Conifer (CNFR) 10-K 1 Apr 24 2023 FY Annual report Financial data

Document and Entity Information

Document and Entity Information - USD ($) $ in Millions	12 Months Ended
	Dec. 31, 2023	Mar. 28, 2024	Jun. 30, 2023
Document Information [Line Items]
Document Type	10-K
Amendment Flag	false
Document Period End Date	Dec. 31, 2023
Document Fiscal Year Focus	2023
Document Fiscal Period Focus	FY
Entity Registrant Name	Conifer Holdings, Inc.
Entity Central Index Key	0001502292
Entity Current Reporting Status	Yes
Entity Voluntary Filers	No
Entity Interactive Data Current	Yes
Current Fiscal Year End Date	--12-31
Entity Filer Category	Non-accelerated Filer
Entity Well-known Seasoned Issuer	No
Entity Public Float			$ 5.4
Entity Common Stock, Shares Outstanding		12,222,881
Entity Shell Company	false
Entity Small Business	true
Entity Emerging Growth Company	false
Document Financial Statement Error Correction [Flag]	false
Entity File Number	001-37536
Entity Incorporation, State or Country Code	MI
Entity Tax Identification Number	27-1298795
Entity Address, Address Line One	3001 West Big Beaver Road
Entity Address, Address Line Two	Suite 200
Entity Address, City or Town	Troy
Entity Address, State or Province	MI
Entity Address, Postal Zip Code	48084
City Area Code	248
Local Phone Number	559-0840
Document Annual Report	true
Document Transition Report	false
Auditor Firm ID	166
Auditor Name	Plante & Moran, PLLC
Auditor Location	East Lansing, Michigan
ICFR Auditor Attestation Flag	false
Documents Incorporated by Reference	Documents Incorporated by Reference Portions of the registrant’s Definitive Proxy Statement to be filed with the Securities and Exchange Commission pursuant to Regulation 14A in connection with the registrant’s 2024 Annual Meeting of Stockholders, to be filed subsequent to the date hereof, are incorporated by reference into Part III of this report. Such Definitive Proxy Statement will be filed with the Securities and Exchange Commission not later than 120 days after the conclusion of the registrant’s fiscal year ended December 31, 2023.
Common stocks
Document Information [Line Items]
Title of 12(b) Security	Common Stock, no par value
Trading Symbol	CNFR
Security Exchange Name	NASDAQ
9.75% Senior Notes due 2028
Document Information [Line Items]
Title of 12(b) Security	9.75% Senior Notes due 2028
Trading Symbol	CNFRZ
Security Exchange Name	NASDAQ

Consolidated Balance Sheets

Consolidated Balance Sheets - USD ($) $ in Thousands	Dec. 31, 2023	Dec. 31, 2022
Investment securities:
Debt securities, at fair value (amortized cost of $135,370 and $127,119, respectively)	$ 122,113	$ 110,201
Equity securities, at fair value (cost of $2,385 and $1,905, respectively)	2,354	1,267
Short-term investments, at fair value	20,838	25,929
Total investments	145,305	137,397
Cash and cash equivalents	11,125	28,035
Premiums and agents' balances receivable, net	29,369	21,802
Reinsurance recoverables on unpaid losses	70,807	82,651
Reinsurance recoverables on paid losses	12,619	6,653
Prepaid reinsurance premiums	28,908	16,399
Deferred policy acquisition costs	6,285	10,290
Other assets	6,339	7,862
Total assets	311,804	312,350
Liabilities:
Unpaid losses and loss adjustment expenses	174,612	165,539
Unearned premiums	65,150	67,887
Reinsurance premium payable	246	6,144
Debt	25,061	33,876
Funds held under reinsurance agreements	24,550	11,084
Premiums payable to other insureds	13,986
Accounts payable and accrued expenses	5,310	8,870
Total liabilities	308,915	293,400
Commitments and contingencies	0	0
Shareholders' equity:
Preferred stock, no par value (10,000,000 shares authorized; 1,000 and 0 issued and outstanding, respectively)	6,000	0
Common stock, no par value (100,000,000 shares authorized; 12,222,881 and 12,215,849 issued and outstanding, respectively)	98,100	97,913
Accumulated deficit	(86,683)	(60,760)
Accumulated other comprehensive income (loss)	(14,528)	(18,203)
Total shareholders' equity	2,889	18,950
Total liabilities and shareholders' equity	311,804	312,350
Affiliated Entity
Investment securities:
Receivable from Affiliate	$ 1,047	$ 1,261

Consolidated Balance Sheets (Pa

Consolidated Balance Sheets (Parenthetical) - USD ($) $ in Thousands	Dec. 31, 2023	Dec. 31, 2022
Statement of Financial Position [Abstract]
Debt securities, amortized cost	$ 135,370	$ 127,119
Equity securities, amortized cost	$ 2,385	$ 1,905
Preferred stock, par value (in dollars per share)	$ 0	$ 0
Preferred stock, shares authorized (in shares)	10,000,000	10,000,000
Preferred stock, shares issued (in shares)	1,000	0
Preferred stock, shares outstanding (in shares)	1,000	0
Common stock, par value (in dollars per share)	$ 0	$ 0
Common stock, shares authorized (in shares)	100,000,000	100,000,000
Common stock, shares issued (in shares)	12,222,881	12,215,849
Common stock, shares outstanding (in shares)	12,222,881	12,215,849

Consolidated Statements of Oper

Consolidated Statements of Operations - USD ($) $ in Thousands		12 Months Ended
		Dec. 31, 2023	Dec. 31, 2022
Revenue and Other Income
Gross earned premiums		$ 146,572	$ 135,401
Ceded earned premiums		(62,637)	(38,690)
Net earned premiums		83,935	96,711
Net investment income		5,526	3,043
Net realized investment gains (losses)		(20)	(1,505)
Change in fair value of equity securities		608	403
Gain from VSRM Transaction		0	8,810
Loss portfolio transfer risk fee		0	(5,400)
Gain from sale of renewal rights		2,335	0
Other gains (losses)		0	59
Agency commission income		5,680	1,414
Other income		694	1,354
Total revenue and other income		98,758	104,889
Expenses
Losses and loss adjustment expenses, net		82,413	81,440
Policy acquisition costs		20,892	22,179
Operating expenses		17,891	18,789
Interest expense		3,206	2,971
Total expenses		124,402	125,379
Income (loss) before income taxes		(25,644)	(20,490)
Equity earnings (losses) in Affiliate, net of tax		(251)	368
Income tax expense (benefit)		9	(9,441)
Net income (loss)		(25,904)	(10,681)
Preferred stock dividends		19
Net income (loss) allocable to common shareholders		$ (25,885)	$ (10,681)
Earnings (loss) per common share, basic		$ (2.12)	$ (1)
Earnings (loss) per common share, diluted		$ (2.12)	$ (1)
Weighted average common shares outstanding, basic	[1]	12,220,511	10,692,090
Weighted average common shares outstanding, diluted	[1]	12,220,511	10,692,090
[1] The preferred shares that may be convertible into a total of 4,000,000 common shares were anti-dilutive and thus did not impact the diluted earnings per share calculation. There were no unvested restricted stock units as of December 31, 2023. The non-vested shares of the restricted stock units and stock options were anti-dilutive as of December 31, 2022. Therefore, the non-vested shares are excluded from earnings (loss) per share for the years ended December 31, 2022 .

Consolidated Statements of Comp

Consolidated Statements of Comprehensive Income (Loss) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2023	Dec. 31, 2022
Statement of Comprehensive Income [Abstract]
Net income (loss)	$ (25,904)	$ (10,681)
Unrealized investment gains (losses):
Unrealized investment gains (losses) during the period	3,624	(16,024)
Income tax expense (benefit)	0	0
Unrealized investment gains (losses), net of tax	3,624	(16,024)
Less: reclassification adjustments to:
Net realized investment gains (losses) included in net income (loss)	(51)	69
Income tax expense (benefit)	0	0
Total reclassifications included in net income (loss), net of tax	(51)	69
Other comprehensive income (loss)	3,675	(16,093)
Total comprehensive income (loss)	$ (22,229)	$ (26,774)

Consolidated Statement of Chang

Consolidated Statement of Changes in Shareholders' Equity - USD ($) $ in Thousands	Total	No Par, Preferred Stock	No Par, Common Stock	Retained Earnings (Accumulated deficit)	Accumulated Other Comprehensive Income (Loss)
Balance at beginning of period at Dec. 31, 2021	$ 40,503		$ 92,692	$ (50,079)	$ (2,110)
Balance at beginning of period (in shares) at Dec. 31, 2021			9,707,817
Net income (loss)	(10,681)			(10,681)
Repurchase of common stock	10		$ 10
Repurchase of common stock (in shares)			(1,968)
Issuance of shares	5,000		$ 5,000
Issuance of shares (in shares)			2,500,000
Stock-based compensation expense	211		$ 211
Stock-based compensation expense, Shares			10,000
Other comprehensive income (loss)	(16,093)				(16,093)
Balance at end of period at Dec. 31, 2022	18,950		$ 97,913	(60,760)	(18,203)
Balance at end of period (in shares) at Dec. 31, 2022			12,215,849
Net income (loss)	(25,904)			(25,904)
Repurchase of common stock	(3)		$ (3)
Repurchase of common stock (in shares)			(1,968)
Issuance of shares	6,000	$ 6,000
Issuance of shares (in shares)		1,000
Cash dividends paid on preferred stock	(19)			(19)
Stock-based compensation expense	190		$ 190
Stock-based compensation expense, Shares			9,000
Other comprehensive income (loss)	3,675				3,675
Balance at end of period at Dec. 31, 2023	$ 2,889	$ 6,000	$ 98,100	$ (86,683)	$ (14,528)
Balance at end of period (in shares) at Dec. 31, 2023		1,000	12,222,881

Consolidated Statements of Cash

Consolidated Statements of Cash Flows - USD ($)		12 Months Ended
		Dec. 31, 2023	Dec. 31, 2022
Cash Flows from Operating Activities
Net income (loss)		$ (25,904,000)	$ (10,681,000)
Adjustments to reconcile net income (loss) to net cash provided by (used in) operating activities:
Gain from sale of renewal rights		(2,335,000)	0
Gain upon consolidation of VSRM and sale of agency business	[1]		(10,052,000)
Depreciation and amortization		545,000	417,000
Amortization of bond premium and discount, net		(871,000)	320,000
Net realized investment (gains) losses		20,000	1,505,000
Change in fair value of equity securities		(608,000)	(403,000)
Loss on sale of fixed assets			33,000
Deferred income tax expense		(17,000)	(9,396,000)
Stock-based compensation expenses		190,000	211,000
Equity (earnings) loss in Affiliate, net of tax		251,000	(368,000)
Other			60,000
(Increase) decrease in:
Premiums, agents' balances and other receivables		(7,549,000)	(594,000)
Reinsurance recoverables		5,878,000	(47,613,000)
Prepaid reinsurance premiums		(12,509,000)	(8,098,000)
Deferred policy acquisition costs		4,005,000	1,977,000
Other assets		250,000	(138,000)
Increase (decrease) in:
Unpaid losses and loss adjustment expenses		9,073,000	26,454,000
Unearned premiums		(2,737,000)	2,618,000
Funds held under reinsurance agreements		13,450,000	11,100,000
Reinsurance premiums payable		(5,898,000)	826,000
Premiums payable to other insureds		13,986,000
Accounts payable and other liabilities		(2,612,000)	1,348,000
Net cash provided by operating activities		(13,392,000)	(40,474,000)
Cash Flows From Investing Activities
Purchases of investments		(234,869,000)	(318,227,000)
Proceeds from maturities and redemptions of investments		10,424,000	20,324,000
Proceeds from sales of investments		222,772,000	324,091,000
Proceeds from sale of renewal rights/agency business		2,335,000	32,759,000	[1]
Purchase of VSRM, net of $3,920 cash acquired	[1]		(1,947,000)
Deconsolidation of SSU	[1]		(497,000)
Contribution to SSU	[1]	(934,000)
Net cash provided by (used in) investing activities		(272,000)	56,503,000
Cash Flows From Financing Activities
Proceeds received from issuance of shares of preferred stock		6,000,000
Proceeds received from issuance of shares of common stock			5,000,000
Proceeds from issuance of long-term debt		6,727,000
Repurchase of common stock		(3,000)	10,000
Borrowings under lines of credit			19,500,000
Repayment of lines of credit			(19,500,000)
Repayment /paydown of long-term debt		(13,971,000)	(2,917,000)
Debt issuance costs		(1,999,000)
Net cash provided by (used in) financing activities		(3,246,000)	2,093,000
Net increase (decrease) in cash		(16,910,000)	18,122,000
Cash at beginning of period		28,035,000	9,913,000
Cash at end of period		11,125,000	28,035,000
Supplemental Disclosure of Cash Flow Information:
Interest paid		3,077,000	2,979,000
Income taxes paid (refunded), net		1,000	$ (11,000)
Exchanging of public senior unsecured notes		11,160,000
Preferred stock dividends declared but not paid at end of period		$ 19,000
[1] See Note 3 ~ VSRM Transaction

Consolidated Statements of Ca_2

Consolidated Statements of Cash Flows (Parenthetical) $ in Thousands	12 Months Ended
	Dec. 31, 2023 USD ($)
Statement of Cash Flows [Abstract]
Cash used	$ 271
Cash acquired	$ 3,920

Pay vs Performance Disclosure

Pay vs Performance Disclosure - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2023	Dec. 31, 2022
Pay vs Performance Disclosure
Net Income (Loss)	$ (25,923)	$ (10,681)

Insider Trading Arrangements

Insider Trading Arrangements	3 Months Ended
	Dec. 31, 2023
Trading Arrangements, by Individual
Rule 10b5-1 Arrangement Adopted	false
Non-Rule 10b5-1 Arrangement Adopted	false
Rule 10b5-1 Arrangement Terminated	false
Non-Rule 10b5-1 Arrangement Terminated	false

