less than $0.1 million that was settled during thesecond* quarter of2024. DDI, based in Wall, New Jersey, is a provider of fully managed outsourced cardiac telemetry services. As further discussed in Note22, "Segmented Information," DDI is included in the Kingsway Search Xcelerator segment. This acquisition was the Company’sfifth acquisition under its novel CEO Accelerator program and further expands the Company’s portfolio of businesses with recurring revenue and low capital intensity.

This acquisition was accounted for as a business combination using the acquisition method of accounting. The purchase price was provisionally allocated to the assets acquired and liabilities assumed based on their estimated fair values at the date of acquisition and are subject to adjustment during a measurement period subsequent to the acquisition date,not to exceedone year as permitted under U.S. GAAP.

During thesecond quarter of2024, the Company finalized its fair value analysis of the assets acquired and liabilities assumed with the assistance of athird party.

The Company records measurement period adjustments in the period in which the adjustments occur. During thesecond quarter of2024, the Company recorded a measurement period adjustment that increased goodwill by $0.2 million compared to the amount recorded at* December* 31, 2023. The measurement period adjustments primarily relate to a decrease in the estimated fair value of property and equipment of $0.4 million, partially offset by an increase to the customer relationships intangible asset of $0.2 million.

Refer to Note9 , " Intangible Assets," for further disclosure of the intangible assets related to this acquisition. The final goodwill recorded of $4.9 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.

53

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

The consolidated statements of operations include the earnings of DDI from the date of acquisition. From the date of acquisition through* December 31, 2023*, DDI earned revenue of$0.9 million and had net income of$1.5 million, primarily related to a tax benefit recognized for the partial release of the Company’s deferred tax valuation allowance related to the acquired deferred tax liabilities.

Unaudited Pro Forma Summary

The following unaudited pro forma summary presents the Company's consolidated financial statements for the years ended* December 31, 2024and December 31, 2023* as if Image Solutions and DDI had been acquired on* January 1of the year prior to the acquisitions. The pro forma summary is presented for illustrative purposes only and doesnot* purport to represent the results of our operations that would have actually occurred had the acquisitions occurred as of the beginning of the period presented or project our results of operations as of any future date or for any future period, as applicable. The pro forma results primarily include purchase accounting adjustments related to the acquisitions of Image Solutions and DDI, interest expense and the amortization of debt issuance costs and discounts associated with the related financing obtained in connection with the Image Solutions and DDI acquisitions (see Note12, "Debt"), tax related adjustments and acqui sition-related expenses. The pro forma effects of the SPI acquisition werenot material to the Company’s consolidated statements of operations for the year ended* December 31, 2023*.

NOTE5 DISPOSAL AND DISCONTINUED OPERATIONS

On* July 29, 2022,the Company sold Professional Warranty Service Corporation ("PWSC"), an 80% majority-owned, indirect subsidiary of the Company. The purchase price was subject to customary adjustments for net working capital. During the year ended December 31, 2023*, the Company recorded an additional gain on disposal of PWSC of $0.3 million related to working capital adjustments and release of escrowed amounts withheld for purposes of indemnification claims.

Leased Real Estate Segment

The Company’s subsidiaries, VA Lafayette, LLC ("VA Lafayette") and CMC, which included CMC’s subsidiaries Texas Rail Terminal LLC and 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*.*

54

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

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 Note24*, "Related Parties," for further disclosure. The purchase price paid by the purchaser at the closing consisted of $1.3 million in cash plus the assumption of the unpaid principal balance, as of the closing, of the LA Mortgage of approximately $11.8 million, netting cash proceeds of $1.1 million to Kingsway after expenses.

During thethird quarter of2024, the Company recognized a loss on disposal of $0.2 million, which is included in loss on disposal of discontinued operations, net of taxes in the consolidated statements of operations for the year ended* December 31, 2024*. As part of recognizing the business as held for sale, the Company was required to measure VA Lafayette at the lower of its carrying amount or fair value less cost to sell. As a result of this analysis, during thefirst quarter of2024 and thefourth quarter of2023, the Company recognized an estimated non-cash, loss on disposal of $0.4 million and $2.0 million, respectively, which is included in loss on disposal of discontinued operations, net of taxes in the consolidated statements of operations for the years ended* December 31, 2024* and* December 31, 2023*, respectively. The losses are a result of adjusting the net carrying value of VA Lafayette to be equal to the estimated selling price and were 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 consolidated statements of operations for the years ended* December 31, 2024and December 31, 2023* is presented below:

For the years ended* December 31, 2024and December 31, 2023*, all of the pre-tax income from discontinued operations disclosed in the table above is attributable to the controlling interest.

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

Loss on disposal of discontinued operations, net of taxes, related to Leased Real Estate, in the consolidated statements of operations for the years ended* December 31, 2024and December 31, 2023* is comprised of the following:

55

NOTE6 VARIABLE INTEREST ENTITIES

Argo Holdings Fund I, LLC

The Company holds a 43.4% investment in Argo Holdings at* December 31, 2024and December 31, 2023*. Argo Holdings makes investments, primarily in established lower middle market companies based in North America, through investments in search funds. The managing member of Argo Holdings is Argo Management Group, LLC ("Argo Management"), a wholly owned subsidiary of the Company. Argo Holdings is considered to be a VIE as the members holding equity at risk lack characteristics of a controlling financial interest. The Company holds a variable interest in Argo Holdings due to its right to absorb significant economics in Argo Holdings and through its controlling interest in Argo Management, through which the Company holds the power to direct the significant activities of Argo Holdings. As such, the Company was the primary beneficiary of Argo Holdings and consolidated Argo Holdings at* December 31, 2024and December 31, 2023*.

The following table summarizes the assets and liabilities related to the VIE consolidated by the Company at* December 31, 2024and December 31, 2023*:

No arrangements exist requiring the Company to provide additional funding to the consolidated VIE in excess of the Company’s unfunded commitments to its consolidated VIE. At* December 31, 2024and December 31, 2023*, the Company hadno unfunded commitments. There areno restrictions on assets consolidated by the VIE. There areno structured settlements of liabilities consolidated by the VIE. Creditors haveno recourse to the general credit of the Company as the primary beneficiary of the VIE.

The Company’s investments include certain non-consolidated investments, primarily in limited liability companies and limited partnerships in which the Company holds variable interests, that are considered VIEs due to the legal entities holding insufficient equity; the holders of equity at risk in the legal entities lacking controlling financial interests; and/or the holders of equity at risk having non-proportional voting rights.

The Company’s risk of loss associated with its non-consolidated VIEs is limited and depends on the investment. Limited liability investments accounted for under the equity method are limited to the Company’s initial investments. At* December 31, 2024and December 31, 2023*, the Company hadno unfunded commitments to its non-consolidated VIEs.

