Kingsway Financial Services (KFS) 10-Q 8 Aug 18 2018 Q2 Quarterly report Financial data

Document and Entity Information

Document and Entity Information Document - shares	6 Months Ended
	Jun. 30, 2018	Aug. 08, 2018
Document Information [Line Items]
Entity Registrant Name	KINGSWAY FINANCIAL SERVICES INC.
Entity Central Index Key	1,072,627
Current Fiscal Year End Date	--06-30
Entity Filer Category	Accelerated Filer
Document Type	10-Q
Document Period End Date	Jun. 30, 2018
Document Fiscal Year Focus	2,018
Document Fiscal Period Focus	Q2
Amendment Flag	false
Entity Common Stock, Shares Outstanding		23,660,855

Consolidated Balance Sheet

Consolidated Balance Sheet - USD ($) $ in Thousands	Jun. 30, 2018	Dec. 31, 2017
Investments [Abstract]
Fixed maturities, at fair value (amortized cost of $11,605 and $14,707, respectively)	$ 11,361	$ 14,541
Marketable Securities, Equity Securities	2,189	4,476
Limited liability investments	5,217	4,922
Limited liability investment, at fair value	4,869	5,771
Other investments, at cost which approximates fair value	1,916	2,321
Short-term investments, at cost which approximates fair value	151	151
Total investments	25,703	32,182
Cash and cash equivalents	24,713	20,781
Investment in investee	4,947	5,230
Accrued investment income	161	331
Service fee receivable, net of allowance for doubtful accounts of $315 and $318, respectively	5,173	4,286
Other receivables, net of allowance for doubtful accounts of zero and zero, respectively	7,907	6,536
Deferred acquisition costs, net	6,662	6,325
Property and equipment, net of accumulated depreciation of $13,794 and $11,633, respectively	105,246	107,327
Goodwill	80,112	80,112
Intangible assets, net of accumulated amortization of $8,876 and $8,333, respectively	79,519	80,062
Other assets	3,592	4,302
Assets held for sale	138,804	137,126
Total Assets	482,539	484,600
Unpaid loss and loss adjustment [Abstract]
Property and casualty	2,594	1,329
Vehicle service agreements	2,615	2,779
Total unpaid loss and loss adjustment expenses	5,209	4,108
Note payable	184,567	186,469
Bank loan	4,417	4,917
Subordinated debt, at fair value	52,822	52,105
Net deferred income tax liabilities	28,796	28,745
Deferred service fees	41,221	39,741
Income taxes payable	2,801	2,644
Accrued expenses and other liabilities	10,946	10,612
Liabilities held for sale	112,866	105,949
Total Liabilities	443,645	435,290
Class A preferred stock, no par value; unlimited number authorized; 222,876 and 222,876 issued and outstanding at June 30, 2018 and December 31, 2017, respectively; redemption amount of $5,572	5,477	5,461
Shareholders' Equity [Abstract]
Additional paid-in capital	356,609	356,021
Accumulated deficit	(364,917)	(313,487)
Accumulated other comprehensive income (loss)	36,322	(3,852)
Shareholders' equity attributable to common shareholders	28,014	38,682
Noncontrolling interests in consolidated subsidiaries	5,403	5,167
Total Shareholders' Equity	33,417	43,849
Total Liabilities, Class A preferred stock and Shareholders' Equity	$ 482,539	$ 484,600

Consolidated Balance Sheet Bala

Consolidated Balance Sheet Balance Sheet Parenthetical - USD ($) $ in Thousands	Jun. 30, 2018	Dec. 31, 2017
Balance Sheet Parenthetical [Abstract]
Fixed maturities, cost	$ 11,605	$ 14,707
Equity investments, cost	2,325	4,854
Premiums receivable, allowance for doubtful accounts	0	0
Other receivables, allowance for doubtful accounts	0	0
Service fee receivable, allowance for doubtful accounts	315	318
Property and equipment, accumulated depreciation	13,794	11,634
Intangible assets accumulated amortization	8,876	8,333
Class A preferred stock, no par value; unlimited number authorized; 222,876 and 222,876 issued and outstanding at June 30, 2018 and December 31, 2017, respectively; redemption amount of $5,572	$ 5,572	$ 6,572
Common stock, shares outstanding	21,708,190	21,708,190

Consolidated Statement of Opera

Consolidated Statement of Operations - USD ($) shares in Thousands, $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2018	Jun. 30, 2017	Jun. 30, 2018	Jun. 30, 2017
Revenues [Abstract]
Service fee and commission income	$ 9,479	$ 6,584	$ 19,670	$ 12,946
Rental income	3,341	3,341	6,682	6,682
Net investment income (loss)	(18)	1,347	613	1,163
Net realized (losses) gains	(1)	(1)	9	(1)
(Loss) gain on change in fair value of equity investments	(248)	0	614	0
Other income	1,081	242	1,308	569
Total revenues	13,670	8,819	27,670	19,033
Operating Expenses [Abstract]
Loss and loss adjustment expenses	2,625	1,338	4,247	2,557
Commissions	932	811	1,817	1,579
Cost of services sold	1,464	1,291	3,716	2,595
General and administrative expenses	7,305	6,508	14,702	12,245
Leased real estate segment interest expense	1,546	1,569	3,098	3,143
Total operating expenses	13,872	11,517	27,580	22,119
Operating (loss) income	(202)	(2,698)	90	(3,086)
Other (revenues) expenses, net: [Abstract]
Interest expense not allocated to segments	1,519	1,216	2,905	2,375
Amortization of intangible assets	271	289	543	580
Contingent consideration benefit	0	(212)	0	(212)
Loss on change in fair value of debt	142	2,702	1,061	4,591
Equity in net loss (income) of investee	385	145	284	(2,240)
Total other expenses, net	2,317	4,140	4,793	5,094
Loss from continuing operations before income tax expense	(2,519)	(6,838)	(4,703)	(8,180)
Income tax expense	187	1,251	438	1,516
Loss from continuing operations	(2,706)	(8,089)	(5,141)	(9,696)
Income (loss) from discontinued operations, net of taxes	911	(570)	1,318	(447)
(Loss) gain on disposal of discontinued operations, net of taxes	(6,611)	1,017	(6,611)	1,017
Net loss	(8,406)	(7,642)	(10,434)	(9,126)
Less: net income attributable to noncontrolling interests in consolidated subsidiaries	108	100	243	205
Less: dividends on preferred stock, net of tax	130	154	259	328
Net loss attributable to common shareholders	$ (8,644)	$ (7,896)	$ (10,936)	$ (9,659)
Loss per share - continuing operations [Abstract]
Basic:	$ (0.14)	$ (0.39)	$ (0.26)	$ (0.48)
Diluted:	(0.14)	(0.39)	(0.26)	(0.48)
(Loss) earnings per share - discontinued operations [Abstract]
Basic:	(0.26)	0.02	(0.24)	0.03
Diluted:	(0.26)	0.02	(0.24)	0.03
Earnings Per Share, Basic and Diluted [Abstract]
Basic:	(0.40)	(0.37)	(0.50)	(0.45)
Diluted:	$ (0.40)	$ (0.37)	$ (0.50)	$ (0.45)
Weighted Average Number of Shares Outstanding, Diluted [Abstract]
Basic:	21,708	21,458	21,708	21,458
Diluted:	21,708	21,458	21,708	21,458

Consolidated Statements of Comp

Consolidated Statements of Comprehensive (Loss) Income - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2018	Jun. 30, 2017	Jun. 30, 2018	Jun. 30, 2017
Net loss	$ (8,406)	$ (7,642)	$ (10,434)	$ (9,126)
Unrealized gains (losses) on fixed maturities and equity investments: [Abstract]
Unrealized losses arising during the period	(72)	(1,064)	(437)	(1,227)
Reclassification adjustment for amounts included in net loss	(4)	478	(11)	(29)
Change in fair value of debt attributable to instrument-specific credit risk	778	0	344	0
Equity in other comprehensive loss of limited liability investment	(224)	0	(224)	0
Other comprehensive income (loss)	478	(586)	(328)	(1,256)
Comprehensive loss	(7,928)	(8,228)	(10,762)	(10,382)
Less: comprehensive income attributable to noncontrolling interests in consolidated subsidiaries	108	102	237	208
Comprehensive loss attributable to common shareholders	$ (8,036)	$ (8,330)	$ (10,999)	$ (10,590)

Consolidated Statement of Cash

Consolidated Statement of Cash Flows - USD ($) $ in Thousands	6 Months Ended
	Jun. 30, 2018	Jun. 30, 2017
Net Cash Provided by (Used in) Operating Activities [Abstract]
Net loss	$ (10,434)	$ (9,126)
Adjustments to Reconcile Net Income (Loss) to Cash Provided by (Used in) Operating Activities [Abstract]
(Income) loss from discontinued operations, net of taxes	(1,318)	447
(Loss) gain on disposal of discontinued operations, net of taxes	(6,611)	1,017
Equity in net loss (income) of investee	284	(2,240)
Equity in net income of limited liability investments	(164)	166
Loss on change in fair value of limited liability investment	(1,152)	(1,473)
Depreciation and amortization expense	2,704	3,187
Contingent consideration benefit	0	(212)
Stock-based compensation expense, net of forfeitures	588	588
Net realized (gains) losses	(9)	1
Gain on change in fair value of equity investments	(614)	0
Loss on change in fair value of debt	1,061	4,591
Deferred income taxes	51	1,090
Amortization of fixed maturities premiums and discounts	32	47
Amortization of note payable premium	(473)	(483)
Increase (Decrease) in Other Operating Assets and Liabilities, Net [Abstract]
Service fee receivable, net	(887)	(88)
Other receivables, net	(1,371)	(1,647)
Deferred acquisition costs, net	(337)	(227)
Unpaid loss and loss adjustment expenses	1,101	(523)
Deferred service fees	1,480	2,061
Other, net	(1,193)	(817)
Cash used in operating activities - continuing operations	(6,387)	(7,847)
Cash used in operating activities - discontinued operations	(4,651)	(5,118)
Net cash used in operating activities	(1,736)	(2,729)
Net Cash Provided by (Used in) Investing Activities [Abstract]
Proceeds from sales and maturities of fixed maturities	4,965	145
Proceeds from sales of equity investments	3,704	0
Purchases of fixed maturities	1,885	192
Purchases of equity investments	806	506
Net acquisitions of limited liability investments	606	1,000
Net proceeds from other investments	405
Net proceeds from short-term investments	0	(250)
Net proceeds from sale of discontinued operations	1,900	1,017
Net proceeds from other investments		373
Net purchases of property and equipment	(80)	(450)
Cash provided by (used in) investing activities - continuing operations	7,260	6,409
Cash (used in) provided by investing activities - discontinued operations	(337)	6,772
Net cash provided by investing activities	7,597	(363)
Net Cash Provided by (Used in) Financing Activities, Continuing Operations [Abstract]
Principal payments on bank loan	(500)	0
Principal payments on note payable	1,429	1,264
Cash used in financing activities - continuing operations	(1,929)	(1,264)
Cash used in financing activities - discontinued operations	0	0
Net cash used in financing activities	(1,929)	(1,264)
Net increase (decrease) in cash and cash equivalents from continuing operations	3,932	(4,356)
Cash and cash equivalents of continuing operations at beginning of period	20,781	31,962
Cash and cash equivalents of continuing operations at end of period	$ 24,713	$ 27,606

Business

Business	6 Months Ended
	Jun. 30, 2018
Business [Abstract]
Nature of Operations [Text Block]	BUSINESS Kingsway Financial Services Inc. (the "Company" or "Kingsway") was incorporated under the Business Corporations Act (Ontario) on September 19, 1989. Kingsway is a Canadian holding company with operating subsidiaries located in the United States. The Company owns or controls subsidiaries primarily in the insurance, extended warranty, asset management and real estate industries.

Basis of Presentation (Notes)

Basis of Presentation (Notes)	6 Months Ended
	Jun. 30, 2018
Basis of Presentation [Abstract]
Basis of Presentation and Significant Accounting Policies [Text Block]	BASIS OF PRESENTATION The accompanying unaudited consolidated interim financial statements have been prepared in accordance with accounting principles generally accepted in the United States of America ("U.S. GAAP") for interim financial information and with the instructions to Form 10-Q and Article 10 of Regulation S-X. Accordingly, they do not include all of the information and notes required by U.S. GAAP for complete financial statements of the Company. In the opinion of management, all adjustments necessary for a fair presentation have been included and are of a normal recurring nature. Interim results are not necessarily indicative of the results that may be expected for the year. Certain prior year amounts have been reclassified to conform to current year presentation. Such reclassifications had no impact on previously reported net loss or total shareholders' equity. The accompanying unaudited consolidated interim financial statements and footnotes should be read in conjunction with the audited consolidated financial statements and footnotes included within our Annual Report on Form 10-K (" 2017 Annual Report") for the year ended December 31, 2017 . The unaudited consolidated interim financial statements include the accounts of the Company and its subsidiaries. All material intercompany transactions and balances have been eliminated in consolidation. The preparation of consolidated 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 critical accounting estimates and assumptions in the accompanying unaudited consolidated interim financial statements include the provision for unpaid loss and loss adjustment expenses; valuation of fixed maturities and equity investments; impairment assessment of investments; valuation of limited liability investment, at fair value; valuation of deferred income taxes; valuation and impairment assessment of intangible assets; goodwill recoverability; deferred acquisition costs; fair value assumptions for performance shares; and fair value assumptions for subordinated debt obligations. The fair values of the Company's investments in fixed maturities and equity investments, limited liability investment, at fair value, performance shares and subordinated debt are 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, short-term investments and certain other assets and other liabilities because of their short-term nature. The Company's financial results contained herein are reported in U.S. dollars unless otherwise indicated.

Summary of Significant Accounti

Summary of Significant Accounting Polocies	6 Months Ended
	Jun. 30, 2018
Summary of significant accounting policies [Abstract]
Significant Accounting Policies [Text Block]	SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES There have been no material changes to our significant accounting policies as reported in our 2017 Annual Report.

Recently Issued Accounting Stan

Recently Issued Accounting Standards	6 Months Ended
	Jun. 30, 2018
Recently Issued Accounting Standards [Abstract]
New Accounting Pronouncements, Policy [Policy Text Block]	RECENTLY ISSUED ACCOUNTING STANDARDS (a) Adoption of New Accounting Standards: Effective January 1, 2018, the Company adopted Accounting Standards Update ("ASU") 2014-09, Revenue from Contracts with Customers ("ASU 2014-09"), and the related amendments, utilizing the modified retrospective approach, which created a new comprehensive revenue recognition standard that serves as the single source of revenue guidance for all contracts with customers to transfer goods or services or contracts for the transfer of nonfinancial assets, unless those contracts are within the scope of other standards. The core principle of ASU 2014-09 is that an entity recognizes revenue to depict the transfer of promised goods or services to customers in an amount that reflects the consideration to which the entity expects to be entitled in exchange for those goods or services. Insurance contracts, lease contracts and investments are not within the scope of ASU 2014-09. ASU 2014-09 is applicable to the Company's service fee and commission income. Service fee and commission income represents vehicle service agreement fees, maintenance support service fees, warranty product commissions and homebuilder warranty service fees and commissions based on terms of various agreements with credit unions, consumers, businesses and homebuilders. The revenue recognition policy we utilize for our service fee and commission income aligns with the new guidance; therefore, there were no changes to the way we recognize revenue for the three and six months ended June 30, 2018 . Since the adoption of the new standard did not have a material impact on the measurement or recognition of revenue, a cumulative effect adjustment to opening accumulated deficit was not deemed necessary. Refer to Note 12 , " Revenue from Contracts with Customers ," for further details. Effective January 1, 2018, the Company adopted ASU 2016-01, Financial Instruments-Overall (Subtopic 825-10): Recognition and Measurement of Financial Assets and Financial Liabilities ("ASU 2016-01"). The amendments in ASU 2016-01 address certain aspects of recognition, measurement, presentation, and disclosure of financial instruments. Most significantly, ASU 2016-01 requires (1) equity investments (except those accounted for under the equity method of accounting or those that result in consolidation of an investee) to be measured at fair value with changes in fair value recognized in net income (loss); and (2) an entity to present separately in other comprehensive income (loss) the portion of the total change in the fair value of a liability resulting from a change in the instrument-specific credit risk when the entity has elected to measure the liability at fair value in accordance with the fair value option for financial instruments. Previously, the Company recorded its equity investments at fair value with net unrealized gains or losses reported in accumulated other comprehensive income (loss) and recorded its subordinated debt at fair value with the total change in fair value reported in net income (loss). As a result of the adoption of ASU 2016-01, at January 1, 2018 cumulative net unrealized losses on equity investments of $0.0 million were reclassified from accumulated other comprehensive income (loss) into accumulated deficit and a cumulative $40.5 million change in fair value of subordinated debt attributable to instrument-specific credit risk was reclassified from accumulated deficit to accumulated other comprehensive income (loss). Prior periods have not been restated to conform to the current presentation. Effective January 1, 2018, the Company adopted ASU 2016-15, Classification of Certain Cash Receipts and Cash Payments ("ASU 2016-15"). The objective of ASU 2016-15 is to reduce diversity in the classification of cash receipts and payments for specific cash flow issues, including debt prepayment or debt extinguishment costs, contingent consideration payments made after a business combination and proceeds from the settlement of insurance claims. The adoption of the standard did not affect the Company's consolidated statements of cash flows. (b) Accounting Standards Not Yet Adopted: In February 2016, the Financial Accounting Standards Board ("FASB") FASB issued ASU 2016-02, Leases ("ASU 2016-02"). ASU 2016-02 was issued to improve the financial reporting of leasing transactions. Under current guidance for lessees, leases are only included on the balance sheet if certain criteria, classifying the agreement as a capital lease, are met. This update will require the recognition of a right-of-use asset and a corresponding lease liability, discounted to the present value, for all leases that extend beyond 12 months. For operating leases, the asset and liability will be expensed over the lease term on a straight-line basis, with all cash flows included in the operating section of the statement of cash flows. For finance leases, interest on the lease liability will be recognized separately from the amortization of the right-of-use asset in the statement of comprehensive income and the repayment of the principal portion of the lease liability will be classified as a financing activity while the interest component will be included in the operating section of the statement of cash flows. The accounting treatment for lessors will remain relatively unchanged. ASU 2016-02 is effective for annual and interim reporting periods beginning after December 15, 2018. Early adoption is permitted. Upon adoption, leases will be recognized and measured at the beginning of the earliest period presented using a modified retrospective approach. The Company is currently evaluating the potential effect of the adoption of ASU 2016-02 on its consolidated financial statements. In June 2016, the FASB issued ASU 2016-13, Financial Instruments-Credit Losses (Topic 326): Measurement of Credit Losses on Financial Instruments ("ASU 2016-13"). ASU 2016-13 replaces the current incurred loss model used to measure impairment losses with an expected loss model for trade, reinsurance, and other receivables as well as financial instruments measured at amortized cost. ASU 2016-13 will require a financial asset measured at amortized cost, including reinsurance balances recoverable, to be presented at the net amount expected to be collected by means of an allowance for credit losses that runs through net loss. Credit losses relating to available-for-sale debt securities will also be recorded through an allowance for credit losses. However, the amendments would limit the amount of the allowance to the amount by which fair value is below amortized cost. The measurement of credit losses on available-for-sale investments is similar under current GAAP, but the update requires the use of the allowance account through which amounts can be reversed, rather than through an irreversible write-down. ASU 2016-13 is effective for annual periods beginning after December 15, 2019, and interim periods within those annual periods with early adoption permitted for fiscal years beginning after December 31, 2018 and interim periods within such year. The Company is currently evaluating ASU 2016-13 to determine the potential impact that adopting this standard will have on its consolidated financial statements. In January 2017, the FASB issued ASU 2017-04, Intangibles - Goodwill and Other (Topic 350): Simplifying the Test for Goodwill Impairment ("ASU 2017-04"). ASU 2017-04 was issued to simplify the subsequent measurement of goodwill. This update changes the impairment test by requiring an entity to compare the fair value of a reporting unit with its carrying amount as opposed to comparing the carrying amount of goodwill with its implied fair value. ASU 2017-04 is effective for annual and interim reporting periods beginning after December 15, 2019. Early adoption is permitted. The Company does not believe the adoption of ASU 2017-04 will have a material effect on its consolidated financial statements.

