Quarterly Report for Quarter Ending June 30, 2025 (Form 10-Q)

Management's Discussion and Analysis of Financial Condition and Results of Operations

FORWARD-LOOKING STATEMENTS

Management's Discussion and Analysis includes "forward-looking statements" within the meaning of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934 that are not historical facts, and involve risks and uncertainties that could cause actual results to differ materially from those expected and projected. Words such as "expects," "believes," "anticipates," "intends," "estimates," "seeks" and variations and similar words and expressions are intended to identify such forward-looking statements. Such forward-looking statements relate to future events or future performance, but reflect Kingsway management's current beliefs, based on information currently available. A number of factors could cause actual events, performance or results to differ materially from the events, performance and results discussed in the forward-looking statements. For information identifying important factors that could cause actual results to differ materially from those anticipated in the forward-looking statements, see Kingsway's securities filings, including its Annual Report on Form 10-K for the year ended December 31, 2024 ("2024 Annual Report"). The Company's securities filings can be accessed on the EDGAR section of the U.S. Securities and Exchange Commission's website at www.sec.gov, on the Canadian Securities Administrators' website at www.sedar.com or through the Company's website at www.kingsway-financial.com. Except as expressly required by applicable securities law, the Company disclaims any intention or obligation to update or revise any forward-looking statements because of new information, future events or otherwise.

OVERVIEW

Kingsway is a Delaware 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. Kingsway conducts its business through two reportable segments: Extended Warranty and Kingsway Search Xcelerator.

Extended Warranty includes the following subsidiaries of the Company: IWS Acquisition Corporation ("IWS"), Geminus Holding Company, Inc. ("Geminus"), PWI Holdings, Inc. ("PWI") and Trinity Warranty Solutions LLC ("Trinity"). Throughout Management's Discussion and Analysis, the term "Extended Warranty" is used to refer to this segment.

IWS is a licensed motor vehicle service agreement company and is a provider of after-market vehicle protection services distributed by credit unions in 28 states and the District of Columbia to their members, with customers in all fifty states.

Geminus primarily sells vehicle service agreements to used car buyers across the United States, through its subsidiaries, The Penn Warranty Corporation ("Penn") and Prime Auto Care, Inc. ("Prime"). Penn and Prime distribute these products in 46 and 35 states, respectively, via independent used car dealerships and franchised car dealerships. Penn also sells and administers a guaranteed asset protection product ("GAP") in states where Penn is approved.

PWI markets, sells and administers vehicle service agreements to used car buyers in all fifty 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 in three states with a white label agreement.

Trinity sells heating, ventilation, air conditioning ("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 the third-party insurance companies that underwrite and guaranty these warranty contracts. Trinity does not 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 includes the following subsidiaries of the Company: CSuite Financial Partners, LLC ("CSuite"), Ravix Group, Inc. ("Ravix"), Secure Nursing Service LLC ("SNS"), Systems Products International, Inc. ("SPI"), Digital Diagnostics Inc. ("DDI"), Image Solutions, LLC ("Image Solutions") and M.L.C. Plumbing, LLC (d/b/a Bud's Plumbing Service, "Bud's Plumbing"). Throughout Management's Discussion and Analysis, the term the term "Kingsway Search Xcelerator" is used to refer to this segment.

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

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

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

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

DDI provides outsourced 24 hours a day and 7 days per week ("24/7") cardiac telemetry services for long-term acute care and inpatient rehabilitation hospitals. Outsourcing cardiac monitoring is intended to allow hospitals to eliminate personnel callouts and human resources issues, remove distractions from onsite operations, and free up facility staff to assist directly with patient care. DDI currently has a presence in 42 states and Puerto Rico.

Image Solutions provides comprehensive information technology managed services, including equipment sales, service, and helpdesk support to customers primarily in North Carolina, Kansas, Georgia, Kentucky and Tennessee.

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

KINGSWAY FINANCIAL SERVICES INC.

NON-U.S. GAAP FINANCIAL MEASURE

Throughout this quarterly report, we present our operations in the way we believe will be most meaningful, useful and transparent to anyone using this financial information to evaluate our performance. Our unaudited consolidated interim financial statements have been prepared in accordance with accounting principles generally accepted in the United States of America ("U.S. GAAP") for interim financial information. In addition to the U.S. GAAP presentation of net loss, we present segment operating income as a non-U.S. GAAP financial measure, which we believe is valuable in managing our business and drawing comparisons to our peers. Below is a definition of our non-U.S. GAAP measure and its relationship to U.S. GAAP.