Summary of Significant Accounti

Summary of Significant Accounting Policies	12 Months Ended
	Dec. 31, 2023
Accounting Policies [Abstract]
Summary of Significant Accounting Policies	1. Summary of Significant Accounting Policies Basis of Presentation and Management Representation The consolidated financial statements include accounts, after elimination of intercompany accounts and transactions, of Conifer Holdings, Inc. (the “Company” or “Conifer”), its wholly owned subsidiaries Conifer Insurance Company ("CIC"), Red Cedar Insurance Company ("RCIC"), White Pine Insurance Company ("WPIC"), Conifer Insurance Services ("CIS") formerly known as Sycamore Insurance Agency, Inc. ("Sycamore"), and VSRM, Inc. ("VSRM"). VSRM has substantially no operations following the contribution to SSU as described in Note 3 ~ VSRM Transaction . CIC, WPIC, and RCIC are collectively referred to as the "Insurance Company Subsidiaries." On a stand-alone basis Conifer Holdings, Inc. is referred to as the "Parent Company." VSRM owns a 50 % non-controlling interest in Sycamore Specialty Underwriters, LLC ("SSU" or "Affiliate"). The accompanying consolidated financial statements have been prepared in conformity with accounting principles generally accepted in the United States of America (“GAAP”), which differ from statutory accounting practices prescribed or permitted for insurance companies by regulatory authorities. Business The Company is engaged in the sale of property and casualty insurance products and has organized its principal operations into three types of insurance businesses: commercial lines, personal lines, and agency business. The Company underwrites a variety of specialty insurance products, including property, general liability, liquor liability, automobile, and homeowners and dwelling policies. The Company markets and sells its insurance products through a network of independent agents, including managing general agents, whereby policies are written in all 50 states in the United States (“U.S.”). The Company’s corporate headquarters are located in Troy, Michigan with additional office facilities in Florida and Michigan. Summary of Significant Accounting Policies Use of Estimates The preparation of financial statements in conformity with GAAP requires management to make estimates and assumptions that affect the reported amounts of assets and liabilities and disclosure of contingent assets and liabilities at the date of the financial statements and the reported amounts of revenues and expenses during the reporting period. In applying these estimates, management makes subjective and complex judgments that frequently require assumptions about matters that are inherently uncertain, including uncertainties associated with the Pandemic. While management believes the amounts included in the consolidated financial statements reflect management's best estimates and assumptions, actual results may differ from these estimates. Cash, Cash Equivalents, and Short-term Investments Cash consists of cash deposits in banks, generally in operating accounts. Cash equivalents consist of money-market funds that are specifically used as overnight investments tied to cash deposit accounts. Short-term investments, consisting of money-market funds, are classified as short-term investments in the consolidated balance sheets as they relate to the Company’s investment activities. Lease Accounting The Company accounts for leases under FASB Accounting Standards Update ("ASU") No. 2016-02, Leases (Topic 842), which required the recognition of a right-of-use asset and a corresponding lease liability, discounted to the present value upon initial recognition, for all leases that extend beyond 12 months. For operating leases, the asset and liability are amortized over the lease term with expense recognized on a straight-line basis and all cash flows included in the operating section of the consolidated statement of cash flows. We do not have any financing leases. Our operating leases consist primarily of real estate utilized in the operation of our businesses with lease terms ranging from 5 to 10 years . Management has determined the appropriate discount rate to use in calculating the right-to-use asset and lease liability is 9.5 %. The Company records a right-of-use asset and lease liabilities included in Other Assets and Other Liabilities in the Consolidated Balance Sheets. As of December 31, 2023 , the Company had a right-of-use asset of $ 960,000 , and lease liabilities of $ 1.0 million. As of December 31, 2022 , the Company had a right-of-use asset of $ 1.3 million, and lease liabilities of $ 1.3 million. Investment Securities Debt securities are classified as available-for-sale and reported at fair value. The Company determines the fair value using the market approach, which uses quoted prices or other relevant data based on market transactions involving identical or comparable assets. The Company purchases available-for-sale debt securities with the expectation that they will be held to maturity, however the Company may sell them if market conditions or credit‑related risk warrant earlier sales. The Company does not have any securities classified as held-to-maturity or trading. We review available-for-sale debt securities for credit losses based on current expected credit loss methodology at the end of each reporting period. We do not have any securities classified as trading or held to maturity. At each quarter-end, for available-for-sale debt securities in an unrealized loss position, the Company first assesses whether it intends to sell or it is more likely than not that it will be required to sell the security before recovery of its amortized cost basis. If either of the criteria regarding intent or requirement to sell is met, the security’s amortized cost basis is written down to fair value through earnings. For debt securities available-for-sale that do not meet the aforementioned criteria, the Company evaluates whether the decline in fair value has resulted from credit losses or other factors. In making this assessment, management considers the extent to which fair value is less than amortized cost, any changes to the rating of the security by a rating agency, and adverse conditions specifically related to the security, among other factors. If this assessment indicates that a credit loss exists, the present value of cash flows expected to be collected from the security are compared to the amortized cost basis of the security. If the present value of cash flows expected to be collected is less than the amortized cost basis, a credit loss exists and an allowance for credit losses is recorded for the credit loss, limited by the amount that the fair value is less than the amortized cost basis. Any impairment that has not been recorded through an allowance for credit losses is recognized in other comprehensive income. Changes in the allowance for credit losses are recorded as provision for (or reversal of) credit loss expense. Losses are charged against the allowance when management believes the uncollectability of an available-for-sale security is confirmed or when either of the criteria regarding intent or requirement to sell is met. Our outside investment managers assist us in this evaluation. The change in unrealized gain and loss on debt securities is recorded as a component of accumulated other comprehensive income (loss), net of the related deferred tax effect, until realized. The debt securities portfolio includes structured securities. The Company recognizes income from these securities using a constant effective yield based on anticipated prepayments and the estimated economic life of the securities. When actual prepayments differ significantly from anticipated prepayments, the estimated economic life is recalculated and the remaining unamortized premium or discount is amortized prospectively over the remaining economic life. Premiums and discounts on structured securities are amortized or accreted over the life of the related available‑for‑sale security as an adjustment to yield using the effective interest method. Such amortization and accretion is included in interest income in the consolidated statements of operations. Dividend and interest income are recognized when earned. Realized gains and losses from the sale of available-for-sale securities are determined on a specific-identification basis and included in earnings on the trade date. Equity securities that do not result in consolidation and are not accounted for under the equity method are measured at fair value and any changes in fair value are recognized in net income in the Consolidated Statements of Operations. Investment company limited partnerships are measured at their net asset value, which approximates fair value. Any changes in the net asset value are recognized in net income in the Consolidated Statements of Operations. The Company carries other equity investments that do not have a readily determinable fair value at cost, less impairment and adjusted for observable price changes under the measurement alternative provided under GAAP. We review these investments for impairment during each reporting period. These investments are a component of Other Assets in the Consolidated Balance Sheets. There were no observable prices changes to the Company's other equity investments during 2023 or 2022. Credit Losses Effective January 1, 2023, the Company adopted ASU 2016-13 Financial Instruments—Credit Losses (Topic 326): Measurement of Credit Losses on Financial Instruments, as amended, which introduces a new process for recognizing credit losses on financial instruments based on expected credit losses. This new standard replaces the incurred loss methodology and the concept of Other-than-Temporary Impairment (or “OTTI”) with an expected credit loss methodology that is sometimes referred to as the Current Expected Credit Loss (CECL) methodology. The guidance applies to Conifer's reinsurance recoverables, premium receivable, and debt securities. Results for reporting periods beginning after January 1, 2023 are presented under ASC 326, while prior period amounts continue to be reported in accordance with previously applicable U.S. GAAP. The adoption of ASC 326 did not have a material impact on the Company's financial statements. Recognition of Premium Revenues All of the property and casualty policies written by our insurance companies are considered short-duration contracts. These policy premiums are earned on a daily pro-rata basis, net of reinsurance, over the term of the policy, which are primarily twelve months in duration. The portion of premiums written that relate to the unexpired terms of policies in force are deferred and reported as unearned premium at the balance sheet date. Reinsurance Reinsurance premiums, commissions, losses and loss adjustment expenses ("LAE") on reinsured business are accounted for on a basis consistent with that used in accounting for the original policies issued and the terms of the reinsurance contracts. The amounts reported as reinsurance recoverables include amounts billed to reinsurers on losses and LAE paid as well as estimates of amounts expected to be recovered from reinsurers on insurance liabilities that have not yet been paid. Reinsurance recoverables on unpaid losses and LAE are estimated based upon assumptions consistent with those used in establishing the gross liabilities as they are applied to the underlying reinsured contracts. The Company records an allowance for uncollectible reinsurance recoverables based on an assessment of the reinsurer’s creditworthiness and collectability of the recorded amounts. Management believes an allowance for uncollectible recoverables from its reinsurers was not necessary for the periods presented. The Company receives ceding commissions in connection with certain ceded reinsurance. The ceding commissions are recorded as a reduction of policy acquisition costs. In 2022, the Company entered into a loss portfolio transfer ("LPT") reinsurance agreement. The LPT is a retroactive reinsurance contract. See Note 9 ~ Reinsurance for further details regarding the LPT. Deferred Policy Acquisition Costs Costs incurred which are incremental and directly related to the successful acquisition of new or renewal insurance business are deferred. These deferred costs consist of commissions paid to agents (net of ceding commissions), premium taxes, and underwriting costs, including compensation and payroll related benefits. Proceeds from reinsurance transactions that represent recovery of acquisition costs reduce applicable unamortized acquisition costs in such a manner that net acquisition costs are capitalized and charged to expense. Amortization of such policy acquisition costs is charged to expense in proportion to premium earned over the estimated policy term. To the extent that unearned premiums on existing policies are not adequate to cover the sum of expected losses and LAE, unamortized acquisition costs and policy maintenance costs, unamortized deferred policy acquisition costs are charged to expense to the extent required to eliminate the premium deficiency. If the premium deficiency is greater than the unamortized policy acquisition costs, a liability is recorded for any such deficiency. As of December 31, 2023 , there was no premium deficiency reserve. The Company considers anticipated investment income in determining whether a premium deficiency exists. Management performs this evaluation at each insurance product line level. Unpaid Losses and Loss Adjustment Expenses The liability for unpaid losses and LAE in the Consolidated Balance Sheets represents the Company’s estimate of the amount it expects to pay for the ultimate cost of all losses and LAE incurred that remain unpaid at the balance sheet date. The liability is recorded on an undiscounted basis. The process of estimating the liability for unpaid losses and LAE is a complex process that requires a high degree of judgment. The liability for unpaid losses and LAE represents the accumulation of individual case estimates for reported losses and LAE, and actuarially determined estimates for incurred but not reported losses and LAE and includes a provision for estimated costs to settle all outstanding claims at the balance sheet date. The liability for unpaid losses and LAE is intended to include the ultimate net cost of all losses and LAE incurred but unpaid as of the balance sheet date. The liability is stated net of anticipated deductibles, salvage and subrogation, and gross of reinsurance ceded. The estimate of the unpaid losses and LAE liability is continually reviewed and updated. Although management believes the liability for losses and LAE is reasonable, the ultimate liability may be more or less than the current estimate. The estimation of ultimate liability for unpaid losses and LAE is a complex, imprecise and inherently uncertain process, and therefore involves a considerable degree of judgment and expertise. The Company utilizes various actuarially‑accepted reserving methodologies in deriving the continuum of expected outcomes and ultimately determining its estimated liability amount. These methodologies utilize various inputs, including but not limited to written and earned premiums, paid and reported losses and LAE, expected initial loss and LAE ratio, which is the ratio of incurred losses and LAE to earned premiums, and expected claim reporting and payout patterns (including company-specific and industry data). The liability for unpaid loss and LAE does not represent an exact measurement of liability, but is an estimate that is not directly or precisely quantifiable, particularly on a prospective basis, and is subject to a significant degree of variability over time. In addition, the establishment of the liability for unpaid losses and LAE makes no provision for the broadening of coverage by legislative action or judicial interpretation or for the extraordinary future emergence of new types of losses not sufficiently represented in the Company’s historical experience or which cannot yet be quantified. As a result, an integral component of estimating the liability for unpaid losses and LAE is the use of informed subjective estimates and judgments about the ultimate exposure to unpaid losses and LAE. The effects of changes in the estimated liability are included in the results of operations in the period in which the estimates are revised. The Company allocates the applicable portion of the unpaid losses and LAE to amounts recoverable from reinsurers under reinsurance contracts and reports those amounts separately as assets on the consolidated balance sheets. Income Taxes Income taxes are accounted for under the asset and liability method. Deferred tax assets and liabilities are recognized for the future tax consequences attributable to differences between the financial statement carrying amounts of existing assets and liabilities and their respective tax bases and operating loss and tax-credit carryforwards. Deferred tax assets and liabilities are measured using enacted tax rates expected to apply to taxable income in the years in which those temporary differences are expected to be recovered or settled. The effect on deferred tax assets and liabilities of a change in tax rates is recognized in income in the period that includes the enactment date. Deferred tax assets are recognized to the extent that there is sufficient positive evidence, as allowed under the Accounting Standard Codification ("ASC") 740, Income Taxes, to support the recoverability of those deferred tax assets. The Company establishes a valuation allowance to the extent that there is insufficient evidence to support the recoverability of the deferred tax asset under ASC 740. In making such a determination, management considers all available positive and negative evidence, including future reversals of existing taxable temporary differences, projected future taxable income, tax‑planning strategies, and results of recent operations. If it is determined that the deferred tax assets would be realizable in the future in excess of their net recorded amount, an adjustment would be made to the deferred tax asset valuation allowance, which would reduce the provision for income taxes. As of December 31, 2023 and 2022 , the Company did no t have any unrecognized tax benefits and had no accrued interest or penalties related to uncertain tax positions. Other Income Other income consists primarily of fees charged to policyholders by the Company for services outside of the premium charge, such as installment billings or policy issuance costs. Commission income is also received by the Company’s insurance agencies for writing policies for third party insurance companies. The Company recognizes commission income on the later of the effective date of the policy, the date when the premium can be reasonably established, or the date when substantially all services related to the insurance placement have been rendered. Agency Commission Income Agency commission income is comprised of commissions earned on policies where the Company has no exposure to underlying risk on the policies written. Agency commission income is earned at the time the policy is written. Operating Expenses Operating expenses consist primarily of other underwriting, compensation and benefits, information technology, facility and other administrative expenses. Accounting Guidance Not Yet Adopted In January 2021, the FASB issued ASU 2022-06, Reference Rate Reform (Topic 848) . This guidance provides optional expedients and exceptions that are intended to ease the burden of updating contracts to contain a new reference rate due to the discontinuation of the London Inter-Bank Offered Rate (LIBOR). This guidance is available immediately and may be implemented in any period prior to the guidance expiration on December 31, 2024. Management does not expect the new guidance to have a material impact on the Company’s consolidated financial statements. In November 2023, the FASB issued ASU 2023-07, Segment Reporting (Topic 280). This guidance is intended to improve reportable segment disclosure requirements, primarily through enhanced disclosures about significant segment expenses, allowing financial statement users to better understand the components of a segment's profit or loss to assess potential future cash flows for each reportable segment and the entity as a whole. The amendments expand a public entity's segment disclosures by requiring disclosure of significant segment expenses that are regularly provided to the chief operating decision maker ("CODM"), clarifying when an entity may report one or more additional measures to assess segment performance, requiring enhanced interim disclosures, providing new disclosure requirements for entities with a single reportable segment, and requiring other new disclosures. ASU 2023-07 is effective for fiscal years beginning after December 31, 2024. Early adoption is permitted. the Company is currently evaluating the impact the adoption of this standard will have on its consolidated financial statements. In December 2023 , the FASB issued ASU 2023-09 , Income Taxes (Topic 740). ASU 2023-09 requires public business entities to disclose additional information with respect to the reconciliation of the effective tax rate to the statutory rate. Additionally, public business entities will need to disaggregate federal, state and foreign taxes paid in their financial statements. ASU 2023-09 is effective for public business entities for fiscal years, and interim periods within those fiscal years, beginning after December 15, 2024. The Company is currently evaluating the impact the adoption of this standard will have on its consolidated financial statements. Risks and Uncertainties The Company is exposed to interest rate risks as it maintains a significant amount of its investment portfolio in debt securities. As of December 31, 2023, total net unrealized losses in the debt securities was $ 13.3 million. Management believes it will not need to sell debt securities at significant losses as it has the ability and intention to hold them until maturity or their values improve. Company Liquidity We conduct our business operations primarily through our Insurance Company Subsidiaries. Our ability to service debt, and pay administrative expenses is primarily reliant upon our intercompany service fees paid by the Insurance Company Subsidiaries to the holding company for management, administrative, and information technology services provided to the Insurance Company Subsidiaries by the Parent Company. The Parent Company may receive dividends from the Insurance Company Subsidiaries; however, this is not the primary means in which the holding company supports its funding as state insurance laws restrict the ability of our Insurance Company Subsidiaries to declare dividends to the Parent Company, and we do not anticipate any dividends being paid to us from our insurance subsidiaries during 2024 and 2025. Due to significant losses in 2023, much of which is attributable to strengthening reserves and severe storm activity affecting the Oklahoma homeowners business, both Insurance Company Subsidiaries lack sufficient capital to continue to underwrite the volume of business they have historically written. We incurred a consolidated net loss of $ 25.9 million. We used cash from the operation activities of $ 13.6 million, and our overall equity at December 31, 2023 totaled $ 2.9 million. As a result of these factors, we were out of compliance with several of our debt covenants and obtained a waiver from our lender. The aforementioned factors have resented additional liquidity and capital challenges on the Company's financial condition. Accordingly, management is in the process of implementing a strategic shift in which the Company will utilize third-party insurers and rely mostly on commission revenues generated by our managed general agency. Management may also consider the sale of other assets to generate additional cash resources available to the Company. In September 2023, the Company repaid its $ 24.4 million of 6.75 % public senior unsecured notes (the "Old Public Notes") and funded it, in part, with issuing 9.75 % public senior unsecured notes (the "New Public Notes") in the amount of $ 17.9 million. The Company also paid down $ 500,000 of principal on its subordinated notes on September 29, 2023. The Company then restructured its existing $ 10.0 million of subordinated notes to Senior Secure Notes with its lender on September 30, 2023. The Senior Secured Notes mature on September 30, 2028 , and bear an interest rate of 12.5 % per annum. Quarterly principal payments of $ 250,000 are required on the Senior Secured Notes starting on December 31, 2023 through September 30, 2028. The requirements on the new Senior Secured Notes will result in $ 1.0 million per year of principal to be paid on the senior secured debt that previously was not required. On December 20, 2023, the Company issued $ 6.0 million of its newly designated Series A Preferred Stock (the "Preferred Stock"). The Company intends to use the proceeds for working capital and general corporate purposes. As of the filing of this Form 10-K, the Insurance Company Subsidiaries are still the primary underwriters for the business produced by CIS and still the primary source of revenues and cash flows. The Insurance Company Subsidiaries are currently both required to provide an action plan with the state of domicile insurance regulator to remediate certain statutory capital and surplus regulatory deficiencies. If we do not remediate the regulatory deficiencies the insurance regulator could suspend or terminate the insurers’ authority to write business. Also, A.M. Best and Kroll downgraded the financial strength ratings of both companies and we terminated the rating relationship. Therefore, neither company is currently rated by a nationally recognized statistical rating organization which can have an impact on the ability to market to policyholders. We believe that the Insurance Company Subsidiaries will both regain compliance with the state insurance regulators, however, as part of the strategic shift, we no longer expect significant revenues to be generated through them after the second quarter of 2024. These circumstances could jeopardize the ability of the Company to generate insurance underwriting revenues which could put into doubt our ability to meet our obligations as they become due. To alleviate these concerns the Company is in the process of implementing the strategic shift mentioned above which will not require the use of either Insurance Company Subsidiary to generate the majority of the Company’s revenues going forward. Rather, the Company will expect to generate the vast majority of its revenue from commissions from third-party insurers. In order to successfully implement the strategic shift the Company must have in place producer agreements with third-party insurers. Currently the Company has executed one producer agreement for approximately 25 % of the existing commercial lines book of business and is expected to execute another producer agreement with a different third-party insurer for the remaining commercial lines business within a week of filing this Form 10-K. We expect to continue to underwrite the existing personal lines business within our Insurance Company Subsidiaries. With these producer agreements in place the Company expects to be able to generate the needed revenues to meeting our obligations as they become due over the next twelve months. In the event there are delays in implementing the strategic shift or other uncertainties arise with respect to completion of our strategic shift during 2024, these events could have a negative effect on our liquidity and ability to satisfy our obligations as they become due. If the Company were to experience any such uncertainties the Company believes it has alternative sources of liquidity available which are sufficient to cover any short-term needs as a result of any such uncertainties encountered. Management believes the current actions being executed to implement the planned strategic shift coupled with additional available sources of available liquidity, will be sufficient to enable the Company to meet its obligations for the foreseeable future.