Acquisition and Discontinued Op

Acquisition and Discontinued Operations (Notes)	6 Months Ended
	Jun. 30, 2018
Acquisition [Abstract]
Business Combination Disclosure [Text Block]	ACQUISITION AND DISCONTINUED OPERATIONS (a) Acquisition Professional Warranty Service Corporation: On October 12, 2017, the Company acquired 100% of the outstanding shares of Professional Warranty Service Corporation ("PWSC") for estimated cash consideration of approximately $9.9 million . The final purchase price is subject to a true-up that will be finalized in 2018. As further discussed in Note 17 , " Segmented Information ," PWSC is included in the Extended Warranty segment. PWSC is based in Virginia and is a leading provider of new home warranty products and administration services to the largest tier of domestic residential construction firms in the United States. This acquisition allows the Company to grow its portfolio of warranty companies and expand into the home warranty business. The Company intends to finalize during 2018 its fair value analysis of the assets acquired and liabilities assumed. The assets acquired and liabilities assumed are recorded in the consolidated financial statements at their estimated fair market values. These estimates, allocations and calculations are subject to change as we obtain further information; therefore, the final fair market values of the assets acquired and liabilities assumed may not agree with the estimates included in the consolidated financial statements. The following table summarizes the estimated allocation of the assets acquired and liabilities assumed at the date of acquisition: (in thousands) October 12, 2017 Cash and cash equivalents $ 2,071 Other receivables 50 Service fee receivable 1,422 Property and equipment 238 Other assets 205 Goodwill 9,051 Total assets $ 13,037 Deferred service fees $ 2,079 Accrued expenses and other liabilities 1,089 Total liabilities $ 3,168 Purchase price $ 9,869 (b) Discontinued Operations Mendota Insurance Company, Mendakota Insurance Company and Mendakota Casualty Company: On July 16, 2018, the Company announced it has entered into a definitive agreement to sell its non-standard automobile insurance companies Mendota Insurance Company, Mendakota Insurance Company and Mendakota Casualty Company (collectively "Mendota") for an aggregate purchase price equal to Mendota's statutory surplus at June 30, 2018, which is approximately $28.9 million . The transaction is expected to be completed during the third quarter of 2018 subject to the receipt of regulatory approvals. As part of the transaction, the Company will indemnify the buyer for any loss and loss adjustment expenses with respect to open claims and certain specified claims in excess of Mendota's carried unpaid loss and loss adjustment expenses at June 30, 2018 . The maximum obligation to the Company with respect to the open claims is $2.5 million . There is no maximum obligation to the Company with respect to the specified claims. As a result of this announcement, Mendota, previously disclosed as part of the Insurance Underwriting segment, has been classified as a discontinued operation and the results of their operations are reported separately for all periods presented. The Company recognized a loss on disposal of $8.0 million during the second quarter of 2018, as a result of adjusting the net carrying value of Mendota to be equal to the estimated purchase price. The assets and liabilities of Mendota are presented as held for sale in the consolidated balance sheets at June 30, 2018 and December 31, 2017 . Itasca Real Estate Investors, LLC: On June 1, 2018, the Company disposed of its subsidiary, Itasca Real Estate Investors, LLC ("Itasca Real Estate"). During the second quarter of 2018, the Company recognized a gain on disposal of Itasca Real Estate of $0.0 million . As a result of the sale, Itasca Real Estate has been classified as a discontinued operation and the results of their operations are reported separately for all periods presented. The assets and liabilities of Itasca Real Estate are presented as held for sale in the consolidated balance sheets at December 31, 2017. Assigned Risk Solutions Ltd.: On April 1, 2015, the Company closed on the sale of its subsidiary, Assigned Risk Solutions Ltd. ("ARS"). The terms of the sale provided for receipt by the Company of future earnout payments equal to 1.25% of ARS' written premium and fee income during the earnout periods. The earnout payments were payable in three annual installments beginning in April 2016 through April 2018. During the second quarter of 2018, the Company received cash consideration, before expenses, for the third annual installment earnout payment of $1.7 million . Net of expenses, the Company recorded an additional gain on disposal of ARS of $1.3 million and $1.0 million for the three and six months ended June 30, 2018 and June 30, 2017 , respectively. As a result of the sale, ARS, previously disclosed as part of the Extended Warranty (formerly Insurance Services) segment, has been classified as a discontinued operation. Summary financial information for Mendota, Itasca Real Estate and ARS included in (loss) income from discontinued operations, net of taxes in the statements of operations for the three and six months ended June 30, 2018 and June 30, 2017 is presented below: (in thousands) Three months ended June 30, Six months ended June 30, 2018 2017 2018 2017 Income (loss) from discontinued operations, net of taxes: Revenues: Net premiums earned $ 22,956 $ 33,518 $ 51,592 $ 66,440 Rental income 4 6 10 12 Net investment income (loss) 570 (1,008 ) 519 (478 ) Net realized (losses) gains (1 ) 735 2 1,133 (Loss) gain on change in fair value of equity investments (77 ) — 237 — Other income 2,445 2,556 4,876 5,027 Total revenues 25,897 35,807 57,236 72,134 Expenses: Loss and loss adjustment expenses 18,927 26,130 41,728 51,321 Commissions 2,251 5,375 6,442 10,688 General and administrative expenses 3,808 4,872 7,748 10,407 Impairment of intangible assets — — — 250 Total expenses 24,986 36,377 55,918 72,666 Income (loss) from discontinued operations before income tax benefit 911 (570 ) 1,318 (532 ) Income tax benefit — — — (85 ) Income (loss) from discontinued operations, net of taxes 911 (570 ) 1,318 (447 ) (Loss) gain on disposal of discontinued operations, net of taxes: (Loss) gain on disposal of discontinued operations before income tax expense (6,611 ) 1,017 (6,611 ) 1,017 Income tax expense — — — — (Loss) gain on disposal of discontinued operations, net of taxes (6,611 ) 1,017 (6,611 ) 1,017 Total (loss) income from discontinued operations, net of taxes $ (5,700 ) $ 447 $ (5,293 ) $ 570 The assets and liabilities of Mendota and Itasca Real Estate are presented as held for sale in the consolidated balance sheets. The carrying amounts of the major classes of assets and liabilities of Mendota and Itasca Real Estate at June 30, 2018 and December 31, 2017 are as follows: (in thousands) June 30, 2018 December 31, 2017 Assets Investments: Fixed maturities, at fair value $ 42,714 $ 38,673 Equity investments, at fair value 3,681 4,518 Limited liability investments 18,427 20,251 Limited liability investment, at fair value 3,629 4,543 Other investments, at cost which approximates fair value 1,400 1,400 Total investments 69,851 69,385 Cash and cash equivalents 18,517 23,505 Accrued investment income 239 195 Premiums receivable, net 27,673 27,855 Other receivables 174 603 Reinsurance recoverable 6,509 108 Prepaid reinsurance premiums 13,493 — Deferred acquisition costs, net 2,048 6,720 Property and equipment, net 162 903 Intangible assets, net — 7,553 Other assets 138 299 Assets held for sale $ 138,804 $ 137,126 Liabilities Unpaid loss and loss adjustment expenses $ 58,817 $ 62,323 Unearned premiums 34,969 36,686 Reinsurance payable 14,869 82 Deferred income tax liability — 1,586 Accrued expenses and other liabilities 4,211 5,272 Liabilities held for sale $ 112,866 $ 105,949

Investments

Investments	6 Months Ended
	Jun. 30, 2018
Investments [Abstract]
Summary of Investments, Other than Investments in Related Parties [Text Block]	INVESTMENTS As further discussed in Note 4 , " Recently Issued Accounting Standards ," effective January 1, 2018, the Company adopted ASU 2016-01. As a result of the adoption, equity investments are no longer classified as available-for-sale. Prior periods have not been restated to conform to the current presentation. The amortized cost, gross unrealized gains and losses, and estimated fair value of the Company's available-for-sale investments at June 30, 2018 and December 31, 2017 are summarized in the tables shown below: (in thousands) June 30, 2018 Amortized Cost Gross Unrealized Gains Gross Unrealized Losses Estimated Fair Value Fixed maturities: U.S. government, government agencies and authorities $ 5,503 $ — $ 76 $ 5,427 States, municipalities and political subdivisions 624 — 19 605 Mortgage-backed 2,902 — 91 2,811 Corporate 2,576 — 58 2,518 Total fixed maturities $ 11,605 $ — $ 244 $ 11,361 (in thousands) December 31, 2017 Amortized Cost Gross Unrealized Gains Gross Unrealized Losses Estimated Fair Value Fixed maturities: U.S. government, government agencies and authorities $ 5,671 $ — $ 59 $ 5,612 States, municipalities and political subdivisions 639 — 13 626 Mortgage-backed 2,933 — 57 2,876 Corporate 5,464 — 37 5,427 Total fixed maturities 14,707 — 166 14,541 Equity investments: Common stock 3,883 — 313 3,570 Warrants - publicly traded 11 47 — 58 Warrants - not publicly traded 960 173 285 848 Total equity investments 4,854 220 598 4,476 Total fixed maturities and equity investments $ 19,561 $ 220 $ 764 $ 19,017 Net unrealized gains and losses in the tables above are reported as other comprehensive income (loss) with the exception of net unrealized losses of $0.1 million , at December 31, 2017 , related to warrants - not publicly traded, which are reported in the consolidated statements of operations. The table below summarizes the Company's fixed maturities at June 30, 2018 by contractual maturity periods. Actual results may differ as issuers may have the right to call or prepay obligations, with or without penalties, prior to the contractual maturity of these obligations. (in thousands) June 30, 2018 Amortized Cost Estimated Fair Value Due in one year or less $ 4,924 $ 4,899 Due after one year through five years 5,378 5,219 Due after five years through ten years 132 125 Due after ten years 1,171 1,118 Total $ 11,605 $ 11,361 The following tables highlight the aggregate unrealized loss position, by security type, of available-for-sale investments in unrealized loss positions as of June 30, 2018 and December 31, 2017 . The tables segregate the holdings based on the period of time the investments have been continuously held in unrealized loss positions. (in thousands) June 30, 2018 Less than 12 Months Greater than 12 Months Total Estimated Fair Value Unrealized Loss Estimated Fair Value Unrealized Loss Estimated Fair Value Unrealized Loss Fixed maturities: U.S. government, government agencies and authorities $ 3,502 $ 34 $ 1,925 $ 42 $ 5,427 $ 76 States, municipalities and political subdivisions 86 2 519 17 605 19 Mortgage-backed 690 13 2,121 78 2,811 91 Corporate 410 5 2,108 53 2,518 58 Total fixed maturities $ 4,688 $ 54 $ 6,673 $ 190 $ 11,361 $ 244 (in thousands) December 31, 2017 Less than 12 Months Greater than 12 Months Total Estimated Fair Value Unrealized Loss Estimated Fair Value Unrealized Loss Estimated Fair Value Unrealized Loss Fixed maturities: U.S. government, government agencies and authorities $ 4,067 $ 50 $ 1,545 $ 9 $ 5,612 $ 59 States, municipalities and political subdivisions 626 13 — — 626 13 Mortgage-backed 2,876 57 — — 2,876 57 Corporate 2,427 37 — — 2,427 37 Total fixed maturities 9,996 157 1,545 9 11,541 166 Equity investments: Common stock 3,570 313 — — 3,570 313 Warrants 675 285 — — 675 285 Total equity investments 4,245 598 — — 4,245 598 Total $ 14,241 $ 755 $ 1,545 $ 9 $ 15,786 $ 764 There are approximately 64 and 68 individual available-for-sale investments that were in unrealized loss positions as of June 30, 2018 and December 31, 2017 , respectively. The establishment of an other-than-temporary impairment on an investment requires a number of judgments and estimates. The Company performs a quarterly analysis of the individual investments to determine if declines in market value are other-than-temporary. The analysis includes some or all of the following procedures as deemed appropriate by the Company: • identifying all unrealized loss positions that have existed for at least six months; • identifying other circumstances management believes may affect the recoverability of the unrealized loss positions; • obtaining a valuation analysis from third-party investment managers regarding the intrinsic value of these investments based on their knowledge and experience together with market-based valuation techniques; • reviewing the trading range of certain investments over the preceding calendar period; • assessing if declines in market value are other-than-temporary for debt instruments based on the investment grade credit ratings from third-party rating agencies; • assessing if declines in market value are other-than-temporary for any debt instrument with a non-investment grade credit rating based on the continuity of its debt service record; • determining the necessary provision for declines in market value that are considered other-than-temporary based on the analyses performed; and • assessing the Company's ability and intent to hold these investments at least until the investment impairment is recovered. The risks and uncertainties inherent in the assessment methodology used to determine declines in market value that are other-than-temporary include, but may not be limited to, the following: • the opinions of professional investment managers could be incorrect; • the past trading patterns of individual investments may not reflect future valuation trends; • the credit ratings assigned by independent credit rating agencies may be incorrect due to unforeseen or unknown facts related to a company's financial situation; and • the debt service pattern of non-investment grade instruments may not reflect future debt service capabilities and may not reflect a company's unknown underlying financial problems. As a result of the analysis performed by the Company to determine declines in market value that are other-than-temporary, there were no write-downs for other-than-temporary impairments related to investments recorded for the three and six months ended June 30, 2018 and June 30, 2017 . The Company has reviewed currently available information regarding investments with estimated fair values less than their carrying amounts and believes these unrealized losses are not other-than-temporary and are primarily due to temporary market and sector-related factors rather than to issuer-specific factors. The Company does not intend to sell those investments, and it is not likely it will be required to sell those investments before recovery of its amortized cost. The Company does not have any exposure to subprime mortgage-backed investments. Limited liability investments include investments in limited liability companies and limited partnerships that primarily invest in income-producing real estate or real estate related investments. The Company's interests in these investments are not 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 is no more than three months. As of June 30, 2018 and December 31, 2017 , the carrying value of limited liability investments totaled $5.2 million and $4.9 million , respectively. 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 (loss). Limited liability investment, at fair value represents the Company's investment in 15.9% of the outstanding units of 1347 Investors LLC ("1347 Investors"). The Company has made an irrevocable election to account for this investment at fair value. As of June 30, 2018 and December 31, 2017 , the carrying value of the Company's limited liability investment, at fair value was $4.9 million and $5.8 million , respectively. Other investments include collateral loans and are reported at their unpaid principal balance. As of June 30, 2018 and December 31, 2017 , the carrying value of other investments totaled $1.9 million and $2.3 million , respectively. The Company had previously entered into two separate performance share grant agreements with 1347 Property Insurance Holdings, Inc. ("PIH"), whereby the Company will be entitled to receive up to an aggregate of 475,000 shares of PIH common stock upon achievement of certain milestones for PIH’s stock price. Pursuant to the performance share grant agreements, if at any time the last sales price of PIH’s common stock equals or exceeds: (i) $10.00 per share (as adjusted for stock splits, stock dividends, reorganizations, recapitalizations and the like) for any 20 trading days within any 30-trading day period, the Company will receive 100,000 shares of PIH common stock; (ii) $12.00 per share (as adjusted for stock splits, stock dividends, reorganizations, recapitalizations and the like) for any 20 trading days within any 30-trading day period, the Company will receive 125,000 shares of PIH common stock (in addition to the 100,000 shares of common stock earned pursuant to clause (i) herein); (iii) $15.00 per share (as adjusted for stock splits, stock dividends, reorganizations, recapitalizations and the like) for any 20 trading days within any 30-trading day period, the Company will receive 125,000 shares of PIH common stock (in addition to the 225,000 shares of common stock earned pursuant to clauses (i) and (ii) herein); and (iv) $18.00 per share (as adjusted for stock splits, stock dividends, reorganizations, recapitalizations and the like) for any 20 trading days within any 30-trading day period, the Company will receive 125,000 shares of PIH common stock (in addition to the 350,000 shares of common stock earned pursuant to clauses (i), (ii) and (iii) herein). To the extent shares of PIH common stock are granted to the Company under either of the performance share grant agreements, they will be recorded at the time the shares are granted and will have a valuation equal to the last sales price of PIH common stock on the day prior to such grant. During the first quarter of 2018, the Company entered into an agreement with PIH to cancel the $10.00 per share Performance Shares Grant Agreement in exchange for cash consideration of $0.3 million . For the six months ended June 30, 2018 , the Company recorded a gain of $0.3 million related to this transaction which is included in gain on change in fair value of equity investments in the consolidated statements of operations. No shares were received by the Company under either of the performance share grant agreements as of June 30, 2018 . On July 24, 2018, the Company entered into an agreement with PIH to cancel the $12.00 per share, $15.00 per share and $18.00 per share Performance Shares Grant Agreements in exchange for cash consideration of $1.0 million . The Company will record this gain during the third quarter of 2018. Refer to Note 18 , " Fair Value of Financial Instruments ," for further details regarding the performance shares. Net investment income (loss) for the three and six months ended June 30, 2018 and June 30, 2017 is comprised as follows: (in thousands) Three months ended June 30, Six months ended June 30, 2018 2017 2018 2017 Investment income (loss): Interest from fixed maturities $ 57 $ 49 $ 90 $ 83 Dividends 53 102 108 196 Income (loss) from limited liability investments 120 (100 ) 164 (166 ) Loss on change in fair value of limited liability investment, at fair value (280 ) (1,292 ) (1,152 ) (1,520 ) (Loss) gain on change in fair value of warrants - not publicly traded — (198 ) — 47 Other 77 100 194 212 Gross investment income (loss) 27 (1,339 ) (596 ) (1,148 ) Investment expenses (9 ) (8 ) (17 ) (15 ) Net investment income (loss) $ 18 $ (1,347 ) $ (613 ) $ (1,163 ) Gross realized gains and losses on available-for-sale investments and limited liability investments for the three and six months ended June 30, 2018 and June 30, 2017 are comprised as follows: (in thousands) Three months ended June 30, Six months ended June 30, 2018 2017 2018 2017 Gross realized gains $ — $ — $ 10 $ — Gross realized losses (1 ) (1 ) (1 ) (1 ) Net realized (losses) gains $ (1 ) $ (1 ) $ 9 $ (1 ) (Loss) gain on change in fair value of equity investments for the three and six months ended June 30, 2018 and June 30, 2017 is comprised as follows: (in thousands) Three months ended June 30, Six months ended June 30, 2018 2017 2018 2017 Net (losses) gains recognized on equity investments sold during the period $ (10 ) $ — $ 545 $ — Change in unrealized (losses) gains on equity investments held at end of the period (238 ) — 69 — (Loss) gain on change in fair value of equity investments $ (248 ) $ — $ 614 $ — Fixed maturities and short-term investments with an estimated fair value of $1.9 million and $1.8 million were on deposit with state and provincial regulatory authorities at June 30, 2018 and December 31, 2017 , respectively. From time to time, the Company pledges investments to third parties as deposits or to collateralize liabilities incurred under its policies of insurance. The amount of such pledged investments was $1.1 million and $1.1 million at June 30, 2018 and December 31, 2017 , respectively.

Investment in Investees (Notes)

Investment in Investees (Notes)	6 Months Ended
	Jun. 30, 2018
Schedule of Equity Method Investments [Line Items]
Equity Method Investments and Joint Ventures Disclosure [Text Block]	INVESTMENT IN INVESTEE Investment in investee includes the Company's investment in the common stock of Itasca Capital Ltd. ("ICL") and is accounted for under the equity method. The Company's investment in ICL is recorded on a three-month lag basis. The carrying value, estimated fair value and approximate equity percentage for the Company's investment in investee at June 30, 2018 and December 31, 2017 were as follows: (in thousands, except for percentages) June 30, 2018 December 31, 2017 Equity Percentage Estimated Fair Value Carrying Value Equity Percentage Estimated Fair Value Carrying Value ICL 31.2 % $ 3,531 $ 4,947 31.2 % $ 3,816 $ 5,230 The estimated fair value of the Company's investment in ICL at June 30, 2018 in the table above is calculated based on the published closing price of ICL at March 31, 2018 to be consistent with the three-month lag in reporting its carrying value under the equity method. The estimated fair value of the Company's investment in ICL based on the published closing price of ICL at June 30, 2018 is $3.3 million . For the three months ended June 30, 2018 and June 30, 2017 , equity in net loss of investee was $0.4 million and $0.1 million , respectively (loss of $0.3 million and income of $2.2 million for the six months ended June 30, 2018 and June 30, 2017 , respectively). On July 30, 2018, the Company executed an agreement to sell 1,813,889 shares of ICL common stock, at a price of Canadian $0.72 per share, for cash proceeds totaling Canadian $1.3 million .

Deferred Acquisition Costs

Deferred Acquisition Costs	6 Months Ended
	Jun. 30, 2018
Deferred Acquisition Costs [Abstract]
Deferred Policy Acquisition Costs [Text Block]	DEFERRED ACQUISITION COSTS Policy acquisition costs consist primarily of commissions and agency expenses incurred related to successful efforts to acquire vehicle service agreements. Acquisition costs deferred on vehicle service agreements are amortized over the period in which the related revenues are earned. The components of deferred acquisition costs and the related amortization expense for the three and six months ended June 30, 2018 and June 30, 2017 are comprised as follows: (in thousands) Three months ended June 30, Six months ended June 30, 2018 2017 2018 2017 Beginning balance, net $ 6,428 $ 5,867 $ 6,325 $ 5,827 Additions 1,256 1,331 2,498 2,317 Amortization (1,022 ) (1,144 ) (2,161 ) (2,090 ) Balance at June 30, net $ 6,662 $ 6,054 $ 6,662 $ 6,054

Intangible Assets

Intangible Assets	6 Months Ended
	Jun. 30, 2018
Intangible Assets [Abstract]
Intangible Assets Disclosure [Text Block]	9 INTANGIBLE ASSETS Intangible assets at June 30, 2018 and December 31, 2017 are comprised as follows: (in thousands) June 30, 2018 Gross Carrying Value Accumulated Amortization Net Carrying Value Intangible assets subject to amortization: Database $ 4,918 $ 2,767 $ 2,151 Vehicle service agreements in-force 3,680 3,656 24 Customer relationships 3,611 2,183 1,428 In-place lease 1,125 123 1,002 Contract-based revenues 731 147 584 Intangible assets not subject to amortization: Tenant relationship 73,667 — 73,667 Trade name 663 — 663 Total $ 88,395 $ 8,876 $ 79,519 (in thousands) December 31, 2017 Gross Carrying Value Accumulated Amortization Net Carrying Value Intangible assets subject to amortization: Database $ 4,918 $ 2,521 $ 2,397 Vehicle service agreements in-force 3,680 3,640 40 Customer relationships 3,611 1,965 1,646 In-place lease 1,125 92 1,033 Contract-based revenues 731 115 616 Intangible assets not subject to amortization: Tenant relationship 73,667 — 73,667 Trade name 663 — 663 Total $ 88,395 $ 8,333 $ 80,062 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 seven to eighteen years. Amortization of intangible assets was $0.3 million and $0.3 million for the three months ended June 30, 2018 and June 30, 2017 , respectively ( $0.5 million and $0.6 million for the six months ended June 30, 2018 and June 30, 2017 , respectively). The tenant relationship and trade name intangible assets have indefinite useful lives and are not amortized. No impairment charges were taken on intangible assets during the three and six months ended June 30, 2018 and June 30, 2017 .

Unpaid Loss and Loss Adjustment

Unpaid Loss and Loss Adjustment Expenses	6 Months Ended
	Jun. 30, 2018
Unpaid loss and loss adjustment [Abstract]
Liability for Future Policy Benefits and Unpaid Claims Disclosure [Text Block]	10 UNPAID LOSS AND LOSS ADJUSTMENT EXPENSES The establishment of the provision for unpaid loss and loss adjustment expenses is based on known facts and interpretation of circumstances and is, therefore, a complex and dynamic process influenced by a large variety of factors. These factors include the Company's experience with similar cases and historical trends involving loss payment patterns, pending levels of unpaid loss and loss adjustment expenses, product mix or concentration, loss severity and loss frequency patterns. Other factors include the continually evolving and changing regulatory and legal environment; actuarial studies; professional experience and expertise of the Company's claims departments' personnel and independent adjusters retained to handle individual claims; the quality of the data used for projection purposes; existing claims management practices including claims-handling and settlement practices; the effect of inflationary trends on future loss settlement costs; court decisions; economic conditions; and public attitudes. Consequently, the process of determining the provision for unpaid loss and loss adjustment expenses necessarily involves risks that the actual loss and loss adjustment expenses incurred by the Company will deviate, perhaps materially, from the estimates recorded. The Company's evaluation of the adequacy of unpaid loss and loss adjustment expenses includes a re-estimation of the liability for unpaid loss and loss adjustment expenses relating to each preceding financial year compared to the liability that was previously established. (a) Property and Casualty The results of this comparison and the changes in the provision for property and casualty unpaid loss and loss adjustment expenses, net of amounts recoverable from reinsurers, as of June 30, 2018 and June 30, 2017 were as follows: (in thousands) June 30, 2018 June 30, 2017 Balance at beginning of period, gross $ 1,329 $ 2,201 Less reinsurance recoverable related to property and casualty unpaid loss and loss adjustment expenses 72 354 Balance at beginning of period, net 1,257 1,847 Incurred related to: Current year — — Prior years 1,647 (1 ) Paid related to: Current year — — Prior years (410 ) (379 ) Balance at end of period, net 2,494 1,467 Plus reinsurance recoverable related to property and casualty unpaid loss and loss adjustment expenses 100 332 Balance at end of period, gross $ 2,594 $ 1,799 The Company reported unfavorable development on property and casualty unpaid loss and loss adjustment expenses of $1.6 million and favorable development of $0.0 million for the six months ended June 30, 2018 and June 30, 2017 , respectively. The unfavorable development for the six months ended June 30, 2018 was related to an increase in property and casualty loss adjustment expenses at Kingsway Amigo Insurance Company ("Amigo"). (b) Vehicle Service Agreements The results of the comparison and the changes in the provision for vehicle service agreement unpaid loss and loss adjustment expenses as of June 30, 2018 and June 30, 2017 were as follows: (in thousands) June 30, 2018 June 30, 2017 Balance at beginning of period $ 2,779 $ 2,915 Incurred related to: Current year 2,600 2,558 Prior years — — Paid related to: Current year (2,502 ) (2,616 ) Prior years (262 ) (63 ) Balance at end of period $ 2,615 $ 2,794

