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KINGSWAY FINANCIAL SERVICES INC

For the period ended Sep 30, 2025. Filed Nov 6, 2025.

View on SEC.gov

About this filing

A company's report for each of its first three quarters. The financial statements are not audited. It shows how the business has moved since the last annual report, and what management says changed.

Sep 30, 2025 · Filed Nov 6, 2025

KWY$8.00-16.3%Stored close · as of Nov 6, 2026

What changed in Management’s Discussion and Analysis?

Read the current filing

Previous report: 10-Q

Period ended 2025-06-30; filed 2025-08-07.

0001437749-25-025403

Item 2. Management's Discussion and Analysis of Financial Condition and Results of Operations

Current report: 10-Q

Period ended 2025-09-30; filed 2025-11-06.

0001437749-25-033593

Item 2. Management's Discussion and Analysis of Financial Condition and Results of Operations

The baseline is this issuer’s latest earlier reporting period of the same form that was filed before the current report. A previous 10-Q is a different quarter, not a year-over-year comparison. Amendments are excluded.

Compared 112 previous paragraphs and 119 current paragraphs.

76 unchanged; 30 reworded; 12 added; 5 removed; 1 previous and 1 current paragraphs rearranged.

Tables are not compared: 18 previous and 23 current tables excluded. Dates, whitespace, punctuation and numbering changes are ignored; changes to financial figures remain significant.

A changed paragraph is not evidence that risk increased or decreased. An unchanged paragraph does not establish that risk stayed the same.

Added paragraphs (12)

Current report

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

Current report

The Extended Warranty operating income was $0.4 million for the three months ended September 30, 2025 compared with $1.7 million for the three months ended September 30, 2024 ( $0.9 million year to date compared to $4.0 million prior year to date).

Current report

As part of the acquisition of Roundhouse on July 1, 2025, Roundhouse became a wholly owned subsidiary of Longhorns Acquisition LLC ("Longhorns LLC"), and together they borrowed from a bank a principal amount of $11.0 million in the form of a term loan, and established a $0.5 million revolver to finance the acquisition of Roundhouse. The Roundhouse term loan requires monthly payments of principal and interest and has an annual interest rate equal to the greater of the one-month term Secured Overnight Financing Rate plus 3.3%, or 5.0%. The term loan and revolver mature on July 1, 2035. At September 30, 2025, the balance of the revolver was zero.

Current report

In 2025, the Company formed Kingsway Plumbing Holdco LLC ("KPH"), whose subsidiaries include Bud's Plumbing, Advanced Plumbing and Southside Plumbing. As part of the acquisition of Southside Plumbing on August 14, 2025, KPH and its subsidiaries borrowed from a bank a principal amount of $3.75 million in the form of a term loan, and established a $0.5 million revolver. The KPH term loan requires monthly payments of interest and has an annual fixed interest rate of 7.5%. Monthly principal payments on the KPH term loan begin September 14, 2026. The term loan matures on August 14, 2032. At September 30, 2025, the balance of the revolver was zero.

Current report

As part of the acquisition of Bud's Plumbing on March 14, 2025, Bud's Plumbing became a wholly owned subsidiary of KPH, 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 was recorded at its estimated fair value of $1.1 million, which included the unpaid principal amount of $1.25 million as of the date of acquisition less a discount of $0.2 million. The KPH Note required monthly payments of principal and interest and had an annual fixed interest rate of 6.00%. The KPH Note was due to mature on April 1, 2030; however on August 7, 2025, the KPH Note was repaid in full to the seller of Bud's Plumbing in exchange for shares of Kingsway common stock. See Note 18, "Shareholders' Equity" for further discussion of the exchange. The settlement of the KPH Note by issuing the Company's common shares is accounted for as a debt extinguishment. The difference between the reacquisition price of the debt and the net carrying amount of the KPH Note at the date of the exchange of $0.1 million is recorded as loss on extinguishment of debt in the unaudited consolidated statement of operations for the three and nine months ended September 30, 2025.