Sale of Renewal Rights

Sale of Renewal Rights	12 Months Ended
	Dec. 31, 2023
Renewal Rights
Collaborative Arrangement and Arrangement Other than Collaborative [Line Items]
Sale of Renewal Rights/Certain Agency Business	2. Sale of Renewal Rights In September 2023, the Company sold the renewal rights of one of its insurance programs to another insurer for $ 2.5 million in cash in addition to agreeing to participate in the Company's issuance of new public debt in September 2023, by purchasing $ 5.0 million of new debt. The program provided mostly liability insurance to the security guard and alarm installation industries. The program produced gross earned premiums of $ 55.9 million and $ 41.0 million in 2023 and 2022, respectively. The buyer began writing new and renewal policies for this program as of September 15, 2023. On September 30, 2023, the Company ceded 100 % of its gross unearned premium of $ 30.9 million in the program to the buyer in return for an $ 8.4 million ceding commission. As of December 31, 2023, the Company retained $ 24.1 million of net cash owed to the buyer under a funds withheld provision. This can be seen in the funds held under reinsurance agreements in the liability section of the Company's Consolidated Balance Sheets. The funds withheld balance is expected to be paid out as premiums are earned and related claims are paid. The Company incurred $ 135,000 in expense related to this transaction. As part of this transaction, five claims staff transferred employment to the buyer. The buyer will handle all of the Company’s run-off claims for this program under a related claims administration agreement.

VSRM Transaction

VSRM Transaction	12 Months Ended
	Dec. 31, 2023
Business Combinations [Abstract]
VSRM Transaction	3. VSRM Transaction Prior to October 13, 2022, CIS, formerly known as Sycamore, owned 50 % of Venture Agency Holdings, Inc. ("Venture") and has accounted for its ownership under the equity method of accounting. On October 13, 2022, CIS purchased the other 50 % of Venture from an individual for $ 9.7 million. Following this purchase, CIS obtained control and owned 100 % of Venture, which was then renamed to VSRM, Inc. ("VSRM"). VRSM and its two wholly owned subsidiaries, The Roots Insurance Agency, Inc. ("Roots") and Mitzel Insurance Agency, Inc. ("Mitzel") were incorporated into the Company's consolidated financial statements as of the date of the acquisition. CIS initially purchased the Venture shares with a promissory note for $ 9.7 million and ultimately settled the note with $ 5.9 million of cash received from the Security & Alarm Business sale, described below, and $ 3.8 million in the form of stock from the buyer of the Security & Alarm Business. The Company acquired the remaining outstanding shares of VSRM, in order to take advantage of net operating tax losses as part of a tax planning strategy to apply to the Security and Alarm Business sale described below, in addition to the strategic focus of getting out of the Security and Alarm line of business. The Company recognized CIS's purchase of the individual's shares of VSRM as a step acquisition and revalued all assets and liabilities upon the acquisition date. This resulted in the recognition of an $ 8.8 million non-operating gain reported in the Consolidated Statement of Operations as Gain from VSRM Transaction in the fourth quarter of 2022. The Company also utilized $ 12.5 million of federal income tax net operating losses carried forward and $ 14.8 million state income tax net operating losses carried forward, for a total net-of-tax benefit of $ 9.4 million. VSRM retained $ 8.9 million of debt, and $ 9.4 million of tax liabilities, as well as other smaller assets and liabilities that did not go with the transaction. A condensed schedule of assets and liabilities incorporated into the consolidated balance sheet from the VSRM acquisition is provided below: Cash $ 3,921 Trade receivables 4,604 Customer relationship intangible assets 37,122 Other assets 574 Total assets $ 46,221 Trade and other payables 7,624 Deferred tax liability 9,407 Note payable to Affiliate 6,000 Senior debt 2,917 Total Liabilities $ 25,948 Fair value of net assets acquired $ 20,273 The following table presents the calculation of the $ 8.8 million revaluation gain related to the Company's equity method investment in VSRM as a result of the VSRM Transaction: Carrying value of equity method investment in VSRM $ 1,773 Fair value of investment in VSRM 10,583 Gain on step acquisition $ 8,810 The fair value of the equity interest of VSRM immediately prior to the acquisition was $ 10.6 million. The fair value techniques used to measure the fair value of VSRM included using the recent valuations performed by third party valuation experts and the net realized proceeds received upon the sale of the Security & Alarm Business sold the following day. There were no material transaction costs incurred in the acquisition of VSRM. Additionally, no results of operations for the Security and Alarm business have been included the consolidated financial statements as that business was immediately disposed of. Results of operations for the retained business have been included from the date of acquisition. On October 14, 2022, VSRM sold all of its security guard and alarm installation insurance brokerage business (the "Security & Alarm Business") to a third party insurance brokerage firm for $ 38.2 million, of which $ 32.8 million was paid in cash and $ 3.8 million was in the form of the buyer's stock. The $ 3.8 million of buyer's stock was immediately used to settle a portion of the $ 9.7 million promissory note that was issued to buy the 50 % of Venture and the remainder of the promissory note was settled with cash from the sale of business. As part of the transaction, the individual who previously owned 50 % of VSRM transitioned employment to the buyer, along with a team of approximately eight other employees of VSRM. Also, the Company transferred to the buyer, $ 4.3 million of accounts receivable, $ 5.8 million of current liabilities, $ 271,000 in cash as well as all books and records of the business being purchased. The buyer held back $ 75,000 of cash for a future true up of the trade balances which the Company reflected as a current receivable. The Company recognized this transaction as the sale of a business. Because all assets and liabilities were just adjusted to fair value from the step acquisition described above, the basis of the net assets sold equaled the net proceeds from the sale, thus there was no gain recognized upon the sale of the Security & Alarm Business. The following table reconciles the net assets disposed of from this transaction: Cash at closing $ 32,759 Net liabilities transferred 1,499 Hold back 75 Stock of acquirer 3,822 Total purchase price $ 38,155 Cash $ 271 Premiums transferred to buyer 4,326 Intangible assets 38,154 Trade payables and accrued liabilities assumed by buyer ( 5,838 ) Net assets disposed of 36,913 Gross gain 1,242 Broker fee transaction costs ( 1,242 ) Net gain $ — The net gain on revaluation of the investment in VSRM and the disposal of the Security and Alarm Business line are summarized below: Gross gains $ 10,052 Broker fee ( 1,242 ) Net gain $ 8,810 On December 30, 2022, VSRM contributed its remaining business, including its two wholly owned subsidiaries (Mitzel and Roots) to a new wholly owned subsidiary, Sycamore Specialty Underwriters, LLC ("SSU"). The business contributed to SSU consisted of customer accounts of substantially all of the personal lines business and a small subset of the commercial lines business underwritten by the Insurance Company Subsidiaries, and all of the customer accounts VSRM produced for third-party insurers, other than the security guard and alarm installation brokerage business previously sold. On December 31, 2022, Sycamore Financial Group, LLC ("SFG"), wholly owned by Andrew D. Petcoff purchased 50 % of SSU from VSRM, Inc. for $ 1,000 . As a result, SSU and its two wholly owned subsidiaries, Roots and Mitzel, are no longer consolidated in the Company's consolidated financial statements as of December 31, 2022, and VSRM's investment in SSU is accounted for using the equity method. The net assets transferred to SSU had a fair value of $ 0 at the time of the contribution. There was no gain or loss recognized upon the sale of half of SSU to SFG. Included in the net assets transferred to SSU was a $ 1.0 million promissory note obligation of VSRM that originated as part of the Venture Transaction described below, and is payable to CIC. The $ 1.0 million promissory note was still outstanding and payable to CIC as of December 31, 2023. The $ 934,000 receivable from VSRM in the table below transferred as part of the deconsolidation resulted in the Company retaining an existing related payable for $ 934,000 which was repaid in 2023. The following table provides the assets and liabilities deconsolidated as a result of this transaction: Cash $ 497 Receivable from VSRM 934 Trade receivables 239 Intangible asset 196 Other assets 514 Total assets $ 2,380 Payable to Affiliates 286 Trade payables 193 Note payable 1,000 Other liabilities 901 Total Liabilities $ 2,380 In order to determine the value of the business contributed to SSU, the Company obtained a third party valuation based on a weighting of discounted cash flows and earnings before interest, taxes, depreciation and amortization (EBITDA) multiple valuation methods. The valuation included significant estimates and assumptions related to (i) forecasted revenue and EBITDA and (ii) the selection of the EBITDA multiple and discount rate.

Sale of Certain Agency Business

Sale of Certain Agency Business	12 Months Ended
	Dec. 31, 2023
Agency Business
Collaborative Arrangement and Arrangement Other than Collaborative [Line Items]
Sale of Renewal Rights/Certain Agency Business	4. Sale of Certain Agency Business In June of 2021, CIS, formerly known as Sycamore, sold the customer accounts and other related assets of some of its personal and commercial lines of business to Venture. Two promissory notes were created as a result of the sale (one for $ 3.0 million and one for $ 6.0 million). In December 2021, Venture paid off the $ 3.0 million note. On October 20, 2022, Venture paid down $ 5.0 million of the $ 6.0 million note. The remaining $ 1.0 million promissory note was assumed by SSU as part of the contribution of business to SSU described in Note 3 ~ Acquisition of Joint Venture and Subsequent Sale of Business , and was still outstanding as a payable to CIC as of December 31, 2023 .

Investments

Investments	12 Months Ended
	Dec. 31, 2023
Investments, Debt and Equity Securities [Abstract]
Investments	5. Invest ments Results for reporting periods occurring before January 1, 2023 continue to be reported in accordance with previously applicable U.S. GAAP and are presented under ASC 326, which was adopted by the Company on January 1, 2023. The Company analyzed its investment portfolio in accordance with its credit loss review policy and determined it did not need to record a credit loss for the twelve months ended December 31, 2023 . The Company holds only investment grade securities from high credit quality issuers. The gross unrealized losses of $ 13.3 million as of December 31, 2023, from the Company's available-for-sale securities are due to market conditions and interest rate changes. Management believes it will not need to sell its available-for-sale securities at significant losses as it has the ability and intention to hold them until maturity or until their values improve. The cost or amortized cost, gross unrealized gain or loss, and estimated fair value of the investments in securities classified as available-for-sale at December 31, 2023 and 2022 were as follows (dollars in thousands): December 31, 2023 Cost or Gross Unrealized Amortized Gains Losses Estimated Debt securities: U.S. Government $ 5,405 $ 3 $ ( 161 ) $ 5,247 State and local government 24,274 — ( 3,810 ) 20,464 Corporate debt 34,002 — ( 3,507 ) 30,495 Asset-backed securities 38,289 47 ( 584 ) 37,752 Mortgage-backed securities 26,768 — ( 4,641 ) 22,127 Commercial mortgage-backed securities 3,404 — ( 160 ) 3,244 Collateralized mortgage obligations 3,228 — ( 444 ) 2,784 Total debt securities available for sale $ 135,370 $ 50 $ ( 13,307 ) $ 122,113 December 31, 2022 Cost or Gross Unrealized Amortized Gains Losses Estimated Debt securities: U.S. Government $ 7,833 $ — $ ( 335 ) $ 7,498 State and local government 25,487 1 ( 4,672 ) 20,816 Corporate debt 35,347 — ( 4,788 ) 30,559 Asset-backed securities 21,742 — ( 1,246 ) 20,496 Mortgage-backed securities 29,194 — ( 5,157 ) 24,037 Commercial mortgage-backed securities 3,414 — ( 186 ) 3,228 Collateralized mortgage obligations 4,102 — ( 535 ) 3,567 Total debt securities available for sale $ 127,119 $ 1 $ ( 16,919 ) $ 110,201 The following table summarizes the aggregate fair value and gross unrealized losses, by security type, of the available-for-sale securities in unrealized loss positions. The table segregates the holdings based on the length of time that individual securities have been in a continuous unrealized loss position (dollars in thousands): December 31, 2023 Less than 12 months 12 months or More Total No. Fair Value of Gross No. Fair Value of Gross No. Fair Value of Gross Debt securities: U.S. Government 1 $ 649 $ ( 7 ) 9 $ 3,400 $ ( 154 ) 10 $ 4,049 $ ( 161 ) State and local government 3 1,193 ( 7 ) 113 19,096 ( 3,803 ) 116 20,289 ( 3,810 ) Corporate debt - - - 66 30,495 ( 3,507 ) 66 30,495 ( 3,507 ) Asset-backed securities 1 1,090 ( 1 ) 21 16,270 ( 583 ) 22 17,360 ( 584 ) Mortgage-backed securities 4 11 ( 1 ) 64 22,116 ( 4,640 ) 68 22,127 ( 4,641 ) Commercial mortgage - - - 4 3,225 ( 160 ) 4 3,225 ( 160 ) Collateralized mortgage - - - 32 2,803 ( 444 ) 32 2,803 ( 444 ) Total debt securities 9 2,943 ( 16 ) 309 97,405 ( 13,291 ) 318 100,348 ( 13,307 ) December 31, 2022 Less than 12 months 12 months or More Total No. Fair Value of Gross No. Fair Value of Gross No. Fair Value of Gross Debt securities: U.S. Government 8 $ 3,534 $ ( 135 ) 5 $ 3,964 $ ( 200 ) 13 $ 7,498 $ ( 335 ) State and local government 77 12,966 ( 2,318 ) 45 7,147 ( 2,354 ) 122 20,113 ( 4,672 ) Corporate debt 27 10,069 ( 1,373 ) 42 20,890 ( 3,415 ) 69 30,959 ( 4,788 ) Asset-backed securities 6 3,188 ( 76 ) 20 17,308 ( 1,170 ) 26 20,496 ( 1,246 ) Mortgage-backed securities 57 4,006 ( 573 ) 12 20,031 ( 4,584 ) 69 24,037 ( 5,157 ) Commercial mortgage 4 3,205 ( 186 ) — — — 4 3,205 ( 186 ) Collateralized mortgage 26 1,789 ( 196 ) 9 1,802 ( 339 ) 35 3,591 ( 535 ) Total debt securities 205 $ 38,757 $ ( 4,857 ) 133 $ 71,142 $ ( 12,062 ) 338 $ 109,899 $ ( 16,919 ) The Company’s sources of net investment income are as follows (dollars in thousands): December 31, 2023 2022 Debt securities $ 4,121 $ 2,517 Equity securities 36 52 Cash, cash equivalents, and short-term investments 1,603 776 Total investment income 5,760 3,345 Investment expenses ( 234 ) ( 302 ) Net investment income $ 5,526 $ 3,043 The following table summarizes the gross realized gains and losses from sales or maturities of available-for-sale debt securities and equity securities, as follows (dollars in thousands): December 31, 2023 2022 Debt securities: Gross realized gains $ — $ 6 Gross realized losses ( 20 ) ( 155 ) Total debt securities ( 20 ) ( 149 ) Equity securities: Gross realized gains — 375 Gross realized losses — ( 1,731 ) Total equity securities — ( 1,356 ) Total net realized investment gains $ ( 20 ) $ ( 1,505 ) Proceeds from the sales of available-for-sale securities were $ 11.9 million and $ 32.0 million for the years ended December 31, 2023 and 2022, respectively. The gross realized gains from sales of available-for-sale securities for the years ended December 31, 2023 and 2022 were $ 0 and $ 5,000 , respectively. The gross realized losses from sales of available-for-sale securities for the years ended December 31, 2023 and 2022 were $ 18,000 and $ 155,000 , respectively. As of December 31, 2023 and 2022 , there were $ 0 of payables from securities purchased, respectively. As of December 31, 2023 and 2022 , there were $ 0 and $ 650,000 of receivables from securities sold, respectively. The Company's gross unrealized losses related to its equity investments were $ 535,000 and $ 638,000 as of December 31, 2023 and 2022, respectively. The Company's gross unrealized gains related to its equity investments were $ 505,000 as of December 31, 2023. The Company had no gross unrealized gains related to its equity investments as of December 31, 2022. The Company also carries other equity investments that do not have a readily determinable fair value and are recorded at cost, less impairment or observable changes in price. We review these investments for impairment during each reporting period. There was no impairment or observable changes in price recorded during 2023 related to the Company's equity securities without readily determinable fair value. These investments are a component of Other Assets in the Consolidated Balance Sheets. The value of these investments as of December 31, 2023 and December 31, 2022 were $ 1.4 million and $ 1.8 million, respectively. The table below summarizes the amortized cost and fair value of available-for-sale debt securities by contractual maturity at December 31, 2023. Actual maturities may differ from contractual maturities because certain borrowers have the right to call or prepay obligations with or without call or prepayment penalties (dollars in thousands): Amortized Estimated Due in one year or less $ 3,212 $ 3,175 Due after one year through five years 30,996 28,983 Due after five years through ten years 18,768 15,904 Due after ten years 10,705 8,144 Securities with contractual maturities 63,681 56,206 Asset-backed securities 38,289 37,752 Mortgage-backed securities 26,768 22,127 Commercial mortgage-backed securities 3,404 3,244 Collateralized mortgage obligations 3,228 2,784 Total debt securities $ 135,370 $ 122,113 At December 31, 2023 and 2022 , the Insurance Companies Subsidiaries had an aggregate of $ 8.2 million and $ 8.0 million, respectively, on deposit in trust accounts to meet the deposit requirements of various state insurance departments. At December 31, 2023 and 2022 , the Company had $ 123.5 million and $ 95.7 million held in trust accounts to meet collateral requirements with other third-party insurers, relating to various fronting arrangements. Approximately $ 111.3 million of the trust account balances are for collateral of gross unearned premiums and gross loss reserves of the fronted business on the Security Program and the quick service restaurant program. There are withdrawal and other restrictions on these deposits, including the type of investments that may be held, however, the Company may generally invest in high-grade bonds and short-term investments and earn interest on the funds. As the unearned premiums run off to zero and loss reserves are paid on these programs, the trust balances will be released and available for general use.