Debt

Debt	6 Months Ended
	Jun. 30, 2018
Debt Instruments [Abstract]
Debt Disclosure [Text Block]	11 DEBT Debt consists of the following instruments at June 30, 2018 and December 31, 2017 : (in thousands) June 30, 2018 December 31, 2017 Principal Carrying Value Fair Value Principal Carrying Value Fair Value Note payable $ 174,707 $ 184,567 $ 163,059 $ 176,136 $ 186,469 $ 168,477 Bank loan 4,417 4,417 4,163 4,917 4,917 4,864 Subordinated debt 90,500 52,822 52,822 90,500 52,105 52,105 Total $ 269,624 $ 241,806 $ 220,044 $ 271,553 $ 243,491 $ 225,446 (a) Note payable: As part of the acquisition of CMC Industries, Inc. ("CMC") in July 2016, the Company assumed a mortgage, which is recorded as note payable in the consolidated balance sheets ("the Mortgage"). The Mortgage is nonrecourse indebtedness with respect to CMC and its subsidiaries, and the Mortgage is not, nor will it be, guaranteed by Kingsway or its affiliates. The Mortgage was recorded at its estimated fair value of $191.7 million , which included the unpaid principal amount of $180.0 million as of the date of acquisition plus a premium of $11.7 million . The Mortgage matures on May 15, 2034 and has a fixed interest rate of 4.07% . The Mortgage is carried in the consolidated balance sheets at its amortized cost, which reflects the monthly pay-down of principal as well as the amortization of the premium using the effective interest rate method. The fair value of the Mortgage disclosed in the table above is derived from quoted market prices of A-rated industrial bonds with similar maturities. (b) Bank loan: On October 12, 2017, the Company borrowed a principal amount of $5.0 million from a bank at a fixed interest rate of 5.0% . The bank loan matures on October 12, 2022. The carrying value of the bank loan represents its unpaid principal balance. The fair value of the bank loan disclosed in the table above is derived from quoted market prices of B and B minus rated industrial bonds with similar maturities. (c) Subordinated debt: The subordinated debt is carried in the consolidated balance sheets at fair value. See Note 18 , " Fair Value of Financial Instruments ," for further discussion of the subordinated debt. As further discussed in Note 4 , " Recently Issued Accounting Standards ," effective January 1, 2018, the Company adopted ASU 2016-01. As a result, the portion of the change in fair value of subordinated debt related to the instrument-specific credit risk is now recognized in other comprehensive income (loss), whereas for 2017, the total change in fair value of subordinated debt was recorded in net income (loss). Of the $0.7 million increase in fair value of the Company’s subordinated debt between December 31, 2017 and June 30, 2018 , $0.4 million is reported as change in fair value of debt attributable to instrument-specific credit risk in the Company's consolidated statements of comprehensive loss and $1.1 million is reported as loss on change in fair value of debt in the Company’s consolidated statements of operations. Subordinated debt consists of the following trust preferred debt instruments: Issuer Principal (in thousands) Issue date Interest Redemption date Kingsway CT Statutory Trust I $ 15,000 12/4/2002 annual interest rate equal to LIBOR, plus 4.00% payable quarterly 12/4/2032 Kingsway CT Statutory Trust II $ 17,500 5/15/2003 annual interest rate equal to LIBOR, plus 4.10% payable quarterly 5/15/2033 Kingsway CT Statutory Trust III $ 20,000 10/29/2003 annual interest rate equal to LIBOR, plus 3.95% payable quarterly 10/29/2033 Kingsway DE Statutory Trust III $ 15,000 5/22/2003 annual interest rate equal to LIBOR, plus 4.20% payable quarterly 5/22/2033 Kingsway DE Statutory Trust IV $ 10,000 9/30/2003 annual interest rate equal to LIBOR, plus 3.85% payable quarterly 9/30/2033 Kingsway DE Statutory Trust VI $ 13,000 12/16/2003 annual interest rate equal to LIBOR, plus 4.00% payable quarterly 1/8/2034

Revenue from Contracts with Cus

Revenue from Contracts with Customers (Notes)	6 Months Ended
	Jun. 30, 2018
Revenue from Contract with Customer [Abstract]
Revenue from Contract with Customer [Text Block]	REVENUE FROM CONTRACTS WITH CUSTOMERS Revenue from contracts with customers relates to Extended Warranty segment service fee and commission income. Service fee and commission income represents vehicle service agreement fees, maintenance support service fees, warranty product commissions and homebuilder warranty service fees and commissions based on terms of various agreements with credit unions, consumers, businesses and homebuilders. The following table disaggregates revenues from contracts with customers by revenue type: (in thousands) Three months ended June 30, Six months ended June 30, 2018 2017 2018 2017 Vehicle service agreement fees - IWS $ 4,474 $ 4,333 $ 9,024 $ 8,611 Maintenance support service fees - Trinity 1,962 1,818 4,935 3,572 Warranty product commissions - Trinity 736 433 1,232 763 Homebuilder warranty service fees and commissions - PWSC 2,307 — 4,479 — Service fee and commission income $ 9,479 $ 6,584 $ 19,670 $ 12,946 IWS' vehicle service agreement fees include the administrative fees from the sale of vehicle service agreements as well as the fees to administer future claims and are earned over the life of the contract. The administrative fee component is recognized in proportion to the costs incurred in acquiring and administering the vehicle service agreements. The claims fee component is earned over the life of the vehicle service agreements based on the greater of expected claims or actual claims experience. Trinity’s maintenance support service fees include the service fees collected to administer equipment breakdown and maintenance support services and are earned as services are rendered. Trinity’s 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 refrigeration equipment. 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. Warranty product commissions are earned at the time of the warranty product sales. PWSC’s homebuilder warranty service fees and commissions include the administrative fees, service fees and commissions collected from the sale of warranties issued by new homebuilders. Homebuilder warranty administrative fees are earned when the home is enrolled and services are rendered. Homebuilder warranty service fees are earned over the warranty period, the majority of which is ten years and is based on homes closed by the builder. The Company estimates deferred service fees for years two through ten of the warranty period, based on historical dispute resolution services experience. Homebuilder warranty commissions are recognized as income on the certification date, which is typically the date of the closing of the sale of the home to the buyer. The Company also earns fees to manage remediation or repair services related to claims on insurance-backed warranty obligations, which are earned when the claims are closed; an incentive bonus on eligible warranties, which is based on expected ultimate loss ratio targets; and a profit-sharing percentage on expected profits, which is recognized at the time the bonus is received. Receivables from contracts with customers are reported as service fee receivable, net in the consolidated balance sheets and at June 30, 2018 and December 31, 2017 were $5.2 million and $4.3 million , respectively. The Company records deferred service fees resulting from contracts with customers when payment is received in advance of satisfying the performance obligations. We expect to recognize within one year as service fee and commission income approximately 38.3% of the deferred service fees as of June 30, 2018 that are related to contracts with customers. Approximately $8.0 million of service fee and commission income recognized during the six months ended June 30, 2018 was included in deferred service fees as of December 31, 2017.

Income Taxes

Income Taxes	6 Months Ended
	Jun. 30, 2018
Income Tax Disclosure [Abstract]
Income Tax Disclosure [Text Block]	INCOME TAXES The Tax Cuts and Jobs Act (the "Tax Act") was enacted on December 22, 2017. The Tax Act makes broad and complex changes to the U.S. tax code, including a permanent reduction in the U.S. federal corporate income tax rate to 21% starting in 2018. Previously, the Company was subject to a 34% U.S. federal corporate income tax rate. Income tax expense for the three and six months ended June 30, 2018 and June 30, 2017 varies from the amount that would result by applying the applicable U.S. federal corporate income tax rate of 21% and 34% , respectively, to loss from continuing operations before income tax expense. The following table summarizes the differences: (in thousands) Three months ended June 30, Six months ended June 30, 2018 2017 2018 2017 Income tax benefit at United States statutory income tax rate $ (529 ) $ (2,325 ) $ (988 ) $ (2,781 ) Valuation allowance 481 2,207 942 2,764 State income tax 67 22 133 35 Non-deductible compensation 62 101 123 200 Change in unrecognized tax benefits (1) 60 160 130 372 Indefinite life intangibles 21 1,058 41 1,090 Foreign operations subject to different tax rates (39 ) 45 (54 ) (94 ) Other 64 (17 ) 111 (70 ) Income tax expense $ 187 $ 1,251 $ 438 $ 1,516 (1) Includes interest and penalty expense related to unrecognized tax benefits. The Company maintains a valuation allowance for its gross deferred tax assets at June 30, 2018 and December 31, 2017 . The Company's operations have generated substantial operating losses in prior years. These losses can be available to reduce income taxes that might otherwise be incurred on future taxable income; however, it is uncertain whether the Company will generate the taxable income necessary to utilize these losses or other reversing temporary differences. This uncertainty has caused management to place a full valuation allowance on its June 30, 2018 and December 31, 2017 net deferred tax asset, excluding the deferred income tax asset and liability amounts set forth in the paragraph below. The Company carries net deferred income tax liabilities of $28.8 million and $28.7 million at June 30, 2018 and December 31, 2017 , respectively. At June 30, 2018 , $8.0 million relates to deferred income tax liabilities scheduled to reverse in periods after the expiration of the Company's consolidated U.S. net operating loss carryforwards, $20.9 million relates to deferred income tax liabilities associated with land and indefinite lived intangible assets and $0.1 million relates to deferred income tax assets associated with alternative minimum tax credits. At December 31, 2017 , $8.0 million relates to deferred income tax liabilities scheduled to reverse in periods after the expiration of the Company's consolidated U.S. net operating loss carryforwards, $20.8 million relates to deferred income tax liabilities associated with land and indefinite lived intangible assets and $0.1 million relates to deferred income tax assets associated with alternative minimum tax credits. The Company considered a tax planning strategy in arriving at its June 30, 2018 and December 31, 2017 net deferred income tax liabilities. As of June 30, 2018 and December 31, 2017 , the Company carried a liability for unrecognized tax benefits of $1.4 million and $1.4 million , respectively, that is included in income taxes payable in the consolidated balance sheets. The Company classifies interest and penalty accruals, if any, related to unrecognized tax benefits as income tax expense. The Company recorded income tax expense of $0.1 million and $0.2 million related to interest and penalty accruals for the three months ended June 30, 2018 and June 30, 2017 , respectively ( $0.1 million and $0.4 million for the six months ended June 30, 2018 and June 30, 2017 , respectively). At June 30, 2018 and December 31, 2017 , the Company carried an accrual for the payment of interest and penalties of $1.0 million and $0.9 million , respectively, included in income taxes payable in the consolidated balance sheets.

Loss from Continuing Operations

Loss from Continuing Operations per Share	6 Months Ended
	Jun. 30, 2018
Net Loss per Share [Abstract]
Earnings Per Share [Text Block]	LOSS FROM CONTINUING OPERATIONS PER SHARE The following table sets forth the reconciliation of numerators and denominators for the basic and diluted loss from continuing operations per share computation for the three and six months ended June 30, 2018 and June 30, 2017 : (in thousands, except per share data) Three months ended June 30, Six months ended June 30, 2018 2017 2018 2017 Numerator: Loss from continuing operations $ (2,706 ) $ (8,089 ) $ (5,141 ) $ (9,696 ) Less: net income attributable to noncontrolling interests (108 ) (100 ) (243 ) (205 ) Less: dividends on preferred stock, net of tax (130 ) (154 ) (259 ) (328 ) Loss from continuing operations attributable to common shareholders $ (2,944 ) $ (8,343 ) $ (5,643 ) $ (10,229 ) Denominator: Weighted average basic shares Weighted average common shares outstanding 21,708 21,458 21,708 21,458 Weighted average diluted shares Weighted average common shares outstanding 21,708 21,458 21,708 21,458 Effect of potentially dilutive securities — — Total weighted average diluted shares 21,708 21,458 21,708 21,458 Basic loss from continuing operations per share $ (0.14 ) $ (0.39 ) $ (0.26 ) $ (0.48 ) Diluted loss from continuing operations per share $ (0.14 ) $ (0.39 ) $ (0.26 ) $ (0.48 ) Basic loss from continuing operations per share is calculated using weighted-average common shares outstanding. Diluted loss from continuing operations 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 consist of stock options, unvested restricted stock awards, unvested restricted stock units, warrants and convertible preferred stock. Because the Company is reporting a loss from continuing operations for the three and six months ended June 30, 2018 and June 30, 2017 , all potentially dilutive securities outstanding were excluded from the calculation of diluted loss from continuing operations per share since their inclusion would have been anti-dilutive.

Stock-Based Compensation

Stock-Based Compensation	6 Months Ended
	Jun. 30, 2018
Stock-Based Compensation [Abstract]
Disclosure of Compensation Related Costs, Share-based Payments [Text Block]	STOCK-BASED COMPENSATION (a) Stock Options The following table summarizes the stock option activity during the six months ended June 30, 2018 : Number of Options Outstanding Weighted-Average Exercise Price Weighted-Average Remaining Contractual Term (in Years) Aggregate Intrinsic Value (in Thousands) Outstanding at December 31, 2017 651,875 $ 4.51 0.4 $ 352 Granted — — Expired — — Outstanding at June 30, 2018 651,875 $ 4.51 0.1 $ — Exercisable at June 30, 2018 651,875 $ 4.51 0.1 $ — The aggregate intrinsic value of stock options outstanding and exercisable is the difference between the June 30, 2018 market price for the Company's common shares and the exercise price of the options, multiplied by the number of options where the fair value exceeds the exercise price. The Company uses the Black-Scholes option pricing model to estimate the fair value of each option on the date of grant. No options were granted during the six months ended June 30, 2018 . (b) Restricted Stock Awards Under the 2013 Equity Incentive Plan, the Company made grants of restricted common stock awards ("Restricted Stock Awards") to certain officers of the Company on March 28, 2014. The Restricted Stock Awards shall become fully vested and the restriction period shall lapse as of March 28, 2024 subject to the officers' continued employment through the vesting date. The Restricted Stock Awards are amortized on a straight-line basis over the ten-year requisite service period. Total unamortized compensation expense related to unvested Restricted Stock Awards at June 30, 2018 was $4.6 million . The grant-date fair value of the Restricted Stock Awards was determined using the closing price of Kingsway common stock on the date of grant. The following table summarizes the activity related to unvested Restricted Stock Awards for the six months ended June 30, 2018 : Number of Restricted Stock Awards Weighted-Average Grant Date Fair Value (per Share) Unvested at December 31, 2017 1,952,665 $ 4.14 Granted — — Forfeited — — Unvested at June 30, 2018 1,952,665 $ 4.14 (c) Restricted Stock Units The Company granted restricted common stock units ("Restricted Stock Units") to an officer of the Company pursuant to a Restricted Stock Unit Agreement dated August 24, 2016. Each Restricted Stock Unit represents a right to receive one common share on the vesting date. The Restricted Stock Units shall become fully vested and the restriction period shall lapse as of March 28, 2024 subject to the officer's continued employment through the vesting date. The Restricted Stock Units are amortized on a straight-line basis over the requisite service period. Total unamortized compensation expense related to unvested Restricted Stock Units at June 30, 2018 was $2.2 million . The grant-date fair value of the Restricted Stock Units was determined using the closing price of Kingsway common stock on the date of grant. The following table summarizes the activity related to unvested Restricted Stock Units for the six months ended June 30, 2018 : Number of Restricted Stock Units Weighted-Average Grant Date Fair Value (per Share) Unvested at December 31, 2017 500,000 $ 5.73 Granted — — Vested — — Forfeited — — Unvested at June 30, 2018 500,000 $ 5.73 Total stock-based compensation expense, net of forfeitures, was $0.3 million and $0.3 million for the three months ended June 30, 2018 and June 30, 2017 , respectively ( $0.6 million and $0.6 million for the six months ended June 30, 2018 and June 30, 2017 , respectively).

Accumulated Other Comprehensive

Accumulated Other Comprehensive Income	6 Months Ended
	Jun. 30, 2018
Accumulated Other Comprehensive Income [Abstract]
Comprehensive Income (Loss) Note [Text Block]	16 ACCUMULATED OTHER COMPREHENSIVE INCOME (LOSS) The tables below detail the changes in the balances of each component of accumulated other comprehensive income (loss), net of tax, for the three and six months ended June 30, 2018 and June 30, 2017 as relates to shareholders' equity attributable to common shareholders on the consolidated balance sheets. On the other hand, the unaudited consolidated statements of comprehensive loss present the components of other comprehensive loss, net of tax, only for the three and six months ended June 30, 2018 and June 30, 2017 and inclusive of the components attributable to noncontrolling interests in consolidated subsidiaries. As further discussed in Note 4 , " Recently Issued Accounting Standards ," effective January 1, 2018, the Company adopted ASU 2016-01. As a result of the adoption, equity investments are no longer classified as available-for-sale with unrealized gains and losses recognized in other comprehensive income (loss); rather, changes in the fair value of equity investments are now recognized in net income (loss). Also as a result of the adoption, the portion of the total change in the fair value of our subordinated debt resulting from the change in instrument-specific credit risk is no longer recognized in net income (loss) and is now presented in other comprehensive income (loss). Prior periods have not been restated to conform to the current presentation. (in thousands) Three months ended June 30, 2018 Unrealized Gains (Losses) on Available-for-Sale Investments Foreign Currency Translation Adjustments Change in Fair Value of Debt Attributable to Instrument-Specific Credit Risk Equity in Other Comprehensive Loss of Limited Liability Investment Total Accumulated Other Comprehensive Income (Loss) Balance at April 1, 2018 $ (891 ) $ (3,286 ) $ 40,021 $ — $ 35,844 Other comprehensive income (loss) arising during the period (72 ) — 778 (224 ) 482 Amounts reclassified from accumulated other comprehensive income (loss) (4 ) — — — (4 ) Net current-period other comprehensive income (loss) (76 ) — 778 (224 ) 478 Balance at June 30, 2018 $ (967 ) $ (3,286 ) $ 40,799 $ (224 ) $ 36,322 (in thousands) Three months ended June 30, 2017 Unrealized Gains (Losses) on Available-for-Sale Investments Foreign Currency Translation Adjustments Total Accumulated Other Comprehensive Loss Balance at April 1, 2017 $ 2,901 $ (3,780 ) $ (879 ) Other comprehensive loss arising during the period (1,066 ) — (1,066 ) Amounts reclassified from accumulated other comprehensive income (loss) 478 — 478 Net current-period other comprehensive loss (588 ) — (588 ) Balance at June 30, 2017 $ 2,313 $ (3,780 ) $ (1,467 ) (in thousands) Six months ended June 30, 2018 Unrealized Gains (Losses) on Available-for-Sale Investments Foreign Currency Translation Adjustments Change in Fair Value of Debt Attributable to Instrument-Specific Credit Risk Equity in Other Comprehensive Loss of Limited Liability Investment Total Accumulated Other Comprehensive Income (Loss) Balance at January 1, 2018 $ (566 ) $ (3,286 ) $ — $ — $ (3,852 ) Cumulative effect of adoption of ASU 2016-01 40 — 40,455 — 40,495 Balance at January 1, 2018, as adjusted (526 ) (3,286 ) 40,455 — 36,643 Other comprehensive income (loss) arising during the period (430 ) — 344 (224 ) (310 ) Amounts reclassified from accumulated other comprehensive income (loss) (11 ) — — — (11 ) Net current-period other comprehensive income (loss) (441 ) — 344 (224 ) (321 ) Balance at June 30, 2018 $ (967 ) $ (3,286 ) $ 40,799 $ (224 ) $ 36,322 (in thousands) Six months ended June 30, 2017 Unrealized Gains (Losses) on Available-for-Sale Investments Foreign Currency Translation Adjustments Total Accumulated Other Comprehensive Loss Balance at January 1, 2017 $ 3,572 $ (3,780 ) $ (208 ) Other comprehensive loss arising during the period (1,230 ) — (1,230 ) Amounts reclassified from accumulated other comprehensive income (loss) (29 ) — (29 ) Net current-period other comprehensive loss (1,259 ) — (1,259 ) Balance at June 30, 2017 $ 2,313 $ (3,780 ) $ (1,467 ) Components of accumulated other comprehensive income (loss) were reclassified to the following lines of the unaudited consolidated statements of operations for the three and six months ended June 30, 2018 and June 30, 2017 : (in thousands) Three months ended June 30, Six months ended June 30, 2018 2017 2018 2017 Reclassification of accumulated other comprehensive income (loss) from unrealized gains (losses) on available-for-sale investments to: Net realized gains $ 5 $ 2 $ 8 $ 2 Other-than-temporary impairment loss — — — — Loss from continuing operations before income tax expense 5 2 8 2 Income tax expense — — — — Loss from continuing operations 5 2 8 2 Income (loss) from discontinued operations, net of taxes (1 ) (480 ) 3 27 Net loss $ 4 $ (478 ) $ 11 $ 29

Segmented Information

Segmented Information	6 Months Ended
	Jun. 30, 2018
Segmented Information [Abstract]
Segment Reporting Disclosure [Text Block]	SEGMENTED INFORMATION The Company conducts its business through the following two reportable segments: Extended Warranty and Leased Real Estate. Prior to the second quarter of 2018, the Company conducted its business through a third reportable segment, Insurance Underwriting. Insurance Underwriting included the following subsidiaries of the Company: Mendota, Amigo and Kingsway Reinsurance Corporation ("Kingsway Re"). As further discussed in Note 5 , " Acquisition and Discontinued Operations ," on July 16, 2018, the Company announced that it had entered into a definitive agreement to sell Mendota. As a result, Mendota has been classified as discontinued operations and the results of their operations are reported separately for all periods presented. As a result of classifying Mendota as discontinued operations, the composition of the Insurance Underwriting segment has changed such that it no longer meets the criteria of a reportable segment. As such, all segmented information has been restated to exclude the Insurance Underwriting segment for all periods presented. Extended Warranty Segment Extended Warranty includes the following subsidiaries of the Company: IWS Acquisition Corporation ("IWS"), Trinity Warranty Solutions LLC ("Trinity") and PWSC (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 23 states and the District of Columbia to their members. Trinity sells HVAC, standby generator, commercial LED lighting and 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 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. PWSC sells new home warranty products and provides administration services to home builders and homeowners across the United States. PWSC distributes its products and services through an in house sales team and through insurance brokers and insurance carriers throughout all states except Alaska and Louisiana. Leased Real Estate Segment Leased Real Estate includes the Company's subsidiary, CMC, which was acquired on July 14, 2016. CMC owns a parcel of real property consisting of approximately 192 acres located in the State of Texas (the "Real Property") that is leased to a third party pursuant to a long-term triple net lease. The Real Property is also subject to the Mortgage. When assessing and measuring the operational and financial performance of the Leased Real Estate segment, interest expense related to the Mortgage is included in Leased Real Estate's segment operating income. Revenues and Operating Income by Reportable Segment Results for the Company's reportable segments are based on the Company's internal financial reporting systems and are consistent with those followed in the preparation of the unaudited consolidated interim financial statements. The following tables provide financial data used by management. Segment assets are not allocated for management use and, therefore, are not included in the segment disclosures below. Revenues by reportable segment reconciled to consolidated revenues for the three and six months ended June 30, 2018 and June 30, 2017 were: (in thousands) Three months ended June 30, Six months ended June 30, 2018 2017 2018 2017 Revenues: Extended Warranty: Service fee and commission income 9,479 6,584 19,670 12,946 Other income 36 51 102 136 Total Extended Warranty 9,515 6,635 19,772 13,082 Leased Real Estate: Rental income 3,341 3,341 6,682 6,682 Other income 72 160 219 372 Total Leased Real Estate 3,413 3,501 6,901 7,054 Total segment revenues 12,928 10,136 26,673 20,136 Net investment income (loss) 18 (1,347 ) (613 ) (1,163 ) Net realized (losses) gains (1 ) (1 ) 9 (1 ) (Loss) gain on change in fair value of equity investments (248 ) — 614 — Other income not allocated to segments 973 31 987 61 Total revenues $ 13,670 $ 8,819 $ 27,670 $ 19,033 The operating income by reportable segment in the following table is before income taxes and includes revenues and direct segment costs. Total segment operating income reconciled to the consolidated loss from continuing operations for the three and six months ended June 30, 2018 and June 30, 2017 were: (in thousands) Three months ended June 30, Six months ended June 30, 2018 2017 2018 2017 Segment operating income: Extended Warranty 1,659 685 3,230 1,271 Leased Real Estate 618 872 1,492 1,790 Total segment operating income 2,277 1,557 4,722 3,061 Net investment income (loss) 18 (1,347 ) (613 ) (1,163 ) Net realized (losses) gains (1 ) (1 ) 9 (1 ) (Loss) gain on change in fair value of equity investments (248 ) — 614 — Interest expense not allocated to segments (1,519 ) (1,216 ) (2,905 ) (2,375 ) Other income and expenses not allocated to segments, net (2,248 ) (2,907 ) (4,642 ) (4,983 ) Amortization of intangible assets (271 ) (289 ) (543 ) (580 ) Contingent consideration benefit — 212 — 212 Loss on change in fair value of debt (142 ) (2,702 ) (1,061 ) (4,591 ) Equity in net (loss) income of investee (385 ) (145 ) (284 ) 2,240 Loss from continuing operations before income tax expense (2,519 ) (6,838 ) (4,703 ) (8,180 ) Income tax expense 187 1,251 438 1,516 Loss from continuing operations $ (2,706 ) $ (8,089 ) $ (5,141 ) $ (9,696 )