Current report

As part of the acquisition of certain assets from The HR Team, Inc. on August 1, 2025, Ravix borrowed from the seller a principal amount of $0.2 million in the form of a promissory note, to partially finance the acquisition of assets (the "Ravix Note"). The Ravix Note requires quarterly payments of principal and interest beginning October 1, 2025 and has an annual fixed interest rate of 8.00%. The Ravix Note matures on August 1, 2027.

Current report

As part of the acquisition of Advanced Plumbing on August 1, 2025, Advanced Plumbing borrowed from the seller of Advanced Plumbing a principal amount of $0.5 million in the form of a promissory note, to partially finance the acquisition of Advanced Plumbing (the "AAA Note"). The AAA Note, which is recorded as notes payable in the consolidated balance sheet at September 30, 2025, was recorded at its estimated fair value of $0.4 million, which included the unpaid principal amount of $0.5 million as of the date of acquisition less a discount of $0.1 million. The AAA Note requires quarterly payments of principal and interest beginning November 1, 2025 and has an annual fixed interest rate of 6.00%. The AAA Note matures on August 1, 2030.
Removed paragraphs (5)

Previous report

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).

Previous report

Loss on change in fair value of debt was less than $0.1 million in the second quarter of 2025 compared to a loss of less than $0.1 million in the second quarter of 2024 (gain of less than $0.1 million year to date compared to a loss of $0.1 million prior year to date). The gain or loss for the three and six months ended June 30, 2025 and June 30, 2024 reflects changes in the fair value of the subordinated debt resulting primarily from changes in interest rates used (not related to instrument-specific credit risk). See "Debt" section below for further information.
Reworded paragraphs (30)

Previous wording

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.

Current wording

Kingsway is a Delaware holding company with operating subsidiaries located in the United States. The Company is the only publicly-traded US company employing the Search Fund model to acquire and build great businesses and owns and operates a collection of high-quality B2B and B2C services companies that are asset-light, growing, profitable, and that have recurring revenues. Kingsway seeks to compound long-term shareholder value on a per share basis via its decentralized management model, its talented team of operators, and its tax-advantaged corporate structure. Kingsway conducts its business through two reportable segments: Kingsway Search Xcelerator and Extended Warranty.

Previous wording

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.

Current wording

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"), Roundhouse Electric & Equipment Co., Inc. ("Roundhouse"), M.L.C. Plumbing, LLC (d/b/a Bud's Plumbing Service, "Bud's Plumbing"), Advanced Plumbing & Drain, LLC (d/b/a AAA Advanced Plumbing & Drain, "Advanced Plumbing") and Efficient Plumbing, LLC (d/b/a Southside Plumbing, "Southside Plumbing"). Throughout Management's Discussion and Analysis, the term the term "Kingsway Search Xcelerator" is used to refer to this segment.

Previous wording

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.

Current wording

Kingsway Skilled Trades includes Bud's Plumbing, Advanced Plumbing and Southside Plumbing. Kingsway Skilled Trades provides a comprehensive range of plumbing services, including emergency repairs, drain cleaning, water heater installations, and water treatment solutions to residential and commercial customers, primarily in Evansville, Indiana (Bud's Plumbing), Cleveland, Ohio (Advanced Plumbing) and Omaha, Nebraska (Southside Plumbing).

Previous wording

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:

Current wording

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

Previous wording

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:

Current wording

The Kingsway Search Xcelerator revenue increased to $19.0 million for the three months ended September 30, 2025 compared to $9.3 million for the three months ended September 30, 2024 (an increase to $43.9 million year to date compared to $28.1 million prior year to date). Kingsway Search Xcelerator operating income was $2.2 million for the three months ended September 30, 2025 compared to $1.1 million for the three months ended September 30, 2024 ($6.0 million year to date compared to $3.9 million prior year to date). Revenue and operating income were primarily impacted by the following:

Previous wording

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).

Current wording

The Extended Warranty service fee and commission revenue was $18.2 million for the three months ended September 30, 2025 compared with $17.8 million for the three months ended September 30, 2024 ($52.5 million year to date compared to $51.6 million prior year to date). However, cash sales were up 14.6% over the prior year (9.2% year to date).

Previous wording

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

Previous wording

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.