Fair Value Measurements

Fair Value Measurements	12 Months Ended
	Dec. 31, 2023
Fair Value Disclosures [Abstract]
Fair Value Measurements	6. Fair Value Measurements The Company’s financial instruments include assets carried at fair value, as well as debt carried at face value, net of unamortized debt issuance costs, which are also disclosed at fair value in this note. All fair values disclosed in this note are determined on a recurring basis other than the debt which is a non-recurring fair value measure. Fair value is defined as the price that would be received for an asset or paid to transfer a liability in the principal most advantageous market for the asset or liability in an orderly transaction between market participants. In determining fair value, the Company applies the market approach, which uses prices and other relevant data based on market transactions involving identical or comparable assets and liabilities. The inputs to valuation techniques used to measure fair value are prioritized into a three-level hierarchy. The hierarchy gives the highest priority to quoted prices from sources independent of the reporting entity (“observable inputs”) and the lowest priority to prices determined by the reporting entity’s own assumptions about market participant assumptions developed based on the best information available in the circumstances (“unobservable inputs”). The fair value hierarchy is as follows: Level 1 —Valuations that are based on quoted prices (unadjusted) in active markets for identical assets or liabilities. Level 2 —Valuations that are based on observable inputs (other than Level 1 prices) such as quoted prices for similar assets or liabilities at the measurement date; quoted prices in markets that are not active; or other inputs that are observable, either directly or indirectly, for substantially the full term of the asset or liability. Level 3 —Unobservable inputs that are supported by little or no market activity. The unobservable inputs represent the Company’s best assumption of how market participants would price the assets or liabilities. Net Asset Value (NAV) —The fair values of investment company limited partnership investments and mutual funds are based on the capital account balances reported by the investment funds subject to their management review and adjustment. These capital account balances reflect the fair value of the investment funds. The following tables present the Company’s assets and liabilities measured at fair value, classified by the valuation hierarchy as of December 31, 2023 and 2022 (dollars in thousands): December 31, 2023 Fair Value Measurements Using Total Level 1 Level 2 Level 3 Assets: Debt Securities: U.S. Government $ 5,247 $ — $ 5,247 $ — State and local government 20,464 — 20,464 — Corporate debt 30,495 — 30,495 — Asset-backed securities 37,752 — 37,752 — Mortgage-backed securities 22,127 — 22,127 — Commercial mortgage-backed securities 3,244 — 3,244 — Collateralized mortgage obligations 2,784 — 2,784 — Total debt securities 122,113 — 122,113 — Equity Securities 896 139 757 — Short-term investments 20,838 20,838 — — Total marketable investments measured at fair value $ 143,847 $ 20,977 $ 122,870 $ — Investments measured at NAV: Investment in limited partnership 1,458 Total assets measured at fair value $ 145,305 Liabilities: Senior Unsecured Notes * $ 11,791 $ — $ 11,791 $ — Senior Secured Notes * 9,965 — — 9,965 Total Liabilities (non-recurring fair value measure) $ 21,756 $ — $ 11,791 $ 9,965 * Carried at face value of debt net of unamortized debt issuance costs on the consolidated balance sheet December 31, 2022 Fair Value Measurements Using Total Level 1 Level 2 Level 3 Assets: Debt Securities: U.S. Government $ 7,498 $ — $ 7,498 $ — State and local government 20,816 — 20,816 — Corporate debt 30,559 — 30,559 — Asset-backed securities 20,496 — 20,496 — Mortgage-backed securities 24,037 — 24,037 — Commercial mortgage-backed securities 3,228 — 3,228 — Collateralized mortgage obligations 3,567 — 3,567 — Total debt securities 110,201 — 110,201 — Equity Securities 917 160 757 — Short-term investments 25,929 25,929 — — Total marketable investments measured at fair value $ 137,047 $ 26,089 $ 110,958 $ — Investments measured at NAV: Investment in limited partnership 350 Total assets measured at fair value $ 137,397 Liabilities: Senior Unsecured Notes * $ 22,430 $ — $ 22,430 $ — Subordinated Notes * 11,300 — — 11,300 Total Liabilities (non-recurring fair value measure) $ 33,730 $ — $ 22,430 $ 11,300 * Carried at face value of debt net of unamortized debt issuance costs on the consolidated balance sheet Level 1 investments consist of equity securities traded in an active exchange market. The Company uses unadjusted quoted prices for identical instruments to measure fair value. Level 1 also includes money market funds and other interest-bearing deposits at banks, which are reported as short-term investments. The fair value measurements that were based on Level 1 inputs comprise 15 % and 18 % of the fair value of the total marketable investments measured at fair value as of December 31, 2023 and December 31, 2022, respectively. Level 2 investments include debt securities and equity securities, which consist of U.S. government agency securities, state and local municipal bonds, corporate debt securities, mortgage-backed and asset-backed securities. The fair value of securities included in the Level 2 category were based on the market values obtained from a third party pricing service that were evaluated using pricing models that vary by asset class and incorporate available trade, bid and other observable market information. The third party pricing service monitors market indicators, as well as industry and economic events. The fair value measurements that were based on Level 2 inputs comprise 85 % and 82 % of the fair value of the total marketable investments measured at fair value as of December 31, 2023 and December 31, 2022, respectively. The Company obtains pricing for each security from independent pricing services, investment managers or consultants to assist in determining fair value for its Level 2 investments. To validate that these quoted prices are reasonable estimates of fair value, the Company performs various quantitative and qualitative procedures, such as (i) evaluation of the underlying methodologies, (ii) analysis of recent sales activity, (iii) analytical review of our fair values against current market prices and (iv) comparison of the pricing services’ fair value to other pricing services’ fair value for the same investment. No markets for the investments were determined to be inactive at period-ends. Based on these procedures, the Company did not adjust the prices or quotes provided from independent pricing services, investment managers or consultants. As of December 31, 2023, the fair value of the Senior Secured Notes reported at amortized cost was considered a Level 3 liability in the fair value hierarchy and is entirely comprised of the Company's Senior Secured Notes. In determining the fair value of the Senior Secured Notes outstanding at December 31, 2023, the security attributes (issue date, maturity, coupon, calls, etc.) were entered into a valuation model. A lognormal trinomial interest rate lattice was created within the model to compute the option adjusted spread (“OAS”) which is the amount, in basis points, of interest rate required to be paid under the debt agreement over the risk-free U.S. Treasury rates. The OAS was then entered back into the model along with the December 31, 2023 U.S. Treasury rates. A new lattice was generated and the fair value was computed from the OAS. There were no changes in assumptions of credit risk from the issuance date. As of December 31, 2022, the fair value of the subordinated debt reported at amortized cost was considered a Level 3 liability in the fair value hierarchy and is entirely comprised of the Company's subordinated notes. In determining the fair value of the subordinated notes outstanding at December 31, 2022, the security attributes (issue date, maturity, coupon, calls, etc.) and market rates on September 24, 2018 (the date of the restated and amended agreement which was repriced at that time) were entered into a valuation model. A lognormal trinomial interest rate lattice was created within the model to compute the option adjusted spread (“OAS”) which is the amount, in basis points, of interest rate required to be paid under the debt agreement over the risk-free U.S. Treasury rates. The OAS was then entered back into the model along with the December 31, 2022 U.S. Treasury rates. A new lattice was generated and the fair value was computed from the OAS. There were no changes in assumptions of credit risk from the issuance date. The Company's policy on recognizing transfers between hierarchies is applied at the end of each reporting period. There were no transfers in or out of Level 3 for the twelve months ended December 31, 2023 and 2022 .

Deferred Policy Acquisition Cos

Deferred Policy Acquisition Costs	12 Months Ended
	Dec. 31, 2023
Deferred Policy Acquisition Costs Disclosures [Abstract]
Deferred Policy Acquisition Costs	7. Deferred Policy Acquisition Costs The Company defers costs incurred which are incremental and directly related to the successful acquisition of new or renewal insurance business, net of corresponding amounts of ceded reinsurance commissions. Net deferred policy acquisition costs are amortized and charged to expense in proportion to premium earned over the estimated policy term. The Company anticipates that its deferred policy acquisition costs will be fully recoverable and there were no premium deficiencies for the years December 31, 2023 and 2022 . The activity in deferred policy acquisition costs, net of reinsurance transactions, is as follows (dollars in thousands): December 31, 2023 2022 Balance at beginning of period $ 10,290 $ 12,267 Deferred policy acquisition costs 16,887 20,202 Amortization of policy acquisition costs ( 16,589 ) ( 22,179 ) Impact from renewal rights sale ( 4,303 ) — Net change ( 4,005 ) ( 1,977 ) Balance at end of period $ 6,285 $ 10,290

Unpaid Losses and Loss Adjustme

Unpaid Losses and Loss Adjustment Expenses	12 Months Ended
	Dec. 31, 2023
Insurance Loss Reserves [Abstract]
Unpaid Losses and Loss Adjustment Expenses	8. Unpaid Losses and Loss Adjustment Expenses The Company establishes reserves for unpaid losses and LAE which represent the estimated ultimate cost of all losses incurred that were both reported and unreported (i.e., incurred but not yet reported losses, or “IBNR”) and LAE incurred as well as a provision for estimated future costs related to claim settlement for all claims that remain unpaid at the balance sheet date. The Company’s reserving process takes into account known facts and interpretations of circumstances and factors including the Company’s experience with similar cases, actual claims paid, historical trends involving claim payment patterns and pending levels of unpaid claims, loss management programs, product mix and contractual terms, changes in law and regulation, judicial decisions, and economic conditions. In the normal course of business, the Company may also supplement its claims processes by utilizing third party adjusters, appraisers, engineers, inspectors, and other professionals and information sources to assess and settle catastrophe and non-catastrophe related claims. The effects of inflation are implicitly considered in the reserving process. Reserves are estimates of unpaid portions of losses that have occurred, including IBNR losses, therefore the establishment of appropriate reserves, is an inherently uncertain and complex process. The ultimate cost of losses may vary materially from recorded amounts, which are based on management’s best estimates. The highest degree of uncertainty is associated with reserves for losses incurred in the current reporting period as it contains the greatest proportion of losses that have not been reported or settled. The Company regularly updates its reserve estimates as new information becomes available and as events unfold that may affect the resolution of unsettled claims. Changes in prior year reserve estimates, which may be material, are reported in the results of operations in the period such changes are determined to be needed and recorded. Management believes that the reserve for losses and LAE, any related estimates of reinsurance recoverables, is appropriately established in the aggregate and adequate to cover the ultimate net cost of reported and unreported claims arising from losses which had occurred by the date of the consolidated financial statements based on available facts and in accordance with applicable laws and regulations. The table below provides the changes in the reserves for losses and LAE, net of recoverables from reinsurers, for the periods indicated (dollars in thousands): December 31, 2023 2022 Gross reserves - beginning of period $ 165,539 $ 139,085 Less: reinsurance recoverables on unpaid losses 82,651 40,344 Net reserves - beginning of period 82,888 98,741 Add: incurred losses and loss adjustment expenses, net Current period 64,580 57,156 Prior period 17,833 24,284 Total net incurred losses and loss adjustment 82,413 81,440 Deduct: loss and loss adjustment expense payments, Current period 27,001 20,894 Prior period 34,495 76,399 Total net loss and loss adjustment expense 61,496 97,293 Net reserves - end of period 103,805 82,888 Plus: reinsurance recoverables on unpaid losses 70,807 82,651 Gross reserves - end of period $ 174,612 $ 165,539 There was $ 17.8 million and $ 24.3 million of adverse development on prior accident year reserves in 2023 and 2022, respectively. There were no significant changes in the key methods utilized in the analysis and calculations of the Company’s reserves during 2023 and 2022. Of the $ 17.8 million of adverse development in 2023, $ 5.9 million was related to the 2022 accident year, $ 6.8 million was related to the 2021 accident year, $ 4.9 million was related to the 2020 accident year, and $ 218,000 was related to the 2019 and prior accident years. The development came primarily from commercial liability lines of business particularly in the longer tail lines of business, as a result of additional loss emergence primarily from the Security Program which represented 58 % of the adverse development while the remainder was substantially in hospitality, most notably the quick service restaurant program. Both the Security Program and the quick service restaurant program are no longer written by the Company. As a result of this loss emergence, the Company increased its expected loss ratio selections on both prior accident years as well as the current accident year, resulting in increases to our carried loss reserves. Of the $ 24.3 million of adverse development in 2022, $ 1.8 million was related to the 2021 accident year, $ 4.0 million was related to the 2020 accident year, $ 9.6 million was related to the 2019 accident year, $ 5.2 million was related to the 2018 accident year, and $ 3.7 million was related to 2017 and prior accident years. The adverse development was mostly related to the Company's commercial liability lines and was driven by multiple factors including significant social inflation generating higher severity than historical experience, and longer tail exposure than anticipated, particularly in certain jurisdictions. Loss Development Tables The following tables represent cumulative incurred loss and allocated loss adjustment expenses ("ALAE"), net of reinsurance, by accident year and cumulative paid loss and ALAE, net of reinsurance, by accident year, for the years ended December 31, 2014 to 2023, as well as total IBNR and the cumulative number of reported claims for the year ended December 31, 2023 , by reportable segment and accident year (dollars in thousands). The tables do not include reinsurance recoverables from the LPT. The 2023 and 2022 columns in the commercial lines incurred and paid loss tables below do not include reinsurance recoverables on reserves of $ 10.9 million and $ 25.9 million and reinsurance recoverables on paid losses of $ 3.8 million and $ 3.9 million, respectively, related to the LPT. Commercial Lines Incurred loss and allocated loss adjustment expenses, net of reinsurance Total Cumulative Accident Year 2014* 2015* 2016* 2017* 2018* 2019* 2020* 2021* 2022* 2023 2023 2023 2014 19,709 19,907 22,711 26,367 28,145 28,766 29,045 29,175 29,011 29,093 — 1,755 2015 22,442 26,633 31,861 34,478 36,372 37,795 38,824 39,093 39,311 — 2,363 2016 32,396 34,935 40,440 44,355 46,089 46,993 48,677 49,162 19 3,559 2017 44,251 44,495 49,749 51,883 55,589 56,649 59,149 234 5,835 2018 42,624 42,432 49,741 55,261 60,102 61,881 568 6,128 2019 41,286 42,129 46,329 55,263 59,028 1,611 6,337 2020 33,867 35,328 39,193 43,918 3,012 3,866 2021 40,388 42,266 48,650 5,557 2,947 2022 41,708 49,751 10,142 2,323 2023 39,456 20,752 1,644 Total $ 479,399 $ 41,895 Commercial lines Cumulative paid loss and allocated loss adjustment expenses, net of reinsurance Accident Year 2014* 2015* 2016* 2017* 2018* 2019* 2020* 2021* 2022* 2023 2014 8,715 13,977 17,458 22,446 25,609 27,544 28,389 28,648 28,608 28,688 2015 10,470 17,817 22,549 30,475 34,497 35,833 37,563 38,685 39,116 2016 10,255 19,135 27,785 37,967 41,945 43,644 46,957 48,557 2017 12,448 23,020 34,205 42,308 47,148 52,800 57,304 2018 10,375 19,799 31,633 41,577 50,508 57,114 2019 10,078 20,462 28,958 39,893 50,369 2020 10,217 17,332 24,225 33,354 2021 12,870 21,313 30,478 2022 12,839 22,892 2023 8,486 Total $ 376,358 Net Unpaid losses and ALAE, years 2014 through 2023 $ 103,041 Unpaid losses and ALAE, prior to 2014* 160 Unpaid Losses, LPT ( 10,928 ) Unpaid losses and ALAE, net of reinsurance $ 92,273 * Presented as unaudited required supplementary information. Personal Lines Incurred loss and allocated loss adjustment expenses, net of reinsurance Total Cumulative Accident For the years ended December 31, Year 2014* 2015* 2016* 2017* 2018* 2019* 2020* 2021* 2022* 2023 2023 2023 2014 17,951 17,471 17,735 17,880 17,929 18,082 18,095 18,097 18,052 18,028 — 3,737 2015 10,877 13,445 14,721 15,285 15,364 15,427 15,427 15,448 15,456 — 2,154 2016 11,619 13,418 14,949 15,550 15,655 15,634 15,679 15,681 — 1,815 2017 14,058 13,550 14,493 14,793 14,911 14,957 14,955 — 2,914 2018 5,893 6,378 6,283 6,382 6,298 6,336 — 803 2019 3,099 2,712 2,898 2,862 2,867 — 341 2020 2,339 2,590 2,636 2,619 — 324 2021 4,409 4,332 4,240 — 48 2022 9,404 8,122 — 714 2023 19,444 1,156 1,584 Total $ 107,748 $ 1,156 Personal lines Cumulative paid loss and allocated loss adjustment expenses, net of reinsurance Accident For the years ended December 31, Year 2014* 2015* 2016* 2017* 2018* 2019* 2020* 2021* 2022* 2023 2014 12,819 16,515 17,260 17,746 17,855 18,047 18,068 18,070 18,025 18,027 2015 7,771 11,873 13,844 15,159 15,250 15,290 15,416 15,444 15,452 2016 7,119 11,238 14,442 15,110 15,351 15,452 15,679 15,681 2017 8,320 12,944 14,004 14,526 14,866 14,957 14,955 2018 4,296 5,618 6,100 6,242 6,244 6,333 2019 2,119 2,604 2,692 2,850 2,859 2020 1,307 2,455 2,605 2,619 2021 3,022 3,980 4,081 2022 5,397 7,923 2023 16,170 Total $ 104,100 Net Unpaid losses and ALAE, years 2014 through 2023 $ 3,648 Unpaid losses and ALAE, prior to 2014* — Unpaid losses and ALAE, net of reinsurance $ 3,648 * Presented as unaudited required supplementary information. Total Lines Incurred loss and allocated loss adjustment expenses, net of reinsurance Total Cumulative number of reported claims Accident For the years ended December 31, Year 2014* 2015* 2016* 2017* 2018* 2019* 2020* 2021* 2022* 2023 2023 2023 2014 37,660 37,378 40,446 44,247 46,074 46,848 47,140 47,272 47,063 47,121 — 5,492 2015 33,319 40,078 46,581 49,763 51,736 53,222 54,251 54,541 54,767 — 4,517 2016 44,015 48,353 55,389 59,905 61,744 62,627 64,356 64,843 19 5,374 2017 58,309 58,045 64,242 66,676 70,500 71,606 74,104 234 8,749 2018 48,517 48,810 56,024 61,643 66,400 68,217 568 6,931 2019 44,385 44,841 49,227 58,125 61,895 1,611 6,678 2020 36,206 37,918 41,829 46,537 3,012 4,190 2021 44,797 46,598 52,890 5,557 2,995 2022 51,112 57,873 10,142 3,037 2023 58,900 21,908 3,228 Total 587,147 43,051 Total lines Cumulative paid loss and allocated loss adjustment expenses, net of reinsurance Accident For the years ended December 31, Year 2014* 2015* 2016* 2017* 2018* 2019* 2020* 2021* 2022* 2023 2014 21,534 30,492 34,718 40,192 43,464 45,591 46,457 46,718 46,633 46,715 2015 18,241 29,690 36,393 45,634 49,747 51,123 52,979 54,129 54,568 2016 17,374 30,373 42,227 53,077 57,296 59,096 62,636 64,238 2017 20,768 35,964 48,209 56,834 62,014 67,757 72,259 2018 14,671 25,417 37,733 47,819 56,752 63,447 2019 12,197 23,066 31,650 42,743 53,228 2020 11,524 19,787 26,830 35,973 2021 15,892 25,293 34,559 2022 18,236 30,815 2023 — 24,656 Total $ 480,458 Net Unpaid losses and ALAE, years 2014 through 2023 $ 106,689 Unpaid losses and ALAE, prior to 2014* 160 Unpaid losses, LPT ( 10,928 ) Unpaid losses and ALAE, net of reinsurance $ 95,921 * Presented as unaudited required supplementary information. The following table reconciles the loss development information to the consolidated balance sheet for the year ended December 31, 2023, by reportable segment (dollars in thousands). December 31, Net unpaid losses claims and ALAE Commercial Lines $ 92,273 Personal Lines 3,648 Total unpaid losses and LAE, net of reinsurance 95,921 Reinsurance recoverable on losses and LAE Commercial Lines 68,981 Personal Lines 1,826 Total reinsurance recoverable on unpaid losses and LAE 70,807 ULAE expense 7,884 Total gross unpaid losses and LAE $ 174,612 Loss Duration Disclosure (unaudited) The following table represents the average annual percentage payout of incurred losses by age, net of reinsurance, for each reportable segment. Average annual percentage payout of incurred losses by age, net of reinsurance Year 1 Year 2 Year 3 Year 4 Year 5 Year 6 Year 7 Year 8 Year 9 Year Commercial Lines 27.3 % 21.6 % 18.6 % 12.8 % 9.2 % 4.9 % 2.9 % 1.5 % 0.7 % 0.5 % Personal Lines 83.1 % 11.3 % 5.3 % 0.3 % 0.0 % 0.0 % 0.0 % 0.0 % 0.0 % 0.0 % Total Lines 29.2 % 21.3 % 18.2 % 12.4 % 8.9 % 4.7 % 2.8 % 1.4 % 0.7 % 0.4 %