Fair Value of Financial Instrum

Fair Value of Financial Instruments	6 Months Ended
	Jun. 30, 2018
Fair Value of Financial Instruments [Abstract]
Fair Value of Financial Instruments, Policy [Policy Text Block]	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 are not 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 are not 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 may use 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 do not 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 is not 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 Level 1: • Level 1 – Quoted prices for identical instruments in active markets. • Level 2 – Quoted prices for similar instruments in active markets; quoted prices for identical or similar instruments in markets that are not active; and model-derived valuations in which all significant inputs are observable in active markets. • Level 3 – Valuations derived from valuation techniques in which one or more significant inputs are not observable. 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, performance shares and subordinated debt are measured and reported at fair value. Fixed maturities - Fair values of fixed maturities for which no active market exists are derived from quoted market prices of similar instruments or other third 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 Level 2. Level 2 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 a third-party vendor who utilizes third-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 independent third-party pricing services as well as, to a lesser extent, quotes from broker-dealers. Our third-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. We have obtained an understanding of our third-party vendor’s valuation methodologies and inputs. Fair values obtained from our third-party vendor are not adjusted by the Company. The following is a description of the significant inputs, by asset class, used by the third-party pricing services to determine the fair values of our fixed maturities included in Level 2: • U.S. government, government agencies and authorities are generally priced using the market approach. Inputs generally consist of trades of identical or similar securities, quoted prices in inactive markets and maturity. • States, municipalities and political subdivisions are generally priced using the market approach. Inputs generally consist of trades of identical or similar securities, quoted prices in inactive markets, new issuances and credit spreads. • Mortgage-backed securities are generally priced using the market approach. Inputs generally consist of trades of identical or similar securities, quoted prices in inactive markets, expected prepayments, expected credit default rates, delinquencies and issue specific information including, but not limited to, collateral type, seniority and vintage. • Corporate securities are generally priced using the market approach using pricing vendors. Inputs generally consist of trades of identical or similar securities, quoted prices in inactive markets, issuer rating, benchmark yields, maturity and credit spreads. Equity investments - Fair values of equity investments, including warrants, reflect quoted market values based on latest bid prices, where active markets exist, or models based on significant market observable inputs, where no active markets exist. Limited liability investment, at fair value - The fair value of the limited liability investment, at fair value is calculated based on a model that distributes the net equity of 1347 Investors to all classes of membership interests. The model uses quoted market prices and significant market observable inputs. Performance shares - The performance shares, for which no active market exists, are required to be valued at fair value as determined in good faith by the Company. Such determination of fair value would require the Company to develop a model based upon relevant observable market inputs as well as significant unobservable inputs, including developing a sufficiently reliable estimate for an appropriate discount to reflect the illiquidity and unique structure of the security. The Company determined its model for the performance shares was not sufficiently reliable. As a result, the Company has assigned a fair value of zero to the performance shares. Refer to Note 6 , " Investments ," for further details regarding the performance shares. Subordinated debt - 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. These inputs include credit spread assumptions developed by a third party and market observable swap rates. 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 June 30, 2018 and December 31, 2017 are as follows: (in thousands) June 30, 2018 Fair Value Measurements at the End of the Reporting Period Using Total Quoted Prices in Active Markets for Identical Assets (Level 1) Significant Other Observable Inputs (Level 2) Significant Unobservable Inputs (Level 3) Recurring fair value measurements: Assets: Fixed maturities: U.S. government, government agencies and authorities $ 5,427 $ — $ 5,427 $ — States, municipalities and political subdivisions 605 — 605 — Mortgage-backed 2,811 — 2,811 — Corporate 2,518 — 2,518 — Total fixed maturities 11,361 — 11,361 — Equity investments: Common stock 1,264 1,264 — — Warrants 925 54 871 — Total equity investments 2,189 1,318 871 — Limited liability investment, at fair value 4,869 — 4,869 — Other investments 1,916 — 1,916 — Short-term investments 151 — 151 — Total assets $ 20,486 $ 1,318 $ 19,168 $ — Liabilities: Subordinated debt $ 52,822 $ — $ 52,822 $ — Total liabilities $ 52,822 $ — $ 52,822 $ — (in thousands) December 31, 2017 Fair Value Measurements at the End of the Reporting Period Using Total Quoted Prices in Active Markets for Identical Assets (Level 1) Significant Other Observable Inputs (Level 2) Significant Unobservable Inputs (Level 3) Recurring fair value measurements: Assets: Fixed maturities: U.S. government, government agencies and authorities $ 5,612 $ — $ 5,612 $ — States municipalities and political subdivisions 626 — 626 — Mortgage-backed 2,876 — 2,876 — Corporate 5,427 — 5,427 — Total fixed maturities 14,541 — 14,541 — Equity investments: Common stock 3,570 3,570 — — Warrants 906 58 848 — Total equity investments 4,476 3,628 848 — Limited liability investment, at fair value 5,771 — 5,771 — Other investments 2,321 — 2,321 — Short-term investments 151 — 151 — Total assets $ 27,260 $ 3,628 $ 23,632 $ — Liabilities: Subordinated debt $ 52,105 $ — $ 52,105 $ — Total liabilities $ 52,105 $ — $ 52,105 $ —

Related Party Transactions

Related Party Transactions	6 Months Ended
	Jun. 30, 2018
Related Party Transactions [Abstract]
Related Party Transactions Disclosure [Text Block]	RELATED PARTY TRANSACTIONS 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. Management believes consideration paid for such services in each case approximates fair value. Except where disclosed elsewhere in these unaudited consolidated interim financial statements, the following is a summary of related party transactions. On October 25, 2017, the Company executed an agreement to sell 900,000 shares of PIH common stock, at a price of $7.85 per share, to Fundamental Global Investors, LLC and/or one or more of its affiliates ("FGI") in two separate transactions for cash proceeds totaling $7.1 million . On November 1, 2017, the Company sold 475,428 of the 900,000 shares of PIH common stock to FGI for cash proceeds totaling $3.7 million . The second transaction, for the sale of the remaining 424,572 shares of PIH common stock for cash proceeds totaling $3.4 million , closed on March 15, 2018 following FGI having obtained the necessary regulatory approvals. On July 30, 2018, the Company executed an agreement to sell 1,813,889 shares of ICL common stock, at a price of Canadian $0.72 per share, to FGI for cash proceeds totaling Canadian $1.3 million . On July 30, 2018, the Company executed an agreement to sell 75,000 shares of PIH common stock, at a price of $7.13 per share, to FGI for cash proceeds totaling $0.5 million . FGI is a greater than 5% shareholder of the Company.

Commitment and Contingencies

Commitment and Contingencies	6 Months Ended
	Jun. 30, 2018
Commitments and Contingencies [Abstract]
Commitments and Contingencies Disclosure [Text Block]	COMMITMENTS AND CONTINGENCIES (a) Legal proceedings: In connection with its operations in the ordinary course of business, the Company and its subsidiaries are named as defendants in various actions for damages and costs allegedly sustained by the plaintiffs. While it is not possible to estimate the loss, or range of loss, if any, that would be incurred in connection with any of the various proceedings at this time, it is possible an individual action would result in a loss having a material adverse effect on the Company's business, results of operations or financial condition. (b) Guarantees: The Company provided indemnity and hold harmless agreements to a third party for certain customs bonds reinsured by Lincoln General Insurance Company ("Lincoln General") during a period of the time Lincoln General was a subsidiary of the Company. These agreements may require the Company to compensate the third party if Lincoln General is unable to fulfill its obligations relating to the customs bonds. The Company's potential exposure under these agreements is not determinable, and no liability has been recorded in the unaudited consolidated interim financial statements at June 30, 2018 . No assurances can be given, however, the Company will not be required to perform under these agreements in a manner that would have a material adverse effect on the Company's business, results of operations or financial condition. As further discussed in Note 5 , " Acquisition and Discontinued Operations ," as part of the transaction to sell Mendota, the Company will indemnify the buyer for loss and loss adjustment expenses with respect to open claims and certain specified claims in excess of Mendota's carried unpaid loss and loss adjustment expenses at June 30, 2018 related to the open claims and specified claims. The Company's potential exposure under these agreements is not determinable, and no liability has been recorded in the unaudited consolidated interim financial statements at June 30, 2018 . (c) Commitments: The Company's subsidiaries, Mendota Insurance Company and Mendakota Casualty Company, have entered into subscription agreements to commit up to $2.7 million of capital to allow for participation in limited liability investments. At June 30, 2018 , the unfunded commitment was $1.0 million .

Acquisition and Discontinued 27

Acquisition and Discontinued Operations Acquisition of PWSC (Tables)	6 Months Ended
	Jun. 30, 2018
Reportable Subsegments [Member]
Business Acquisition [Line Items]
Schedule of Recognized Identified Assets Acquired and Liabilities Assumed [Table Text Block]	The following table summarizes the estimated allocation of the assets acquired and liabilities assumed at the date of acquisition: (in thousands) October 12, 2017 Cash and cash equivalents $ 2,071 Other receivables 50 Service fee receivable 1,422 Property and equipment 238 Other assets 205 Goodwill 9,051 Total assets $ 13,037 Deferred service fees $ 2,079 Accrued expenses and other liabilities 1,089 Total liabilities $ 3,168 Purchase price $ 9,869

Acquisition and Discontinued 28

Acquisition and Discontinued Operations Discontinued operations (Tables)	6 Months Ended
	Jun. 30, 2018
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Disposal Groups, Including Discontinued Operations [Table Text Block]	On April 1, 2015, the Company closed on the sale of its subsidiary, Assigned Risk Solutions Ltd. ("ARS"). The terms of the sale provided for receipt by the Company of future earnout payments equal to 1.25% of ARS' written premium and fee income during the earnout periods. The earnout payments were payable in three annual installments beginning in April 2016 through April 2018. During the second quarter of 2018, the Company received cash consideration, before expenses, for the third annual installment earnout payment of $1.7 million . Net of

Investments (Tables)

Investments (Tables)	6 Months Ended
	Jun. 30, 2018
Investments [Abstract]
Schedule of Unrealized Loss on Investments [Table Text Block]	(in thousands) June 30, 2018 Amortized Cost Gross Unrealized Gains Gross Unrealized Losses Estimated Fair Value Fixed maturities: U.S. government, government agencies and authorities $ 5,503 $ — $ 76 $ 5,427 States, municipalities and political subdivisions 624 — 19 605 Mortgage-backed 2,902 — 91 2,811 Corporate 2,576 — 58 2,518 Total fixed maturities $ 11,605 $ — $ 244 $ 11,361 (in thousands) December 31, 2017 Amortized Cost Gross Unrealized Gains Gross Unrealized Losses Estimated Fair Value Fixed maturities: U.S. government, government agencies and authorities $ 5,671 $ — $ 59 $ 5,612 States, municipalities and political subdivisions 639 — 13 626 Mortgage-backed 2,933 — 57 2,876 Corporate 5,464 — 37 5,427 Total fixed maturities 14,707 — 166 14,541 Equity investments: Common stock 3,883 — 313 3,570 Warrants - publicly traded 11 47 — 58 Warrants - not publicly traded 960 173 285 848 Total equity investments 4,854 220 598 4,476 Total fixed maturities and equity investments $ 19,561 $ 220 $ 764 $ 19,017
Investments Classified by Contractual Maturity Date [Table Text Block]	(in thousands) June 30, 2018 Amortized Cost Estimated Fair Value Due in one year or less $ 4,924 $ 4,899 Due after one year through five years 5,378 5,219 Due after five years through ten years 132 125 Due after ten years 1,171 1,118 Total $ 11,605 $ 11,361
Available-for-sale Securities, Continuous Unrealized Loss Position, Fair Value [Table Text Block]	(in thousands) June 30, 2018 Less than 12 Months Greater than 12 Months Total Estimated Fair Value Unrealized Loss Estimated Fair Value Unrealized Loss Estimated Fair Value Unrealized Loss Fixed maturities: U.S. government, government agencies and authorities $ 3,502 $ 34 $ 1,925 $ 42 $ 5,427 $ 76 States, municipalities and political subdivisions 86 2 519 17 605 19 Mortgage-backed 690 13 2,121 78 2,811 91 Corporate 410 5 2,108 53 2,518 58 Total fixed maturities $ 4,688 $ 54 $ 6,673 $ 190 $ 11,361 $ 244 (in thousands) December 31, 2017 Less than 12 Months Greater than 12 Months Total Estimated Fair Value Unrealized Loss Estimated Fair Value Unrealized Loss Estimated Fair Value Unrealized Loss Fixed maturities: U.S. government, government agencies and authorities $ 4,067 $ 50 $ 1,545 $ 9 $ 5,612 $ 59 States, municipalities and political subdivisions 626 13 — — 626 13 Mortgage-backed 2,876 57 — — 2,876 57 Corporate 2,427 37 — — 2,427 37 Total fixed maturities 9,996 157 1,545 9 11,541 166 Equity investments: Common stock 3,570 313 — — 3,570 313 Warrants 675 285 — — 675 285 Total equity investments 4,245 598 — — 4,245 598 Total $ 14,241 $ 755 $ 1,545 $ 9 $ 15,786 $ 764
Schedule of Realized Gain (Loss) [Table Text Block]	(in thousands) Three months ended June 30, Six months ended June 30, 2018 2017 2018 2017 Gross realized gains $ — $ — $ 10 $ — Gross realized losses (1 ) (1 ) (1 ) (1 ) Net realized (losses) gains $ (1 ) $ (1 ) $ 9 $ (1 )
Investment Income [Table Text Block]	Net investment income (loss) for the three and six months ended June 30, 2018 and June 30, 2017 is comprised as follows: (in thousands) Three months ended June 30, Six months ended June 30, 2018 2017 2018 2017 Investment income (loss): Interest from fixed maturities $ 57 $ 49 $ 90 $ 83 Dividends 53 102 108 196 Income (loss) from limited liability investments 120 (100 ) 164 (166 ) Loss on change in fair value of limited liability investment, at fair value (280 ) (1,292 ) (1,152 ) (1,520 ) (Loss) gain on change in fair value of warrants - not publicly traded — (198 ) — 47 Other 77 100 194 212 Gross investment income (loss) 27 (1,339 ) (596 ) (1,148 ) Investment expenses (9 ) (8 ) (17 ) (15 ) Net investment income (loss) $ 18 $ (1,347 ) $ (613 ) $ (1,163 )

Investments Amortized cost, gro

Investments Amortized cost, gross unrealized gains and losses, and estimated fair value (Tables)	6 Months Ended
	Jun. 30, 2018
Schedule of Available-for-sale Securities [Line Items]
Schedule of Unrealized Loss on Investments [Table Text Block]	(in thousands) June 30, 2018 Amortized Cost Gross Unrealized Gains Gross Unrealized Losses Estimated Fair Value Fixed maturities: U.S. government, government agencies and authorities $ 5,503 $ — $ 76 $ 5,427 States, municipalities and political subdivisions 624 — 19 605 Mortgage-backed 2,902 — 91 2,811 Corporate 2,576 — 58 2,518 Total fixed maturities $ 11,605 $ — $ 244 $ 11,361 (in thousands) December 31, 2017 Amortized Cost Gross Unrealized Gains Gross Unrealized Losses Estimated Fair Value Fixed maturities: U.S. government, government agencies and authorities $ 5,671 $ — $ 59 $ 5,612 States, municipalities and political subdivisions 639 — 13 626 Mortgage-backed 2,933 — 57 2,876 Corporate 5,464 — 37 5,427 Total fixed maturities 14,707 — 166 14,541 Equity investments: Common stock 3,883 — 313 3,570 Warrants - publicly traded 11 47 — 58 Warrants - not publicly traded 960 173 285 848 Total equity investments 4,854 220 598 4,476 Total fixed maturities and equity investments $ 19,561 $ 220 $ 764 $ 19,017

Investments Fixed maturities by

Investments Fixed maturities by contractual periods (Tables)	6 Months Ended
	Jun. 30, 2018
Schedule of Held-to-maturity Securities [Line Items]
Investments Classified by Contractual Maturity Date [Table Text Block]	(in thousands) June 30, 2018 Amortized Cost Estimated Fair Value Due in one year or less $ 4,924 $ 4,899 Due after one year through five years 5,378 5,219 Due after five years through ten years 132 125 Due after ten years 1,171 1,118 Total $ 11,605 $ 11,361
Schedule of Realized Gain (Loss) [Table Text Block]	(in thousands) Three months ended June 30, Six months ended June 30, 2018 2017 2018 2017 Gross realized gains $ — $ — $ 10 $ — Gross realized losses (1 ) (1 ) (1 ) (1 ) Net realized (losses) gains $ (1 ) $ (1 ) $ 9 $ (1 )

Investments Continuous Unrealiz

Investments Continuous Unrealized Loss Position (Tables)	6 Months Ended
	Jun. 30, 2018
Schedule of Available-for-sale Securities [Line Items]
Available-for-sale Securities, Continuous Unrealized Loss Position, Fair Value [Table Text Block]	(in thousands) June 30, 2018 Less than 12 Months Greater than 12 Months Total Estimated Fair Value Unrealized Loss Estimated Fair Value Unrealized Loss Estimated Fair Value Unrealized Loss Fixed maturities: U.S. government, government agencies and authorities $ 3,502 $ 34 $ 1,925 $ 42 $ 5,427 $ 76 States, municipalities and political subdivisions 86 2 519 17 605 19 Mortgage-backed 690 13 2,121 78 2,811 91 Corporate 410 5 2,108 53 2,518 58 Total fixed maturities $ 4,688 $ 54 $ 6,673 $ 190 $ 11,361 $ 244 (in thousands) December 31, 2017 Less than 12 Months Greater than 12 Months Total Estimated Fair Value Unrealized Loss Estimated Fair Value Unrealized Loss Estimated Fair Value Unrealized Loss Fixed maturities: U.S. government, government agencies and authorities $ 4,067 $ 50 $ 1,545 $ 9 $ 5,612 $ 59 States, municipalities and political subdivisions 626 13 — — 626 13 Mortgage-backed 2,876 57 — — 2,876 57 Corporate 2,427 37 — — 2,427 37 Total fixed maturities 9,996 157 1,545 9 11,541 166 Equity investments: Common stock 3,570 313 — — 3,570 313 Warrants 675 285 — — 675 285 Total equity investments 4,245 598 — — 4,245 598 Total $ 14,241 $ 755 $ 1,545 $ 9 $ 15,786 $ 764

Investments Gross realized gain

Investments Gross realized gains and losses (Tables)	6 Months Ended
	Jun. 30, 2018
Gain (Loss) on Investments [Line Items]
Schedule of Realized Gain (Loss) [Table Text Block]	(in thousands) Three months ended June 30, Six months ended June 30, 2018 2017 2018 2017 Gross realized gains $ — $ — $ 10 $ — Gross realized losses (1 ) (1 ) (1 ) (1 ) Net realized (losses) gains $ (1 ) $ (1 ) $ 9 $ (1 )

Investments Investments income

Investments Investments income (Tables)	6 Months Ended
	Jun. 30, 2018
Net Investment Income [Line Items]
Investment Income [Table Text Block]	Net investment income (loss) for the three and six months ended June 30, 2018 and June 30, 2017 is comprised as follows: (in thousands) Three months ended June 30, Six months ended June 30, 2018 2017 2018 2017 Investment income (loss): Interest from fixed maturities $ 57 $ 49 $ 90 $ 83 Dividends 53 102 108 196 Income (loss) from limited liability investments 120 (100 ) 164 (166 ) Loss on change in fair value of limited liability investment, at fair value (280 ) (1,292 ) (1,152 ) (1,520 ) (Loss) gain on change in fair value of warrants - not publicly traded — (198 ) — 47 Other 77 100 194 212 Gross investment income (loss) 27 (1,339 ) (596 ) (1,148 ) Investment expenses (9 ) (8 ) (17 ) (15 ) Net investment income (loss) $ 18 $ (1,347 ) $ (613 ) $ (1,163 )

Investments Change in fair valu

Investments Change in fair value of equity investments (Tables)	6 Months Ended
	Jun. 30, 2018
Schedule of Available-for-sale Securities [Line Items]
Fair Value, Measured on Recurring Basis, Gain (Loss) Included in Earnings [Table Text Block]	ain on change in fair value of equity investments for the three and six months ended June 30, 2018 and June 30, 2017 is comprised as follows: (in thousands) Three months ended June 30, Six months ended June 30, 2018 2017 2018 2017 Net (losses) gains recognized on equity investments sold during the period $ (10 ) $ — $ 545 $ — Change in unrealized (losses) gains on equity investments held at end of the period (238 ) — 69 — (Loss) gain on change in fair value of equity investments $ (248 ) $ — $ 614 $ —

Investment in Investees (Tables

Investment in Investees (Tables)	6 Months Ended
	Jun. 30, 2018
Investment in Investee [Abstract]
Equity Method Investments [Table Text Block]	The carrying value, estimated fair value and approximate equity percentage for the Company's investment in investee at June 30, 2018 and December 31, 2017 were as follows: (in thousands, except for percentages) June 30, 2018 December 31, 2017 Equity Percentage Estimated Fair Value Carrying Value Equity Percentage Estimated Fair Value Carrying Value ICL 31.2 % $ 3,531 $ 4,947 31.2 % $ 3,816 $ 5,230

Deferred Acquisition Costs (Tab

Deferred Acquisition Costs (Tables)	6 Months Ended
	Jun. 30, 2018
Deferred Acquisition Costs [Line Items]
Deferred Costs, Capitalized, Prepaid, and Other Assets Disclosure [Table Text Block]	The components of deferred acquisition costs and the related amortization expense for the three and six months ended June 30, 2018 and June 30, 2017 are comprised as follows: (in thousands) Three months ended June 30, Six months ended June 30, 2018 2017 2018 2017 Beginning balance, net $ 6,428 $ 5,867 $ 6,325 $ 5,827 Additions 1,256 1,331 2,498 2,317 Amortization (1,022 ) (1,144 ) (2,161 ) (2,090 ) Balance at June 30, net $ 6,662 $ 6,054 $ 6,662 $ 6,054

Intangible Assets (Tables)

Intangible Assets (Tables)	6 Months Ended
	Jun. 30, 2018
Finite-Lived Intangible Assets [Line Items]
Schedule of Finite-Lived Intangible Assets [Table Text Block]	Intangible assets at June 30, 2018 and December 31, 2017 are comprised as follows: (in thousands) June 30, 2018 Gross Carrying Value Accumulated Amortization Net Carrying Value Intangible assets subject to amortization: Database $ 4,918 $ 2,767 $ 2,151 Vehicle service agreements in-force 3,680 3,656 24 Customer relationships 3,611 2,183 1,428 In-place lease 1,125 123 1,002 Contract-based revenues 731 147 584 Intangible assets not subject to amortization: Tenant relationship 73,667 — 73,667 Trade name 663 — 663 Total $ 88,395 $ 8,876 $ 79,519 (in thousands) December 31, 2017 Gross Carrying Value Accumulated Amortization Net Carrying Value Intangible assets subject to amortization: Database $ 4,918 $ 2,521 $ 2,397 Vehicle service agreements in-force 3,680 3,640 40 Customer relationships 3,611 1,965 1,646 In-place lease 1,125 92 1,033 Contract-based revenues 731 115 616 Intangible assets not subject to amortization: Tenant relationship 73,667 — 73,667 Trade name 663 — 663 Total $ 88,395 $ 8,333 $ 80,062