Current wording

Net investment income was $0.4 million in the third quarter of 2025 compared to $0.4 million in the third quarter of 2024 ($1.2 million year to date compared to $1.0 million prior year to date). The increase in investment income for the nine months ended September 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.

Previous wording

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.

Current wording

Net realized losses were less than $0.1 million in the third quarter of 2025 compared to net realized gains of $1.0 million in the third quarter of 2024 (net realized gains of $0.1 million year to date compared to $1.4 million prior year to date). The net realized gains for the three and nine months ended September 30, 2024 primarily relate to realized gains recognized by Argo Holdings Fund I, LLC ("Argo Holdings") and a net realized gain related to the sale of one of the private company investments.

Previous wording

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:

Current wording

Interest expense for the third quarter of 2025 was $1.5 million compared to $1.2 million in the third quarter of 2024 ($4.0 million year to date compared to $3.5 million prior year to date). Interest expense was impacted by the following for the three and nine months ended September 30, 2025:

Previous wording

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.

Current wording

General and administrative expenses and other revenue not allocated to segments was a net expense of $3.3 million in the third quarter of 2025 compared to $3.3 million in the third quarter of 2024 ($9.0 million year to date compared to $7.1 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.

Previous wording

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.

Current wording

The increase in net expense for the nine months ended September 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 nine months ended September 30, 2025 compared to the same period in 2024.

Previous wording

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.

Current wording

Amortization of intangible assets was $2.4 million in the third quarter of 2025 compared to $1.4 million in the third quarter of 2024 ($5.8 million year to date compared to $4.3 million prior year to date). The increase is primarily due to the inclusion of Image Solutions (acquired September 26, 2024) and Roundhouse, Advanced Plumbing and Southside Plumbing (acquired in the third quarter of 2025) for the three and nine months ended September 30, 2025, partially offset by decreased amortization expense for the Company's other intangible assets.

Previous wording

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

Current wording

Impairment of intangible assets was $0.2 million in the third quarter of 2025 compared to $0.6 million in the third quarter of 2024 ($0.5 million year to date compared to $1.8 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 through third 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 $0.2 million during the third quarter of 2025 ($0.5 million year to date) related to the CSuite and Ravix indefinite-lived trade names; and an impairment charge of $0.6 million during the third quarter of 2024 related to the CSuite and Ravix indefinite-lived trade names ($1.8 million prior year to date, related to the SNS, CSuite and Ravix 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

Previous wording

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.

Current wording

During the third quarter of 2025, the KPH Note was repaid in full to the seller of Bud's Plumbing in exchange for shares of Kingsway common stock. See Note 18 "Shareholders' Equity for further discussion of the exchange. The settlement of the KPH Note by issuing the Company's common shares is accounted for as a debt extinguishment. The difference between the reacquisition price of the debt and the net carrying amount of $0.1 million is recorded as loss on extinguishment of debt on the unaudited consolidated statement of operations for the three and nine months ended September 30, 2025. During the first quarter of 2025, there was a modification to the 2021 Ravix Loan. Loss on extinguishment of debt for the nine months ended September 30, 2025 includes $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.

Previous wording

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.

Current wording

During the second quarter of 2024, there was a modification to the 2020 KWH Loan. For the nine months ended September 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.

Previous wording

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.

Current wording

Income tax benefit for the third quarter of 2025 was $2.1 million compared to an expense of less than $0.1 million in the third quarter of 2024 (benefit of $2.4 million year to date compared to an expense of $0.2 million prior year to date). For the three and nine months ended September 30, 2025, the Company reported a tax benefit primarily due to the partial release of its valuation allowance related to deferred tax liabilities from corporate acquisitions. For the three and nine months ended September 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 nine months ended September 30, 2025 and September 30, 2024.

Previous wording

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.

Current wording

At September 30, 2025, we held cash and cash equivalents, restricted cash and investments with a carrying value of $58.8 million. Our operations typically invest in U.S. dollar-denominated instruments to mitigate their exposure to currency rate fluctuations.

Previous wording

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

Current wording

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

Previous wording

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.