Segment Operating Income

Segment operating income represents one measure of the pretax profitability of our segments and is derived by subtracting direct segment expenses from direct segment revenues. Revenues and expenses are presented in the unaudited consolidated interim statements of operations, but are not subtotaled by segment; however, this information is available in total and by segment in Note 19, "Segmented Information," to the unaudited consolidated interim financial statements, regarding reportable segment information. The nearest comparable U.S. GAAP measure to total segment operating income is operating (loss) income that, in addition to total segment operating income, includes corporate general and administrative expenses and excludes segment non-operating other revenue (expense).

SIGNIFICANT ACCOUNTING POLICIES AND CRITICAL ESTIMATES

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

The Company's most critical accounting policies are those that are most important to the portrayal of its financial condition and results of operations, and that require the Company to make its most difficult and subjective judgments, often as a result of the need to make estimates of matters that are inherently uncertain. The critical accounting policies and judgments in the accompanying unaudited consolidated interim financial statements include 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. Although management believes that its estimates and assumptions are reasonable, they are based upon information available when they are made, and therefore, actual results may differ from these estimates under different assumptions or conditions.

The Company's significant accounting policies and critical estimates are described in Management's Discussion and Analysis of Financial Condition and Results of Operations included in the 2024 Annual Report. There has been no material change subsequent to December 31, 2024 to the information previously disclosed in the 2024 Annual Report with respect to these significant accounting policies and critical estimates.

RESULTS OF CONTINUING OPERATIONS

A reconciliation of total segment operating income to net loss for the three and six months ended June 30, 2025 and June 30, 2024 is presented in Table 1 below:

Table 1 Segment Operating Income

(in thousands of dollars)

		For the three months ended June 30,												For the six months ended June 30,
		2025				2024				Change				2025				2024				Change
Segment operating income:
Extended Warranty		$	(63	)		$	1,244			$	(1,307	)		$	452			$	2,320			$	(1,868	)
KSX			2,049				1,441				608				3,792				2,784				1,008
Total segment operating income			1,986				2,685				(699	)			4,244				5,104				(860	)
Net investment income			410				308				102				790				634				156
Net realized gains			128				277				(149	)			57				401				(344	)
Net loss on equity investments			-				-				-				-				(3	)			3
Gain on change in fair value of limited liability investment, at fair value			177				86				91				178				78				100
Interest expense			(1,265	)			(1,162	)			(103	)			(2,495	)			(2,307	)			(188	)
General and administrative expenses and other revenue not allocated to segments, net			(2,886	)			(2,087	)			(799	)			(5,719	)			(3,826	)			(1,893	)
Amortization of intangible assets			(1,710	)			(1,457	)			(253	)			(3,392	)			(2,871	)			(521	)
Impairment of intangible assets			(135	)			(690	)			555				(219	)			(1,201	)			982
Loss on change in fair value of debt			(1	)			(49	)			48				19				(129	)			148
Loss on extinguishment of debt			-				(160	)			160				(115	)			(160	)			45
Loss from continuing operations before income tax (benefit) expense			(3,296	)			(2,249	)			(1,047	)			(6,652	)			(4,280	)			(2,372	)
Income tax (benefit) expense			(131	)			104				(235	)			(395	)			188				(583	)
Loss from continuing operations			(3,165	)			(2,353	)			(812	)			(6,257	)			(4,468	)			(1,789	)
Income from discontinued operations, net of taxes (a)			-				167				(167	)			-				358				(358	)
Loss on disposal of discontinued operations, net of taxes (a)			-				-				-				-				(404	)			404
Net loss		$	(3,165	)		$	(2,186	)		$	(979	)		$	(6,257	)		$	(4,514	)		$	(1,743	)

(a)

The income from discontinued operations and the loss on disposal of discontinued operations is related to VA Lafayette. See Note 5, "Acquisitions and Discontinued Operations," to the unaudited consolidated interim financial statements, for further information.

KINGSWAY FINANCIAL SERVICES INC.