Unpaid Loss and Loss Adjustme39

Unpaid Loss and Loss Adjustment Expenses (Tables)	6 Months Ended
	Jun. 30, 2018
Liability for Future Policy Benefit, by Product Segment [Line Items]
Liability for Future Policy Benefits and Unpaid Claims Disclosure [Text Block]	10 UNPAID LOSS AND LOSS ADJUSTMENT EXPENSES The establishment of the provision for unpaid loss and loss adjustment expenses is based on known facts and interpretation of circumstances and is, therefore, a complex and dynamic process influenced by a large variety of factors. These factors include the Company's experience with similar cases and historical trends involving loss payment patterns, pending levels of unpaid loss and loss adjustment expenses, product mix or concentration, loss severity and loss frequency patterns. Other factors include the continually evolving and changing regulatory and legal environment; actuarial studies; professional experience and expertise of the Company's claims departments' personnel and independent adjusters retained to handle individual claims; the quality of the data used for projection purposes; existing claims management practices including claims-handling and settlement practices; the effect of inflationary trends on future loss settlement costs; court decisions; economic conditions; and public attitudes. Consequently, the process of determining the provision for unpaid loss and loss adjustment expenses necessarily involves risks that the actual loss and loss adjustment expenses incurred by the Company will deviate, perhaps materially, from the estimates recorded. The Company's evaluation of the adequacy of unpaid loss and loss adjustment expenses includes a re-estimation of the liability for unpaid loss and loss adjustment expenses relating to each preceding financial year compared to the liability that was previously established. (a) Property and Casualty The results of this comparison and the changes in the provision for property and casualty unpaid loss and loss adjustment expenses, net of amounts recoverable from reinsurers, as of June 30, 2018 and June 30, 2017 were as follows: (in thousands) June 30, 2018 June 30, 2017 Balance at beginning of period, gross $ 1,329 $ 2,201 Less reinsurance recoverable related to property and casualty unpaid loss and loss adjustment expenses 72 354 Balance at beginning of period, net 1,257 1,847 Incurred related to: Current year — — Prior years 1,647 (1 ) Paid related to: Current year — — Prior years (410 ) (379 ) Balance at end of period, net 2,494 1,467 Plus reinsurance recoverable related to property and casualty unpaid loss and loss adjustment expenses 100 332 Balance at end of period, gross $ 2,594 $ 1,799 The Company reported unfavorable development on property and casualty unpaid loss and loss adjustment expenses of $1.6 million and favorable development of $0.0 million for the six months ended June 30, 2018 and June 30, 2017 , respectively. The unfavorable development for the six months ended June 30, 2018 was related to an increase in property and casualty loss adjustment expenses at Kingsway Amigo Insurance Company ("Amigo"). (b) Vehicle Service Agreements The results of the comparison and the changes in the provision for vehicle service agreement unpaid loss and loss adjustment expenses as of June 30, 2018 and June 30, 2017 were as follows: (in thousands) June 30, 2018 June 30, 2017 Balance at beginning of period $ 2,779 $ 2,915 Incurred related to: Current year 2,600 2,558 Prior years — — Paid related to: Current year (2,502 ) (2,616 ) Prior years (262 ) (63 ) Balance at end of period $ 2,615 $ 2,794

Unpaid Loss and Loss Adjustme40

Unpaid Loss and Loss Adjustment Expenses Insurance Product Line (Tables)	6 Months Ended
	Jun. 30, 2018
Liability for Claims and Claims Adjustment Expense [Line Items]
Liability for Future Policy Benefits and Unpaid Claims Disclosure [Text Block]	10 UNPAID LOSS AND LOSS ADJUSTMENT EXPENSES The establishment of the provision for unpaid loss and loss adjustment expenses is based on known facts and interpretation of circumstances and is, therefore, a complex and dynamic process influenced by a large variety of factors. These factors include the Company's experience with similar cases and historical trends involving loss payment patterns, pending levels of unpaid loss and loss adjustment expenses, product mix or concentration, loss severity and loss frequency patterns. Other factors include the continually evolving and changing regulatory and legal environment; actuarial studies; professional experience and expertise of the Company's claims departments' personnel and independent adjusters retained to handle individual claims; the quality of the data used for projection purposes; existing claims management practices including claims-handling and settlement practices; the effect of inflationary trends on future loss settlement costs; court decisions; economic conditions; and public attitudes. Consequently, the process of determining the provision for unpaid loss and loss adjustment expenses necessarily involves risks that the actual loss and loss adjustment expenses incurred by the Company will deviate, perhaps materially, from the estimates recorded. The Company's evaluation of the adequacy of unpaid loss and loss adjustment expenses includes a re-estimation of the liability for unpaid loss and loss adjustment expenses relating to each preceding financial year compared to the liability that was previously established. (a) Property and Casualty The results of this comparison and the changes in the provision for property and casualty unpaid loss and loss adjustment expenses, net of amounts recoverable from reinsurers, as of June 30, 2018 and June 30, 2017 were as follows: (in thousands) June 30, 2018 June 30, 2017 Balance at beginning of period, gross $ 1,329 $ 2,201 Less reinsurance recoverable related to property and casualty unpaid loss and loss adjustment expenses 72 354 Balance at beginning of period, net 1,257 1,847 Incurred related to: Current year — — Prior years 1,647 (1 ) Paid related to: Current year — — Prior years (410 ) (379 ) Balance at end of period, net 2,494 1,467 Plus reinsurance recoverable related to property and casualty unpaid loss and loss adjustment expenses 100 332 Balance at end of period, gross $ 2,594 $ 1,799 The Company reported unfavorable development on property and casualty unpaid loss and loss adjustment expenses of $1.6 million and favorable development of $0.0 million for the six months ended June 30, 2018 and June 30, 2017 , respectively. The unfavorable development for the six months ended June 30, 2018 was related to an increase in property and casualty loss adjustment expenses at Kingsway Amigo Insurance Company ("Amigo"). (b) Vehicle Service Agreements The results of the comparison and the changes in the provision for vehicle service agreement unpaid loss and loss adjustment expenses as of June 30, 2018 and June 30, 2017 were as follows: (in thousands) June 30, 2018 June 30, 2017 Balance at beginning of period $ 2,779 $ 2,915 Incurred related to: Current year 2,600 2,558 Prior years — — Paid related to: Current year (2,502 ) (2,616 ) Prior years (262 ) (63 ) Balance at end of period $ 2,615 $ 2,794
Property, Liability and Casualty Insurance Product Line [Member]
Liability for Claims and Claims Adjustment Expense [Line Items]
Liability for Future Policy Benefits and Unpaid Claims Disclosure [Text Block]	The results of this comparison and the changes in the provision for property and casualty unpaid loss and loss adjustment expenses, net of amounts recoverable from reinsurers, as of June 30, 2018 and June 30, 2017 were as follows: (in thousands) June 30, 2018 June 30, 2017 Balance at beginning of period, gross $ 1,329 $ 2,201 Less reinsurance recoverable related to property and casualty unpaid loss and loss adjustment expenses 72 354 Balance at beginning of period, net 1,257 1,847 Incurred related to: Current year — — Prior years 1,647 (1 ) Paid related to: Current year — — Prior years (410 ) (379 ) Balance at end of period, net 2,494 1,467 Plus reinsurance recoverable related to property and casualty unpaid loss and loss adjustment expenses 100 332 Balance at end of period, gross $ 2,594 $ 1,799

Unpaid Loss and Loss Adjustme41

Unpaid Loss and Loss Adjustment Expenses Vehicle Service Agreements (Tables)	6 Months Ended
	Jun. 30, 2018
Other Insurance Product Line [Member]
Liability for Claims and Claims Adjustment Expense [Line Items]
Schedule of Liability for Unpaid Claims and Claims Adjustment Expense [Table Text Block]	The results of the comparison and the changes in the provision for vehicle service agreement unpaid loss and loss adjustment expenses as of June 30, 2018 and June 30, 2017 were as follows: (in thousands) June 30, 2018 June 30, 2017 Balance at beginning of period $ 2,779 $ 2,915 Incurred related to: Current year 2,600 2,558 Prior years — — Paid related to: Current year (2,502 ) (2,616 ) Prior years (262 ) (63 ) Balance at end of period $ 2,615 $ 2,794

Debt (Tables)

Debt (Tables)	6 Months Ended
	Jun. 30, 2018
Debt Instrument [Line Items]
Schedule of Carrying Values and Estimated Fair Values of Debt Instruments [Table Text Block]	Debt consists of the following instruments at June 30, 2018 and December 31, 2017 : (in thousands) June 30, 2018 December 31, 2017 Principal Carrying Value Fair Value Principal Carrying Value Fair Value Note payable $ 174,707 $ 184,567 $ 163,059 $ 176,136 $ 186,469 $ 168,477 Bank loan 4,417 4,417 4,163 4,917 4,917 4,864 Subordinated debt 90,500 52,822 52,822 90,500 52,105 52,105 Total $ 269,624 $ 241,806 $ 220,044 $ 271,553 $ 243,491 $ 225,446
Schedule of Subordinated Borrowing [Table Text Block]	Subordinated debt consists of the following trust preferred debt instruments: Issuer Principal (in thousands) Issue date Interest Redemption date Kingsway CT Statutory Trust I $ 15,000 12/4/2002 annual interest rate equal to LIBOR, plus 4.00% payable quarterly 12/4/2032 Kingsway CT Statutory Trust II $ 17,500 5/15/2003 annual interest rate equal to LIBOR, plus 4.10% payable quarterly 5/15/2033 Kingsway CT Statutory Trust III $ 20,000 10/29/2003 annual interest rate equal to LIBOR, plus 3.95% payable quarterly 10/29/2033 Kingsway DE Statutory Trust III $ 15,000 5/22/2003 annual interest rate equal to LIBOR, plus 4.20% payable quarterly 5/22/2033 Kingsway DE Statutory Trust IV $ 10,000 9/30/2003 annual interest rate equal to LIBOR, plus 3.85% payable quarterly 9/30/2033 Kingsway DE Statutory Trust VI $ 13,000 12/16/2003 annual interest rate equal to LIBOR, plus 4.00% payable quarterly 1/8/2034

Revenue from Contracts with C43

Revenue from Contracts with Customers Disaggregates revenues from contracts with customer by revenue type (Tables)	6 Months Ended
	Jun. 30, 2018
Disaggregation of Revenue [Line Items]
Disaggregation of Revenue [Table Text Block]	The following table disaggregates revenues from contracts with customers by revenue type: (in thousands) Three months ended June 30, Six months ended June 30, 2018 2017 2018 2017 Vehicle service agreement fees - IWS $ 4,474 $ 4,333 $ 9,024 $ 8,611 Maintenance support service fees - Trinity 1,962 1,818 4,935 3,572 Warranty product commissions - Trinity 736 433 1,232 763 Homebuilder warranty service fees and commissions - PWSC 2,307 — 4,479 — Service fee and commission income $ 9,479 $ 6,584 $ 19,670 $ 12,946

Income Taxes Income Taxes (tabl

Income Taxes Income Taxes (table) (Tables)	6 Months Ended
	Jun. 30, 2018
Income Tax (table) [Abstract]
Income Tax (Benefit) Expense [Table Text Block]	The following table summarizes the differences: (in thousands) Three months ended June 30, Six months ended June 30, 2018 2017 2018 2017 Income tax benefit at United States statutory income tax rate $ (529 ) $ (2,325 ) $ (988 ) $ (2,781 ) Valuation allowance 481 2,207 942 2,764 State income tax 67 22 133 35 Non-deductible compensation 62 101 123 200 Change in unrecognized tax benefits (1) 60 160 130 372 Indefinite life intangibles 21 1,058 41 1,090 Foreign operations subject to different tax rates (39 ) 45 (54 ) (94 ) Other 64 (17 ) 111 (70 ) Income tax expense $ 187 $ 1,251 $ 438 $ 1,516 (1) Includes interest and penalty expense related to unrecognized tax benefits.

Loss from Continuing Operatio45

Loss from Continuing Operations per Share Net Loss per Share (Tables)	6 Months Ended
	Jun. 30, 2018
Earnings Per Share, Basic, by Common Class, Including Two Class Method [Line Items]
Schedule of Earnings Per Share, Basic and Diluted [Table Text Block]	The following table sets forth the reconciliation of numerators and denominators for the basic and diluted loss from continuing operations per share computation for the three and six months ended June 30, 2018 and June 30, 2017 : (in thousands, except per share data) Three months ended June 30, Six months ended June 30, 2018 2017 2018 2017 Numerator: Loss from continuing operations $ (2,706 ) $ (8,089 ) $ (5,141 ) $ (9,696 ) Less: net income attributable to noncontrolling interests (108 ) (100 ) (243 ) (205 ) Less: dividends on preferred stock, net of tax (130 ) (154 ) (259 ) (328 ) Loss from continuing operations attributable to common shareholders $ (2,944 ) $ (8,343 ) $ (5,643 ) $ (10,229 ) Denominator: Weighted average basic shares Weighted average common shares outstanding 21,708 21,458 21,708 21,458 Weighted average diluted shares Weighted average common shares outstanding 21,708 21,458 21,708 21,458 Effect of potentially dilutive securities — — Total weighted average diluted shares 21,708 21,458 21,708 21,458 Basic loss from continuing operations per share $ (0.14 ) $ (0.39 ) $ (0.26 ) $ (0.48 ) Diluted loss from continuing operations per share $ (0.14 ) $ (0.39 ) $ (0.26 ) $ (0.48 )

Stock-Based Compensation (Table

Stock-Based Compensation (Tables)	6 Months Ended
	Jun. 30, 2018
Stock-Based Compensation [Abstract]
Share-based Compensation, Stock Options, Activity [Table Text Block]	The following table summarizes the stock option activity during the six months ended June 30, 2018 : Number of Options Outstanding Weighted-Average Exercise Price Weighted-Average Remaining Contractual Term (in Years) Aggregate Intrinsic Value (in Thousands) Outstanding at December 31, 2017 651,875 $ 4.51 0.4 $ 352 Granted — — Expired — — Outstanding at June 30, 2018 651,875 $ 4.51 0.1 $ — Exercisable at June 30, 2018 651,875 $ 4.51 0.1 $ —
Schedule of Share-based Payment Award, Stock Options, Valuation Assumptions [Table Text Block]	No options were granted during the six months ended June 30, 2018 .
Schedule of Share-based Compensation, Restricted Stock and Restricted Stock Units Activity [Table Text Block]	The grant-date fair value of the Restricted Stock Awards was determined using the closing price of Kingsway common stock on the date of grant. The following table summarizes the activity related to unvested Restricted Stock Awards for the six months ended June 30, 2018 : Number of Restricted Stock Awards Weighted-Average Grant Date Fair Value (per Share) Unvested at December 31, 2017 1,952,665 $ 4.14 Granted — — Forfeited — — Unvested at June 30, 2018 1,952,665 $ 4.14
Schedule of Share-based Compensation, Restricted Stock Units Award Activity [Table Text Block]	The following table summarizes the activity related to unvested Restricted Stock Units for the six months ended June 30, 2018 : Number of Restricted Stock Units Weighted-Average Grant Date Fair Value (per Share) Unvested at December 31, 2017 500,000 $ 5.73 Granted — — Vested — — Forfeited — — Unvested at June 30, 2018 500,000 $ 5.73

Accumulated Other Comprehensi47

Accumulated Other Comprehensive Income (Tables)	6 Months Ended
	Jun. 30, 2018
Accumulated Other Comprehensive Income [Abstract]
Schedule of Accumulated Other Comprehensive Income (Loss) [Table Text Block]	On the other hand, the unaudited consolidated statements of comprehensive loss present the components of other comprehensive loss, net of tax, only for the three and six months ended June 30, 2018 and June 30, 2017 and inclusive of the components attributable to noncontrolling interests in consolidated subsidiaries. As further discussed in Note 4 , " Recently Issued Accounting Standards ," effective January 1, 2018, the Company adopted ASU 2016-01. As a result of the adoption, equity investments are no longer classified as available-for-sale with unrealized gains and losses recognized in other comprehensive income (loss); rather, changes in the fair value of equity investments are now recognized in net income (loss). Also as a result of the adoption, the portion of the total change in the fair value of our subordinated debt resulting from the change in instrument-specific credit risk is no longer recognized in net income (loss) and is now presented in other comprehensive income (loss). Prior periods have not been restated to conform to the current presentation. (in thousands) Three months ended June 30, 2018 Unrealized Gains (Losses) on Available-for-Sale Investments Foreign Currency Translation Adjustments Change in Fair Value of Debt Attributable to Instrument-Specific Credit Risk Equity in Other Comprehensive Loss of Limited Liability Investment Total Accumulated Other Comprehensive Income (Loss) Balance at April 1, 2018 $ (891 ) $ (3,286 ) $ 40,021 $ — $ 35,844 Other comprehensive income (loss) arising during the period (72 ) — 778 (224 ) 482 Amounts reclassified from accumulated other comprehensive income (loss) (4 ) — — — (4 ) Net current-period other comprehensive income (loss) (76 ) — 778 (224 ) 478 Balance at June 30, 2018 $ (967 ) $ (3,286 ) $ 40,799 $ (224 ) $ 36,322 (in thousands) Three months ended June 30, 2017 Unrealized Gains (Losses) on Available-for-Sale Investments Foreign Currency Translation Adjustments Total Accumulated Other Comprehensive Loss Balance at April 1, 2017 $ 2,901 $ (3,780 ) $ (879 ) Other comprehensive loss arising during the period (1,066 ) — (1,066 ) Amounts reclassified from accumulated other comprehensive income (loss) 478 — 478 Net current-period other comprehensive loss (588 ) — (588 ) Balance at June 30, 2017 $ 2,313 $ (3,780 ) $ (1,467 ) (in thousands) Six months ended June 30, 2018 Unrealized Gains (Losses) on Available-for-Sale Investments Foreign Currency Translation Adjustments Change in Fair Value of Debt Attributable to Instrument-Specific Credit Risk Equity in Other Comprehensive Loss of Limited Liability Investment Total Accumulated Other Comprehensive Income (Loss) Balance at January 1, 2018 $ (566 ) $ (3,286 ) $ — $ — $ (3,852 ) Cumulative effect of adoption of ASU 2016-01 40 — 40,455 — 40,495 Balance at January 1, 2018, as adjusted (526 ) (3,286 ) 40,455 — 36,643 Other comprehensive income (loss) arising during the period (430 ) — 344 (224 ) (310 ) Amounts reclassified from accumulated other comprehensive income (loss) (11 ) — — — (11 ) Net current-period other comprehensive income (loss) (441 ) — 344 (224 ) (321 ) Balance at June 30, 2018 $ (967 ) $ (3,286 ) $ 40,799 $ (224 ) $ 36,322 (in thousands) Six months ended June 30, 2017 Unrealized Gains (Losses) on Available-for-Sale Investments Foreign Currency Translation Adjustments Total Accumulated Other Comprehensive Loss Balance at January 1, 2017 $ 3,572 $ (3,780 ) $ (208 ) Other comprehensive loss arising during the period (1,230 ) — (1,230 ) Amounts reclassified from accumulated other comprehensive income (loss) (29 ) — (29 ) Net current-period other comprehensive loss (1,259 ) — (1,259 ) Balance at June 30, 2017 $ 2,313 $ (3,780 ) $ (1,467 )
Reclassification out of Accumulated Other Comprehensive Income [Table Text Block]	(in thousands) Three months ended June 30, 2018 Unrealized Gains (Losses) on Available-for-Sale Investments Foreign Currency Translation Adjustments Change in Fair Value of Debt Attributable to Instrument-Specific Credit Risk Equity in Other Comprehensive Loss of Limited Liability Investment Total Accumulated Other Comprehensive Income (Loss) Balance at April 1, 2018 $ (891 ) $ (3,286 ) $ 40,021 $ — $ 35,844 Other comprehensive income (loss) arising during the period (72 ) — 778 (224 ) 482 Amounts reclassified from accumulated other comprehensive income (loss) (4 ) — — — (4 ) Net current-period other comprehensive income (loss) (76 ) — 778 (224 ) 478 Balance at June 30, 2018 $ (967 ) $ (3,286 ) $ 40,799 $ (224 ) $ 36,322 (in thousands) Three months ended June 30, 2017 Unrealized Gains (Losses) on Available-for-Sale Investments Foreign Currency Translation Adjustments Total Accumulated Other Comprehensive Loss Balance at April 1, 2017 $ 2,901 $ (3,780 ) $ (879 ) Other comprehensive loss arising during the period (1,066 ) — (1,066 ) Amounts reclassified from accumulated other comprehensive income (loss) 478 — 478 Net current-period other comprehensive loss (588 ) — (588 ) Balance at June 30, 2017 $ 2,313 $ (3,780 ) $ (1,467 ) (in thousands) Six months ended June 30, 2018 Unrealized Gains (Losses) on Available-for-Sale Investments Foreign Currency Translation Adjustments Change in Fair Value of Debt Attributable to Instrument-Specific Credit Risk Equity in Other Comprehensive Loss of Limited Liability Investment Total Accumulated Other Comprehensive Income (Loss) Balance at January 1, 2018 $ (566 ) $ (3,286 ) $ — $ — $ (3,852 ) Cumulative effect of adoption of ASU 2016-01 40 — 40,455 — 40,495 Balance at January 1, 2018, as adjusted (526 ) (3,286 ) 40,455 — 36,643 Other comprehensive income (loss) arising during the period (430 ) — 344 (224 ) (310 ) Amounts reclassified from accumulated other comprehensive income (loss) (11 ) — — — (11 ) Net current-period other comprehensive income (loss) (441 ) — 344 (224 ) (321 ) Balance at June 30, 2018 $ (967 ) $ (3,286 ) $ 40,799 $ (224 ) $ 36,322 (in thousands) Six months ended June 30, 2017 Unrealized Gains (Losses) on Available-for-Sale Investments Foreign Currency Translation Adjustments Total Accumulated Other Comprehensive Loss Balance at January 1, 2017 $ 3,572 $ (3,780 ) $ (208 ) Other comprehensive loss arising during the period (1,230 ) — (1,230 ) Amounts reclassified from accumulated other comprehensive income (loss) (29 ) — (29 ) Net current-period other comprehensive loss (1,259 ) — (1,259 ) Balance at June 30, 2017 $ 2,313 $ (3,780 ) $ (1,467 ) Components of accumulated other comprehensive income (loss) were reclassified to the following lines of the unaudited consolidated statements of operations for the three and six months ended June 30, 2018 and June 30, 2017 : (in thousands) Three months ended June 30, Six months ended June 30, 2018 2017 2018 2017 Reclassification of accumulated other comprehensive income (loss) from unrealized gains (losses) on available-for-sale investments to: Net realized gains $ 5 $ 2 $ 8 $ 2 Other-than-temporary impairment loss — — — — Loss from continuing operations before income tax expense 5 2 8 2 Income tax expense — — — — Loss from continuing operations 5 2 8 2 Income (loss) from discontinued operations, net of taxes (1 ) (480 ) 3 27 Net loss $ 4 $ (478 ) $ 11 $ 29

Segmented Information (Tables)