The following table summarizes the carrying value and maximum loss exposure of the Company’s non-consolidated VIEs at* December 31, 2024and December 31, 2023*:

The following table summarizes the Company’s non-consolidated VIEs by category at* December 31, 2024and December 31, 2023*:

56

The following table presents aggregated summarized financial information of the Company’s non-consolidated VIEs at* December 31, 2024and December 31, 2023*. For certain of the non-consolidated VIEs, the financial information is presented on a lag basis, consistent with how the changes in the Company’s share of the net asset values of these equity method investees are recorded in net investment income. The difference between the end of the reporting period of an equity method investee and that of the Company is typicallyno more thanthree months.

NOTE7 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* December 31, 2024and December 31, 2023* are summarized in the tables shown below:

The table below summarizes the Company's fixed maturities at* December 31, 2024* by contractual maturity periods. Actual results* maydiffer as issuers may*have the right to call or prepay obligations, with or without penalties, prior to the contractual maturity of these obligations.

57

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 has been established as of* December 31, 2024and December 31, 2023*. The tables segregate the holdings based on the period of time the investments have been continuously held in unrealized loss positions.

At* December 31, 2024* and* December 31, 2023*, there are approximately 191 and 181 individual available-for-sale investments, respectively, that were in unrealized loss positions, for which an allowance for credit losses hadnot 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* December 31, 2024* and* December 31, 2023*. The Company considers many factors in evaluating whether the unrealized losses were credit-related, including, butnot limited to, the extent to which the fair value has been less than amortized cost, conditions related to the security, industry, or geographic area, payment structure of the investment and the likelihood of the issuer’s ability to make contractual cashflows, defaults or other collectability concerns related to the issuer, changes in the ratings assigned by a rating agency, and other credit enhancements that affect the investment’s expected performance. The Company determined that the unrealized losses on the fixed maturity investments were due to non-credit related factors at* December 31, 2024* and* December 31, 2023*.

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 & Analysis 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 the years ended* December 31, 2024and December 31, 2023*.

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

As of* December 31, 2024and December 31, 2023*, the carrying value of limited liability investments totaled$0.7 million and$0.8 million, respectively. The Company recorded impairments related to limited liability investments ofzero and $0.1 million for the years ended* December 31, 2024and December 31, 2023*, respectively, which are included in impairment losses on investments in the consolidated statements of operations. At* December 31, 2024*, the Company hasno unfunded commitments related to limited liability investments.

58

Limited liability investment, at fair value represents the underlying investments of the Company’s consolidated entity, Argo Holdings. As of* December 31, 2024and December 31, 2023*, the carrying value of the Company's limited liability investment, at fair value was $2.9 million and $3.5 million, respectively. At* December 31, 2024*, the Company hasno unfunded commitments related to limited liability investment, at fair value.

Prior to thesecond quarter of2023, the Company's limited liability investments, at fair value included the underlying investments of the Company's consolidated entity, Net Lease Investment Grade Portfolio LLC ("Net Lease"). The Company consolidated the financial statements of Net Lease on athree-month lag. Net Lease owned investments in limited liability companies that held investment properties.

As of* December 31, 2024and December 31, 2023*, the carrying value of the Company’s investments in private companies totaled$0.7 million and$0.9 million, respectively. For the years ended* December 31, 2024and December 31, 2023*, the Company recorded adjustments ofzero and $0.1 million, respectively, to increase the fair value of certain investments in private companies for observable price changes, which are included in unrealized gain on private company investments in the consolidated statements of operations.

The Company performs a quarterly impairment analysis of its investments in private companies. As a result of the analysis performed, the Company didnot record any impairments related to investments in private companies for the years ended* December 31, 2024and December 31, 2023*.

Net investment income for the years ended* December 31, 2024and December 31, 2023*, respectively, is comprised as follows:

Net realized gains on investments for the years ended* December 31, 2024and December 31, 2023* are comprised as follows:

Net (loss) gain on equity investments for the years ended* December 31, 2024and December 31, 2023* is comprised as follows:

59

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

NOTE*8* GOODWILL

The following table summarizes goodwill activity for the years ended* December 31, 2024and December 31, 2023*:

As further discussed in Note4, "Acquisitions," during2024 the Company recorded goodwill of$6.5 million related to the acquisition of Image Solutions on* September 26, 2024*. The goodwill related to this acquisition is provisional and subject to adjustment during the measurement period. The Company expects to complete its purchase price allocations within the nextsix months. The estimates, allocations and calculations recorded at* December 31, 2024* are subject to change as we obtain further information; therefore, the final fair values of the assets acquired and liabilities assumed* may**not* agree with the estimates included in these consolidated financial statements.

During2023 the Company recorded goodwill of$0.1 million related to the acquisition of SPI on* September 7, 2023and$4.8 million related to the acquisition of DDI on October 26, 2023.The goodwill recorded at December 31, 2023related to these acquisitions was provisional and subject to adjustment during the measurement period. As further discussed in Note4*, "Acquisitions," during thesecond quarter of2024, the Company recorded measurement period adjustments, related to acquisitions of SPI and DDI, that increased goodwill by $0.4 million.

During the2023 the Company settled the working capital true-up, related to the acquisition of CSuite on* November 1, 2021,*that decreased goodwill by less than $0.1 million.

As of* December 31, 2024and December 31, 2023*, accumulated goodwill impairment losses were $0.7 million and zero, respectively.

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.

Based upon the impairment assessments performed at* November 30,*2024, the Company recorded an impairment charge of $0.7 million during2024 related to the Argo Management reporting unit. The fair value of the Argo Management reporting unit was estimated using a discounted cash flow analysis that includes estimates of future cash flows expected to be generated by the business and recent market transactions related to the investments owned by Argo Holdings. The decline in fair value is primarily due to reduced estimated future cash flows as a result of fewer investments remaining in the Argo Holdings, which is an expected result as Argo Holdings’ investments continue to be acquired. No impairment charges were recorded against goodwill for the Company's other reporting units in2024, as the estimated fair values of the Company's other reporting units exceeded their respective carrying values. No impairment charges were recorded against goodwill in2023.

60

NOTE9 INTANGIBLE ASSETS

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

As further discussed in Note4, "Acquisitions," the Company recorded the following intangible assets related to the acquisitions that occurred during2024 and2023:

The intangible assets related to the Image Solutions acquisition are provisional and subject to adjustment during the measurement period. The Company expects to complete its purchase price within the nextsix months. The estimates, allocations and calculations recorded at* December 31, 2024* are subject to change as we obtain further information; therefore, the final fair values of the assets acquired and liabilities assumed* may**not* agree with the estimates included in these consolidated financial statements.