Reinsurance

Reinsurance	12 Months Ended
	Dec. 31, 2023
Reinsurance Disclosures [Abstract]
Reinsurance	9. Reinsurance In the normal course of business, the Company participates in reinsurance agreements in order to limit losses that may arise from catastrophes or other individually severe events. The Company primarily ceded all specific loss commercial liability risks in excess of $ 400,000 in 2023 and $ 340,000 in 2022. The Company ceded specific loss commercial property risks in excess of $ 400,000 in 2023 and $ 300,000 in 2022. The Company ceded homeowners specific risks in excess of $ 300,000 in 2023 and 2022. A "treaty" is a reinsurance agreement in which coverage is provided for a class of risks and does not require policy by policy underwriting of the reinsurer. "Facultative" reinsurance is where a reinsurer negotiates an individual reinsurance agreement for every policy it will reinsure on a policy-by-policy basis. A loss is covered under a reinsurance contract if the loss occurs within the effective dates of the agreement notwithstanding when the loss is reported. The Company entered into new specific loss reinsurance treaties on December 31, 2021 and January 1, 2022 which included a 40 % ceding commission. The reinsurance premiums related to these treaties increased by the same amount as the ceding commission. The ceding commissions were carried forward under the 2023 treaties with substantially similar terms. Reinsurance does not discharge the Company, as the direct insurer, from liability to its policyholders. Failure of reinsurers to honor their obligations could result in losses to the Company. The Company evaluates the financial condition of its reinsurers and monitors the concentration of credit risk arising from similar geographic regions, activities, or economic characteristics of the reinsurers to minimize its exposure to significant losses from reinsurer insolvencies. To date, the Company has not experienced any significant difficulties in collecting reinsurance recoverables. The Company's current reinsurance structure includes the following primary categories: Casualty Clash • Clash coverage is a type of reinsurance that provides additional coverage in the event that one casualty loss event results in two or more claims and recovery under the reinsurance treaties may otherwise be limited due to the amount, type or number of claims. Clash reinsurance further protects the balance sheet as it reduces the potential maximum loss on either a single risk or a large number of risks. • Effective January 1, 2022 through December 31, 2023, the Company was party to a workers’ compensation and casualty clash reinsurance treaty with a limit of $ 29.0 million in excess of $ 1.0 million. Facultative • The Company was party to a facultative reinsurance agreement with a large reinsurer for commercial auto physical damage risks primarily in excess of $ 400,000 . • The Company was party to a facultative reinsurance agreement with a large reinsurer for property risks with total insured values above the other reinsurance treaty limits. Liability • Effective January 1, 2019 through December 31, 2023, the Company was party to an excess of loss reinsurance treaty for commercial liability coverage with a limit of $ 600,000 in excess of $ 400,000 . Property • Effective January 1, 2020 through December 31, 2023, the Company was party to an excess of loss reinsurance treaty for personal property coverage with a limit of $ 1.7 million in excess of $ 300,000 , for homeowners' and dwelling fire business. • Effective January 1, 2023 through December 31, 2023, the Company was party to an excess of loss reinsurance treaty for commercial property coverage with a limit of $ 7.6 million in excess of $ 400,000 . • Effective January 1, 2022 through December 31, 2022, the Company was party to an excess of loss reinsurance treaty for commercial property coverage with a limit of $ 7.7 million in excess of $ 300,000 . • At December 31, 2023, the Company was covered for property catastrophe losses up to $ 27.0 million in excess of $ 3.0 million retention for the first event. This treaty terminates on June 1, 2024 . • At December 31, 2022, the Company was covered for property catastrophe losses up to $ 28.0 million in excess of a $ 2.0 million retention for the first event. This treaty terminates on June 1, 2023 . Quota Share • Under a quota share agreement, the reinsurer pays a percentage of all losses the insurer sustains in return for a similar percent of the premiums written on that risk. A ceding commission is paid by the reinsurer to the insurer to cover acquisition and operating expenses. • The Company ceded 90 % to 100 % of its commercial umbrella coverages under a quota share treaty. • The Company ceded 50 % of its cannabis program net written premiums under a quota share treaty. • The Company ceded 100 % of a small number of equipment breakdown, employment practices liability, data compromise, and cannabis cyber liability coverages that are occasionally bundled with other products under separate quota share agreements. Sale of Renewal Rights • On September 30, 2023, the Company entered into a 100% quota share reinsurance agreement with the buyer of the renewal rights described in Note 2 ~ Sale of Renewal Rights. The Company ceded $ 30.9 million of its gross unearned premiums relating to the security guard and alarm installation program in exchange for 22 % - 27 % ceding commission. Loss Portfolio Transfer • On November 1, 2022, the Company entered into a loss portfolio transfer (“LPT”) reinsurance agreement with Fleming Reinsurance Ltd (“Fleming Re”). Under the agreement, Fleming Re will cover an aggregate limit of $ 66.3 million of paid losses on $ 40.8 million of stated net reserves as of June 30, 2022, relating to accident years 2019 and prior. This covers substantially all of the commercial liability lines underwritten by the Company. Within the aggregate limit, there is a $ 5.5 million loss corridor in which the Company retains losses in excess of $ 40.8 million. Fleming Re is then responsible to cover paid losses in excess of $ 46.3 million up to $ 66.3 million. Accordingly, there is $ 20.0 million of adverse development cover for accident years 2019 and prior. Under the agreement, Fleming Re was compensated with $ 40.8 million for stated net reserves as of June 30, 2022, plus a one-time risk fee of $ 5.4 million. Recoverables due to the Company under this agreement are recorded as reinsurance recoverables. The agreement is between CIC and WPIC and Fleming Re. As of December 31, 2022, the Company has recorded losses through the $ 5.5 million corridor and $ 644,000 into the $ 20.0 million layer. As of December 31, 2022, the Consolidated Balance Sheet included $ 3.9 million of reinsurance recoverables on paid losses related to the LPT, and $ 25.9 million of reinsurance recoverables on unpaid losses related to the LPT. As of December, 31, 2023, the Company has recorded losses through the $ 5.5 million corridor and $ 9.1 million into the $ 20.0 million layer. As of December 31, 2023, the Consolidated Balance Sheet included $ 3.8 million of reinsurance recoverables on paid losses related to the LPT, and $ 10.9 million of reinsurance recoverables on unpaid losses related to the LPT. The Company assumes written premiums under a few fronting arrangements. The fronting arrangements are with unaffiliated insurers who write on behalf of the Company in markets that require a higher A.M. Best rating than the Company’s rating, or where the policies are written in a state where the Company is not licensed or for other strategic reasons. The Company assumed $ 43.6 million and $ 42.2 million of written premiums under the insurance fronting arrangements for the years ended December 31, 2023 and 2022, respectively. The following table presents the effects of reinsurance and assumed reinsurance transactions on written premiums, earned premiums and losses and LAE (dollars in thousands). In 2023, ceded written and earned premium amounts included $ 91,000 of reinsurance reinstatement costs related to catastrophe losses. In 2022, ceded written and earned premium amounts included $ 1.6 million of reinsurance reinstatement costs relating to Hurricane Ian. Year Ended December 31, 2023 2022 Written premiums: Direct $ 100,214 $ 95,832 Assumed 43,620 42,187 Ceded ( 75,146 ) ( 46,787 ) Net written premiums $ 68,688 $ 91,232 Earned premiums: Direct $ 96,595 $ 97,843 Assumed 49,977 37,558 Ceded ( 62,637 ) ( 38,690 ) Net earned premiums $ 83,935 $ 96,711 Loss and loss adjustment expenses: Direct $ 75,175 $ 73,000 Assumed 45,662 43,487 Ceded ( 38,424 ) ( 35,047 ) Net loss and LAE $ 82,413 $ 81,440

Debt

Debt	12 Months Ended
	Dec. 31, 2023
Debt Disclosure [Abstract]
Debt	10. Debt As of December 31, 2023 , the Company’s debt was comprised of two instruments: $ 17.9 million of 9.75 % public senior unsecured notes (the "New Public Notes") which were issued during the third quarter of 2023, and $ 9.8 million of privately placed 12.5 % senior secured notes ("Senior Secured Notes"), which were issued on September 30, 2023. The New Public Notes have substantially the same terms as the 6.75 % public senior unsecured notes (the "Old Public Notes") which matured on September 30, 2023 , except for the coupon. A summary of the Company's outstanding debt is as follows (dollars in thousands): As of December 31, 2023 As of December 31, 2022 Gross Debt Unamortized Net Debt Gross Debt Unamortized Net Debt Public Notes $ 17,887 $ 1,679 $ 16,208 $ 24,381 $ 195 $ 24,186 Senior Secured Notes 9,750 897 8,853 — — — Subordinated notes — — — 10,500 810 9,690 Total $ 27,637 $ 2,576 $ 25,061 $ 34,881 $ 1,005 $ 33,876 Public Note repayment and new issuance The Company repaid all the $ 24.4 million of its Old Public Notes which matured on September 30, 2023, by paying off $ 13.2 million in cash and exchanging $ 11.2 million for the New Public Notes. The New Public Notes have substantially the same terms as the Old Public Notes, except for the coupon. The Company funded the repayment of the Old Public Notes with several different fundraising initiatives. In August and September of 2023, the Company raised $ 6.7 million in cash under and S-1 registration statement for the New Public Notes. The Company also raised $ 6.2 million under an S-4 registration statement exchange offering for the New Public Notes and the Company's lender of its subordinated notes also exchanged its $ 5.0 million holding of the Company's Old Public Notes for $ 5.0 million of the New Public Notes under the S-1 registration statement. As such, there was a non-cash exchange of $ 11.2 million of Old Public Notes for New Public Notes. The remaining $ 6.5 million of cash needed to pay down the Old Public Notes was provided with cash on hand. New Public Notes The Company issued $ 17.9 million of New Public Notes during the third quarter of 2023. The new notes bear an interest rate of 9.75 % per annum, payable quarterly at the end of March, June, September and December and mature on September 30, 2028 . The Company may redeem the new notes, in whole or in part, at face value at any time after September 30, 2025. Senior Secured Notes The Company paid down $ 500,000 of principal on its subordinated notes on September 29, 2023. The Company then restructured its existing $ 10.0 million of subordinated notes to Senior Secured Notes with its lender on September 30, 2023. The Senior Secured Notes mature on September 30, 2028 , and bear an interest rate of 12.5 % per annum. Interest is payable quarterly at the end of March, June, September, and December . Quarterly principal payments of $ 250,000 are required starting on December 31, 2023 through September 30, 2028. The Company may redeem the senior secured notes, in whole or in part, for a call premium of $ 1.8 million less 22 % of the interest payment amounts that were paid prior to the date of redemption. The Company accounted for this restructuring as a debt modification because there was no concession made to the lender. Debt issuance costs The Company incurred $ 173,000 of restructuring costs from the lender related to the Senior Secured Notes. These costs were capitalized as debt issuance costs as of September 30, 2023. As of December 31, 2023 , the carrying value of the New Public Notes and Senior Secured Notes were offset by $ 1.7 million and $ 897,000 of capitalized costs, respectively. The debt issuance costs are amortized through interest expense over the life of the loans. Debt covenants The Senior Secured Notes contain various restrictive financial debt covenants that relate to the Company’s minimum tangible net worth, minimum fixed-charge coverage ratios, dividend paying capacity, reinsurance retentions, and risk-based capital ratios. The Senior Secured Notes also require that any proceeds the Company receives from asset sales be used to pay down the principal. As of December 31, 2023, the Company was not in compliance with the tangible net worth, dividend paying capacity, risk-based capital and consolidated debt to capital covenants. On March 27, 2024, the holders of the Senior Secured Notes waived the December 31, 2023 covenants and modified the minimum requirements of the financial debt covenants. Management expects to be in compliance with all debt covenants in future periods. The following table shows the scheduled principal payments of the Company's debt as of December 31, 2023 (dollars in thousands): Year Senior unsecured notes Senior secured notes 2024 1,000 — 2025 1,000 — 2026 1,000 — 2027 1,000 — 2028 5,750 17,887 Total $ 9,750 $ 17,887 Line of credit The Company maintained a $ 10.0 million line of credit with a national bank during 2022. The line of credit carried an interest rate at LIBOR plus 2.75 % per annum, payable monthly. The line of credit agreement matured on December 1, 2022, and was not renewed.