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

The discussion below highlights the key drivers of the current and prior year results.

Extended Warranty

The Extended Warranty service fee and commission revenue was $17.6 million for the three months ended June 30, 2025 compared with $17.1 million for the three months ended June 30, 2024 ($34.3 million year to date compared to $33.8 million prior year to date). However, cash sales were up 9.2% over the prior year (6.5% year to date).

The Extended Warranty operating loss was $0.1 million for the three months ended June 30, 2025 compared with operating income of $1.2 million for the three months ended June 30, 2024 (operating income of $0.5 million year to date compared to $2.3 million prior year to date).

Operating (loss) income was primarily impacted by the following:

•

A $1.3 million increase in loss at a combined Geminus and PWI to an operating loss of $0.8 million for the three months ended June 30, 2025 (an increase in loss of $1.3 million year to date to an operating loss of $0.7 million), due to:

	•	For the quarter, a decrease in revenue (cash sales up 9.3% in the quarter), higher claims and higher general and administrative expenses;
	•	For the year to date, a decrease in revenue (cash sales up 3.2% year to date), higher commission expense and higher general and administrative expenses; partially offset by lower claims expense;
	•	Note that quarter general and administrative expenses included $0.3 million of costs associated with severance and redundant salaries, as a new President & CEO was hired March 31, 2025 to run both Geminus and PWI.

•

A less than $0.1 million decrease at IWS to operating income of $0.4 million for the three months ended June 30, 2025 (a decrease of $0.3 million year to date to operating income of $0.9 million), due to higher claims and general and administrative expenses, which essentially offset the benefits from increased revenue (cash sales up 11.4% for the quarter and 15.3% year to date) for the quarter and year to date; and

•

A less than $0.1 million decrease at Trinity to operating income of $0.3 million for the three months ended June 30, 2025 (a decrease of $0.2 million year to date to operating income of $0.3 million), due to higher cost of sales (driven by higher maintenance revenue, which has a lower margin), commission and general and administrative expenses, which essentially offset the benefits from increased revenue for the quarter and year to date.

Kingsway Search Xcelerator

The Kingsway Search Xcelerator revenue increased to $13.3 million for the three months ended June 30, 2025 compared to $9.3 million for the three months ended June 30, 2024 (an increase to $25.0 million year to date compared to $18.8 million prior year to date). Kingsway Search Xcelerator operating income was $2.0 million for the three months ended June 30, 2025 compared to $1.4 million for the three months ended June 30, 2024 ($3.8 million year to date compared to $2.8 million prior year to date). Revenue and operating income were primarily impacted by the following:

•

The inclusion of Image Solutions for the three and six months ended June 30, 2025 following its acquisition effective September 26, 2024. For the three months ended June 30, 2025, Image Solutions had revenue and operating income of $2.0 million and $0.5 million, respectively (revenue and operating income of $3.9 million and $0.8 million, respectively for the six months ended June 30, 2025);

•

SPI operating income increased $0.2 million to $0.4 million for the three months ended June 30, 2025 (an increase of $0.2 million year to date to $0.3 million), primarily due to an increase in revenue from new customer go-lives for the quarter and year to date;

•

DDI operating income increased $0.1 million to $0.3 million for the three months ended June 30, 2025 (an increase of $0.1 million year to date to $0.6 million), primarily due to an increase in revenue and lower general and administrative expenses, partially offset by higher cost of sales for the quarter and year to date;

•

CSuite operating income increased $0.1 million to $0.1 million for the three months ended June 30, 2025 (an increase of $0.2 million year to date to $0.2 million), due to an increase in revenue (primarily driven by interim assignments lasting longer) and less general and administrative expenses, partially offset by higher cost of sales;

•

Ravix operating income decreased $0.4 million to $0.5 million for the three months ended June 30, 2025 (a decrease of $0.5 million year to date to $1.4 million), due to decreased revenue (primarily due to loss of retained customers as they were acquired, as well as financially distressed customers spending less on Ravix services) and bad debt expense of $0.1 million, partially offset by a decrease in costs of services sold and general and administrative expenses;

•

SNS operating income decreased by less than $0.1 million to $0.2 million for the three months ended June 30, 2025 (a decrease of $0.1 million year to date to $0.3 million), primarily due to higher cost of sales and general and administrative expenses, partially offset by an increase in revenue (travel shifts are up 11% for the quarter and 17% year to date, while per diem shifts are up 10% for the quarter and 5% year to date); and

•

Bud's Plumbing had revenue and operating income of $1.8 million and $0.1 million, respectively, for the three months ended June 30, 2025 (revenue and operating income of $2.0 million and $0.2 million, respectively, for the period from the date of acquisition through June 30, 2025.