As further discussed in Note4, "Acquisitions," during thesecond quarter of2024, the Company recorded a measurement period adjustment related to acquisition of DDI that increased the customer relationships intangible asset by $0.2 million compared to the amount recorded at* December 31, 2023.*

The Company's intangible assets with definite useful lives are amortized either based on the patterns in which the economic benefits of the intangible assets are expected to be consumed or using the straight-line method over their estimated useful lives, which range from 7 to 15 years. Amortization of intangible assets was$6.3 million and$5.9 million for the years ended* December 31, 2024and December 31, 2023*, respectively. The estimated aggregate future amortization expense of all intangible assets is$6.6 million for2025, $5.1 million for2026, $3.9 million for2027, $3.0 million for2028, $2.2 million for2029 and $5.1 million thereafter.

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.

61

At* March 31, 2024,** June 30, 2024,** September 30, 2024and November 30, 2024,the Company determined that certain trade names should be further examined under a quantitative approach due to actual revenue coming in lower than previous projections. Based upon these assessments, the Company recorded impairment charges of $2.1 million for the year ended December 31, 2024*, related to the SNS, CSuite and Ravix indefinite-lived trade names. The fair value of the SNS, CSuite and Ravix trade names were estimated using the relief-from-royalty method. The significant unobservable inputs used in the relief-from-royalty method, which are level3 inputs, include a royalty rate and discount rate. The reduction in value is primarily due to higher discount rates and a reduction in projected revenue. Future impairments* maybe recorded if discount rates increase further, or if actual revenue falls short of current projections. The valuation of these assets isnot* dependent on the underlying profit or loss generated by the respective business. Therefore, even if a change in revenue doesnot have a significant impact on operating results, it could significantly impact the fair value of the trade name. No impairment charges were recorded during the year ended* December 31, 2023*.

NOTE10 PROPERTY AND EQUIPMENT

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

For the years ended* December 31, 2024and December 31, 2023*, depreciation expense on medical equipment and certain computer hardware of $0.2 million andzero, respectively, is included in cost of services sold in the consolidated statements of operations. For the years ended* December 31, 2024and December 31, 2023*, depreciation expense on all other property and equipment of $0.5 million and$0.3 million, respectively, is included in general and administrative expenses in the consolidated statements of operations.

As discussed in Note4, "Acquisitions," during thesecond quarter of2024, the Company recorded a measurement period adjustment related to acquisition of DDI that decreased property and equipment, specifically medical equipment, by $0.4 million.

NOTE11 DERIVATIVES

On* April 1, 2021,the Company entered into an interest rate swap agreement with CIBC Bank USA to convert the variable London interbank offered interest rate forthree*-month U.S. dollar deposits ("LIBOR") interest rate on a portion of its2020 KWH Loan (as defined below in Note12, "Debt") to a fixed interest rate of 1.18%. On* September 15, 2022,the interest rate swap agreement was amended to convert from a variable Secured Overnight Financing Rate ("SOFR") to a fixed interest rate of 1.103%. The interest rate swap had an initial notional amount of $11.9 million. On February**29,* 2024, the interest rate swap matured and the Company didnot enter into any additional interest rate swap agreement upon its expiration.

62

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

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

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

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

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

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

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

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

In* February 2023,the Company entered into amendments to the repurchase agreements described above that gave the Company an additional discount on the total repurchase price if the Company effected a 100% repurchase on or before March 15, 2023.On March 2, 2023,the Company gave notice to the holders of its intent to exercise its options to repurchase 100% of the principal. On March 22, 2023,the Company completed the repurchases. See Note12*, "Debt," for further discussion.

The* AugustOption, September 20Option and September 26Options (collectively "the TruPs Options") are derivative contracts. The Company's accounting policies donot* apply hedge accounting treatment to derivative instruments. The TruPs options were recorded in the consolidated balance sheet at fair value with changes in fair value recorded in the consolidated statements of operations. See Note23, "Fair Value of Financial Instruments," for further discussion.

During the year ended* December 31, 2023*, the Company recognized a loss on change in fair value of the TruPs Options contracts of $1.4 million, which is included in loss on change in fair value of derivative asset option contracts in the consolidated statements of operations and as an adjustment to calculate cash flows provided by (used in) operating activities in the consolidated statements of cash flows. Cash payments of $56.5 million were made to repurchase the TruPs during theyear ended* December 31, 2023*with respect to the TruPs Options contracts.

63

NOTE12 DEBT

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

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

The contractual maturities of the Company's principal debt balances as of* December 31, 2024* were as follows:

Ravix

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

64

The2021 Ravix Loan has an annual interest rate equal to the greater of the Prime Rate plus 0.5%, or 3.75%. At* December 31, 2024*, the interest rate was 8.00%. The term loan matures on* October**1,* 2027. The Company also recorded as a discount to the carrying value of the2021 Ravix Loan issuance costs of $0.2 million specifically related to the2021 Ravix Loan. The2021 Ravix Loan is carried in the consolidated balance sheets at itsunpaid 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 requires monthly payments of principal and interest. The2022 Ravix Loan matures on* November 16, 2028and has an annual interest rate equal to the Prime Rate plus 0.75%. At December 31, 2024*, the interest rate was 8.25%. The2022 Ravix Revolver was to mature on* November 16, 2024prior to thethird* amendment to the2021 Ravix Loan on* October 24, 2024,which extended the maturity date on the2022* Ravix Revolver to* February 13, 2025.The2022* Ravix Revolver has an annual interest rate equal to the Prime Rate plus 0.50%. At* December 31, 2024*, the interest rate was 8.00%.

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 itsamortized cost, which reflects the monthly pay-down of principal as well as the amortization of the debt discount and issuance costs using the effective interest rate method.

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

On* July 23, 2024,Ravix, 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 Revolver and the remainder to be paid with available cash; and (2) amending the loan amortization payment schedule to provide for equal monthly payments through the loan maturity date. The2021 Ravix Loan wasnot deemed to be substantially different as a result of thesecond amendment; therefore, the amended2021 Ravix Loan is accounted for as a modification of the original2021 Ravix Loan.

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 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.

The fair values of the2021 Ravix Loan and the2022 Ravix 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. The2021 Ravix Loan and the2022 Ravix Loan are secured by certain of the equity interests and assets of Ravix and CSuite.

The2021 Ravix Loan and the2022 Ravix Loan 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 the2021 Ravix Loan and2022 Ravix Loan that, among other things, restrict Ravix and CSuite’s ability to incur additional indebtedness, create liens, make dividends and distributions, engage in mergers, acquisitions and consolidations, make certain payments and investments and dispose of certain assets.