Income Taxes

Income Taxes	12 Months Ended
	Dec. 31, 2023
Income Tax Disclosure [Abstract]
Income Taxes	11. Income Taxes At December 31, 2023 , the Company had current income tax receivable of $ 65,000 included in other assets in the consolidated balance sheets. At December 31, 2022 , the Company had current income tax receivable of $ 58,000 included in other assets in the consolidated balance sheets. The income tax expense (benefit) is comprised of the following (dollars in thousands): Year Ended December 31, 2023 2022 Current tax expense (benefit) $ 26 $ ( 45 ) Deferred tax expense (benefit) ( 17 ) ( 9,396 ) Total income tax expense (benefit) $ 9 $ ( 9,441 ) The income tax expense (benefit) differed from the amounts computed by applying the statutory U.S. federal income tax rate of 21 % in 2023 and 2022 to pretax income as a result of the following (dollars in thousands): Year Ended December 31, 2023 2022 Income (loss) before income taxes $ ( 25,644 ) $ ( 20,490 ) Statutory U.S. federal income tax rate ( 5,385 ) ( 4,303 ) State income taxes, net of federal benefit ( 1,503 ) ( 5,984 ) Tax‑exempt investment income and dividend received deduction ( 13 ) ( 22 ) Nondeductible meals and entertainment 73 79 Valuation allowance on deferred tax assets 7,254 3,715 Equity-earnings from Affiliate — 195 Net gain from sale of agency assets — ( 2,848 ) Utilization of state NOLs — ( 386 ) Deferred corrections ( 476 ) — PPP Loan forgiveness — — Other 59 113 Income tax expense (benefit) $ 9 $ ( 9,441 ) Effective tax rate — 46.1 % The tax effects of temporary differences that give rise to significant portions of the deferred tax assets and deferred tax liabilities are presented below (dollars in thousands): December 31, 2023 2022 Deferred tax assets: Discounted unpaid losses and loss adjustment expenses $ 1,749 $ 1,217 Unearned premiums 1,648 2,324 Net operating loss carryforwards 16,960 12,152 Net unrealized losses on investments 2,780 3,687 State net operating loss carryforwards 6,523 5,097 Other 112 403 Gross deferred tax assets 29,772 24,880 Less valuation allowance ( 28,013 ) ( 21,663 ) Total deferred tax assets, net of allowance 1,759 3,217 Deferred tax liabilities: Investment basis difference 208 23 Tax rate change transition discounting 92 137 Equity investment in Affiliate — 691 Deferred policy acquisition costs 1,320 2,161 Intangible assets 115 115 Property and equipment 24 41 Other — 49 Total deferred tax liabilities 1,759 3,217 Net deferred tax liability $ — $ — The net deferred tax liability is recorded in accounts payable and accrued expenses in the consolidated balance sheets. As of December 31, 2023 , the Company has NOL carryforwards for federal income tax purposes of $ 80.8 million, of which $ 78.2 million expire in tax years 2030 through 2043 and $ 10.3 million never expire. Of this amount, $ 19.5 million are limited in the amount that can be utilized in any one year and may expire before they are realized under Section 382 of the Internal Revenue Code. The Company has state net operating loss carryforwards of $ 120.3 million, which expire in tax years 2024 through 2043. Management assesses the available positive and negative evidence to estimate whether sufficient future taxable income will be generated to permit the use of the existing deferred tax assets under the guidance of ASC 740. A significant piece of objective negative evidence evaluated was the cumulative loss incurred over the three‑year period ended December 31, 2023. Such objective evidence limits the Company's ability to consider other subjective evidence, such as management's projections for future growth. Based on its evaluation, the Company has recorded a valuation allowance of $ 28.0 million and $ 21.7 million at December 31, 2023 and 2022, respectively, to reduce the deferred tax assets to an amount that is more likely than not to be realized based on the provisions in ASC 740. The amount of the deferred tax assets considered realizable, however, could be adjusted if estimates of future taxable income during the carryforward period are reduced or if objective negative evidence in the form of cumulative losses is no longer present, and additional weight may be given to subjective evidence, such as the Company’s projections for growth. The Company files consolidated federal income tax returns. For the years before 2020, the Company is no longer subject to U.S. federal examinations; however, the Internal Revenue Service has the ability to review years prior to 2020 to the extent the Company utilized tax attributes carried forward from those prior years. The statute of limitations on state filings is generally three to four years .

Statutory Financial Data, Risk-

Statutory Financial Data, Risk-Based Capital and Dividend Restrictions	12 Months Ended
	Dec. 31, 2023
Insurance [Abstract]
Statutory Financial Data, Risk-Based Capital and Dividend Restrictions	12. Statutory Financial Data, Risk-Based Capital and Dividend Restrictions U.S. state insurance laws and regulations prescribe accounting practices for determining statutory net income and capital and surplus for insurance companies. In addition, state regulators may permit statutory accounting practices that differ from prescribed practices. Statutory accounting practices prescribed or permitted by regulatory authorities for the Company’s Insurance Company Subsidiaries differ from GAAP. The principal differences between statutory accounting practices ("SAP") and GAAP as they relate to the financial statements of the Company’s Insurance Company Subsidiaries are (i) policy acquisition costs are expensed as incurred under SAP, whereas they are deferred and amortized under GAAP, (ii) deferred tax assets are subject to more limitations regarding what amounts can be recorded under SAP and (iii) bonds are recorded at amortized cost under SAP and fair value under GAAP. Risk-Based Capital ("RBC") requirements as promulgated by the National Association of Insurance Commissioners (‘‘NAIC’’) require property and casualty insurers to maintain minimum capitalization levels determined based on formulas incorporating various business risks (e.g., investment risk, underwriting profitability, etc.) of the Insurance Company Subsidiaries. As of December 31, 2023, CIC fell within the Company Action Level and WPIC fell within the Regulatory Action Level of the RBC formula. WPIC also fell below two other regulatory thresholds which are necessary to stay in compliance. Management is required to provide a plan to its domiciliary regulator that shows how the Companies will get above the minimum level requirements. Management believes that the planned reduction in premium anticipated by a strategic shift to use third-party insurers for substantially all of its commercial lines business will be sufficient to bring the Companies back into compliance by December 31, 2024. Management expects to substantially cease all writings in WPIC by the end of the second quarter of 2024. In the event the Companies do not regain compliance, the director may suspend, revoke, or limit the certificate of authority of the Companies. As of December 31, 2022, the Insurance Company Subsidiaries’ adjusted capital and surplus exceeded their authorized control level as determined by the NAIC’s risk-based capital models. Summarized 2023 and 2022 statutory basis information for the non-captive Insurance Company Subsidiaries, which differs from generally accepted accounting principles, is as follows (dollars in thousands). CIC WPIC 2023 Statutory capital and surplus $ 32,117 $ 7,494 RBC authorized control level 19,050 5,268 Statutory net income (loss) ( 14,014 ) ( 9,841 ) RBC % 169 % 142 % CIC WPIC 2022 Statutory capital and surplus $ 47,827 $ 20,651 RBC authorized control level 15,541 5,098 Statutory net income (loss) ( 6,846 ) ( 4,171 ) RBC % 308 % 405 % Dividend Restrictions The state insurance statutes in which the Insurance Company Subsidiaries are domiciled limit the amount of dividends that they may pay annually without first obtaining regulatory approval. Generally, the limitations are based on the greater of statutory net income for the preceding year or 10 % of statutory surplus at the end of the preceding year. The Insurance Company Subsidiaries must receive regulatory approval in order to pay dividends to the Parent Company from its Insurance Company Subsidiaries.

Shareholders' Equity

Shareholders' Equity	12 Months Ended
	Dec. 31, 2023
Stockholders' Equity Note [Abstract]
Shareholders' Equity	13. Shareholders’ Equity Preferred Stock On December 20, 2023, the Company issued $ 6.0 million of its newly designated Series A Preferred Stock (the "Preferred Stock"), no par value, through a private placement of 1,000 shares priced at $ 6,000 per share that matures on June 30, 2026 . The Preferred Stock was sold to Clarkston 91 West LLC (the "Purchaser"), an entity affiliated with Gerald and Jeffrey Hakala, members of the Board of Directors of the Company. The Company intends to use the proceeds for working capital and general corporate purposes. Preferred Stock shareholders have no voting rights and optional redemption is only in the control of the Company. The Preferred Stock requires quarterly dividend payments. The Preferred Stock dividend rate is equal to the prime rate of Waterford Bank, N.A. ("Waterford Bank"), or 8.0 %, whichever is higher, plus 200 basis points. As of December 31, 2023 , this equated to an annualized rate of 10.5 %. The Company has the option to redeem the Preferred Stock at the end of any fiscal quarter, in whole or in part, at a price equal to issue price, plus the amount that would result in a 20.0 %, compounded annually, annualized return to the holder (inclusive of the dividends paid), on the portion being redeemed. On the maturity date, each outstanding share of the Preferred Stock, that has not otherwise been redeemed, shall, without any further action by the holders, automatically convert into 4,000 shares of the Company's common stock, subject to adjustment for reverse and forward stock splits, stock dividends, stock combinations and other similar transactions of the common stock that occur after the initial issue date. As of December 31, 2023 and 2022 , the Company had 1,000 and 0 issued and outstanding shares of Preferred Stock, respectively. Common Stock On August 10, 2022, the Company issued $ 5.0 million of common equity through a private placement of 2,500,000 shares priced at $ 2.00 per share. The participants in the private placement consisted of members of the Company's Board of Directors. The Company used the proceeds for growth capital in the Company's specialty core business segments. For the year ended December 31, 2023 , the Company repurchased 1,968 shares of stock valued at approximately $ 3,000 related to the vesting of the Company’s restricted stock units. Upon the repurchase of the Company’s shares, the shares remain authorized, but not issued or outstanding. For the year ended December 31, 2022 , the Company repurchased 1,968 shares of stock valued at approximately $ 4,000 related to the vesting of the Company’s restricted stock units. The Company's additional paid-in capital relating to the Company's stock repurchases was $ 10,000 for the year ended December 31, 2022. The capital increase was due to a $ 14,000 adjustment for cash returned related to the Company's stock repurchase program. As of December 31, 2023 and 2022 , the Company had 12,222,881 and 12,215,849 issued and outstanding shares of common stock, respectively. Holders of common stock are entitled to one vote per share and to receive dividends only when and if declared by the board of directors. The holders have no preemptive, conversion or subscription rights.

Accumulated Other Comprehensive

Accumulated Other Comprehensive Income (Loss)	12 Months Ended
	Dec. 31, 2023
Equity [Abstract]
Accumulated Other Comprehensive Income (Loss)	14. Accumulated Other Comprehensive Income (Loss) The following table presents changes in accumulated other comprehensive income (loss) for unrealized gains and losses on available-for-sale securities (dollars in thousands): Year Ended 2023 2022 Balance at beginning of period $ ( 18,203 ) $ ( 2,110 ) Other comprehensive income (loss) before reclassifications 3,624 ( 16,024 ) Less: amounts reclassified from accumulated other comprehensive income (loss) ( 51 ) 69 Net current period other comprehensive income (loss) 3,675 ( 16,093 ) Balance at end of period $ ( 14,528 ) $ ( 18,203 )

Earnings Per Share

Earnings Per Share	12 Months Ended
	Dec. 31, 2023
Earnings Per Share [Abstract]
Earnings Per Share	15. Earnings Per Share Basic and diluted earnings (loss) per share are computed by dividing net income allocable to common shareholders by the weighted average number of common shares outstanding during the period. The dividends on preferred stock are deducted from the net income to arrive at net income allocable to common shareholders. The following table presents the calculation of basic and diluted earnings (loss) per common share, as follows (dollars in thousands, except share and per share amounts): Year Ended 2023 2022 Net income (loss) $ ( 25,904 ) $ ( 10,681 ) Preferred stock dividends 19 - Net income (loss) allocable to common shareholders $ ( 25,923 ) $ ( 10,681 ) Weighted average common shares, basic and diluted* 12,220,511 10,692,090 Earnings (loss) per share, basic and diluted $ ( 2.12 ) $ ( 1.00 ) * The preferred shares that may be convertible into a total of 4,000,000 common shares were anti-dilutive and thus did not impact the diluted earnings per share calculation. There were no unvested restricted stock units as of December 31, 2023. The non-vested shares of the restricted stock units and stock options were anti-dilutive as of December 31, 2022. Therefore, the non-vested shares are excluded from earnings (loss) per share for the years ended December 31, 2022 .

Stock-based Compensation

Stock-based Compensation	12 Months Ended
	Dec. 31, 2023
Share-Based Payment Arrangement [Abstract]
Stock-based Compensation	16. Stock-based Compensation On March 8, 2022 the Company issued options to purchase 630,000 shares of the Company's common stock to two named executive officers. The right to exercise the options will vest over a five-year period on a straight-line basis. The options have a strike price of $ 4.53 per share and will expire on March 8, 2032 . The estimated grant date fair value of these options is $ 612,000 , which is being expensed ratably over the vesting period. A Black Scholes model was used to determine the fair value of the options at the time the options were issued, using the Company’s historical 5-year market price of its stock to determine volatility (equating to 65.04 %), an estimated 5-year term to exercise the options, a 5-year risk-free rate of return of 1.8 %, and the market price for the Company’s stock of $ 2.40 per share. On June 30, 2020, the Company issued options to purchase 280,000 shares of the Company’s common stock to certain executive officers and other employees. The right to exercise the options will vest over a five-year period on a straight-line basis. The options have a strike price of $ 3.81 per share and expire on June 30, 2030 . The estimated grant date fair value of these options is $ 290,000 , which will be expensed ratably over the vesting period. In 2016 and 2018, the Company issued 111,281 and 70,000 , respectively, of restricted stock units (“RSUs”) to various employees to be settled in shares of common stock, which were valued at $ 909,000 , and $ 404,000 , respectively, on the dates of grant. The Company recorded $ 17,000 and $ 56,000 of compensation expense related to the RSUs for the years ended December 31, 2023, and 2022 , respectively. There are no unvested RSUs as of December 31, 2023. The Company recorded $ 51,000 and $ 53,000 of compensation expense for the years ended December 31, 2023 and 2022 , respectively, related to the stock options granted on June 30, 2020. There were 100,000 options outstanding and unvested as of December 31, 2023 , which will generate an estimated future expense of $ 78,000 . The Company recorded $ 122,000 and $ 102,000 of compensation expense for the years ended December 31, 2023, and 2022 , respectively, related to the stock options granted on March 8, 2022. There were 504,000 options outstanding and unvested as of December 31, 2023 , which will generate an estimated future expense of $ 387,000 .

Related Party Transactions

Related Party Transactions	12 Months Ended
	Dec. 31, 2023
Related Party Transactions [Abstract]
Related Party Transactions	17. Related Party Transactions J. Grant Smith joined the Company’s Board on January 12, 2024. J. Grant Smith is the President and Chief Operating Officer of Waterford Bank. As of December 31, 2023, the Company owned $ 528,000 of Waterford Bank's common stock. The Company employs Nicholas J. Petcoff as its Chief Executive Officer and a Director of the Company's Board of Directors. Nicholas J. Petcoff became the Company's sole Chief Executive Officer on December 31, 2023. The Company employed Andrew D. Petcoff as its Senior Vice President of Personal Lines and as President of CIS, until June 30, 2021. The Company’s employment of Andrew D. Petcoff ended as the result of the Venture Transaction. See Note 4 ~ Sale of Certain Agency Business for additional details. Andrew D. Petcoff resigned from the Company's Board of Directors on December 31, 2022. Andrew D. Petcoff is now the President of Sycamore Specialty Underwriters, LLC ("SSU"), a related Affiliate to the Company as of December 31, 2022. See Note 3 ~ VSRM Transaction for additional details. Nicholas J. Petcoff has been employed with the Company since 2009. Andrew D. Petcoff had formerly been employed with the Company since 2009. They are the sons of the Company's former Executive Chairman and Co-Chief Executive Officer, James G. Petcoff. James G. Petcoff stepped down as the Company's Executive Chairman and Co-Chief Executive Officer on December 31, 2023. The Company employed B. Matthew Petcoff as Vice President of CIS until June 30, 2021. B. Matthew Petcoff is the brother of the Executive Chairman and Co-Chief Executive Officer, James G. Petcoff. The Company also employed Hilary Petcoff as its Vice President of Enterprise Risk Management until June 30, 2021. Ms. Petcoff is the daughter of the Company’s Executive Chairman and Co-Chief Executive Officer, James G. Petcoff. As a result of the transaction in Note 3 ~ VSRM Transaction , B. Matthew Petcoff and Hilary Petcoff are no longer employees of Venture Agency Holdings, Inc., and are no longer affiliated with the Company as of December 31, 2022. In October 2022, the Company acquired control over Venture (a previous equity method investee) for total consideration of $ 9.7 million as further described in Note 3 ~ VRSM Transaction. See Note 13 ~ Shareholders' Equity for the preferred and common stock issuances to members of the Company's Board.

Employee Benefit Plans

Employee Benefit Plans	12 Months Ended
	Dec. 31, 2023
Retirement Benefits [Abstract]
Employee Benefit Plans	18. Employee Benefit Plans The Company maintains a retirement savings plan under section 401(k) of the Internal Revenue Code (the “Plan”) for certain eligible employees. Eligible employees electing to participate in the 401(k) plan may defer and contribute from 1 % to 100 % of their compensation on a pre‑tax or post-tax basis, subject to statutory limits. The Company will match the employees’ contributions up to the first 4 % of their compensation. The Company’s Plan expense amounted to $ 411,000 and $ 457,000 for the years ended December 31, 2023 and 2022 , respectively.

Commitments and Contingencies

Commitments and Contingencies	12 Months Ended
	Dec. 31, 2023
Commitments and Contingencies Disclosure [Abstract]
Commitments and Contingencies	19. Commitments and Contingencies Legal proceedings The Company and its subsidiaries are subject at times to various claims, lawsuits and proceedings relating principally to alleged errors or omissions in the placement of insurance, claims administration, and other business transactions arising in the ordinary course of business. Where appropriate, the Company vigorously defends such claims, lawsuits and proceedings. Some of these claims, lawsuits and proceedings seek damages, including consequential, exemplary or punitive damages, in amounts that could, if awarded, be significant. Most of the claims, lawsuits and proceedings arising in the ordinary course of business are covered by the insurance policy at issue. We account for such activity through the establishment of unpaid losses and LAE reserves. In accordance with accounting guidance, if it is probable that a liability has been incurred as of the date of the financial statements and the amount of loss is reasonably estimable; then an accrual for the costs to resolve these claims is recorded by the Company in the accompanying consolidated balance sheets. Periodic expenses related to the defense of such claims are included in the accompanying consolidated statements of operations. On the basis of current information, the Company does not believe that there is a reasonable possibility that any material loss exceeding amounts already accrued, if any, will result from any of the claims, lawsuits and proceedings to which the Company is subject to, either individually, or in the aggregate. Commitments The Company is party to an agreement with an unaffiliated company to provide a policy administration, billing, and claims system for the Company. The scope of work and fee structure has changed over time. Currently, the agreement requires a minimum monthly payment of $ 30,000 with a fee schedule that is scalable with the premium volume, and expires on November 1, 2026. The Company incurred $ 1.9 million of expenses from its use of the system in 2023 and 2022, respectively.