Net Investment Income

Net investment income was $0.4 million in the second quarter of 2025 compared to $0.3 million in the second quarter of 2024 ($0.8 million year to date compared to $0.6 million prior year to date). The increase in investment income for the three and six months ended June 30, 2025 primarily relates to an increase in investment income from fixed maturities and less loss related to limited liability investments, which are accounted for using the equity method.

KINGSWAY FINANCIAL SERVICES INC.

Net Realized Gains

Net realized gains were $0.1 million in the second quarter of 2025 compared to $0.3 million in the second quarter of 2024 ($0.1 million year to date compared to $0.4 million prior year to date). The net realized gains for the three and six months ended June 30, 2025 primarily relate to realized gains recognized by Argo Holdings Fund I, LLC ("Argo Holdings") and investments in private companies, partially offset by realized losses on sales of fixed maturity investments. The net realized gains for the three and six months ended June 30, 2024 primarily relate to realized gains recognized by Argo Holdings.

Interest Expense

Interest expense for the second quarter of 2025 was $1.3 million compared to $1.2 million in the second quarter of 2024 ($2.5 million year to date compared to $2.3 million prior year to date). Interest expense was impacted by the following for the three and six months ended June 30, 2025:

•

An increase of $0.2 million for the three months ended June 30, 2025 related to the Image Solutions Loan (increase of $0.3 million year to date), which was effective September 26, 2024 and has an annual interest rate equal to the greater of the Prime Rate plus 0.5%, or 7.25% (current rate of 8.00%);

	•	An increase of less than $0.1 million for the three months ended June 30, 2025 (increase of $0.1 million year to date) related to the 2020 KWH Loan. During 2024, KWH entered into an amendment to the 2020 KWH Loan whereby KWH borrowed $15.0 million and used the proceeds to repay the existing loan balances. During the third and fourth quarters of 2024, KWH borrowed $6.0 million under the KWH DDTL and $1.0 million under the KWH Revolver. These events resulted in higher interest expense related to the KWH Loan for the three and six months ended June 30, 2025 compared to the same periods in 2024;
	•	A decrease of less than $0.1 million for the three months ended June 30, 2025 (decrease of $0.4 million year to date) related to the 2021, 2022 and 2025 Ravix Loans. During the first quarter of 2025, Ravix entered into an amendment to the 2021 Ravix Loan whereby Ravix borrowed $9.1 million and used the proceeds to repay the existing loan balances. This resulted in lower overall interest expense related to the Ravix Loans for the three and six months ended June 30, 2025 compared to the same periods in 2024. The amended loan has an annual interest rate equal to the Prime Rate plus 0.5% (current rate of 8.00%);
	•	A decrease of less than $0.1 million for the three months ended June 30, 2025 (decrease of $0.1 million year to date) on the Company's subordinated debt. The Company's subordinated debt bears interest at the rate of CME Term SOFR, plus a spread of 4.20%;
	•	A decrease of less than $0.1 million for the three months ended June 30, 2025 (decrease of $0.1 million year to date) related to the SNS Loan, which has an annual interest rate equal to the greater of the Prime Rate plus 0.5%, or 5.00% (current rate of 8.00%); and
	•	A decrease of less than $0.1 million for the three and six months ended June 30, 2025 related to the DDI Loan, which has an annual interest rate equal to the greater of the Prime Rate plus 0.5%, or 5.00% (current rate of 8.00%).

See Note 10, "Debt," to the unaudited consolidated interim financial statements for further details.

General and Administrative Expenses and Other Revenue and Expenses not Allocated to Segments, Net

General and administrative expenses and other revenue not allocated to segments was a net expense of $2.9 million in the second quarter of 2025 compared to $2.1 million in the second quarter of 2024 ($5.7 million year to date compared to $3.8 million prior year to date). Included are primarily expenses associated with our corporate holding company, expenses associated with our Operator-in-Residence who search for our next acquisition, as well as revenue and expenses associated with our various other investments that are accounted for on a consolidated basis.