65

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 to finance the acquisition of Secure Nursing Service, Inc. (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 December 31, 2024*, the interest rate was 8.00%. Monthly principal payments on the term loan began on* November 15, 2023.The revolver matures on May 2, 2025* and the term loan matures on* November 18, 2028*. During thefirst quarter of2024, the Company borrowed $0.2 million under the SNS Loan Revolver. During thesecond quarter of2024, the SNS Loan Revolver of $0.2 million was repaid. During thefourth quarter of2024, the Company borrowed $0.5 million under the SNS Loan 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 sheet at its amortized cost, which reflects the monthly pay-down of principal, as well as 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* December 31,** September 30,** June 30,and March 31, 2024,SNS was in default under the SNS Loan due to debt covenant violations related to the leverage and fixed charge ratios. The Company has entered into an amendment to the SNS Loan that waives the events of default for the fiscal quarter ended December 31, 2024*. As of the report date, there is some uncertainty as to whether the Company will be in compliance with the covenants in future periods, and ifnot, when the Company will be able to cure any potential violations. A default* may*permit the lender to declare the amounts owed under the SNS Loan immediately due and payable, exercise their rights with respect to collateral securing the obligation, and/or exercise any other rights and remedies available.

DDI

As part of the asset acquisition of DDI on* October 26, 2023,DDI became a wholly owned subsidiary of DDI Acquisition, LLC ("DDI LLC"), and together they borrowed from a bank a principal amount of $5.6 million in the form of a term loan, and established a $0.4 million revolver to finance the acquisition of DDI (together, the "DDI Loan"). The DDI Loan has an annual interest rate equal to the greater of the Prime Rate plus 0.5%, or 5.00%. At December 31, 2024*, the interest rate was 8.00%. Monthly principal payments on the term loan began on* December 15, 2024.The revolver matured on September 1, 2024* and the term loan matures on* October 26, 2029*. On* December 12, 2024,the DDI Loan was amended to extend the maturity date on the revolver to November 1, 2025.At December 31, 2024* and* December 31, 2023*, the balance of the DDI Loan revolver waszero.

The Company also recorded as a discount to the carrying value of the DDI Loan issuance costs of $0.1 million specifically related to the DDI Loan. The DDI Loan is carried in the consolidated balance sheet at its amortized cost, which reflects themonthly pay-down of principal starting* December 15, 2024,as well as 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 plus, BB and BB minusr ated 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 December 31, 2024*, the interest rate was 8.00%. The revolver matures on* September 26, 2026and the term loan matures on September 26, 2030.At 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 sheet at its amortized cost, which reflects the monthly pay-down of principal as well as the amortization of the debt discount and issuance costs using the effective interest rate method. The fair value of the Image Solutions Loan disclosed in the table above is derived from quoted market prices of BB plus rated industrial bonds with similar maturities and is categorized within Level2 of the fair value hierarchy. The Image Solutions Loan is secured by certain of the equity interests and assets of Image Solutions.

66

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 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"2020* KWH Loan"). The proceeds from the2020 KWH Loan were used to partially fund the acquisition of PWI and to fully repay the prior outstanding loan at KWH, which occurred on* December 1, 2020.*

The2020 KWH Loan has an annual interest rate equal to SOFR, having a floor of 0.75%, plus spreads ranging from 2.62% to 3.12%. At* December 31, 2024*, the interest rate was 7.46%. The2020 KWH Loan was to mature on* December 1, 2025,prior to entering into thethird* amendment to the KWH Loan further discussed below. The Company also recorded as a discount to the carrying value of the2020 KWH Loan issuance costs of $0.4 million specifically related to the2020 KWH Loan.

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

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

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

The2020 KWH Loan and the2024 KWH Loan werenot deemed to be substantially different; therefore, the2024 KWH Loan is accounted for as a modification of the2020 KHW Loan. The unamortized debt discount and issuance costs from the2020 KWH Loan at the modification date of $0.2 million were recorded as loss on extinguishment of debt during the year ended* December 31, 2024* 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, 2024*, 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. The2020 KWH Loan and2024 KWH Loan are carried in the consolidated balance sheets at amortized cost, which reflects the quarterly pay-down of principal as well as the amortization of the debt discount and issuance costs using the effective interest rate method. The fair values of the2020 KWH Loan,2024 KWH Loan,2024 KWH DDTL and KWH Revolver disclosed in the table above are derived from quoted market prices of BB and BB minus rated industrial bonds (2020 KWH Loan) and B plus, BB and BB minus rated industrial bonds (2024 KWH Loan) with similar maturities and is categorized within Level2 of the fair value hierarchy. The2020 KWH Loan is secured by certain of the equity interests and assets of KWH and its subsidiaries.

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

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

The subordinated debt, or TruPs, is carried in the consolidated balance sheets at fair value. See Note23, "Fair Value of Financial Instruments," for further discussion of the subordinated debt. The portion of the change in fair value of subordinated debt related to the instrument-specific credit risk is recognized in other comprehensive income (loss).

Of the $0.2 million decrease in the Company’s subordinated debt between* December 31, 2023* and* December 31, 2024*, $0.4 million is reported as decrease in fair value of debt attributable to instrument-specific credit risk in the Company's consolidated statements of comprehensive loss and $0.2 million is reported as loss on change in fair value of debt in the Company's consolidated statement of operations.

67

In* February 2023,the Company entered into amendments to the trust preferred option repurchase agreements described in Note11*, "Derivatives," that would give the Company an additional discount on the total repurchase price of the TruPs if the Company effected a100% repurchase on or before* March 15, 2023.On March 2, 2023,the Company gave notice to the holders offive* of its TruPs that it intended to exercise its options to repurchase100% of the principal. On* March 22, 2023,the Company completed the repurchases of thefive* TruPs using available funds from working capital to fund the repurchases. The total amount paid for thefive TruPs was $56.5 million, which included a credit for the $2.3 million that the Company previously paid at the time of entering into the trust preferred option repurchase agreements. As a result, the Company repurchased $75.5 million of TruPs principal and $23.0 million of deferred interest payable. The Company recognized a gain of $31.6 million, which is included in gain on extinguishment of debt in the consolidated statement of operations for the year ended* December 31, 2023*. At* December 31, 2024*, the Company has $15.0 million of principal outstanding related to the remaining trust preferred debt instrument.

At* December 31, 2022*, the fair value of the subordinated debt was $67.8 million. The $54.2 million decrease in the Company’s subordinated debt between* December 31, 2022* and* December 31, 2023* is attributed to the following:

Of the $1.9 million net increase in fair value of the Company’s subordinated debt between * December 31, 2022* and* December 31, 2023* described above,$1.8 million is reported as increase in fair value of debt attributable to instrument-specific credit risk in the Company's consolidated statements of comprehen sive loss and $0.1 million is reported as loss on change in fair value of debt in the Company’s consolidated statements of operations.

The consolidated statements of comprehensive loss for the year ended* December 31, 2023* also includes a reclassification adjustment of $27.2 million from accumulated other comprehensive income to gain on extinguishment of debt related to the instrument-specific credit risk related to the repurchased TruPs.

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

The agreements governing the subordinated debt contain 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.