Segment Information

Segment Information	12 Months Ended
	Dec. 31, 2023
Segment Reporting [Abstract]
Segment Information	20. Segment Information The Company is engaged in the sale of property and casualty insurance products and has organized its business model around three classes of insurance businesses: commercial lines, personal lines, and wholesale agency business. Within these three businesses, the Company offers various insurance products and insurance agency services. Such insurance businesses are engaged in underwriting and marketing insurance coverages, and administering claims processing for such policies. The Company views the commercial and personal lines segments as underwriting business (business that takes on insurance underwriting risk). The wholesale agency business provides non-risk bearing revenue through commissions and policy fees. The wholesale agency business increases the product options to the Company’s independent retail agents by offering both insurance products from the Insurance Company Subsidiaries as well as products offered by other insurers. The Company defines its operating segments as components of the business where separate financial information is available and used by the chief operating decision makers in deciding how to allocate resources to its segments and in assessing its performance. In assessing performance of its operating segments, the Company’s chief operating decision makers, the Chief Executive Officer, review a number of financial measures including gross written premiums, net earned premiums, losses and LAE, net of reinsurance recoveries, and other revenue and expenses. The primary measure used for making decisions about resources to be allocated to an operating segment and assessing its performance is segment underwriting gain or loss which is defined as segment revenues, consisting of net earned premiums and other income, less segment expenses, consisting of losses and LAE, policy acquisition costs and operating expenses of the operating segments. Operating expenses primarily include compensation and related benefits for personnel, policy issuance and claims systems, rent and utilities. The Company markets, distributes and sells its insurance products through its own insurance agencies and a network of independent agents. All of the Company’s insurance activities are conducted in the United States with a concentration of activity in Michigan, Texas, Oklahoma and California. For the years ended December 31, 2023 and 2022 , gross written premiums attributable to these four states were 59.9 % and 52.8 %, respectively, of the Company’s total gross written premiums. The following table summarizes our net earned premiums: Net Earned Premium 2023 2022 Commercial 71 % 84 % Personal 29 % 16 % Total 100 % 100 % The wholesale agency business sells insurance products on behalf of the Company’s commercial and personal lines businesses as well as to third-party insurers. Certain acquisition costs incurred by the commercial and personal lines businesses are reflected as commission revenue for the wholesale agency business and are eliminated in the Eliminations category. In addition to the reportable segments, the Company maintains a Corporate and Other category to reconcile segment results to the consolidated totals. The Corporate and Other category includes: (i) corporate operating expenses such as salaries and related benefits of the Company’s executive management team, some finance and information technology personnel, and other corporate headquarters expenses, (ii) interest expense on the Company’s debt obligations; (iii) depreciation and amortization on property and equipment, and (iv) all investment income activity. All investment income activity is reported within net investment income, net realized investment gains, and change in fair value of equity securities on the consolidated statements of operations. The Company’s assets on the consolidated balance sheet are not allocated to the reportable segments. The following tables present information by reportable segment (dollars in thousands): Year Ended December 31, 2023 Commercial Personal Under-writing Wholesale Agency Corp-orate Elim-inations Total Gross written premiums $ 107,078 $ 36,756 $ 143,834 $ — $ — $ — $ 143,834 Net written premiums $ 36,580 $ 32,108 $ 68,688 $ — $ — $ — $ 68,688 Net earned premiums $ 59,221 $ 24,714 $ 83,935 $ — $ — $ — $ 83,935 Agency commission income — — — 5,680 — — 5,680 Other income 217 96 313 1,379 239 ( 1,237 ) 694 Segment revenue 59,438 24,810 84,248 7,059 239 ( 1,237 ) 90,309 Loss and loss adjustment expenses, net 62,828 19,585 82,413 — — — 82,413 Policy acquisition costs 9,134 6,663 15,797 6,401 — ( 1,306 ) 20,892 Operating expenses 11,988 3,444 15,432 1,153 1,306 — 17,891 Segment expenses 83,950 29,692 113,642 7,554 1,306 ( 1,306 ) 121,196 Segment underwriting gain (loss) ( 24,512 ) ( 4,882 ) ( 29,394 ) ( 495 ) ( 1,067 ) 69 ( 30,887 ) Net investment income 5,526 5,526 Net realized investment gains (losses) ( 20 ) ( 20 ) Change in fair value of equity securities 608 608 Gain on sale of renewal rights 2,335 2,335 Other gains — — Interest expense ( 3,206 ) ( 3,206 ) Income (loss) before income taxes $ ( 24,512 ) $ ( 4,882 ) $ ( 29,394 ) $ ( 495 ) $ 4,176 $ 69 $ ( 25,644 ) Selected Balance Sheet Data: Deferred policy acquisition costs $ 2,047 $ 4,357 $ ( 119 ) $ 6,285 Unearned premiums 45,494 19,656 65,150 Unpaid losses and loss adjustment expenses 169,039 5,573 174,612 Year Ended December 31, 2022 Commercial Personal Under-writing Wholesale Agency Corp-orate Elim-inations Total Gross written premiums $ 116,868 $ 21,151 $ 138,019 $ — $ — $ — $ 138,019 Net written premiums $ 72,318 $ 18,914 $ 91,232 $ — $ — $ — $ 91,232 Net earned premiums $ 80,823 $ 15,888 $ 96,711 $ — $ — $ — $ 96,711 Agency commission income — — — 1,414 — — 1,414 Other income 245 82 327 4,298 271 ( 3,542 ) 1,354 Segment revenue 81,068 15,970 97,038 5,712 271 ( 3,542 ) 99,479 Loss and loss adjustment expenses, net 70,762 10,678 81,440 — — — 81,440 Policy acquisition costs 17,682 4,604 22,286 3,653 — ( 3,760 ) 22,179 Operating expenses 13,069 1,936 15,005 2,612 1,192 ( 20 ) 18,789 Loss portfolio transfer risk fee 5,400 — 5,400 — — — 5,400 Segment expenses 106,913 17,218 124,131 6,265 1,192 ( 3,780 ) 127,808 Segment underwriting gain (loss) ( 25,845 ) ( 1,248 ) ( 27,093 ) ( 553 ) ( 921 ) $ 238 ( 28,329 ) Net investment income 32 3,011 3,043 Net realized investment gains (losses) ( 1,505 ) ( 1,505 ) Change in fair value of equity securities 403 403 Gain from VSRM Transaction 8,810 8,810 Other gains ( 1 ) 60 59 Interest expense ( 42 ) ( 2,929 ) ( 2,971 ) Income (loss) before income taxes $ ( 25,845 ) $ ( 1,248 ) $ ( 27,093 ) $ ( 564 ) $ 6,929 $ 238 $ ( 20,490 ) Selected Balance Sheet Data: Deferred policy acquisition costs $ 7,683 $ 2,796 $ ( 189 ) $ 10,290 Unearned premiums 56,565 11,322 67,887 Unpaid losses and loss adjustment expenses 159,558 5,981 165,539

Subsequent Events

Subsequent Events	12 Months Ended
	Dec. 31, 2023
Subsequent Events [Abstract]
Subsequent Events	21. Subsequent Events The Company performed an evaluation of subsequent events through the date the financial statements were issued and determined there were no recognized or unrecognized subsequent events that would require an adjustment or additional disclosure in the condensed consolidated financial statements as of December 31, 2023 .

Schedule II - Condensed Financi

Schedule II - Condensed Financial Information of Registrant	12 Months Ended
	Dec. 31, 2023
Condensed Financial Information Disclosure [Abstract]
Schedule II - Condensed Financial Information of Registrant	Sched ule II Conifer Holdings, Inc. Condensed Financial Information of Registrant Balance Sheets – Parent Company Only (dollars in thousands) December 31, 2023 2022 Assets Investment in subsidiaries $ 31,157 $ 56,670 Cash 3,174 9,022 Due from Affiliate 33 113 Other assets 1,457 2,434 Total assets $ 35,821 $ 68,239 Liabilities and Shareholders' Equity Liabilities: Debt $ 29,061 $ 33,876 Due to subsidiaries 3,436 9,754 Other liabilities 1,798 5,659 Total liabilities 34,295 49,289 Shareholders' equity: Preferred stock, no par value ( 10,000,000 shares authorized; 1,000 and 0 issued and outstanding, respectively) 6,000 — Common stock, no par value ( 100,000,000 shares authorized; 12,222,881 12,215,849 issued and outstanding, respectively) 98,100 97,913 Accumulated deficit ( 86,683 ) ( 60,760 ) Accumulated other comprehensive income (loss) ( 15,891 ) ( 18,203 ) Total shareholders' equity 1,526 18,950 Total liabilities and shareholders' equity $ 35,821 $ 68,239 The accompanying notes are an integral part of the Condensed Financial Information of Registrant. Schedule II Conifer Holdings, Inc. Condensed Financial Information of Registrant Statements of Comprehensive Income (Loss) – Parent Company Only (dollars in thousands) Year Ended December 31, 2023 2022 Revenue Management fees from subsidiaries $ 17,367 $ 4,980 Other income 819 190 Total revenue 18,186 5,170 Expenses Operating expenses 14,133 14,365 Interest expense 3,079 2,816 Total expenses 17,212 17,181 Income (loss) before equity in earnings (losses) of subsidiaries and income tax expense (benefit) 974 ( 12,011 ) Income tax expense (benefit) 73 ( 4,078 ) Income (loss) before equity earnings (losses) of subsidiaries 901 ( 7,933 ) Equity earnings (losses) in subsidiaries ( 26,805 ) ( 2,748 ) Net income (loss) ( 25,904 ) ( 10,681 ) Other Comprehensive Income Equity in other comprehensive income (loss) of subsidiaries 2,312 ( 16,093 ) Total Comprehensive income (loss) $ ( 23,592 ) $ ( 26,774 ) The accompanying notes are an integral part of the Condensed Financial Information of Registrant. Schedule II Conifer Holdings, Inc. Condensed Financial Information of Registrant Statement of Cash Flows – Parent Company Only (dollars in thousands) Year Ended December 31, 2023 2022 Cash Flows from Operating Activities Net income (loss) $ ( 25,904 ) $ ( 10,681 ) Adjustments to reconcile net income (loss) to net cash used in Depreciation and amortization 545 436 Equity in undistributed (income) loss of subsidiaries 26,805 2,748 Stock-based compensation expense 190 211 Deferred income tax expense ( 3,806 ) 3,884 Other (gain) loss — — Changes in operating assets and liabilities: Due from subsidiaries ( 6,318 ) 2,699 Due from Affiliate 80 107 Current income tax recoverable — — Other assets 860 62 Other liabilities ( 73 ) ( 203 ) Net cash provided by (used in) operating activities ( 7,621 ) ( 737 ) Cash Flows From Investing Activities Contributions to subsidiaries 1,019 4,000 Dividends received from subsidiaries — — Purchases of investments — — Purchases of property and equipment — — Net cash provided by (used in) investing activities 1,019 4,000 Cash Flows From Financing Activities Proceeds received from issuance of shares of preferred stock 6,000 — Proceeds received from issuance of shares of common stock — 5,000 Proceeds from issuance of long-term debt 10,727 — Repurchase of common stock ( 3 ) 10 Borrowings under debt arrangements — 5,000 Repayment of borrowings under debt arrangements — ( 5,000 ) Paydown of long-term debt ( 13,971 ) — Debt issuance costs ( 1,999 ) — Net cash provided by financing activities 754 5,010 Net increase (decrease) in cash ( 5,848 ) 8,273 Cash at beginning of period 9,022 749 Cash at end of period $ 3,174 $ 9,022 Supplemental Disclosure of Cash Flow Information: Interest paid 2,949 2,979 Preferred stock dividends declared but not paid at end of period 19 — The accompanying notes are an integral part of the Condensed Financial Information of Registrant. 1. Accounting Policies Organization Conifer Holdings, Inc. (the “Parent”) is a Michigan‑domiciled holding company organized for the purpose of managing its insurance entities. The Parent conducts its principal operations through these entities. Basis of Presentation The accompanying condensed financial information should be read in conjunction with the Consolidated Financial Statements and related Notes of Conifer Holdings, Inc. and Subsidiaries. Investments in subsidiaries are accounted for using the equity method. Under the equity method, the investment in subsidiaries is stated at cost plus contributions and equity in undistributed income (loss) of consolidated subsidiaries less dividends received since the date of acquisition. The Parent’s operations consist of income earned from management and administrative services performed for the insurance entities pursuant to intercompany services agreements. These management and administrative services include providing management, marketing, offices and equipment, and premium collection, for which the insurance companies pay fees based on a percentage of gross premiums written. Also, the Parent receives commission income for performing agency services. The primary operating costs of the Parent are salaries and related costs of personnel, information technology, administrative expenses, and professional fees. The income received from the management and administrative services is used to cover operating costs, meet debt service requirements and cover other holding company obligations. Estimates and Assumptions Preparation of the condensed financial statements in conformity with GAAP requires management to make estimates and assumptions that affect the amounts reported in the condensed financial statements and accompanying disclosures. Those estimates are inherently subject to change, and actual results may ultimately differ from those estimates. Dividends The Parent received $ 1.4 million in cash dividends from RCIC in 2023. The Parent received a $ 10.8 million dividend from CIS during the fourth quarter of 2022. 2. Guarantees The Parent has guaranteed the principal and interest obligations of a $ 10.0 million surplus note issued by Conifer Insurance Company to White Pine Insurance Company (both wholly owned subsidiaries). The note pays interest annually at a per annum rate of 4 % and has no maturity. As of December 31, 2023, the surplus note was adjusted to a fair value of $ 6.8 million as a result of KBRA downgrading CIC's surplus note rating from BBB- to BB+. This change in CIC's rating required a change in the statutory statement presentation from a cost basis to a fair value basis of accounting.

Schedule V - Valuation and Qual

Schedule V - Valuation and Qualifying Accounts	12 Months Ended
	Dec. 31, 2023
SEC Schedule, 12-09, Valuation and Qualifying Accounts [Abstract]
Schedule V - Valuation and Qualifying Accounts	Balance at Charged to Decrease to Deductions from Balance at Valuation for Deferred Tax Assets 2023 21,663 7,254 ( 904 ) — 28,013 2022 14,594 3,715 3,354 — 21,663