The increase in net expense for the three months ended June 30, 2025 is primarily attributable to reimbursement payments made to Aegis in connection with the Settlement Agreement and higher search related expenses during the three months ended June 30, 2025 compared to the same period in 2024.

The increase in net expense for the six months ended June 30, 2025 is primarily attributable to reimbursement payments made to Aegis in connection with the Settlement Agreement and higher acquisition, search and compensation related expenses, partially offset by zero expense related to the Ravix contingent consideration liability during the six months ended June 30, 2025 compared to the same period in 2024.

See Note 22, "Commitments and Contingencies," to the unaudited consolidated interim financial statements for further details related to the Aegis Settlement Agreement.

Amortization of Intangible Assets

Amortization of intangible assets was $1.7 million in the second quarter of 2025 compared to $1.5 million in the second quarter of 2024 ($3.4 million year to date compared to $2.9 million prior year to date). The increase is primarily due to the inclusion of Image Solutions for the three and six months ended June 30, 2025 following its acquisition effective September 26, 2024, partially offset by decreased amortization expense for the Company's other intangible assets.

Impairment of Intangible Assets

Impairment of intangible assets was $0.1 million in the second quarter of 2025 compared to $0.7 million in the second quarter of 2024 ($0.2 million year to date compared to $1.2 million prior year to date). The Company's indefinite-lived intangible assets consist of trade names, which 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. At each quarter end of the first and second quarters of 2025 and 2024, the Company determined that certain of its trade name intangible assets should be further examined under a quantitative approach due to actual revenue coming in lower than previous projections. Based upon this assessment, the Company recorded an impairment charge of $0.1 million during the second quarter of 2025 ($0.2 million year to date) related to the Ravix indefinite-lived trade name; and an impairment charge of $0.7 million during the second quarter of 2024 ($1.2 million prior year to date), related to the SNS and CSuite indefinite-lived trade names. The reductions in value are primarily due to higher discount rates and a reduction in projected revenue. See Note 8,"Intangible Assets," to the unaudited consolidated interim financial statements, for further discussion

KINGSWAY FINANCIAL SERVICES INC.

Loss on Extinguishment of Debt

During the first quarter of 2025, there was a modification to the 2021 Ravix Loan. For the six months ended June 30, 2025, loss on extinguishment of debt of $0.1 million relates to the write-down of the unamortized debt discount and issuance costs from the 2022 Ravix Loan at the modification date, since the original debt was fully repaid as part of the modification.

During the second quarter of 2024, there was a modification to the 2020 KWH Loan. For the three and six months ended June 30, 2024, loss on extinguishment of debt of $0.2 million relates to the write-down of the unamortized debt discount and issuance costs from the 2020 KWH Loan at the modification date, since the original debt was fully repaid as part of the modification.

See Note 10 "Debt," to the unaudited consolidated interim financial statements, for further discussion.

Income Tax (Benefit) Expense

Income tax benefit for the second quarter of 2025 was $0.1 million compared to an expense of $0.1 million in the second quarter of 2024 (benefit of $0.4 million year to date compared to an expense of $0.2 million prior year to date). For the three and six months ended June 30, 2025, the Company reported a tax benefit primarily due to the release of its valuation allowance associated with indefinite life business interest expense carryforwards. For the three and six months ended June 30, 2024, the Company reported income tax expense primarily due to state tax expense. See Note 13, "Income Taxes," to the unaudited consolidated interim financial statements, for additional detail of the income tax (benefit) expense recorded for the three and six months ended June 30, 2025 and June 30, 2024.

INVESTMENTS

Portfolio Composition

See Note 2(d), "Summary of Significant Accounting Policies - Investments," to the consolidated financial statements in the 2024 Annual Report for an overview of how we account for our various investments.

At June 30, 2025, we held cash and cash equivalents, restricted cash and investments with a carrying value of $61.5 million. Our operations typically invest in U.S. dollar-denominated instruments to mitigate their exposure to currency rate fluctuations.

Table 2 below summarizes the carrying value of investments, including cash and cash equivalents and restricted cash, at the dates indicated.