NOTE13 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 the years ended* December 31, 2024* and* December 31, 2023* were as follows:

The annual maturities of lease liabilities as of* December 31, 2024* were as follows:

68

The weighted-average remaining lease term for operating leases was 4.61 years as of* December 31, 2024*. The weighted average discount rate of operating leases was 6.07% as of* December 31, 2024*. Cash paid for amounts included in the measurement of lease liabilities was$0.6 million and $0.5 million for the years ended* December 31, 2024and December 31, 2023*, respectively.

Supplemental non-cash information related to leases for the years ended* December 31, 2024and December 31, 2023* includes right-of-use assets acquired of$2.0 million and $0.4 million, respectively, in exchange for lease obligations of$2.0 million and $0.4 million, respectively.

NOTE14 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, GAP commissions, maintenance support service fees, warranty product commissions, business services consulting revenue, healthcare services revenue and software license and support revenue. Revenue is based on terms of various agreements with credit unions, consumers and businesses. Customers either pay in full at the inception of a warranty contract or commission product sale, or when consulting, healthcare and software license and support services are billed, or on terms subject to the Company’s customary credit reviews.

The following table disaggregates revenues from contracts with customers by revenue type:

Service fee receivables

Receivables from contracts with customers are reported as service fee receivable, net in the consolidated balance sheets and at* December 31, 2024and December 31, 2023* were$9.4 million and$10.1 million, respectively. The decrease in receivables from contracts with customers is primarily due to the timing difference between the Company's satisfaction of performance obligations and customer payments; partially offset by an increase related to Image Solutions receivables which were acquired om* September 26, 2024.At December 31, 2022*, service fee receivable, net was $10.3 million. The decrease in receivables from contracts with customers from* December 31, 2022* to* December 31, 2023* 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 lossesat* December 31, 2024and December 31, 2023* of $0.6 million and $0.2 million, respectively. During the years ended* December 31, 2024* and* December 31, 2023*, the Company recorded an increase to its allowance for credit losses of $0.6 million and $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 $0.2 million and less than $0.1 million during the years ended* December 31, 2024and December 31, 2023*, 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. The Company didnot have a contract asset priorto the acquisition of SPI on* September 7, 2023*. Changes in contract asset for the years ended* December 31, 2024* and* December 31, 2023* were as follows:

69

The contract asset is reported net of an estimated allowance for credit losses ofzero at* December 31, 2024and December 31, 2023*. Contract assets that are deemed to be uncollectible are written off against the allowance for credit losses when identified. During the years ended* December 31, 2024and December 31, 2023*, the Company recorded write-offs to the contract asset for amounts that were deemed to be uncollectible of less than $0.1 million andzero, respectively. As discussed in Note4, "Acquisitions," during thesecond quarter of2024, the Company recorded a measurement period adjustment related to acquisition of SPI that decreased the estimated value of the contract asset of $0.3 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 the years ended* December 31, 2024and December 31, 2023* were as follows:

The decrease in deferred service fees during the year ended* December 31, 2024* is primarily due to deferred service fees recognized in excess of additions to deferred service fees during the year ended* December 31, 2024*. The increase in deferred service fees during the year ended* December 31, 2023* is primarily due to additions to deferred service fees in excess of deferred service fees recognized during the year ended* December 31, 2023*.

Approximately $44.3 million and$44.6 million of service fee and commission revenue recognized during the years ended* December 31, 2024and December 31, 2023* was included in deferred service fees as of* December 31, 2023* and* December 31, 2022*, respectively.

Remaining performance obligations

The Company expects to recognize withinone year as service fee and commission revenue approximately 53.1% of the outstanding performance obligationsof* December 31, 2024*. 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. The deferred contract costs balances and related amortization expense for the years ended* December 31, 2024and December 31, 2023* are comprised as follows:

No impairment losses related to deferred contract costs were recorded in2024 or2023.

NOTE15 INCOME TAXES

The Company and all of its eligible U.S. subsidiaries file a U.S. consolidated federal income tax return ("KFSI Tax Group"). The method of allocating federal income taxes among the companies in the KFSI Tax Group is subject to written agreement, approved by each company's Board of Directors. The allocation is made primarily on a separate return basis, with current credit for any net operating losses or other items utilized in the consolidated federal income tax return. The Company’s non-U.S. subsidiaries file separate foreign income tax returns.

70

Income tax benefit consists of the following:

Income tax benefit varies from the amount that would result by applying the applicable U.S. corporate income tax rate of 21% to (loss) income from continuing operations before income tax benefit. The following table summarizes the differences:

The tax effects of temporary differences that give rise to significant portions of the deferred income tax assets and liabilities are presented as follows:

71

The Company maintains a valuation allowance for its gross deferred income tax assets of $130.7 million (U.S. operations- $130.7 million; Other - less than $0.1 million) and $129.4 million (U.S. operations - $129.4 million; Other - less than $0.1 million) at* December 31, 2024and December 31, 2023*, respectively. The Company's businesses 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* December 31, 2024and December 31, 2023* net deferred income tax assets, excluding the deferred income tax asset and liability amounts set forth in the paragraph below.

In2024, the Company (i) increased by $0.1 millionits valuation allowance primarily due to deferred tax liabilities assumed from corporate acquisitions; (ii) decreased by $0.2 million its valuation allowance relating to a change in indefinite life deferred income tax liabilities; and (iii) decreased by $0.2 million its valuation allowance associated with business interest expense with an indefinite life.

In2023, the Company (i) decreased by $2.1 million its valuation allowance primarily due to deferred tax liabilities assumed from corporate acquisitions; and (ii) increased by $0.3 million its valuation allowance relating to a change in indefinite life deferred income tax liabilities.

The Company carries net deferred income tax liabilities of$4.4 million and$5.0 millionat* December 31, 2024and December 31, 2023*, respectively, that consists of:

The Tax Cuts and Jobs Act (the "Tax Act") modified the U.S. net operating loss deduction, effective with respect to losses arising in tax years beginning after* December 31, 2017.The Tax Act, however, didnot* limit the utilization, in2018 and later tax years, of U.S. net operating losses generated in2017 and prior tax years.

Amounts, originating dates and expiration dates of the KFSI Tax Group's consolidated U.S. net operating loss carryforwards, totaling $622.3 million, are as follows:

In addition,not reflected in the table above, are net operating loss carryforwards of(i) $4.0 million relating to losses generated in separate U.S. tax return years, which losses will expire over various years through2037 and (ii) $0.1 million relating to non-U.S. operations, which losses will expire over various years through2044.

At* December 31, 2024and December 31, 2023*, the Company hadno unrecognized tax benefits. The Company classifies interest and penalty accruals, if any, related to unrecognized tax benefits as income tax expense (benefit).

The federal income tax returns of the Company's U.S. operat ions for the years through2020 are closed for Internal Revenue Service ("IRS") examination. The Company's federal income tax returns arenot currently under examination by the IRS for any open tax years. The federal income tax returns of the Company's Canadian operations for the years through2019 are closed for Canada Revenue Agency ("CRA") examination. The Company's Canadian federal income tax returns arenot currently under examination by the CRA for any open tax years.