Segmented Information (Tables)	6 Months Ended
	Jun. 30, 2018
Segmented Information [Abstract]
Segment Reporting Disclosure [Text Block]	SEGMENTED INFORMATION The Company conducts its business through the following two reportable segments: Extended Warranty and Leased Real Estate. Prior to the second quarter of 2018, the Company conducted its business through a third reportable segment, Insurance Underwriting. Insurance Underwriting included the following subsidiaries of the Company: Mendota, Amigo and Kingsway Reinsurance Corporation ("Kingsway Re"). As further discussed in Note 5 , " Acquisition and Discontinued Operations ," on July 16, 2018, the Company announced that it had entered into a definitive agreement to sell Mendota. As a result, Mendota has been classified as discontinued operations and the results of their operations are reported separately for all periods presented. As a result of classifying Mendota as discontinued operations, the composition of the Insurance Underwriting segment has changed such that it no longer meets the criteria of a reportable segment. As such, all segmented information has been restated to exclude the Insurance Underwriting segment for all periods presented. Extended Warranty Segment Extended Warranty includes the following subsidiaries of the Company: IWS Acquisition Corporation ("IWS"), Trinity Warranty Solutions LLC ("Trinity") and PWSC (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 23 states and the District of Columbia to their members. Trinity sells HVAC, standby generator, commercial LED lighting and 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 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. PWSC sells new home warranty products and provides administration services to home builders and homeowners across the United States. PWSC distributes its products and services through an in house sales team and through insurance brokers and insurance carriers throughout all states except Alaska and Louisiana. Leased Real Estate Segment Leased Real Estate includes the Company's subsidiary, CMC, which was acquired on July 14, 2016. CMC owns a parcel of real property consisting of approximately 192 acres located in the State of Texas (the "Real Property") that is leased to a third party pursuant to a long-term triple net lease. The Real Property is also subject to the Mortgage. When assessing and measuring the operational and financial performance of the Leased Real Estate segment, interest expense related to the Mortgage is included in Leased Real Estate's segment operating income. Revenues and Operating Income by Reportable Segment Results for the Company's reportable segments are based on the Company's internal financial reporting systems and are consistent with those followed in the preparation of the unaudited consolidated interim financial statements. The following tables provide financial data used by management. Segment assets are not allocated for management use and, therefore, are not included in the segment disclosures below. Revenues by reportable segment reconciled to consolidated revenues for the three and six months ended June 30, 2018 and June 30, 2017 were: (in thousands) Three months ended June 30, Six months ended June 30, 2018 2017 2018 2017 Revenues: Extended Warranty: Service fee and commission income 9,479 6,584 19,670 12,946 Other income 36 51 102 136 Total Extended Warranty 9,515 6,635 19,772 13,082 Leased Real Estate: Rental income 3,341 3,341 6,682 6,682 Other income 72 160 219 372 Total Leased Real Estate 3,413 3,501 6,901 7,054 Total segment revenues 12,928 10,136 26,673 20,136 Net investment income (loss) 18 (1,347 ) (613 ) (1,163 ) Net realized (losses) gains (1 ) (1 ) 9 (1 ) (Loss) gain on change in fair value of equity investments (248 ) — 614 — Other income not allocated to segments 973 31 987 61 Total revenues $ 13,670 $ 8,819 $ 27,670 $ 19,033 The operating income by reportable segment in the following table is before income taxes and includes revenues and direct segment costs. Total segment operating income reconciled to the consolidated loss from continuing operations for the three and six months ended June 30, 2018 and June 30, 2017 were: (in thousands) Three months ended June 30, Six months ended June 30, 2018 2017 2018 2017 Segment operating income: Extended Warranty 1,659 685 3,230 1,271 Leased Real Estate 618 872 1,492 1,790 Total segment operating income 2,277 1,557 4,722 3,061 Net investment income (loss) 18 (1,347 ) (613 ) (1,163 ) Net realized (losses) gains (1 ) (1 ) 9 (1 ) (Loss) gain on change in fair value of equity investments (248 ) — 614 — Interest expense not allocated to segments (1,519 ) (1,216 ) (2,905 ) (2,375 ) Other income and expenses not allocated to segments, net (2,248 ) (2,907 ) (4,642 ) (4,983 ) Amortization of intangible assets (271 ) (289 ) (543 ) (580 ) Contingent consideration benefit — 212 — 212 Loss on change in fair value of debt (142 ) (2,702 ) (1,061 ) (4,591 ) Equity in net (loss) income of investee (385 ) (145 ) (284 ) 2,240 Loss from continuing operations before income tax expense (2,519 ) (6,838 ) (4,703 ) (8,180 ) Income tax expense 187 1,251 438 1,516 Loss from continuing operations $ (2,706 ) $ (8,089 ) $ (5,141 ) $ (9,696 )
Reconciliation of Revenue from Segments to Consolidated [Table Text Block]	Revenues by reportable segment reconciled to consolidated revenues for the three and six months ended June 30, 2018 and June 30, 2017 were: (in thousands) Three months ended June 30, Six months ended June 30, 2018 2017 2018 2017 Revenues: Extended Warranty: Service fee and commission income 9,479 6,584 19,670 12,946 Other income 36 51 102 136 Total Extended Warranty 9,515 6,635 19,772 13,082 Leased Real Estate: Rental income 3,341 3,341 6,682 6,682 Other income 72 160 219 372 Total Leased Real Estate 3,413 3,501 6,901 7,054 Total segment revenues 12,928 10,136 26,673 20,136 Net investment income (loss) 18 (1,347 ) (613 ) (1,163 ) Net realized (losses) gains (1 ) (1 ) 9 (1 ) (Loss) gain on change in fair value of equity investments (248 ) — 614 — Other income not allocated to segments 973 31 987 61 Total revenues $ 13,670 $ 8,819 $ 27,670 $ 19,033
Reconciliation of Operating Profit (Loss) from Segments to Consolidated [Table Text Block]	egment operating income reconciled to the consolidated loss from continuing operations for the three and six months ended June 30, 2018 and June 30, 2017 were: (in thousands) Three months ended June 30, Six months ended June 30, 2018 2017 2018 2017 Segment operating income: Extended Warranty 1,659 685 3,230 1,271 Leased Real Estate 618 872 1,492 1,790 Total segment operating income 2,277 1,557 4,722 3,061 Net investment income (loss) 18 (1,347 ) (613 ) (1,163 ) Net realized (losses) gains (1 ) (1 ) 9 (1 ) (Loss) gain on change in fair value of equity investments (248 ) — 614 — Interest expense not allocated to segments (1,519 ) (1,216 ) (2,905 ) (2,375 ) Other income and expenses not allocated to segments, net (2,248 ) (2,907 ) (4,642 ) (4,983 ) Amortization of intangible assets (271 ) (289 ) (543 ) (580 ) Contingent consideration benefit — 212 — 212 Loss on change in fair value of debt (142 ) (2,702 ) (1,061 ) (4,591 ) Equity in net (loss) income of investee (385 ) (145 ) (284 ) 2,240 Loss from continuing operations before income tax expense (2,519 ) (6,838 ) (4,703 ) (8,180 ) Income tax expense 187 1,251 438 1,516 Loss from continuing operations $ (2,706 ) $ (8,089 ) $ (5,141 ) $ (9,696 )
Revenue from External Customers by Geographic Areas [Table Text Block]	(in thousands) Three months ended June 30, Six months ended June 30, 2018 2017 2018 2017 Segment operating income: Extended Warranty 1,659 685 3,230 1,271 Leased Real Estate 618 872 1,492 1,790 Total segment operating income 2,277 1,557 4,722 3,061 Net investment income (loss) 18 (1,347 ) (613 ) (1,163 ) Net realized (losses) gains (1 ) (1 ) 9 (1 ) (Loss) gain on change in fair value of equity investments (248 ) — 614 — Interest expense not allocated to segments (1,519 ) (1,216 ) (2,905 ) (2,375 ) Other income and expenses not allocated to segments, net (2,248 ) (2,907 ) (4,642 ) (4,983 ) Amortization of intangible assets (271 ) (289 ) (543 ) (580 ) Contingent consideration benefit — 212 — 212 Loss on change in fair value of debt (142 ) (2,702 ) (1,061 ) (4,591 ) Equity in net (loss) income of investee (385 ) (145 ) (284 ) 2,240 Loss from continuing operations before income tax expense (2,519 ) (6,838 ) (4,703 ) (8,180 ) Income tax expense 187 1,251 438 1,516 Loss from continuing operations $ (2,706 ) $ (8,089 ) $ (5,141 ) $ (9,696 )

Fair Value of Financial Instr49

Fair Value of Financial Instruments (Tables)	6 Months Ended
	Jun. 30, 2018
Fair Value of Financial Instruments [Abstract]
Fair Value Inputs, Assets, Quantitative Information [Table Text Block]	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 June 30, 2018 and December 31, 2017 are as follows: (in thousands) June 30, 2018 Fair Value Measurements at the End of the Reporting Period Using Total Quoted Prices in Active Markets for Identical Assets (Level 1) Significant Other Observable Inputs (Level 2) Significant Unobservable Inputs (Level 3) Recurring fair value measurements: Assets: Fixed maturities: U.S. government, government agencies and authorities $ 5,427 $ — $ 5,427 $ — States, municipalities and political subdivisions 605 — 605 — Mortgage-backed 2,811 — 2,811 — Corporate 2,518 — 2,518 — Total fixed maturities 11,361 — 11,361 — Equity investments: Common stock 1,264 1,264 — — Warrants 925 54 871 — Total equity investments 2,189 1,318 871 — Limited liability investment, at fair value 4,869 — 4,869 — Other investments 1,916 — 1,916 — Short-term investments 151 — 151 — Total assets $ 20,486 $ 1,318 $ 19,168 $ — Liabilities: Subordinated debt $ 52,822 $ — $ 52,822 $ — Total liabilities $ 52,822 $ — $ 52,822 $ — (in thousands) December 31, 2017 Fair Value Measurements at the End of the Reporting Period Using Total Quoted Prices in Active Markets for Identical Assets (Level 1) Significant Other Observable Inputs (Level 2) Significant Unobservable Inputs (Level 3) Recurring fair value measurements: Assets: Fixed maturities: U.S. government, government agencies and authorities $ 5,612 $ — $ 5,612 $ — States municipalities and political subdivisions 626 — 626 — Mortgage-backed 2,876 — 2,876 — Corporate 5,427 — 5,427 — Total fixed maturities 14,541 — 14,541 — Equity investments: Common stock 3,570 3,570 — — Warrants 906 58 848 — Total equity investments 4,476 3,628 848 — Limited liability investment, at fair value 5,771 — 5,771 — Other investments 2,321 — 2,321 — Short-term investments 151 — 151 — Total assets $ 27,260 $ 3,628 $ 23,632 $ — Liabilities: Subordinated debt $ 52,105 $ — $ 52,105 $ — Total liabilities $ 52,105 $ — $ 52,105 $ —

Acquisition and Discontinued 50

Acquisition and Discontinued Operations Acquisition of PWSC (Details) - USD ($) $ in Thousands	3 Months Ended
	Dec. 31, 2017	Jun. 30, 2018	Oct. 12, 2017
Business Acquisition [Line Items]
Cash and cash equivalents			$ 2,071
Other receivables			50
Service fee receivable			1,422
Property and equipment			238
Other assets	$ 4,302	$ 3,592	205
Goodwill	80,112	80,112	9,051
Total assets	484,600	482,539	13,037
Deferred service fees			2,079
Accrued expenses and other liabilities	10,612	10,946	1,089
Total liabilities	435,290	$ 443,645	$ 3,168
Purchase price	$ 9,900

Acquisition and Discontinued 51

Acquisition and Discontinued Operations Discontinued Operations - NSA (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2018	Jun. 30, 2017	Jun. 30, 2018	Jun. 30, 2017
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Statutory Accounting Practices, Statutory Capital and Surplus, Balance	$ 28,900		$ 28,900
Liability for Unpaid Claims and Claims Adjustment Expense, Reported Claims, Amount	2,500		2,500
(Loss) gain on disposal of discontinued operations, net of taxes	(6,611)	$ 1,017	$ (6,611)	$ 1,017
Discontinued Operations [Member]
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
(Loss) gain on disposal of discontinued operations, net of taxes	1,335			$ 1,017
Other Segments [Member] | Sale of Subsidiary Gain (Loss) [Member]
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
(Loss) gain on disposal of discontinued operations, net of taxes	(7,964)
Operating Segments [Member]
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
(Loss) gain on disposal of discontinued operations, net of taxes	$ 17

Acquisition and Discontinued 52

Acquisition and Discontinued Operations Discontinued operations - ARS (Details) - USD ($) $ in Thousands, number in Millions	3 Months Ended		6 Months Ended
	Jun. 30, 2018	Jun. 30, 2017	Jun. 30, 2018	Jun. 30, 2017	Jun. 30, 2015
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Disposal Group, Including Discontinued Operation, Consideration	$ 1,700		$ 1,700
(Loss) gain on disposal of discontinued operations, net of taxes	(6,611)	$ 1,017	$ (6,611)	$ 1,017
Discontinued Operations, Disposed of by Sale [Member]
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Premiums, Percentage Assumed to Net					0.00%
Discontinued Operations [Member]
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
(Loss) gain on disposal of discontinued operations, net of taxes	$ 1,335			$ 1,017

Acquisition and Discontinued 53

Acquisition and Discontinued Operations Income from discontinued operations (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2018	Jun. 30, 2017	Jun. 30, 2018	Jun. 30, 2017
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Disposal Group, Including Discontinued Operation, Revenue	$ 25,897	$ 35,807	$ 57,236	$ 72,134
Loss and loss adjustment expenses	2,625	1,338	4,247	2,557
Disposal Group, Including Discontinued Operation, Operating Expense	24,986	36,377	55,918	72,666
Disposal Group, Including Discontinued Operation, Other Expense	2,251	5,375	6,442	10,688
Disposal Group, Including Discontinued Operation, Rental Income	4	6	10	12
Net investment income (loss)	18	(1,347)	(613)	(1,163)
Net realized (losses) gains	(1)	(1)	9	(1)
(Loss) gain on change in fair value of equity investments	(248)	0	614	0
Disposal Group, Including Discontinued Operation, Other Income	2,445	2,556	4,876	5,027
Disposal Group, Including Discontinued Operation, General and Administrative Expense	3,808	4,872	7,748	10,407
Impairment of Intangible Assets, Indefinite-lived (Excluding Goodwill)	0	0	0	250
Discontinued Operation, Income (Loss) from Discontinued Operation, before Income Tax	911	(570)	1,318	(532)
Discontinued Operation, Tax Effect of Discontinued Operation	0	0	0	(85)
Discontinued Operation, Tax Effect of Gain (Loss) from Disposal of Discontinued Operation	0	0	0	0
Income (loss) from discontinued operations, net of taxes	911	(570)	1,318	(447)
Discontinued Operation, Gain (Loss) from Disposal of Discontinued Operation, before Income Tax	(6,611)	1,017	(6,611)	1,017
(Loss) gain on disposal of discontinued operations, net of taxes	(6,611)	1,017	(6,611)	1,017
Operating Income (Loss) [Member]
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Disposal Group, Including Discontinued Operation, Revenue	22,956	33,518	51,592	66,440
Discontinued Operations [Member]
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Loss and loss adjustment expenses	18,927	26,130	41,728	51,321
Net investment income (loss)	570	(1,008)	519	(478)
Net realized (losses) gains	(1)	735	2	1,133
(Loss) gain on change in fair value of equity investments	(77)	0	237	0
(Loss) gain on disposal of discontinued operations, net of taxes	1,335			1,017
Discontinued Operations, Held-for-sale or Disposed of by Sale [Member]
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
(Loss) gain on disposal of discontinued operations, net of taxes	$ (5,700)	$ 447	$ (5,293)	$ 570

Acquisition and Discontinued 54

Acquisition and Discontinued Operations Held for sale in the consolidated balance sheets (Details) - USD ($) $ in Thousands	Jun. 30, 2018	Mar. 31, 2018	Dec. 31, 2017	Jun. 30, 2017	Mar. 31, 2017	Dec. 31, 2016
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Marketable Securities, Fixed Maturities	$ 11,361		$ 14,541
Investments	25,703		32,182
Marketable Securities, Equity Securities	2,189		4,476
Limited liability investments	5,217		4,922
Limited liability investments	4,869		5,771
Other Investments	1,916		2,321
Less: cash and cash equivalents of discontinued operations at begininng of period			23,505			$ 4,513
Accrued investment income	161		331
Disposal Group, Including Discontinued Operation, Other Assets, Current	138		299
Other receivables, net of allowance for doubtful accounts of zero and zero, respectively	7,907		6,536
Deferred acquisition costs, net	6,662	$ 6,428	6,325	$ 6,054	$ 5,867	$ 5,827
Disposal Group, Including Discontinued Operation, Property, Plant and Equipment	162		903
Disposal Group, Including Discontinued Operation, Intangible Assets	0		7,553
Assets held for sale	138,804		137,126
Property and casualty	2,594		1,329	$ 1,799
Unearned Premiums	34,969		36,686
Reinsurance Payable	14,869		82
Disposal Group, Including Discontinued Operation, Accrued Income Tax Payable, Current	0		1,586
Disposal Group, Including Discontinued Operation, Accounts Payable and Accrued Liabilities	4,211		5,272
Liabilities held for sale	112,866		105,949
Discontinued Operations [Member]
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Marketable Securities, Fixed Maturities	42,714		38,673
Investments	69,851		69,385
Marketable Securities, Equity Securities	3,681		4,518
Limited liability investments	18,427		20,251
Limited liability investments	3,629		4,543
Other Investments	1,400		1,400
Less: cash and cash equivalents of discontinued operations at begininng of period	18,517		23,505
Accrued investment income	239		195
Premiums Receivable, Net	27,673		27,855
Disposal Group, Including Discontinued Operation, Other Assets, Current	174
Other receivables, net of allowance for doubtful accounts of zero and zero, respectively			603
Reinsurance Recoverable for Paid Claims and Claims Adjustments	6,509		108
Prepaid Reinsurance Premiums	13,493		0
Deferred acquisition costs, net	2,048		6,720
Property and casualty	$ 58,817		$ 62,323

Investments (Details)

Investments (Details) $ / shares in Units, $ in Thousands	3 Months Ended			6 Months Ended
	Jun. 30, 2018USD ($)	Jun. 30, 2017USD ($)	Mar. 31, 2017USD ($)	Jun. 30, 2018USD ($)	Jun. 30, 2017USD ($)	Dec. 31, 2017USD ($)$ / shares	Jun. 30, 2014$ / sharesshares
Schedule of Available-for-sale Securities [Line Items]
(Loss) gain on change in fair value of equity investments	$ (248)	$ 0		$ 614	$ 0
Fixed maturities and equity investments unrealized loss positions	64,000			64,000		68,000
Limited liability investments	$ 5,217			$ 5,217		$ 4,922
Limited liability investments	4,869			$ 4,869		5,771
Limited Liability Company or Limited Partnership, Members or Limited Partners, Ownership Interest				15.90%
Other investments, at cost which approximates fair value	1,916			$ 1,916		2,321
Available-for-sale Securities Pledged as Collateral	1,854			1,854		1,843
Pledged Assets Separately Reported, Nonsecuritized Investments Pledged as Collateral, at Fair Value	1,100			1,100		1,100
Minimum [Member]
Schedule of Available-for-sale Securities [Line Items]
Common Stock, Capital Shares Reserved for Future Issuance | shares							100,000
Share Price | $ / shares							$ 10
Maximum [Member]
Schedule of Available-for-sale Securities [Line Items]
Share Price | $ / shares							$ 18
Fair Value, Inputs, Level 1 [Member]
Schedule of Available-for-sale Securities [Line Items]
Other investments, at cost which approximates fair value	0			$ 0		0
Fair Value, Inputs, Level 1 [Member] | Warrant [Member]
Schedule of Available-for-sale Securities [Line Items]
(Loss) gain on change in fair value of equity investments			$ (112)
Available-for-sale Equity Securities, Accumulated Gross Unrealized Gain, before Tax						47
Fair Value, Inputs, Level 2 [Member] | Warrant [Member]
Schedule of Available-for-sale Securities [Line Items]
Available-for-sale Equity Securities, Accumulated Gross Unrealized Gain, before Tax						$ 173
Performance Share Grant Agreement [Member]
Schedule of Available-for-sale Securities [Line Items]
Common Stock, Capital Shares Reserved for Future Issuance | shares							475,000
Clause 2 [Member]
Schedule of Available-for-sale Securities [Line Items]
Common Stock, Capital Shares Reserved for Future Issuance | shares							125,000
Share Price | $ / shares							$ 12
Clause 3 [Member]
Schedule of Available-for-sale Securities [Line Items]
Share Price | $ / shares							$ 15
Clause 1, 2 and 3 [Member]
Schedule of Available-for-sale Securities [Line Items]
Common Stock, Capital Shares Reserved for Future Issuance | shares							350,000
Clause 1 and 2 [Member]
Schedule of Available-for-sale Securities [Line Items]
Common Stock, Capital Shares Reserved for Future Issuance | shares							225,000
Management [Member]
Schedule of Available-for-sale Securities [Line Items]
Share Price | $ / shares						$ 7.85
Effect on Future Cash Flows, Amount	300
Effect on Future Cash Flows, Amount	$ 1,000

Investments Amortized cost, g56

Investments Amortized cost, gross unrealized gains and losses, and estimated fair value (Details) - USD ($) $ in Thousands	Jun. 30, 2018	Dec. 31, 2017
Schedule of Available-for-sale Securities [Line Items]
Fixed maturities, cost	$ 11,605	$ 14,707
Gross Unrealized Gain, Fixed Maturities	0	0
Gross Unrealized Loss, Fixed Maturities	244	166
Total Fixed Maturities	11,361	14,541
Equity investments, cost	2,325	4,854
Total Equity Investments	2,189	4,476
Amortized Cost		19,561
Gross Unrealized Gain		220
Gross Unrealized Loss		764
Estimated Fair Value, Fixed Maturities and Equity Investments		19,017
US Government Agencies Debt Securities [Member]
Schedule of Available-for-sale Securities [Line Items]
Fixed maturities, cost	5,503	5,671
Gross Unrealized Gain, Fixed Maturities	0	0
Gross Unrealized Loss, Fixed Maturities	76	59
Total Fixed Maturities	5,427	5,612
Gross Unrealized Loss	76	59
US States and Political Subdivisions Debt Securities [Member]
Schedule of Available-for-sale Securities [Line Items]
Fixed maturities, cost	624	639
Gross Unrealized Gain, Fixed Maturities	0	0
Gross Unrealized Loss, Fixed Maturities	19	13
Total Fixed Maturities	605	626
Gross Unrealized Loss	19	13
Mortgage-backed Securities, Issued by US Government Sponsored Enterprises [Member]
Schedule of Available-for-sale Securities [Line Items]
Fixed maturities, cost	2,902	2,933
Gross Unrealized Gain, Fixed Maturities	0	0
Gross Unrealized Loss, Fixed Maturities	91	57
Total Fixed Maturities	2,811	2,876
Gross Unrealized Loss	91	57
Corporate Debt Securities [Member]
Schedule of Available-for-sale Securities [Line Items]
Fixed maturities, cost	2,576	5,464
Gross Unrealized Gain, Fixed Maturities	0	0
Gross Unrealized Loss, Fixed Maturities	58	37
Total Fixed Maturities	2,518	5,427
Gross Unrealized Loss	58	37
Common Stock [Member]
Schedule of Available-for-sale Securities [Line Items]
Equity investments, cost		3,883
Total Equity Investments		3,570
Unrealized Gain, Equity Investments		0
Gross Unrealized Loss, Equity Investments		313
Gross Unrealized Loss		313
Warrant [Member]
Schedule of Available-for-sale Securities [Line Items]
Gross Unrealized Loss		285
Equity Securities [Member]
Schedule of Available-for-sale Securities [Line Items]
Equity investments, cost		4,854
Total Equity Investments		4,476
Unrealized Gain, Equity Investments		220
Gross Unrealized Loss, Equity Investments		598
Gross Unrealized Loss		598
Fair Value, Inputs, Level 1 [Member]
Schedule of Available-for-sale Securities [Line Items]
Total Fixed Maturities	0	0
Total Equity Investments	1,318	3,628
Fair Value, Inputs, Level 1 [Member] | US States and Political Subdivisions Debt Securities [Member]
Schedule of Available-for-sale Securities [Line Items]
Total Fixed Maturities	0	0
Fair Value, Inputs, Level 1 [Member] | Mortgage-backed Securities, Issued by US Government Sponsored Enterprises [Member]
Schedule of Available-for-sale Securities [Line Items]
Total Fixed Maturities	0	0
Fair Value, Inputs, Level 1 [Member] | Corporate Debt Securities [Member]
Schedule of Available-for-sale Securities [Line Items]
Total Fixed Maturities	0	0
Fair Value, Inputs, Level 1 [Member] | Warrant [Member]
Schedule of Available-for-sale Securities [Line Items]
Equity investments, cost		11
Total Equity Investments		58
Unrealized Gain, Equity Investments		47
Gross Unrealized Loss, Equity Investments		0
Fair Value, Inputs, Level 2 [Member]
Schedule of Available-for-sale Securities [Line Items]
Total Fixed Maturities	11,361	14,541
Total Equity Investments	871	848
Fair Value, Inputs, Level 2 [Member] | US Government Agencies Debt Securities [Member]
Schedule of Available-for-sale Securities [Line Items]
Total Fixed Maturities	5,427	5,612
Fair Value, Inputs, Level 2 [Member] | US States and Political Subdivisions Debt Securities [Member]
Schedule of Available-for-sale Securities [Line Items]
Total Fixed Maturities	605	626
Fair Value, Inputs, Level 2 [Member] | Mortgage-backed Securities, Issued by US Government Sponsored Enterprises [Member]
Schedule of Available-for-sale Securities [Line Items]
Total Fixed Maturities	2,811	2,876
Fair Value, Inputs, Level 2 [Member] | Corporate Debt Securities [Member]
Schedule of Available-for-sale Securities [Line Items]
Total Fixed Maturities	$ 2,518	5,427
Fair Value, Inputs, Level 2 [Member] | Warrant [Member]
Schedule of Available-for-sale Securities [Line Items]
Equity investments, cost		960
Total Equity Investments		848
Unrealized Gain, Equity Investments		173
Gross Unrealized Loss, Equity Investments		$ 285