TABLE 2 Carrying value of investments, including cash and cash equivalents and restricted cash
(in thousands of dollars, except for percentages)

Type of investment		June 30, 2025				% of Total				December 31, 2024				% of Total
Fixed maturities:
U.S. government, government agencies and authorities			13,715				22.3	%			13,354				24.5	%
States, municipalities and political subdivisions			2,249				3.7	%			2,775				5.1	%
Mortgage-backed			10,254				16.7	%			9,886				18.1	%
Asset-backed			1,455				2.4	%			1,326				2.4	%
Corporate			9,857				16.0	%			9,622				17.7	%
Total fixed maturities			37,530				61.0	%			36,963				67.9	%
Limited liability investments			650				1.1	%			650				1.2	%
Limited liability investment, at fair value			3,037				4.9	%			2,859				5.2	%
Investments in private companies			628				1.0	%			696				1.3	%
Short-term investments			173				0.3	%			169				0.3	%
Total investments			42,018				68.3	%			41,337				75.9	%
Cash and cash equivalents			12,079				19.6	%			5,493				10.1	%
Restricted cash			7,378				12.0	%			7,643				14.0	%
Total			61,475				100.0	%			54,473				100.0	%

Investment Impairment

The Company performs a quarterly analysis of its investments to determine if declines in fair value may result in the recognition of impairment losses in net loss. Factors considered in the determination of whether or not an impairment loss is recognized in net loss include a current intention or need to sell the security or an indication that a credit loss exists. See the "Significant Accounting Policies and Critical Estimates" section of Management's Discussion and Analysis of Financial Condition included in the 2024 Annual Report for further information regarding the Company's detailed analysis and factors considered in establishing an impairment loss on an investment.

KINGSWAY FINANCIAL SERVICES INC.

The Company's fixed maturities are subject to declines in fair value below amortized cost that may result in the recognition of impairment losses in net loss. If the decline in fair value is due to credit factors and the Company does not expect to receive cash flows sufficient to support the entire amortized cost basis, the credit loss is reported in the consolidated statements of operations in the period that the declines are evaluated. Significant judgment is required in the determination of whether a credit loss has occurred for a security. The Company considers all available evidence when determining whether a security requires a credit allowance to be recorded, including the financial condition and expected near-term and long term prospects of the issuer, whether the issuer is current with interest and principal payments, credit ratings on the security or changes in ratings over time, general market conditions, industry, sector or other specific factors and whether the Company expects to receive cash flows sufficient to recover the entire amortized cost basis of the security. The Company performs a quarterly analysis of its available for-sale fixed maturity investments and other investments to determine if an impairment loss has occurred.

There were no impairment losses recorded related to investments during the three and six months ended June 30, 2025 and June 30, 2024.

At June 30, 2025 and December 31, 2024, the gross unrealized losses for fixed maturities amounted to $0.7 million and $1.2 million, respectively, and there were no unrealized losses attributable to non-investment grade fixed maturities.

DEBT

The principal and carrying value of the Company's debt instruments at June 30, 2025 and December 31, 2024 are as follows:

(in thousands)		June 30, 2025								December 31, 2024
		Principal				Carrying Value				Principal				Carrying Value
Bank loans:
2021 Ravix Loan		$	-			$	-			$	2,288			$	2,288
2022 Ravix Loan			-				-				4,300				4,182
2022 Ravix Revolver			500				500				500				500
2025 Ravix Loan			8,821				8,787				-				-
SNS Term Loan			3,192				3,137				3,842				3,779
SNS Revolver			750				750				450				450
DDI Term Loan			4,947				4,898				5,507				5,452
DDI Revolver			23				23				-				-
Image Solutions Loan			7,169				7,025				7,556				7,399
2024 KWH Term Loan			12,188				12,112				13,313				13,228
2024 KWH DDTL			5,119				5,119				5,850				5,850
KWH Revolver			1,000				1,000				1,000				1,000
Total bank loans			43,709				43,351				44,606				44,128
Note payable			1,196				1,053				-				-
Subordinated debt			15,000				13,928				15,000				13,409
Total		$	59,905			$	58,332			$	59,606			$	57,537

See Note 10, "Debt," to the unaudited consolidated interim financial statements for a detailed discussion of the Company's debt instruments. Changes related to the Company's debt during the six months ended June 30, 2025 are further described below.