72

NOTE16 (LOSS) EARNINGS PER SHARE

The following table sets forth the reconciliation of numerators and denominators for the basic and diluted (loss) earnings per share computation for the years ended* December 31, 2024and December 31, 2023*:

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

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

NOTE17 STOCK-BASED COMPENSATION

On* September 21, 2020,the Company's shareholders approved the2020* Equity Incentive Plan (the*"2020* Plan"). The2020 Plan replaced the Company's previous2013 Equity Incentive Plan (the*"2013* Plan") with respect to the granting of future equity awards. The2020 Plan permits the grant of Nonqualified Stock Options, Incentive Stock Options, Stock Appreciation Rights, Restricted Shares, Restricted Stock Units, Performance Share Awards, Dividend Equivalent Rights, Other Stock-Based Awards and Cash-Based Awards (collectively "Awards"). Under the2020 Plan, an aggregate of 1.6 million common shares will be available for all Awards, subject to adjustment in the event of certain corporate transactions.

73

Under the2013 Plan, the Company granted 500,000 restricted common stock awards to an officer on* September 5, 2018 (the"2018* Restricted Stock Award"). The2018 Restricted Stock Award fully vested on* March 28, 2024.The2018* Restricted Stock Award was amortized on a straight-line basis over the requisite service period. The grant-date fair value of the2018 Restricted Stock Award was determined using the closing price of Kingsway common stock on the date of grant. Total unamortized compensation expense related to unvested2018 Restricted Stock Award at* December 31, 2024* waszero.

Under the2020 Plan, the Company has granted restricted common stock awards to certain officers of the Company (the*"2020* Plan Restricted Stock Awards"). The2020 Plan Restricted Stock Awards vest according to a graded vesting schedule and shall become fully vested subject to the officers' continued employment through the applicable vesting dates. The2020 Plan Restricted Stock Awards are amortized on a straight-line basis over the requisite service periods. The grant-date fair values of the2020 Plan Restricted Stock Awards were determined using the closing price of Kingsway common stock on the date of grant. During the year ended* December 31, 2024*,126,390 shares of the2020 Plan Restricted Stock Awards became fully vested. Total unamortized compensation expense related to unvested2020 Plan Restricted Stock Awards at* December 31, 2024* was $2.1 million.

The following table summarizes the activity related to unvested2020 Plan Restricted Stock Awards and2018 Restricted Stock Award (collectively "Restricted Stock Awards") during the year ended* December 31, 2024*:

The unvested balance at* December 31, 2024* in the table above is comprised of 443,302 shares of the2020 Plan Restricted Stock Awards andzero shares of the2018 Restricted Stock Award.

Stock-based compensation expense related to the Restricted Stock Awards was$0.7 million and$1.0 million for the years ended* December 31, 2024and December 31, 2023*, respectively.

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

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

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

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

During the year ended* December 31, 2024*,20,833 units of the2021 Ravix RUA became fully vested. At* December 31, 2024and December 31, 2023*, there were 49,695 and 70,528 unvested units, respectively, of the2021 Ravix RUA with a weighted-average grant date fair value of $3.08 per Class B common unit. Total unamortized compensation expense related to unvested2021 Ravix RUA at* December 31, 2024* was$0.1 million.

74

Stock-based compensation expense related to the2021 Ravix RUA was$0.1 million and$0.1 million for the years ended* December 31, 2024and December 31, 2023*, respectively.

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

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

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

During the year ended* December 31, 2024*,6,250 units of the SNS RUA became fully vested. At* December 31, 2024and December 31, 2023*, there were 36,979 and 43,229 unvested units, respectively, of the SNS RUA with a weighted-average grant date fair value of $5.70 and$5.84 per Class B common unit, respectively. Total unamortized compensation expense related to unvested SNS RUA at* December 31, 2024*was$0.1 million.

Stock-based compensation expense related to the SNS RUA was$0.1 million and $0.1 million for the years ended* December 31, 2024and December 31, 2023*, respectively.

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

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

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

During the year ended* December 31, 2024*,26,042 units of the SPI RUA became fully vested. At * December 31, 2024and December 31, 2023*, there were 89,625 and 115,667 unvested units, respectively, of the SPI RUA with a weighted-average grant date fair value of $1.09 and $1.11 per Class B common unit , respectively . Total unamortized compensation expense related to unvested SPI RUA at * December 31, 2024* was $0.1 million.

Stock-based compensation expense related to the SPI RUA was less than $0.1 million and $0.1 million for the years ended* December 31, 2024and December 31, 2023*, respectively.

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

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

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

During the year ended* December 31, 2024*,24,306 units of the DDI RUA became fully vested. At* December 31, 2024and December 31, 2023*, there were 91,361 and 115,667 unvested units, respectively, of the DDI RUA with a weighted-average grant date fair value of $4.07 and $4.16 per Class B common unit, respectively . Total unamortized compensation expense related to unvested DDI RUA at * December 31, 2024* was $0.3 million.

Stock-based compensation expense related to the DDI RUA was $0.1 million and $0.4 million for the years ended* December 31, 2024and December 31, 2023*, respectively.

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

75

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

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

At* December 31, 2024*, there were 115,667 unvested units of the IMSO RUA with a weighted-average grant date fair value of $6.12 per Class B common unit. Total unamortized compensation expense related to unvested IMSO RUA at* December 31, 2024* was $0.7 million.

Stock-based compensation expense related to the IMSO RUA was $0.6 million for the year ended* December 31, 2024*.

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

The following table summarizes the stock option activity during the year ended* December 31, 2024*:

The aggregate intrinsic value of stock options outstanding and exercisable is the difference between the* December 31, 2024* market price for the Company's common shares and the exercise price of the options, multiplied by the number of options where the* December 31, 2024* market price exceeds the exercise price.

Stock-based compensation expense related to the Stock Options was$0.1 million for the year ended* December 31, 2024*. Total unamortized compensation expense related to unvested Stock Options at* December 31, 2024* was $0.9 million.

The Company uses the Black-Scholes option pricing model to estimate the fair value of each option on the date of grant. The fair value of grants and the related assumptions used in the Black-Scholes pricing model for the Stock Options granted during the year ended* December 31, 2024* were as follows:

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

The Company has an employee share purchase plan ("ESPP Plan") whereby qualifying employees can choose each year to have up to 5% of their annual base earnings withheld to purchase the Company's common shares. Afterone year of employment, the Company matches 100% of the employee contribution amount, and the contributions vest immediately. All contributions are used by the plan administrator to purchase common shares in the open market. The Company's contribution is expensed as paid and for the years ended* December 31, 2024and December 31, 2023* totaled$0.2 million and $0.2 million, respectively.