Investments Fixed Maturities 57

Investments Fixed Maturities by Contractual Maturity Periods (Details) - USD ($) $ in Thousands	Jun. 30, 2018	Dec. 31, 2017
Schedule of Held-to-maturity Securities [Line Items]
Due In One Year or Less, Amortized Cost	$ 4,924
Due In One Year or Less, Fair Value	4,899
Due After One Year Through Five Years, Amortized Cost	5,378
Due After One Year Through Five Years, Fair Value	5,219
Due After Five Year Through Ten Years, Amortized Cost	132
Due After Five Year Through Ten Years, Fair Value	125
Due After Ten Years, Amortized Cost	1,171
Due After Ten Years, Fair Value	1,118
Fixed maturities, cost	11,605	$ 14,707
Estimated Fair Value, Fixed Maturities	$ 11,361	$ 14,541

Investments Unrealized Loss Pos

Investments Unrealized Loss Position (Details) - USD ($) $ in Thousands	Jun. 30, 2018	Dec. 31, 2017
Gain (Loss) on Investments [Line Items]
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax		$ 764
US Government Agencies Debt Securities [Member]
Gain (Loss) on Investments [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value	$ 3,502	4,067
Continuous Unrealized Loss Position, Less than 12 Months, Aggregate Loss	34	50
Continuous Unrealized Loss Position, 12 Months or Longer, Aggregate Loss	42	9
Continuous Unrealized Loss Position, Twelve Months or Longer, Fair Value	1,925	1,545
Continuous Unrealized Loss Position, Fair Value	5,427	5,612
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax	76	59
US States and Political Subdivisions Debt Securities [Member]
Gain (Loss) on Investments [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value	86	626
Continuous Unrealized Loss Position, Less than 12 Months, Aggregate Loss	2	13
Continuous Unrealized Loss Position, 12 Months or Longer, Aggregate Loss	17	0
Continuous Unrealized Loss Position, Twelve Months or Longer, Fair Value	519	0
Continuous Unrealized Loss Position, Fair Value	605	626
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax	19	13
Fixed Maturities [Member]
Gain (Loss) on Investments [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value	4,688	9,996
Continuous Unrealized Loss Position, Less than 12 Months, Aggregate Loss	54	157
Continuous Unrealized Loss Position, 12 Months or Longer, Aggregate Loss	190	9
Continuous Unrealized Loss Position, Twelve Months or Longer, Fair Value	6,673	1,545
Continuous Unrealized Loss Position, Fair Value	11,361	11,541
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax	244	166
Mortgage-backed Securities, Issued by US Government Sponsored Enterprises [Member]
Gain (Loss) on Investments [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value	690	2,876
Continuous Unrealized Loss Position, Less than 12 Months, Aggregate Loss	13	57
Continuous Unrealized Loss Position, 12 Months or Longer, Aggregate Loss	78	0
Continuous Unrealized Loss Position, Twelve Months or Longer, Fair Value	2,121	0
Continuous Unrealized Loss Position, Fair Value	2,811	2,876
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax	91	57
Corporate Debt Securities [Member]
Gain (Loss) on Investments [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value	410	2,427
Continuous Unrealized Loss Position, Less than 12 Months, Aggregate Loss	5	37
Continuous Unrealized Loss Position, 12 Months or Longer, Aggregate Loss	53	0
Continuous Unrealized Loss Position, Twelve Months or Longer, Fair Value	2,108	0
Continuous Unrealized Loss Position, Fair Value	2,518	2,427
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax	$ 58	37
Equity Securities [Member]
Gain (Loss) on Investments [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value		3,570
Continuous Unrealized Loss Position, Less than 12 Months, Aggregate Loss		313
Continuous Unrealized Loss Position, 12 Months or Longer, Aggregate Loss		0
Continuous Unrealized Loss Position, Twelve Months or Longer, Fair Value		0
Continuous Unrealized Loss Position, Fair Value		3,570
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax		313
Warrant [Member]
Gain (Loss) on Investments [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value		675
Continuous Unrealized Loss Position, Less than 12 Months, Aggregate Loss		285
Continuous Unrealized Loss Position, 12 Months or Longer, Aggregate Loss		0
Continuous Unrealized Loss Position, Twelve Months or Longer, Fair Value		0
Continuous Unrealized Loss Position, Fair Value		675
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax		285
Equity Securities [Member]
Gain (Loss) on Investments [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value		4,245
Continuous Unrealized Loss Position, Less than 12 Months, Aggregate Loss		598
Continuous Unrealized Loss Position, 12 Months or Longer, Aggregate Loss		0
Continuous Unrealized Loss Position, Twelve Months or Longer, Fair Value		0
Continuous Unrealized Loss Position, Fair Value		4,245
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax		598
Available-for-sale Securities [Member]
Gain (Loss) on Investments [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value		14,241
Continuous Unrealized Loss Position, Less than 12 Months, Aggregate Loss		755
Continuous Unrealized Loss Position, 12 Months or Longer, Aggregate Loss		9
Continuous Unrealized Loss Position, Twelve Months or Longer, Fair Value		1,545
Continuous Unrealized Loss Position, Fair Value		15,786
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax		$ 764

Investments Continuous Unreal59

Investments Continuous Unrealized Loss Position (Details) - USD ($) $ in Thousands	Jun. 30, 2018	Dec. 31, 2017
Schedule of Available-for-sale Securities [Line Items]
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax		$ 764
US Government Agencies Debt Securities [Member]
Schedule of Available-for-sale Securities [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value	$ 3,502	4,067
Continuous Unrealized Loss Position, 12 Months or Longer, Accumulated Loss	42	9
Continuous Unrealized Loss Position, Fair Value	5,427	5,612
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax	76	59
US States and Political Subdivisions Debt Securities [Member]
Schedule of Available-for-sale Securities [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value	86	626
Continuous Unrealized Loss Position, 12 Months or Longer, Accumulated Loss	17	0
Continuous Unrealized Loss Position, Fair Value	605	626
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax	19	13
Mortgage-backed Securities, Issued by US Government Sponsored Enterprises [Member]
Schedule of Available-for-sale Securities [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value	690	2,876
Continuous Unrealized Loss Position, 12 Months or Longer, Accumulated Loss	78	0
Continuous Unrealized Loss Position, Fair Value	2,811	2,876
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax	91	57
Corporate Debt Securities [Member]
Schedule of Available-for-sale Securities [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value	410	2,427
Continuous Unrealized Loss Position, 12 Months or Longer, Accumulated Loss	53	0
Continuous Unrealized Loss Position, Fair Value	2,518	2,427
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax	58	37
Fixed Maturities [Member]
Schedule of Available-for-sale Securities [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value	4,688	9,996
Continuous Unrealized Loss Position, 12 Months or Longer, Accumulated Loss	190	9
Continuous Unrealized Loss Position, Fair Value	11,361	11,541
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax	$ 244	166
Common Stock [Member]
Schedule of Available-for-sale Securities [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value		3,570
Continuous Unrealized Loss Position, 12 Months or Longer, Accumulated Loss		0
Continuous Unrealized Loss Position, Fair Value		3,570
Available-for-sale Equity Securities, Accumulated Gross Unrealized Loss, before Tax		313
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax		313
Warrant [Member]
Schedule of Available-for-sale Securities [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value		675
Continuous Unrealized Loss Position, 12 Months or Longer, Accumulated Loss		0
Continuous Unrealized Loss Position, Fair Value		675
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax		285
Available-for-sale Securities [Member]
Schedule of Available-for-sale Securities [Line Items]
Continuous Unrealized Loss Position, Less than Twelve Months, Fair Value		14,241
Continuous Unrealized Loss Position, 12 Months or Longer, Accumulated Loss		9
Continuous Unrealized Loss Position, Fair Value		15,786
Available-for-sale Securities, Accumulated Gross Unrealized Loss, before Tax		$ 764

Investments Net Investment Inco

Investments Net Investment Income (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2018	Jun. 30, 2017	Jun. 30, 2018	Jun. 30, 2017
Net Investment Income [Line Items]
Interest from fixed maturities	$ 57	$ 49	$ 90	$ 83
Dividends	53	102	108	196
Income (loss) from limited liability investments	(120)	100	(164)	166
Loss on change in fair value of limited liability investment, at fair value	(280)	(1,292)	(1,152)	(1,520)
Other	77	100	194	212
Gross investment income (loss)	27	1,339	596	1,148
Investment expenses	(9)	(8)	(17)	(15)
Net investment income (loss)	18	(1,347)	(613)	(1,163)
Warrant [Member]
Net Investment Income [Line Items]
Loss on change in fair value of limited liability investment, at fair value	$ 0	$ (198)	$ 0	$ 47

Investments Gross Realized Ga61

Investments Gross Realized Gains and Losses on Fixed Maturities (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2018	Jun. 30, 2017	Jun. 30, 2018	Jun. 30, 2017
Gain (Loss) on Investments [Line Items]
Gross realized gains	$ 0	$ 0	$ 10	$ 0
Gross realized losses	(1)	(1)	(1)	(1)
Net realized (losses) gains	$ (1)	$ (1)	$ 9	$ (1)

Investments Gain in change fair

Investments Gain in change fair value of equity investments (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2018	Jun. 30, 2017	Jun. 30, 2018	Jun. 30, 2017
Schedule of Available-for-sale Securities [Line Items]
Net (losses) gains recognized on equity investments sold during the period	$ (10)	$ 0	$ 545	$ 0
Change in unrealized (losses) gains on equity investments held at end of the period	(238)	0	69	0
(Loss) gain on change in fair value of equity investments	$ (248)	$ 0	$ 614	$ 0

Investment in Investees (Detail

Investment in Investees (Details) - USD ($) $ / shares in Units, shares in Thousands, $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2018	Jun. 30, 2017	Jun. 30, 2018	Jun. 30, 2017	Mar. 31, 2018	Dec. 31, 2017	Sep. 30, 2017
Schedule of Equity Method Investments [Line Items]
Carrying Value	$ 4,947		$ 4,947			$ 5,230
Equity in net loss of investees	(385)	$ (145)	(284)	$ 2,240
Corporate Segment [Member]
Schedule of Equity Method Investments [Line Items]
Equity Percentage					31.20%		31.20%
Carrying Value	$ 3,259		$ 3,259		$ 3,531		$ 3,816
Carrying Value					$ 4,947		$ 5,230
Investment Owned, Balance, Shares	1,814		1,814
Sale of Stock, Price Per Share	$ 0.72		$ 0.72
Effect on Future Cash Flows, Amount			$ 1,300

Deferred Acquisition Costs (Det

Deferred Acquisition Costs (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2018	Jun. 30, 2017	Jun. 30, 2018	Jun. 30, 2017	Mar. 31, 2018	Dec. 31, 2017	Mar. 31, 2017	Dec. 31, 2016
Deferred Acquisition Costs [Line Items]
Beginning balance, net	$ (6,662)	$ (6,054)	$ (6,662)	$ (6,054)	$ (6,428)	$ (6,325)	$ (5,867)	$ (5,827)
Additions	1,256	1,331	2,498	2,317
Amortization	1,022	1,144	2,161	2,090
Balance at June 30, net	$ 6,662	$ 6,054	$ 6,662	$ 6,054

Intangible Assets (Details)

Intangible Assets (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2018	Jun. 30, 2017	Jun. 30, 2018	Jun. 30, 2017	Dec. 31, 2017
Finite-Lived Intangible Assets [Line Items]
Intangible assets, net of accumulated amortization of $8,876 and $8,333, respectively	$ 79,519		$ 79,519		$ 80,062
Finite-Lived Intangible Assets, Gross	88,395		88,395		88,395
Amortization of Intangible Assets	271	$ 289	$ 543	$ 580
Noncompete Agreements [Member]
Finite-Lived Intangible Assets [Line Items]
Finite-Lived Intangible Asset, Useful Life			18 years
Finite-Lived Intangible Assets, Gross	4,918		$ 4,918		1,125
Contract-Based Intangible Assets [Member]
Finite-Lived Intangible Assets [Line Items]
Finite-Lived Intangible Asset, Useful Life			9 years
Finite-Lived Intangible Assets, Gross	$ 731		$ 731		$ 731
Minimum [Member]
Finite-Lived Intangible Assets [Line Items]
Finite-Lived Intangible Asset, Useful Life			7 years
Maximum [Member]
Finite-Lived Intangible Assets [Line Items]
Finite-Lived Intangible Asset, Useful Life			15 years

Intangible Assets Intangible As

Intangible Assets Intangible Assets (Tables) (Details) - USD ($) $ in Thousands	Jun. 30, 2018	Dec. 31, 2017
Acquired Finite-Lived Intangible Assets [Line Items]
Finite-Lived Intangible Assets, Gross	$ 88,395	$ 88,395
Finite-Lived Intangible Assets, Accumulated Amortization	8,876	8,333
Intangible Assets, Net (Excluding Goodwill)	79,519	80,062
Database Rights [Member]
Acquired Finite-Lived Intangible Assets [Line Items]
Finite-Lived Intangible Assets, Gross	3,680	4,918
Finite-Lived Intangible Assets, Accumulated Amortization	3,656	2,521
Finite-Lived Intangible Assets, Net	2,151	2,397
Service Agreements [Member]
Acquired Finite-Lived Intangible Assets [Line Items]
Finite-Lived Intangible Assets, Gross	3,611	3,680
Finite-Lived Intangible Assets, Accumulated Amortization	2,183	3,640
Finite-Lived Intangible Assets, Net	24	40
Customer Relationships [Member]
Acquired Finite-Lived Intangible Assets [Line Items]
Finite-Lived Intangible Assets, Gross	1,125	3,611
Finite-Lived Intangible Assets, Accumulated Amortization	123	1,965
Finite-Lived Intangible Assets, Net	1,428	1,646
Noncompete Agreements [Member]
Acquired Finite-Lived Intangible Assets [Line Items]
Finite-Lived Intangible Assets, Gross	4,918	1,125
Finite-Lived Intangible Assets, Accumulated Amortization	2,767	92
Finite-Lived Intangible Assets, Net	1,002	1,033
Contract-Based Intangible Assets [Member]
Acquired Finite-Lived Intangible Assets [Line Items]
Finite-Lived Intangible Assets, Gross	731	731
Finite-Lived Intangible Assets, Accumulated Amortization	147	115
Finite-Lived Intangible Assets, Net		616
Other Intangible Assets [Member]
Acquired Finite-Lived Intangible Assets [Line Items]
Finite-Lived Intangible Assets, Net	584
Insurance Contracts Acquired in Business Combination [Member]
Acquired Finite-Lived Intangible Assets [Line Items]
Finite-Lived Intangible Assets, Accumulated Amortization	0	0
Indefinite-Lived Intangible Assets (Excluding Goodwill)	73,667	73,667
Indefinite-Lived License Agreements	73,667	73,667
Trademarks and Trade Names [Member]
Acquired Finite-Lived Intangible Assets [Line Items]
Finite-Lived Intangible Assets, Accumulated Amortization	0	0
Indefinite-Lived Intangible Assets (Excluding Goodwill)	663	663
Indefinite-Lived License Agreements	$ 663	$ 663

Unpaid Loss and Loss Adjustme67

Unpaid Loss and Loss Adjustment Expenses Property and Casualty (tables) (Details) - USD ($) $ in Thousands	6 Months Ended
	Jun. 30, 2018	Jun. 30, 2017	Dec. 31, 2017	Dec. 31, 2016
Liability for Claims and Claims Adjustment Expense [Line Items]
Property and casualty	$ 2,594	$ 1,799	$ 1,329
Balance at end of period, gross	2,594	1,799
Property, Liability and Casualty Insurance Product Line [Member]
Liability for Claims and Claims Adjustment Expense [Line Items]
Property and casualty			1,329	$ 2,201
Less reinsurance recoverable related to property and casualty unpaid loss and loss adjustment expenses	100	332
Balance at beginning of period, net	2,494	1,467
Current year	0	0
Prior years	(1,647)	1
Current year	0	0
Prior years	410	379
Balance at end of period, net	2,494	1,467	1,257	1,847
Plus reinsurance recoverable related to property and casualty unpaid loss and loss adjustment expenses	$ 100	$ 332	$ 72	$ 354

Unpaid Loss and Loss Adjustme68

Unpaid Loss and Loss Adjustment Expenses Vehicle Service Agreements (Details) - USD ($) $ in Thousands	6 Months Ended
	Jun. 30, 2018	Jun. 30, 2017	Dec. 31, 2017	Dec. 31, 2016
Liability for Claims and Claims Adjustment Expense [Line Items]
Vehicle service agreements	$ 2,615	$ 2,794	$ 2,779
Other Insurance Product Line [Member]
Liability for Claims and Claims Adjustment Expense [Line Items]
Current year	2,600	2,558
Prior years	0	0
Current year	2,502	2,616
Prior years	$ (262)	$ (63)
Vehicle service agreements			$ 2,779	$ 2,915

Debt Carrying Value of Debt Ins

Debt Carrying Value of Debt Instruments (Tables) (Details) - USD ($) $ in Thousands	Jun. 30, 2018	Dec. 31, 2017	Jul. 14, 2016
Debt Instrument [Line Items]
Debt Instrument, Principal Value	$ 269,624	$ 271,553
Bank loan	4,417	4,917
Notes Payable	184,567	186,469
Debt Instrument, Unamortized Discount (Premium), Net	241,806	243,491
Total liabilities	220,044	225,446
Long-term Debt, Fair Value	163,059	168,477
Subordinated debt, at fair value	52,822	52,105
Long-term Debt [Member]
Debt Instrument [Line Items]
Debt Instrument, Principal Value	174,707	176,136
Total liabilities	52,822	52,105
Long-term Debt, Fair Value			$ 191,700
Subordinated Debt [Member]
Debt Instrument [Line Items]
Debt Instrument, Principal Value	90,500	90,500
Debt Instrument, Unamortized Discount (Premium), Net	$ 52,822	$ 52,105

Debt Subordinated Borrowing (Ta

Debt Subordinated Borrowing (Table) (Details) - USD ($)	6 Months Ended
	Jun. 30, 2018	Jul. 14, 2016
Debt Instrument [Line Items]
Debt Instrument, Face Amount		$ 180,000,000
Annual Interest Rate		4.07%
Fair Value, Measurement with Unobservable Inputs Reconciliation, Recurring Basis, Liability, Gain (Loss) Included in Earnings	$ 700,000
Connecticut Statutory Trust I [Member]
Debt Instrument [Line Items]
Debt Instrument, Face Amount	$ 15,000
Issue date of trust	Dec. 4, 2002
Redemption date	Dec. 4, 2032
Annual Interest Rate	0.00%
Connecticut Statutory Trust II [Member]
Debt Instrument [Line Items]
Debt Instrument, Face Amount	$ 17,500
Issue date of trust	May 15, 2003
Redemption date	May 15, 2033
Annual Interest Rate	0.00%
Connecticut Statutory Trust III [Member]
Debt Instrument [Line Items]
Debt Instrument, Face Amount	$ 20,000
Issue date of trust	Oct. 29, 2003
Redemption date	Oct. 29, 2033
Annual Interest Rate	0.00%
Delaware Statutory Trust III [Member]
Debt Instrument [Line Items]
Debt Instrument, Face Amount	$ 15,000
Issue date of trust	May 22, 2003
Redemption date	May 22, 2033
Annual Interest Rate	0.00%
Delaware Statutory Trust IV [Member]
Debt Instrument [Line Items]
Debt Instrument, Face Amount	$ 10,000
Issue date of trust	Sep. 30, 2003
Redemption date	Sep. 30, 2033
Annual Interest Rate	0.00%
Delaware Statutory Trust VI [Member]
Debt Instrument [Line Items]
Debt Instrument, Face Amount	$ 13,000
Issue date of trust	Dec. 16, 2003
Redemption date	Jan. 8, 2034
Annual Interest Rate	0.00%

Debt Debt (Details)

Debt Debt (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2018	Jun. 30, 2017	Jun. 30, 2018	Jun. 30, 2017	Dec. 31, 2017	Oct. 12, 2017	Jul. 14, 2016
Debt Instrument [Line Items]
Prior Period Reclassification Adjustment	$ 778	$ 0	$ 344	$ 0
Long-term Debt, Fair Value	163,059		163,059		$ 168,477
Debt Instrument, Face Amount							$ 180,000
Debt Instrument, Unamortized Premium							$ 11,700
Debt Instrument, Interest Rate, Stated Percentage							4.07%
Debt Instrument, Principal Value	269,624		269,624		271,553
Loss on change in fair value of debt	(142)	$ (2,702)	(1,061)	$ (4,591)
Bank loan	4,417		4,417		4,917
Long-term Debt [Member]
Debt Instrument [Line Items]
Long-term Debt, Fair Value							$ 191,700
Debt Instrument, Principal Value	174,707		174,707		176,136
Notes Payable to Banks [Member]
Debt Instrument [Line Items]
Debt Instrument, Interest Rate, Stated Percentage						5.00%
Debt Instrument, Principal Value	4,417		4,417		4,917	$ 5,000
Long-term Debt, Current Maturities	$ 4,163		4,163		$ 4,864
Accumulated Gain (Loss), Financial Liability, Fair Value Option, Including Portion Attributable to Noncontrolling Interest [Member]
Debt Instrument [Line Items]
Prior Period Reclassification Adjustment			$ 354

Revenue from Contracts with C72

Revenue from Contracts with Customers (Details) - USD ($) $ in Millions	6 Months Ended
	Jun. 30, 2018	Dec. 31, 2017
Revenue from Contract with Customer [Abstract]
Revenue, Remaining Performance Obligation, Expected Timing of Satisfaction, Period	10 years
Contract with Customer, Liability	$ 5.2	$ 4.3

Revenue from Contracts with C73

Revenue from Contracts with Customers Disaggregates revenues from contracts with customer by revenue type (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2018	Jun. 30, 2017	Jun. 30, 2018	Jun. 30, 2017
Disaggregation of Revenue [Line Items]
Maintenance Revenue	$ 1,962	$ 1,818	$ 4,935	$ 3,572
Fees and Commissions, Other	2,307	0	4,479	0
Insurance Commissions and Fees	9,479	6,584	19,670	12,946
Product [Member]
Disaggregation of Revenue [Line Items]
Insurance Commissions and Fees	4,474	4,333	9,024	8,611
Warranty product commissions [Member]
Disaggregation of Revenue [Line Items]
Insurance Commissions and Fees	736	433	1,232	763
Reportable Subsegments [Member]
Disaggregation of Revenue [Line Items]
Insurance Commissions and Fees	$ 9,479	$ 6,584	$ 19,670	$ 12,946

