Kingsway Financial Services Inc. is a holding company. The Company operates as a merchant bank primarily engaged, through its subsidiaries, in the property and casualty insurance business. The Company operates through Insurance Underwriting segment. Its Insurance Underwriting segment provides non-standard automobile insurance to individuals who do not meet the criteria for coverage by standard automobile insurers. The Insurance Underwriting segment markets automobile insurance products that provide coverage in three areas: liability, accident benefits and physical damage. The Insurance Underwriting's products and services are marketed through over 3,700 independent agencies. The Company's property and casualty insurance business operations are conducted through its subsidiaries, such as Mendota Insurance Company (Mendota), Mendakota Insurance Company (Mendakota), Mendakota Casualty Company (MCC), Kingsway Amigo Insurance Company (Amigo) and Kingsway Reinsurance Corporation.