Current wording

At September 30, 2025 and December 31, 2024, the gross unrealized losses for fixed maturities amounted to $0.6 million and $1.2 million, respectively, and there were no unrealized losses attributable to non-investment grade fixed maturities.

Previous wording

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.

Current wording

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 nine months ended September 30, 2025 are further described below.

Previous wording

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.

Current wording

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 nine months ended September 30, 2025 since the original debt related the 2021 Ravix Loan and 2022 Ravix Loan were fully repaid as part of the modification.

Previous wording

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

Current wording

During the nine months ended September 30, 2025, the Company borrowed $0.6 million under the SNS Revolver.

Previous wording

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.

Current wording

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

Previous wording

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.

Current wording

As part of the acquisition of Southside Plumbing on March 14, 2025, Southside Plumbing became a wholly owned subsidiary of KPH, and together they borrowed from the seller of Southside Plumbing a principal amount of $0.5 million in the form of a promissory note, to partially finance the acquisition of Southside Plumbing (the "Southside Note"). The Southside Note, which is recorded as note payable in the consolidated balance sheet at September 30, 2025, was recorded at its estimated fair value of $0.4 million, which included the unpaid principal amount of $0.5 million as of the date of acquisition less a discount of $0.1 million. The Southside Note requires quarterly payments of principal and interest beginning November 1, 2025 and has an annual fixed interest rate of 6.00%. The Southside Note matures on August 1, 2030.

Previous wording

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

Current wording

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

Previous wording

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.

Current wording

During the nine months ended September 30, 2025, the Company reported less than $0.1 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, partially offset by cash paid to settle the Ravix contingent liability of $2.3 million that is reported as an operating activity. During the nine months ended September 30, 2024, the Company reported $0.7 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.

Previous wording

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.

Current wording

During the nine months ended September 30, 2025, the net cash used in investing activities from continuing operations was $29.9 million. This use of cash is primarily attributed to the acquisitions of Bud's Plumbing, Roundhouse, Advanced Plumbing and Southside Plumbing, net of cash acquired. During the nine months ended September 30, 2024, the net cash used in investing activities from continuing operations was $16.4 million. This use of cash is primarily attributed to the acquisition of Image Solutions, net of cash acquired and purchases of fixed maturities in excess of proceeds from sales and maturities of fixed maturities, distributions received by Argo Holdings from three of its underlying limited liability investment companies, proceeds from the sale of a private company investment and proceeds from the sale of VA Lafayette.

Previous wording

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.

Current wording

During the nine months ended September 30, 2025, the net cash provided by financing activities from continuing operations was $33.6 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 $24.1 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 $12.6 million, cash paid to settle the Ravix contingent liability of $0.4 million, payment of preferred stock dividends of $0.7 million and cash paid for repurchases of common stock of $0.3 million. During the nine months ended September 30, 2024, the net cash provided by financing activities from continuing operations was $13.3 million. This source of cash was primarily attributed to principal proceeds from bank loans of $33.7 million and proceeds from the issuance of Class B preferred stock of $8.3 million, partially offset by principal repayment on bank loans of $20.0 million, taxes paid related to net share settlements of restricted stock awards of $2.2 million, cash paid for repurchases of common stock of $2.5 million, cash paid to acquire the IWS noncontrolling interest of $2.5 million and distributions to noncontrolling interest holders of $1.4 million.

Previous wording

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.

Current wording

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 $1.3 million and $0.9 million at September 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 $9.3 million and $5.5 million reported at September 30, 2025 and December 31, 2024, respectively, on the Company’s consolidated balance sheets.
Rearranged current paragraphs (1)

Current report — wording carried from elsewhere

The DDI Loan contains a number of covenants, including, but not 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. As of September 30, 2025, DDI was in default under the DDI Loan due to a debt covenant violation related to the fixed charge ratio. The Company has entered into an amendment to the DDI Loan that waives the event of default for the fiscal quarter ended September 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 DDI Loan immediately due and payable, exercise their rights with respect to collateral securing the obligation, and/or exercise any other rights and remedies available.
Rearranged previous paragraphs (1)

Previous report — wording carried elsewhere

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.