Revenue from Contracts with C74

Revenue from Contracts with Customers Deferred Service Fees (Details) $ in Millions	6 Months Ended
	Jun. 30, 2018USD ($)
Deferred Service Fees [Abstract]
Contracts with Customers, Performance Obligation Satisfied within One Year	38.30%
Deferred Revenue, Revenue Recognized	$ 8

Income Taxes Income Taxes Table

Income Taxes Income Taxes Table (Details) - USD ($) $ in Thousands	3 Months Ended			6 Months Ended
	Jun. 30, 2018	Jun. 30, 2017	Mar. 31, 2016	Jun. 30, 2018	Jun. 30, 2017
Income Tax Contingency [Line Items]
Effective Income Tax Rate Reconciliation at Federal Statutory Income Tax Rate, Amount	$ (529)	$ (2,325)		$ (988)	$ (2,781)
Income tax expense	187	1,251		438	1,516
Effective Income Tax Rate Reconciliation, Change in Deferred Tax Assets Valuation Allowance, Amount	481	2,207
Effective Income Tax Rate Reconciliation, Other Reconciling Items, Amount			$ 942		2,764
Unrecognized Tax Benefits, Period Increase (Decrease)	62	101		123	200
Effective Income Tax Rate Reconciliation, State and Local Income Taxes, Amount	67	22		133	35
Effective Income Tax Rate Reconciliation, Deduction, Other, Amount	60	160		130	372
Effective Income Tax Rate Reconciliation, Nondeductible Expense, Depreciation and Amortization, Amount	21	1,058		41	1,090
Effective Income Tax Rate Reconciliation, Tax Contingency, Foreign, Amount	(39)	45		(54)	(94)
Effective Income Tax Rate Reconciliation, Other Adjustments, Amount	$ 64	$ (17)		$ 111	$ (70)

Income Taxes (Details)

Income Taxes (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2018	Jun. 30, 2017	Jun. 30, 2018	Jun. 30, 2017	Dec. 31, 2017
Income Tax Disclosure [Abstract]
Effective Income Tax Rate Reconciliation, Change in Enacted Tax Rate, Percent			21.00%
Net deferred income tax liabilities	$ 28,796		$ 28,796		$ 28,745
Deferred Tax Assets, Operating Loss Carryforwards, Subject to Expiration	8,000		8,000		8,000
Deferred Tax Liabilities, Other					20,800
Deferred Tax Liabilities, Goodwill and Intangible Assets	20,900		20,900
Unrecognized Tax Benefits	1,400		1,400		1,400
Income Tax Examination, Penalties and Interest Expense	100	$ 200	100	$ 400
Income Tax Examination, Penalties and Interest Accrued	$ 1,000		$ 1,000		$ 900

Loss from Continuing Operatio77

Loss from Continuing Operations per Share Net Loss Per Share (Tables) (Details) - USD ($) $ / shares in Units, shares in Thousands, $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2018	Jun. 30, 2017	Jun. 30, 2018	Jun. 30, 2017
Earnings Per Share, Basic, by Common Class, Including Two Class Method [Line Items]
Loss from continuing operations	$ (2,706)	$ (8,089)	$ (5,141)	$ (9,696)
Less: net income attributable to noncontrolling interests in consolidated subsidiaries	108	100	243	205
Less: dividends on preferred stock, net of tax	(130)	(154)	(259)	(328)
Loss from continuing operations attributable to common shareholders	$ (2,944)	$ (8,343)	$ (5,643)	$ (10,229)
Weighted average common shares outstanding	21,708	21,458	21,708	21,458
Diluted:	21,708	21,458	21,708	21,458
Basic:	$ (0.14)	$ (0.39)	$ (0.26)	$ (0.48)
Diluted:	$ (0.14)	$ (0.39)	$ (0.26)	$ (0.48)

Stock-Based Compensation (Detai

Stock-Based Compensation (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2018	Jun. 30, 2017	Jun. 30, 2018	Jun. 30, 2017
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Stock-based compensation expense, net of forfeitures	$ (300)	$ (300)	$ (588)	$ (588)
Restricted Stock [Member]
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Deferred Compensation Equity	4,600		4,600
Stock Compensation Plan [Member]
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Deferred Compensation Equity	$ 2,200		$ 2,200

Stock-Based Compensation Stock

Stock-Based Compensation Stock Option Activity (Table) (Details)	3 Months Ended	6 Months Ended
	Mar. 31, 2018$ / sharesshares	Jun. 30, 2018USD ($)$ / sharesshares	Dec. 31, 2017USD ($)$ / sharesshares
Class of Stock [Line Items]
Share-based Compensation, Shares Authorized under Stock Option Plans, Exercise Price Range, Number of Outstanding Options | shares		651,875	651,875
Share-based Compensation, Shares Authorized under Stock Option Plans, Exercise Price Range, Outstanding Options, Weighted Average Exercise Price | $ / shares		$ 4.51	$ 4.51
Remaining Contractual Life (Years)		0
Share-based Compensation Arrangement by Share-based Payment Award, Options, Vested and Expected to Vest, Outstanding, Aggregate Intrinsic Value | $		$ 0
Share-based Compensation Arrangement by Share-based Payment Award, Options, Grants in Period, Gross | shares	0
Share-based Compensation Arrangements by Share-based Payment Award, Options, Grants in Period, Weighted Average Exercise Price | $ / shares	$ 0	$ 0
Share-based Compensation Arrangement by Share-based Payment Award, Options, Expirations in Period | shares	0
Share-based Compensation Arrangement by Share-based Payment Award, Options, Outstanding, Weighted Average Exercise Price | $ / shares			$ 4.51
Share-based Compensation Arrangement by Share-based Payment Award, Options, Outstanding, Number | shares		651,875
Options Expired [Member]
Class of Stock [Line Items]
Share-based Compensation Arrangements by Share-based Payment Award, Options, Expirations in Period, Weighted Average Exercise Price | $ / shares	$ 0
Options Outstanding [Member]
Class of Stock [Line Items]
Remaining Contractual Life (Years)			0
Share-based Compensation Arrangement by Share-based Payment Award, Options, Vested and Expected to Vest, Outstanding, Aggregate Intrinsic Value | $			$ 352

Stock-Based Compensation Restri

Stock-Based Compensation Restricted Stock Awards (Tables) (Details) - $ / shares	6 Months Ended
	Jun. 30, 2018	Dec. 31, 2017
Share-based Compensation, Shares Authorized under Stock Option Plans, Exercise Price Range [Line Items]
Share-based Compensation Arrangement by Share-based Payment Award, Equity Instruments Other than Options, Nonvested, Number	500,000	500,000
Share-based Compensation, Shares Authorized under Stock Option Plans, Exercise Price Range, Exercisable Options, Weighted Average Exercise Price		$ 5.73
Share-based Compensation Arrangement by Share-based Payment Award, Equity Instruments Other than Options, Nonvested, Weighted Average Grant Date Fair Value	$ 5.73
Restricted Stock [Member]
Share-based Compensation, Shares Authorized under Stock Option Plans, Exercise Price Range [Line Items]
Share-based Compensation Arrangement by Share-based Payment Award, Equity Instruments Other than Options, Nonvested, Number	1,952,665	1,952,665
Share-based Compensation, Shares Authorized under Stock Option Plans, Exercise Price Range, Exercisable Options, Weighted Average Exercise Price		$ 4.14
Stock Issued During Period, Shares, Restricted Stock Award, Forfeited	0
Share-based Compensation Arrangement by Share-based Payment Award, Equity Instruments Other than Options, Nonvested, Weighted Average Grant Date Fair Value	$ 4.14
Share-based Compensation Arrangement by Share-based Payment Award, Options, Nonvested Options Forfeited, Weighted Average Grant Date Fair Value	$ 0

Stock-Based Compensation Rest81

Stock-Based Compensation Restricted Stock Units (Details) - USD ($) $ / shares in Units, $ in Thousands	3 Months Ended			6 Months Ended
	Jun. 30, 2018	Mar. 31, 2018	Jun. 30, 2017	Jun. 30, 2018	Jun. 30, 2017	Dec. 31, 2017
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share-based Compensation	$ 300		$ 300	$ 588	$ 588
Share-based Compensation Arrangement by Share-based Payment Award, Equity Instruments Other than Options, Nonvested, Number	500,000			500,000		500,000
Share-based Compensation, Shares Authorized under Stock Option Plans, Exercise Price Range, Exercisable Options, Weighted Average Exercise Price						$ 5.73
Share-based Compensation Arrangement by Share-based Payment Award, Equity Instruments Other than Options, Grants in Period				0
Share-based Compensation Arrangements by Share-based Payment Award, Options, Grants in Period, Weighted Average Exercise Price		$ 0		$ 0
Share-based Compensation Arrangement by Share-based Payment Award, Equity Instruments Other than Options, Nonvested, Weighted Average Grant Date Fair Value	$ 5.73			$ 5.73
Stock Compensation Plan [Member]
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Deferred Compensation Equity	$ 2,200			$ 2,200

Accumulated Other Comprehensi82

Accumulated Other Comprehensive Income AOCI (Table) (Details) - USD ($) $ in Thousands	3 Months Ended			6 Months Ended		12 Months Ended
	Jun. 30, 2018	Dec. 31, 2017	Jun. 30, 2017	Jun. 30, 2018	Jun. 30, 2017	Dec. 31, 2017	Mar. 31, 2018	Mar. 31, 2017	Dec. 31, 2016
Accumulated Other Comprehensive Income (Loss) [Line Items]
Accumulated Other Comprehensive Income (Loss), Net of Tax	$ 36,322	$ (3,852)		$ 36,322		$ (3,852)
Equity in other comprehensive loss of limited liability investment	(224)		$ 0	(224)	$ 0
Other Comprehensive Income (Loss), Net of Tax	478		(586)	(328)	(1,256)
Change in fair value of debt attributable to instrument-specific credit risk	778		0	344	0
Accumulated Net Investment Gain (Loss) Including Portion Attributable to Noncontrolling Interest [Member]
Accumulated Other Comprehensive Income (Loss) [Line Items]
Accumulated Other Comprehensive Income (Loss), Net of Tax	(967)	(566)	2,313	(967)	2,313	(566)	$ (891)	$ 2,901	$ 3,572
Prior Period Reclassification Adjustment		40
New Accounting Pronouncement or Change in Accounting Principle, Cumulative Effect of Change on Equity or Net Assets		(526)				(526)
Other Comprehensive Income (Loss), before Reclassifications, Net of Tax	(72)		(1,066)	(430)	(1,230)
Reclassification from Accumulated Other Comprehensive Income, Current Period, Net of Tax	4		478	11	(29)
Other Comprehensive Income (Loss), Reclassification Adjustment from AOCI for Sale of Securities, before Tax	(76)		(588)	(441)	(1,259)
Accumulated Foreign Currency Adjustment Including Portion Attributable to Noncontrolling Interest [Member]
Accumulated Other Comprehensive Income (Loss) [Line Items]
Accumulated Other Comprehensive Income (Loss), Net of Tax	(3,286)	(3,286)	(3,780)	(3,286)	(3,780)	(3,286)	(3,286)	(3,780)	(3,780)
Prior Period Reclassification Adjustment						0
New Accounting Pronouncement or Change in Accounting Principle, Cumulative Effect of Change on Equity or Net Assets		(3,286)				(3,286)
Other Comprehensive Income (Loss), before Reclassifications, Net of Tax	0		0	0	0
Reclassification from Accumulated Other Comprehensive Income, Current Period, Net of Tax	0		0	0	0
Other Comprehensive Income (Loss), Net of Tax	0		0	0	0
Accumulated Gain (Loss), Financial Liability, Fair Value Option, Including Portion Attributable to Noncontrolling Interest [Member]
Accumulated Other Comprehensive Income (Loss) [Line Items]
Accumulated Other Comprehensive Income (Loss), Net of Tax	40,799	0		40,799		0	40,021
Prior Period Reclassification Adjustment						40,455
New Accounting Pronouncement or Change in Accounting Principle, Cumulative Effect of Change on Equity or Net Assets		40,455				40,455
Other Comprehensive Income (Loss), Net of Tax	778			344
Change in fair value of debt attributable to instrument-specific credit risk				354
Comprehensive Income [Member]
Accumulated Other Comprehensive Income (Loss) [Line Items]
Accumulated Other Comprehensive Income (Loss), Net of Tax	36,322	(3,852)	(1,467)	36,322	(1,467)	(3,852)	35,844	$ (879)	$ (208)
Prior Period Reclassification Adjustment		40,495
New Accounting Pronouncement or Change in Accounting Principle, Cumulative Effect of Change on Equity or Net Assets		36,643				36,643
Other Comprehensive Income (Loss), before Reclassifications, Net of Tax	482		(1,066)	(310)	(1,230)
Reclassification from Accumulated Other Comprehensive Income, Current Period, Net of Tax	4		478	11	(29)
Other Comprehensive Income (Loss), Net of Tax	478		$ (588)	(321)	$ (1,259)
Other Comprehensive Income (Loss) [Member]
Accumulated Other Comprehensive Income (Loss) [Line Items]
Accumulated Other Comprehensive Income (Loss), Net of Tax	$ (224)	0		(224)		0	$ 0
Prior Period Reclassification Adjustment		0
New Accounting Pronouncement or Change in Accounting Principle, Cumulative Effect of Change on Equity or Net Assets		$ 0				$ 0
Equity in other comprehensive loss of limited liability investment				$ (224)

Accumulated Other Comprehensi83

Accumulated Other Comprehensive Income Reclassification of AOCI (table) (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2018	Jun. 30, 2017	Jun. 30, 2018	Jun. 30, 2017
Reclassification Adjustment out of Accumulated Other Comprehensive Income [Line Items]
Other comprehensive income (loss)	$ 478	$ (586)	$ (328)	$ (1,256)
Net loss	(7,928)	(8,228)	(10,762)	(10,382)
Reclassification out of Accumulated Other Comprehensive Income [Member]
Reclassification Adjustment out of Accumulated Other Comprehensive Income [Line Items]
Net realized gains	(5)	(2)	(8)	(2)
Other-than-temporary impairment loss	0	0		0
Loss from continuing operations before income tax expense	(5)	(2)	(8)	2
Income tax expense	0	0	0	0
Loss from continuing operations	(5)	(2)	(8)	(2)
Net loss	4	(478)	11	29
Comprehensive Income [Member]
Reclassification Adjustment out of Accumulated Other Comprehensive Income [Line Items]
Other comprehensive income (loss)	478	(588)	(321)	(1,259)
Other-than-temporary impairment loss			0
Loss from continuing operations	(4)	(478)	(11)	29
Discontinued Operations [Member] | Reclassification out of Accumulated Other Comprehensive Income [Member]
Reclassification Adjustment out of Accumulated Other Comprehensive Income [Line Items]
Other comprehensive income (loss)	$ 1	$ (480)	$ (3)	$ 27

Segmented Information (Details)

Segmented Information (Details) number in Thousands, a in Thousands	Jun. 30, 2018	Jul. 14, 2016a
Segment Reporting Information [Line Items]
Land Subject to Ground Leases		0
Reportable Subsegments [Member]
Segment Reporting Information [Line Items]
Number of States in which Entity Operates	0

Segmented Information Revenues

Segmented Information Revenues (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2018	Jun. 30, 2017	Jun. 30, 2018	Jun. 30, 2017
Segment Reporting Information [Line Items]
Service fee and commission income	$ 9,479	$ 6,584	$ 19,670	$ 12,946
Other income	1,081	242	1,308	569
Rental income	3,341	3,341	6,682	6,682
Total segment revenues	13,670	8,819	27,670	19,033
Net investment income (loss)	18	(1,347)	(613)	(1,163)
Net realized (losses) gains	(1)	(1)	9	(1)
(Loss) gain on change in fair value of equity investments	(248)	0	614	0
Other income not allocated to segments	973	31	987	61
Loss from continuing operations before income tax expense	(2,519)	(6,838)	(4,703)	(8,180)
Reportable Subsegments [Member]
Segment Reporting Information [Line Items]
Service fee and commission income	9,479	6,584	19,670	12,946
Other income	36	51	102	136
Total segment revenues	9,515	6,635	19,772	13,082
Reportable Legal Entities [Member]
Segment Reporting Information [Line Items]
Other income	72	160	219	372
Rental income	3,341	3,341	6,682	6,682
Total segment revenues	3,413	3,501	6,901	7,054
Operating Segments [Member]
Segment Reporting Information [Line Items]
Total segment revenues	$ 12,928	$ 10,136	$ 26,673	$ 20,136

Segmented Information Segment (

Segmented Information Segment (loss) income (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2018	Jun. 30, 2017	Jun. 30, 2018	Jun. 30, 2017
Segment Reporting Information [Line Items]
Total segment operating income	$ 2,277	$ 1,557	$ 4,722	$ 3,061
Net investment income (loss)	18	(1,347)	(613)	(1,163)
Net realized (losses) gains	(1)	(1)	9	(1)
(Loss) gain on change in fair value of equity investments	(248)	0	614	0
Interest expense not allocated to segments	1,519	1,216	2,905	2,375
Other income and expenses not allocated to segments, net	(2,248)	(2,907)	(4,642)	(4,983)
Amortization of intangible assets	271	289	543	580
Contingent consideration benefit	0	212	0	212
Loss on change in fair value of debt	(142)	(2,702)	(1,061)	(4,591)
Equity in net (loss) income of investee	(385)	(145)	(284)	2,240
Loss from continuing operations before income tax expense	(2,519)	(6,838)	(4,703)	(8,180)
Income tax expense	187	1,251	438	1,516
Loss from continuing operations	(2,706)	(8,089)	(5,141)	(9,696)
Reportable Subsegments [Member]
Segment Reporting Information [Line Items]
Total segment operating income	1,659	685	3,230	1,271
Reportable Legal Entities [Member]
Segment Reporting Information [Line Items]
Total segment operating income	$ 618	$ 872	$ 1,492	$ 1,790

Fair Value of Financial Instr87

Fair Value of Financial Instruments Fair Value Inputs (Table) (Details) - USD ($) $ in Thousands	Jun. 30, 2018	Dec. 31, 2017
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	$ 11,361	$ 14,541
Marketable Securities, Equity Securities	2,189	4,476
Total equity investments	2,189	4,476
Limited liability investment, at fair value	4,869	5,771
Other investments, at cost which approximates fair value	1,916	2,321
Short-term investments, at cost which approximates fair value	151	151
Total assets	25,703	32,182
Subordinated debt, at fair value	52,822	52,105
Total liabilities	220,044	225,446
Fair Value, Inputs, Level 1 [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	0	0
Warrants	54	58
Total equity investments	1,318	3,628
Other investments, at cost which approximates fair value	0	0
Short-term investments, at cost which approximates fair value		0
Total assets	1,318	3,628
Subordinated debt, at fair value	0	0
Total liabilities	0	0
Fair Value, Inputs, Level 3 [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	0	0
Other investments, at cost which approximates fair value	0	0
Short-term investments, at cost which approximates fair value		0
Total assets	0	0
Subordinated debt, at fair value		0
Total liabilities	0	0
Fair Value, Inputs, Level 2 [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	11,361	14,541
Warrants	871	848
Total equity investments	871	848
Total assets	19,168	23,632
Total liabilities	52,822	52,105
US States and Political Subdivisions Debt Securities [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	605	626
US States and Political Subdivisions Debt Securities [Member] | Fair Value, Inputs, Level 1 [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	0	0
US States and Political Subdivisions Debt Securities [Member] | Fair Value, Inputs, Level 3 [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	0	0
US States and Political Subdivisions Debt Securities [Member] | Fair Value, Inputs, Level 2 [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	605	626
US Government Agencies Debt Securities [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	5,427	5,612
US Government Agencies Debt Securities [Member] | Fair Value, Inputs, Level 2 [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	5,427	5,612
Mortgage-backed Securities, Issued by US Government Sponsored Enterprises [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	2,811	2,876
Mortgage-backed Securities, Issued by US Government Sponsored Enterprises [Member] | Fair Value, Inputs, Level 1 [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	0	0
Mortgage-backed Securities, Issued by US Government Sponsored Enterprises [Member] | Fair Value, Inputs, Level 3 [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	0	0
Mortgage-backed Securities, Issued by US Government Sponsored Enterprises [Member] | Fair Value, Inputs, Level 2 [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	2,811	2,876
Corporate Debt Securities [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	2,518	5,427
Corporate Debt Securities [Member] | Fair Value, Inputs, Level 1 [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	0	0
Corporate Debt Securities [Member] | Fair Value, Inputs, Level 3 [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	0	0
Corporate Debt Securities [Member] | Fair Value, Inputs, Level 2 [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total fixed maturities	2,518	5,427
Equity Securities [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total equity investments		4,476
Equity Securities [Member] | Fair Value, Inputs, Level 1 [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Marketable Securities, Equity Securities	1,264	3,570
Long-term Debt [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total liabilities	52,822	52,105
Common Stock [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Marketable Securities, Equity Securities		3,570
Equity Securities [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Marketable Securities, Equity Securities	1,264
Warrants	925	906
Other Security Investments [Member]
Fair Value Inputs, Assets, Quantitative Information [Line Items]
Total assets	$ 20,486	$ 27,260

Related Party Transactions (Det

Related Party Transactions (Details) - USD ($) $ / shares in Units, $ in Thousands	3 Months Ended		6 Months Ended		12 Months Ended
	Jun. 30, 2018	Dec. 31, 2017	Jun. 30, 2018	Jun. 30, 2017	Dec. 31, 2017
Related Party Transaction [Line Items]
Proceeds from sales of equity investments			$ 3,704	$ 0
Management [Member]
Related Party Transaction [Line Items]
Proceeds from sales of equity investments	$ 3,400
Sale of Stock, Number of Shares Issued in Transaction		900,000			475,428
Proceeds from Sale of Treasury Stock					$ 3,700
Share Price		$ 7.85			$ 7.85
Effect on Future Cash Flows, Amount	$ 1,000
Related Party Transaction, Rate			5.00%
Common Stock [Member] | Management [Member]
Related Party Transaction [Line Items]
Stockholders' Equity, Other Shares		425,000
Effect on Future Cash Flows, Amount					$ 7,100
Corporate Segment [Member]
Related Party Transaction [Line Items]
Effect on Future Cash Flows, Amount			$ 1,300
Investment Owned, Balance, Shares	1,814,000		1,814,000
Sale of Stock, Price Per Share	$ 0.72		$ 0.72
Common Stock [Member] | Management [Member]
Related Party Transaction [Line Items]
Effect on Future Cash Flows, Amount	$ 500
Investment Owned, Balance, Shares	75,000		75,000
Sale of Stock, Price Per Share	$ 7.13		$ 7.13

Commitment and Contingencies (D

Commitment and Contingencies (Details) $ in Millions	6 Months Ended
	Jun. 30, 2018USD ($)
Commitments and Contingencies [Abstract]
Long-term Purchase Commitment, Amount	$ 2.7
Fair Value, Investments, Entities that Calculate Net Asset Value Per Share, Unfunded Commitments	$ 1

Uncategorized Items - kfs-20180

Label	Element	Value
Cash, Cash Equivalents, Restricted Cash and Restricted Cash Equivalents, Including Disposal Group and Discontinued Operations	us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsIncludingDisposalGroupAndDiscontinuedOperations	$ 36,475,000
Cash, Cash Equivalents, Restricted Cash and Restricted Cash Equivalents, Including Disposal Group and Discontinued Operations	us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsIncludingDisposalGroupAndDiscontinuedOperations	$ 44,286,000