NOTE18 EMPLOYEE BENEFIT PLAN

The Company maintains a defined contribution plan in the United States for all of its qualified employees. Qualifying employees can choose to voluntarily contribute up to 60% of their annual earnings subject to an overall limitation of $23,000 and $22,500 in2024 and2023, respectively. The Company matches an amount equal to 50% of each participant's contribution, limited to the lesser of contributions up to 5% of a participant's earnings or $7,250.

76

The contributions for the plan vest based on years of service with 100% vesting afterfive years of service. The Company's contribution is expensed as paid and for the years ended* December 31, 2024and December 31, 2023* totaled$0.5 million and $0.5 million, respectively. All Company obligations to the plans were fully funded as of* December 31, 2024*.

NOTE19 REDEEMABLE CLASS B PREFERRED STOCK

Following approval by the Company's Board of Directors, on* September 24, 2024,the Company closed on a private placement for aggregate proceeds totaling $8.3 million, resulting from the sale and issuance of 330,000 shares of a new series of Class B Preferred Stock, par value $0.01 per share ("Class B Preferred Stock") for a purchase price of $25.00 per share. The Class B Preferred Stock ranks senior to the Company's common shares. There were 330,000 shares of Class B Preferred Stock outstanding at 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* December 31, 2024*, accrued dividends declared of $0.2 million were included in accrued expenses and other liabilities in the consolidated balance sheet. The redemption amount of the Class B Preferred Stock was $8.3 million at* 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.

NOTE20 SHAREHOLDERS' EQUITY

The Company is authorized to issue 50,000,000 shares of $0.01 par value common stock. There were 27,136,749 and 27,101,613 shares of common stock outstanding at* December 31, 2024and December 31, 2023*, respectively.

There wereno common stock dividends declared during the years ended* December 31, 2024and December 31, 2023*.

During2024, the Company declared dividends to be paid to the holders of its Class B Preferred Stock of $0.2 million. Cash dividends paid during the year ended* December 31, 2024* were less than $0.1 million.

Prior to* December 31, 2023,the Company had redeemable Class A Preferred Shares outstanding. During the year ended December 31, 2023*,149,733 Class A Preferred Shares were converted into 935,831 common shares, at the conversion price of $4.00 per common share at the option of the holders. As a result, during2023, $6.1 million was reclassified from redeemable Class A preferred stock to additional paid-in capital on the consolidated balance sheet as of* December 31, 2023*. There areno Class A Preferred Shares outstanding at* December 31, 2023*.

On* March 21, 2023,the Company's Board of Directors approved a security repurchase program under which the Company is authorized to repurchase up to $10.0 million of its currently issued and outstanding securities through March 22,2024. On March 22, 2024,the Company entered into aone* year extension of its existing share repurchase program. As amended, the share repurchase program will now expire on* March 21, 2025;however, in January 2025the Company fully utilized the authorized amount. The timing and amount of any repurchases are determined based on market and economic conditions, share price and other factors, and the program maybe terminated, modified or suspended at any time at the Company's discretion. During the year ended December 31, 2024*, the Company repurchased 312,850 shares of common stock for an aggregate purchase price of approximately $2.5 million, including fees and commissions. During the year ended* December 31, 2023*, the Company repurchased, in the aggregate,1,516,588 shares of common stock and warrants to purchase common stock for an aggregate purchase price of approximately $7.2 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* December 31, 2024and December 31, 2023*.

There were 983,027 and 670,177 shares of treasury stock outstanding at* December 31, 2024and December 31, 2023*, respectively. The Company records treasury stock at cost.

The Company previously had warrants outstanding that expired on* September 15, 2023.Prior to the expiration thereof, the warrants were recorded in shareholders' equity and entitled each subscriber to purchaseone common share of Kingsway at an exercise price of $5.00 for each warrant. During the year ended December 31, 2023*, warrants to purchase 3,331,661 shares of common stock were exercised, resulting in cash proceeds of $16.7 million. Any warrants that werenot exercised prior to the expiration date became null and void on the expiration date.

77

NOTE21 ACCUMULATED OTHER COMPREHENSIVE LOSS

The table below details the change in the balance of each component of accumulated other comprehensive loss, net of tax, for the years ended* December 31, 2024and December 31, 2023*, as it relates to shareholders' equity attributable to common shareholders on the consolidated balance sheets.

It should be noted that the consolidated statements of comprehensive loss present the components of other comprehensive income (loss), net of tax, only for the years ended* December 31, 2024and December 31, 2023* and inclusive of the components attributable to noncontrolling interests in consolidated subsidiaries.

Components of accumulated other comprehensive loss were reclassified to the following lines of the consolidated statements of operations for the years ended* December 31, 2024and December 31, 2023*:

As further discussed in Note12, "Debt," during thefirst quarter of2023, the Company completed the repurchases offive TruPs. The consolidated statements of comprehensive loss for the year ended* December 31, 2023*includes a reclassification adjustment of $27.2 million from accumulated other comprehensive income to gain on extinguishment of debt related to the instrument-specific credit risk portion of the repurchased TruPs.

NOTE22 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 Operating Officer. The Company conducts its business through the followingtwo reportable segments: Extended Warranty and Kingsway Search Xcelerator.

78

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 unions in 26 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 34 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.

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

Kingsway Search Xcelerator Segment

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

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

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

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

DDIprovides 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 39 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.

Revenues and Operating Income by Reportable Segment

Revenues by reportable segment reconciled to consolidated revenues for the years ended* December 31, 2024and December 31, 2023* were:

79

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 consolidated 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.

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 (loss) income from continuing operations for the years ended* December 31, 2024and December 31, 2023* is as follows:

80

NOTE23 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 equity investments, limited liability investment, at fair value, subordinated debt, derivative contracts (interest rate swap and trust preferred debt repurchase options) andcontingent 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:

81

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

Limited liability investment, at fair value- Limited liability investment, at fair value* *includes 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.

Derivative contract- interest rate swap -As described in Note11, "Derivatives," the Company entered into an interest rate swap agreement effective* April 1, 2021to convert the variable interest rate on a portion of the2020* KWH Loan to a fixed interest rate. On* February**29,* 2024, the interest rate swap matured and the Company didnot enter into any additional interest rate swap agreement upon its expiration. The interest rate swap contract was measured and reported at fair value and is included in other receivables in the consolidated balance sheet at* December 31, 2023.The fair value of the interest rate swap contract was estimated using inputs which the Company obtained from the counterparty and was determined using a discounted cash flow analysis on the expected cash flows of the derivative. The discounted cash flow valuation technique reflected the contractual term of the derivative contract, including the period to maturity, and used observable market based inputs, including quoted mid-market prices orthird*-party consensus pricing, interest rate curves and implied volatilities. The interest rate swap contract is categorized in Level2 of the fair value hierarchy.