Bank Loans

On February 7, 2025, Ravix, Ravix LLC and CSuite entered into a fourth amendment to the 2021 Ravix Loan that provides for: (1) a new 2025 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 the 2022 Ravix Revolver to February 7, 2027. In connection with the fourth amendment, Ravix used a portion of the proceeds from the 2025 Ravix Loan to repay the following outstanding principal balances under the 2021 and 2022 Ravix Loans: (1) $2.2 million related to the 2021 Ravix term loan; and (2) $4.2 million related to the 2022 Ravix term loan. The Company also recorded as a discount to the carrying value of the 2025 Ravix Loan issuance costs of less than $0.1 million specifically related to the 2025 Ravix Loan.

The 2025 Ravix Loan was not deemed to be substantially different as a result of the fourth amendment; therefore, the amended 2021 Ravix Loan is accounted for as a modification of the second amended 2021 Ravix Loan. The unamortized debt discount and issuance costs from the 2022 Ravix Loan at the modification date of $0.1 million were recorded as loss on extinguishment of debt during the six months ended June 30, 2025 since the original debt related the 2021 Ravix Loan and 2022 Ravix Loan were fully repaid as part of the modification.

During the six months ended June 30, 2025, the Company borrowed $0.3 million under the SNS Revolver.

The SNS Loan contains a number of covenants, including, but not limited to, a leverage ratio and a fixed charge ratio and limits on annual capital expenditures, all of which are as defined in and calculated pursuant to the SNS Loan that, among other things, restrict SNS's ability to incur additional indebtedness, create liens, make dividends and distributions, engage in mergers, acquisitions and consolidations, make certain payments and investments and dispose of certain assets. At each quarter end beginning March 31, 2024 through June 30, 2025, the Company was in default under the SNS Loan due to debt covenant violations related to the leverage and fixed charge ratios. The Company has entered into an amendment to the SNS Loan that waives the events of default for the fiscal quarter ended June 30, 2025. As of the report date, there is some uncertainty as to whether the Company will be in compliance with the covenants in future periods, and if not, 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.

During the six months ended June 30, 2025, the Company borrowed $0.1 million and made principal repayments of less than $0.1 million under the DDI Revolver.

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

KINGSWAY FINANCIAL SERVICES INC.

Note Payable

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

Subordinated Debt

The Company's subordinated debt is measured and reported at fair value. At June 30, 2025, the carrying value of the subordinated debt is $13.9 million. The fair value of the subordinated debt is calculated using a model based on significant market observable inputs and inputs developed by a third party. For a description of the market observable inputs and inputs developed by a third party used in determining fair value of debt, see Note 20, "Fair Value of Financial Instruments," to the unaudited consolidated interim financial statements.

Though changes in the market observable swap rates will continue to introduce some volatility each quarter to the Company's reported gain or loss on change in fair value of debt, changes in the credit spread assumption developed by the third party does not introduce volatility to the Company's consolidated statements of operations. The fair value of the Company's subordinated debt will eventually equal the principal value totaling $15.0 million of the subordinated debt by the time of the stated redemption date of the remaining trust, which matures on May 22, 2033.

RECENTLY ISSUED ACCOUNTING STANDARDS

See Note 4, "Recently Issued Accounting Standards," to the unaudited consolidated interim financial statements, for discussion of certain accounting standards that may be applicable to the Company's current and future consolidated financial statements.

LIQUIDITY AND CAPITAL RESOURCES

The purpose of liquidity management is to ensure there is sufficient cash to meet all financial commitments and obligations as they fall due. The liquidity requirements of the Company and its subsidiaries have been met primarily by funds generated from operations, capital raising, disposal of subsidiaries, investment maturities and investment income, and other returns received on investments and from the sale of investments.

A significant portion of the cash provided by our Extended Warranty companies is required to be placed into restricted trust accounts, as determined by the insurers who back-up our service contracts, in order to fund future expected claims. On a periodic basis (quarterly or annually), we may be required to contribute more into the restricted accounts or we may be permitted to draw additional funds from the restricted accounts, dependent upon actuarial analyses performed by the insurers regarding sufficiency of funds to cover future expected claims. A substantial portion of the restricted trust accounts are invested in fixed maturities and other instruments that have durations similar to the expected future claim projections.