Derivative contracts - trust preferred debt repurchase options - As described in Note11, "Derivatives," the Company entered into three TruPs Options contracts during thethird quarter of2022. During thefirst quarter of2023, the Company executed the TruPs Options contracts. The TruPs Options contracts were measured and reported at fair value. The fair value of the TruPs Options contracts was estimated using the binomial lattice model. Key inputs in the valuation included credit spread assumptions, interest rate volatility, debt coupon interest rate and time to maturity. The TruPs Options contracts are categorized in Level3 of the fair value hierarchy.

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

82

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* December 31, 2024and December 31, 2023* are as follows:

83

The following table provides a reconciliation of the fair value of recurring Level3 fair value measurements for the years ended* December 31, 2024and December 31, 2023*:

The following table summarizes the valuation techniques and significant unobservable inputs utilized in determining fair values for the Company's investments that are categorized as Level3 at* December 31, 2024*:

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

84

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 the years ended* December 31, 2024and December 31, 2023*, the Company recorded adjustments to increase the fair value of certain investments in private companies for observable price changes ofzero and $0.1 million, respectively, which are included in net change in unrealized gain on private company investments in the consolidated statements of operations. The Company didnot record any impairments related to investments in private companies for the years ended* December 31, 2024and December 31, 2023*. To determine the fair value of investments in these private companies, the Company considered rounds of financing andthird-party transactions, discounted cash flow analyses and market-based information, including comparable transactions, trading multiples and changes in market outlook, among other factors. The Company has classified the fair value measurements of these investments in private companies as Level3 because they involve significant unobservable inputs.

Goodwill and indefinite-lived intangible assets are recorded at carrying value, and, if impaired, are adjusted to fair value using Level3 inputs. Refer to Note8, "Goodwill" and Note9, "Intangible Assets" for further information regarding the process of determining the fair value of goodwill and indefinite-lived intangible assets, respectively, and the impairment charges recorded for the year ended* December 31, 2024*.

As further discussed in Note4, "Acquisitions," the Company acquired SPI on* September 7, 2023and allocated the purchase price to the assets acquired and liabilities assumed. The fair values of intangible assets associated with the acquisition of SPI were determined to be Level3* under the fair value hierarchy.

As further discussed in Note4, "Acquisitions," the Company acquired DDI on* October 26, 2023and allocated the purchase price to the assets acquired and liabilities assumed. The fair values of intangible assets associated with the acquisition of DDI were determined to be Level3* under the fair value hierarchy.

85

As further discussed in Note4, " Acquisitions," the Company acquired Image Solutions on* September 26, 2024and provisionally allocated the purchase price to the assets acquired and liabilities assumed. The fair values of intangible assets associated with the acquisition of Image Solutions were determined to be Level3* under the fair value hierarchy.

NOTE24 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 consolidated financial statements, the following is a summary of related party relationships and transactions.

Argo Management Group, LLC

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

Private Placements

As further described in Note19 " Redeemable Class B Preferred Stock," on* September 24, 2024,*the Company closed on a private placement for aggregate proceeds totaling $8.3 million, resulting from the sale and issuance of 330,000 shares of Class B Preferred Stock. Fitzgerald,one of Fitzgerald’s immediate family members, certain members of the Company's Board of Directors and members of the KSX Advisory Board invested a total of $5.2 million in the Class B Preferred Stock private placement transaction.

As further described in Note26 " Subsequent Events," on* February 12through February 24, 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 Class C Preferred Stock. Certain members of the Company's Board of Directors andone* of Fitzgerald’s immediate family members invested a total of $3.7 million in the Class C Preferred Stock private placement transaction.

VA Lafayette

On* August 16, 2024,the Company closed on the sale of 100% of the membership interests in VA Lafayette to athird*-party, who subsequently invested in the Company's private placement transaction that closed on* September 24, 2024and is a current holder of the Company’s Class B Preferred Stock (refer to Note5*, "Disposal and Discontinued Operations," for further detail of the sale of VA Lafayette and Note19, "Redeemable Class B Preferred Stock," for further detail of the private placement). The Company determined the sale was an arms-length transaction based upon the purchase price paid compared to the pricing of similarthird-party transactions, and given the fact that the terms of the sale were negotiated before the private placement was contemplated.

NOTE25 COMMITMENTS AND CONTINGENT LIABILITIES

In* May 2016,Aegis Security Insurance Company ("Aegis") filed a complaint for breach of contract and declaratory relief against the Company in the Eastern District of Pennsylvania alleging, among other things, that the Company breached a contractual obligation to indemnify Aegis for certain customs bond losses incurred by Aegis under the indemnity and hold harmless agreements provided by the Company to Aegis for certain customs bonds reinsured by Lincoln General Insurance Company ("Lincoln General") during the period of time that Lincoln General was a subsidiary of the Company. Lincoln General was placed into liquidation in November 2015and Aegis subsequently invoked its rights to indemnity under the indemnity and hold harmless agreements. Effective January 20, 2020,Aegis and the Company entered into a Settlement Agreement with respect to such litigation pursuant to which the Company agreed to pay Aegis aone*-time settlement amount of $0.9 million, and to reimburse Aegis for 60% of future losses that Aegis* maysustain in connection with such customs bonds, up to a maximum reimbursement amount of $4.8 million. From2020* through2022, the Company made reimbursement payments to Aegis of $1.0 million in connection with the Settlement Agreement. During2024 and2023, the Company made reimbursement payments to Aegis of $0.2 million and $0.5 million, respectively, in connection with the Settlement Agreement, which is included in general and administrative expenses in its consolidated statements of operations for the years ended* December 31, 2024* and* December 31, 2023*, respectively. The remaining maximum reimbursement amount is $3.1 million as of* December 31, 2024*. The Company’s potential exposure under these agreements wasnot reasonably determinable at* December 31, 2024*, andno liability has been recorded in the consolidated financial statements at* December 31, 2024*.

86

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

The Company also has restricted cash of $7.6 million and$8.4 million at* December 31, 2024and December 31, 2023*, respectively. Included in restricted cash are:

NOTE26 SUBSEQUENT EVENTS

On* February 12,13 and14, 2025, the Company closed on a private placement for aggregate proceeds totaling $4.4 million ("Initial Closing"), resulting from the sale and issuance of 176,756 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. On February 18through February 24, 2025,the Company issued and sold, in asecond* closing of the private placement (the “Second Closing”),63,244 shares of Class C Preferred Stock for aggregate proceeds of $1.6 million 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.

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.

On* March 14, 2025,*the Company acquired 100% of the outstanding membership interests of M.L.C. Plumbing, LLC (dba Bud’s Plumbing Service, “Bud’s Plumbing”), a provider of various plumbing installation and repair services for $5 million, plus transaction expenses and a working capital adjustment, in cash and a $1.25 million seller note.