Cash provided from these sources is used primarily for warranty expenses, business service expenses, debt servicing, acquisitions and operating expenses of the holding company.

The Company's Extended Warranty and Kingsway Search Xcelerator subsidiaries fund their obligations primarily through service fee and commission revenue.

Cash Flows from Continuing Operations

During the six months ended June 30, 2025, the Company reported $1.5 million of net cash used in operating activities from continuing operations, primarily due to cash paid to settle the Ravix contingent liability of $2.3 million that is reported as an operating activity, partially offset by operating income from the Extended Warranty and Kingsway Search Xcelerator segments. During the six months ended June 30, 2024, the Company reported $0.5 million of net cash provided by operating activities from continuing operations, primarily due to operating income from the Extended Warranty and Kingsway Search Xcelerator segments.

During the six months ended June 30, 2025, the net cash used in investing activities from continuing operations was $13.7 million. This use of cash is primarily attributed to the acquisition of Bud's Plumbing, net of cash acquired, and cash paid on June 30, 2025 to pre-fund the acquisition of Roundhouse that occurred on July 1, 2025 of $10.3 million ($8.0 million is included in prepaid expenses and $2.3 million is included in other receivables in the consolidated balance sheet at June 30, 2025). During the six months ended June 30, 2024, the net cash provided by investing activities from continuing operations was $0.9 million. This source of cash is primarily attributed to distributions received by Argo Holdings from two of its underlying limited liability investment companies, partially offset by purchases of fixed maturities and property and equipment, net in excess of proceeds from sales and maturities of fixed maturities and sales of equity securities.

During the six months ended June 30, 2025, the net cash provided by financing activities from continuing operations was $21.5 million. This source of cash was primarily attributed to net proceeds from the issuance of common stock of $15.6 million, principal proceeds from bank loans of $9.4 million and proceeds from the issuance of Class C and Class D preferred stock of $6.0 and $2.0 million, respectively, partially offset by principal repayment on bank loans of $10.3 million, cash paid to settle the Ravix contingent liability of $0.4 million, payment of preferred stock dividends of $0.4 million and cash paid for repurchases of common stock of $0.3 million. During the six months ended June 30, 2024, the net cash used in financing activities from continuing operations was $1.0 million. This use of cash was primarily attributed to principal repayment on bank loans of $16.6 million, taxes paid related to net share settlements of restricted stock awards of $1.8 million, cash paid for repurchases of common stock of $1.0 million and distributions to noncontrolling interest holders of $0.7 million, partially offset by principal proceeds from bank loans of $19.1 million.

Holding Company Liquidity

The liquidity of the holding company is managed separately from its subsidiaries. The obligations of the holding company primarily consist of holding company operating expenses; transaction-related expenses; investments; stock repurchases; and any other extraordinary demands on the holding company.

KINGSWAY FINANCIAL SERVICES INC.

Pursuant to satisfying the covenants under the 2020 KWH Loan, distributions to the holding company in an aggregate amount not to exceed $1.5 million in any 12-month period are permitted. Also, beginning in 2022, the holding company is permitted to receive a portion of the excess cash flow (as defined in the 2020 KWH Loan document) generated by the KWH Subs in the previous year.

The amount of excess cash flow the Company is entitled to retain is dependent upon the leverage ratio (as defined in the 2020 KWH Loan document):

		Percent of excess cash flow
If leverage ratio is		retained by the Company
Greater than 1.75:1.00		50%
Less than 1.75:1.00 but greater than 0.75:1.00		75%
Less than 0.75:1.0		100%

The holding company's liquidity, defined as the amount of cash in the bank accounts of Kingsway Financial Services Inc. and Kingsway America Inc., was $6.2 million and $0.9 million at June 30, 2025 and December 31, 2024, respectively, which excludes future actions available to the holding company that could be taken to generate liquidity. Such future actions include, but are not limited to, issuance of equity securities and distributions from the Extended Warranty and Kingsway Search Xcelerator operating companies subject to certain loan covenants that may be in place at each operating company. The holding company cash amounts are reflected in the cash and cash equivalents of $12.1 million and $5.5 million reported at June 30, 2025 and December 31, 2024, respectively, on the Company's consolidated balance sheets.