Summary of Significant Accoun_2

Summary of Significant Accounting Policies (Policies)	12 Months Ended
	Dec. 31, 2023
Accounting Policies [Abstract]
Basis of Presentation and Management Representation	Basis of Presentation and Management Representation The consolidated financial statements include accounts, after elimination of intercompany accounts and transactions, of Conifer Holdings, Inc. (the “Company” or “Conifer”), its wholly owned subsidiaries Conifer Insurance Company ("CIC"), Red Cedar Insurance Company ("RCIC"), White Pine Insurance Company ("WPIC"), Conifer Insurance Services ("CIS") formerly known as Sycamore Insurance Agency, Inc. ("Sycamore"), and VSRM, Inc. ("VSRM"). VSRM has substantially no operations following the contribution to SSU as described in Note 3 ~ VSRM Transaction . CIC, WPIC, and RCIC are collectively referred to as the "Insurance Company Subsidiaries." On a stand-alone basis Conifer Holdings, Inc. is referred to as the "Parent Company." VSRM owns a 50 % non-controlling interest in Sycamore Specialty Underwriters, LLC ("SSU" or "Affiliate"). The accompanying consolidated financial statements have been prepared in conformity with accounting principles generally accepted in the United States of America (“GAAP”), which differ from statutory accounting practices prescribed or permitted for insurance companies by regulatory authorities.
Business	Business The Company is engaged in the sale of property and casualty insurance products and has organized its principal operations into three types of insurance businesses: commercial lines, personal lines, and agency business. The Company underwrites a variety of specialty insurance products, including property, general liability, liquor liability, automobile, and homeowners and dwelling policies. The Company markets and sells its insurance products through a network of independent agents, including managing general agents, whereby policies are written in all 50 states in the United States (“U.S.”). The Company’s corporate headquarters are located in Troy, Michigan with additional office facilities in Florida and Michigan.
Use of Estimates	Use of Estimates The preparation of financial statements in conformity with GAAP requires management to make estimates and assumptions that affect the reported amounts of assets and liabilities and disclosure of contingent assets and liabilities at the date of the financial statements and the reported amounts of revenues and expenses during the reporting period. In applying these estimates, management makes subjective and complex judgments that frequently require assumptions about matters that are inherently uncertain, including uncertainties associated with the Pandemic. While management believes the amounts included in the consolidated financial statements reflect management's best estimates and assumptions, actual results may differ from these estimates.
Cash, Cash Equivalents, and Short-term Investments	Cash, Cash Equivalents, and Short-term Investments Cash consists of cash deposits in banks, generally in operating accounts. Cash equivalents consist of money-market funds that are specifically used as overnight investments tied to cash deposit accounts. Short-term investments, consisting of money-market funds, are classified as short-term investments in the consolidated balance sheets as they relate to the Company’s investment activities.
Lease Accounting	Lease Accounting The Company accounts for leases under FASB Accounting Standards Update ("ASU") No. 2016-02, Leases (Topic 842), which required the recognition of a right-of-use asset and a corresponding lease liability, discounted to the present value upon initial recognition, for all leases that extend beyond 12 months. For operating leases, the asset and liability are amortized over the lease term with expense recognized on a straight-line basis and all cash flows included in the operating section of the consolidated statement of cash flows. We do not have any financing leases. Our operating leases consist primarily of real estate utilized in the operation of our businesses with lease terms ranging from 5 to 10 years . Management has determined the appropriate discount rate to use in calculating the right-to-use asset and lease liability is 9.5 %. The Company records a right-of-use asset and lease liabilities included in Other Assets and Other Liabilities in the Consolidated Balance Sheets. As of December 31, 2023 , the Company had a right-of-use asset of $ 960,000 , and lease liabilities of $ 1.0 million. As of December 31, 2022 , the Company had a right-of-use asset of $ 1.3 million, and lease liabilities of $ 1.3 million.
Investment Securities	Investment Securities Debt securities are classified as available-for-sale and reported at fair value. The Company determines the fair value using the market approach, which uses quoted prices or other relevant data based on market transactions involving identical or comparable assets. The Company purchases available-for-sale debt securities with the expectation that they will be held to maturity, however the Company may sell them if market conditions or credit‑related risk warrant earlier sales. The Company does not have any securities classified as held-to-maturity or trading. We review available-for-sale debt securities for credit losses based on current expected credit loss methodology at the end of each reporting period. We do not have any securities classified as trading or held to maturity. At each quarter-end, for available-for-sale debt securities in an unrealized loss position, the Company first assesses whether it intends to sell or it is more likely than not that it will be required to sell the security before recovery of its amortized cost basis. If either of the criteria regarding intent or requirement to sell is met, the security’s amortized cost basis is written down to fair value through earnings. For debt securities available-for-sale that do not meet the aforementioned criteria, the Company evaluates whether the decline in fair value has resulted from credit losses or other factors. In making this assessment, management considers the extent to which fair value is less than amortized cost, any changes to the rating of the security by a rating agency, and adverse conditions specifically related to the security, among other factors. If this assessment indicates that a credit loss exists, the present value of cash flows expected to be collected from the security are compared to the amortized cost basis of the security. If the present value of cash flows expected to be collected is less than the amortized cost basis, a credit loss exists and an allowance for credit losses is recorded for the credit loss, limited by the amount that the fair value is less than the amortized cost basis. Any impairment that has not been recorded through an allowance for credit losses is recognized in other comprehensive income. Changes in the allowance for credit losses are recorded as provision for (or reversal of) credit loss expense. Losses are charged against the allowance when management believes the uncollectability of an available-for-sale security is confirmed or when either of the criteria regarding intent or requirement to sell is met. Our outside investment managers assist us in this evaluation. The change in unrealized gain and loss on debt securities is recorded as a component of accumulated other comprehensive income (loss), net of the related deferred tax effect, until realized. The debt securities portfolio includes structured securities. The Company recognizes income from these securities using a constant effective yield based on anticipated prepayments and the estimated economic life of the securities. When actual prepayments differ significantly from anticipated prepayments, the estimated economic life is recalculated and the remaining unamortized premium or discount is amortized prospectively over the remaining economic life. Premiums and discounts on structured securities are amortized or accreted over the life of the related available‑for‑sale security as an adjustment to yield using the effective interest method. Such amortization and accretion is included in interest income in the consolidated statements of operations. Dividend and interest income are recognized when earned. Realized gains and losses from the sale of available-for-sale securities are determined on a specific-identification basis and included in earnings on the trade date. Equity securities that do not result in consolidation and are not accounted for under the equity method are measured at fair value and any changes in fair value are recognized in net income in the Consolidated Statements of Operations. Investment company limited partnerships are measured at their net asset value, which approximates fair value. Any changes in the net asset value are recognized in net income in the Consolidated Statements of Operations. The Company carries other equity investments that do not have a readily determinable fair value at cost, less impairment and adjusted for observable price changes under the measurement alternative provided under GAAP. We review these investments for impairment during each reporting period. These investments are a component of Other Assets in the Consolidated Balance Sheets. There were no observable prices changes to the Company's other equity investments during 2023 or 2022.
Credit Losses	Credit Losses Effective January 1, 2023, the Company adopted ASU 2016-13 Financial Instruments—Credit Losses (Topic 326): Measurement of Credit Losses on Financial Instruments, as amended, which introduces a new process for recognizing credit losses on financial instruments based on expected credit losses. This new standard replaces the incurred loss methodology and the concept of Other-than-Temporary Impairment (or “OTTI”) with an expected credit loss methodology that is sometimes referred to as the Current Expected Credit Loss (CECL) methodology. The guidance applies to Conifer's reinsurance recoverables, premium receivable, and debt securities. Results for reporting periods beginning after January 1, 2023 are presented under ASC 326, while prior period amounts continue to be reported in accordance with previously applicable U.S. GAAP. The adoption of ASC 326 did not have a material impact on the Company's financial statements.
Recognition of Premium Revenues	Recognition of Premium Revenues All of the property and casualty policies written by our insurance companies are considered short-duration contracts. These policy premiums are earned on a daily pro-rata basis, net of reinsurance, over the term of the policy, which are primarily twelve months in duration. The portion of premiums written that relate to the unexpired terms of policies in force are deferred and reported as unearned premium at the balance sheet date.
Reinsurance	Reinsurance Reinsurance premiums, commissions, losses and loss adjustment expenses ("LAE") on reinsured business are accounted for on a basis consistent with that used in accounting for the original policies issued and the terms of the reinsurance contracts. The amounts reported as reinsurance recoverables include amounts billed to reinsurers on losses and LAE paid as well as estimates of amounts expected to be recovered from reinsurers on insurance liabilities that have not yet been paid. Reinsurance recoverables on unpaid losses and LAE are estimated based upon assumptions consistent with those used in establishing the gross liabilities as they are applied to the underlying reinsured contracts. The Company records an allowance for uncollectible reinsurance recoverables based on an assessment of the reinsurer’s creditworthiness and collectability of the recorded amounts. Management believes an allowance for uncollectible recoverables from its reinsurers was not necessary for the periods presented. The Company receives ceding commissions in connection with certain ceded reinsurance. The ceding commissions are recorded as a reduction of policy acquisition costs. In 2022, the Company entered into a loss portfolio transfer ("LPT") reinsurance agreement. The LPT is a retroactive reinsurance contract. See Note 9 ~ Reinsurance for further details regarding the LPT.
Deferred Policy Acquisition Costs	Deferred Policy Acquisition Costs Costs incurred which are incremental and directly related to the successful acquisition of new or renewal insurance business are deferred. These deferred costs consist of commissions paid to agents (net of ceding commissions), premium taxes, and underwriting costs, including compensation and payroll related benefits. Proceeds from reinsurance transactions that represent recovery of acquisition costs reduce applicable unamortized acquisition costs in such a manner that net acquisition costs are capitalized and charged to expense. Amortization of such policy acquisition costs is charged to expense in proportion to premium earned over the estimated policy term. To the extent that unearned premiums on existing policies are not adequate to cover the sum of expected losses and LAE, unamortized acquisition costs and policy maintenance costs, unamortized deferred policy acquisition costs are charged to expense to the extent required to eliminate the premium deficiency. If the premium deficiency is greater than the unamortized policy acquisition costs, a liability is recorded for any such deficiency. As of December 31, 2023 , there was no premium deficiency reserve. The Company considers anticipated investment income in determining whether a premium deficiency exists. Management performs this evaluation at each insurance product line level.
Unpaid Losses and Loss Adjustment Expenses	Unpaid Losses and Loss Adjustment Expenses The liability for unpaid losses and LAE in the Consolidated Balance Sheets represents the Company’s estimate of the amount it expects to pay for the ultimate cost of all losses and LAE incurred that remain unpaid at the balance sheet date. The liability is recorded on an undiscounted basis. The process of estimating the liability for unpaid losses and LAE is a complex process that requires a high degree of judgment. The liability for unpaid losses and LAE represents the accumulation of individual case estimates for reported losses and LAE, and actuarially determined estimates for incurred but not reported losses and LAE and includes a provision for estimated costs to settle all outstanding claims at the balance sheet date. The liability for unpaid losses and LAE is intended to include the ultimate net cost of all losses and LAE incurred but unpaid as of the balance sheet date. The liability is stated net of anticipated deductibles, salvage and subrogation, and gross of reinsurance ceded. The estimate of the unpaid losses and LAE liability is continually reviewed and updated. Although management believes the liability for losses and LAE is reasonable, the ultimate liability may be more or less than the current estimate. The estimation of ultimate liability for unpaid losses and LAE is a complex, imprecise and inherently uncertain process, and therefore involves a considerable degree of judgment and expertise. The Company utilizes various actuarially‑accepted reserving methodologies in deriving the continuum of expected outcomes and ultimately determining its estimated liability amount. These methodologies utilize various inputs, including but not limited to written and earned premiums, paid and reported losses and LAE, expected initial loss and LAE ratio, which is the ratio of incurred losses and LAE to earned premiums, and expected claim reporting and payout patterns (including company-specific and industry data). The liability for unpaid loss and LAE does not represent an exact measurement of liability, but is an estimate that is not directly or precisely quantifiable, particularly on a prospective basis, and is subject to a significant degree of variability over time. In addition, the establishment of the liability for unpaid losses and LAE makes no provision for the broadening of coverage by legislative action or judicial interpretation or for the extraordinary future emergence of new types of losses not sufficiently represented in the Company’s historical experience or which cannot yet be quantified. As a result, an integral component of estimating the liability for unpaid losses and LAE is the use of informed subjective estimates and judgments about the ultimate exposure to unpaid losses and LAE. The effects of changes in the estimated liability are included in the results of operations in the period in which the estimates are revised. The Company allocates the applicable portion of the unpaid losses and LAE to amounts recoverable from reinsurers under reinsurance contracts and reports those amounts separately as assets on the consolidated balance sheets.
Income Taxes	Income Taxes Income taxes are accounted for under the asset and liability method. Deferred tax assets and liabilities are recognized for the future tax consequences attributable to differences between the financial statement carrying amounts of existing assets and liabilities and their respective tax bases and operating loss and tax-credit carryforwards. Deferred tax assets and liabilities are measured using enacted tax rates expected to apply to taxable income in the years in which those temporary differences are expected to be recovered or settled. The effect on deferred tax assets and liabilities of a change in tax rates is recognized in income in the period that includes the enactment date. Deferred tax assets are recognized to the extent that there is sufficient positive evidence, as allowed under the Accounting Standard Codification ("ASC") 740, Income Taxes, to support the recoverability of those deferred tax assets. The Company establishes a valuation allowance to the extent that there is insufficient evidence to support the recoverability of the deferred tax asset under ASC 740. In making such a determination, management considers all available positive and negative evidence, including future reversals of existing taxable temporary differences, projected future taxable income, tax‑planning strategies, and results of recent operations. If it is determined that the deferred tax assets would be realizable in the future in excess of their net recorded amount, an adjustment would be made to the deferred tax asset valuation allowance, which would reduce the provision for income taxes. As of December 31, 2023 and 2022 , the Company did no t have any unrecognized tax benefits and had no accrued interest or penalties related to uncertain tax positions.
Other Income	Other Income Other income consists primarily of fees charged to policyholders by the Company for services outside of the premium charge, such as installment billings or policy issuance costs. Commission income is also received by the Company’s insurance agencies for writing policies for third party insurance companies. The Company recognizes commission income on the later of the effective date of the policy, the date when the premium can be reasonably established, or the date when substantially all services related to the insurance placement have been rendered. Agency Commission Income Agency commission income is comprised of commissions earned on policies where the Company has no exposure to underlying risk on the policies written. Agency commission income is earned at the time the policy is written.
Agency Commission Income	Agency Commission Income Agency commission income is comprised of commissions earned on policies where the Company has no exposure to underlying risk on the policies written. Agency commission income is earned at the time the policy is written.
Operating Expenses	Operating Expenses Operating expenses consist primarily of other underwriting, compensation and benefits, information technology, facility and other administrative expenses.
Accounting Guidance Not Yet Adopted	Accounting Guidance Not Yet Adopted In January 2021, the FASB issued ASU 2022-06, Reference Rate Reform (Topic 848) . This guidance provides optional expedients and exceptions that are intended to ease the burden of updating contracts to contain a new reference rate due to the discontinuation of the London Inter-Bank Offered Rate (LIBOR). This guidance is available immediately and may be implemented in any period prior to the guidance expiration on December 31, 2024. Management does not expect the new guidance to have a material impact on the Company’s consolidated financial statements. In November 2023, the FASB issued ASU 2023-07, Segment Reporting (Topic 280). This guidance is intended to improve reportable segment disclosure requirements, primarily through enhanced disclosures about significant segment expenses, allowing financial statement users to better understand the components of a segment's profit or loss to assess potential future cash flows for each reportable segment and the entity as a whole. The amendments expand a public entity's segment disclosures by requiring disclosure of significant segment expenses that are regularly provided to the chief operating decision maker ("CODM"), clarifying when an entity may report one or more additional measures to assess segment performance, requiring enhanced interim disclosures, providing new disclosure requirements for entities with a single reportable segment, and requiring other new disclosures. ASU 2023-07 is effective for fiscal years beginning after December 31, 2024. Early adoption is permitted. the Company is currently evaluating the impact the adoption of this standard will have on its consolidated financial statements. In December 2023 , the FASB issued ASU 2023-09 , Income Taxes (Topic 740). ASU 2023-09 requires public business entities to disclose additional information with respect to the reconciliation of the effective tax rate to the statutory rate. Additionally, public business entities will need to disaggregate federal, state and foreign taxes paid in their financial statements. ASU 2023-09 is effective for public business entities for fiscal years, and interim periods within those fiscal years, beginning after December 15, 2024. The Company is currently evaluating the impact the adoption of this standard will have on its consolidated financial statements.
Risks and Uncertainties	Risks and Uncertainties The Company is exposed to interest rate risks as it maintains a significant amount of its investment portfolio in debt securities. As of December 31, 2023, total net unrealized losses in the debt securities was $ 13.3 million. Management believes it will not need to sell debt securities at significant losses as it has the ability and intention to hold them until maturity or their values improve.
Company Liquidity	Company Liquidity We conduct our business operations primarily through our Insurance Company Subsidiaries. Our ability to service debt, and pay administrative expenses is primarily reliant upon our intercompany service fees paid by the Insurance Company Subsidiaries to the holding company for management, administrative, and information technology services provided to the Insurance Company Subsidiaries by the Parent Company. The Parent Company may receive dividends from the Insurance Company Subsidiaries; however, this is not the primary means in which the holding company supports its funding as state insurance laws restrict the ability of our Insurance Company Subsidiaries to declare dividends to the Parent Company, and we do not anticipate any dividends being paid to us from our insurance subsidiaries during 2024 and 2025. Due to significant losses in 2023, much of which is attributable to strengthening reserves and severe storm activity affecting the Oklahoma homeowners business, both Insurance Company Subsidiaries lack sufficient capital to continue to underwrite the volume of business they have historically written. We incurred a consolidated net loss of $ 25.9 million. We used cash from the operation activities of $ 13.6 million, and our overall equity at December 31, 2023 totaled $ 2.9 million. As a result of these factors, we were out of compliance with several of our debt covenants and obtained a waiver from our lender. The aforementioned factors have resented additional liquidity and capital challenges on the Company's financial condition. Accordingly, management is in the process of implementing a strategic shift in which the Company will utilize third-party insurers and rely mostly on commission revenues generated by our managed general agency. Management may also consider the sale of other assets to generate additional cash resources available to the Company. In September 2023, the Company repaid its $ 24.4 million of 6.75 % public senior unsecured notes (the "Old Public Notes") and funded it, in part, with issuing 9.75 % public senior unsecured notes (the "New Public Notes") in the amount of $ 17.9 million. The Company also paid down $ 500,000 of principal on its subordinated notes on September 29, 2023. The Company then restructured its existing $ 10.0 million of subordinated notes to Senior Secure Notes with its lender on September 30, 2023. The Senior Secured Notes mature on September 30, 2028 , and bear an interest rate of 12.5 % per annum. Quarterly principal payments of $ 250,000 are required on the Senior Secured Notes starting on December 31, 2023 through September 30, 2028. The requirements on the new Senior Secured Notes will result in $ 1.0 million per year of principal to be paid on the senior secured debt that previously was not required. On December 20, 2023, the Company issued $ 6.0 million of its newly designated Series A Preferred Stock (the "Preferred Stock"). The Company intends to use the proceeds for working capital and general corporate purposes. As of the filing of this Form 10-K, the Insurance Company Subsidiaries are still the primary underwriters for the business produced by CIS and still the primary source of revenues and cash flows. The Insurance Company Subsidiaries are currently both required to provide an action plan with the state of domicile insurance regulator to remediate certain statutory capital and surplus regulatory deficiencies. If we do not remediate the regulatory deficiencies the insurance regulator could suspend or terminate the insurers’ authority to write business. Also, A.M. Best and Kroll downgraded the financial strength ratings of both companies and we terminated the rating relationship. Therefore, neither company is currently rated by a nationally recognized statistical rating organization which can have an impact on the ability to market to policyholders. We believe that the Insurance Company Subsidiaries will both regain compliance with the state insurance regulators, however, as part of the strategic shift, we no longer expect significant revenues to be generated through them after the second quarter of 2024. These circumstances could jeopardize the ability of the Company to generate insurance underwriting revenues which could put into doubt our ability to meet our obligations as they become due. To alleviate these concerns the Company is in the process of implementing the strategic shift mentioned above which will not require the use of either Insurance Company Subsidiary to generate the majority of the Company’s revenues going forward. Rather, the Company will expect to generate the vast majority of its revenue from commissions from third-party insurers. In order to successfully implement the strategic shift the Company must have in place producer agreements with third-party insurers. Currently the Company has executed one producer agreement for approximately 25 % of the existing commercial lines book of business and is expected to execute another producer agreement with a different third-party insurer for the remaining commercial lines business within a week of filing this Form 10-K. We expect to continue to underwrite the existing personal lines business within our Insurance Company Subsidiaries. With these producer agreements in place the Company expects to be able to generate the needed revenues to meeting our obligations as they become due over the next twelve months. In the event there are delays in implementing the strategic shift or other uncertainties arise with respect to completion of our strategic shift during 2024, these events could have a negative effect on our liquidity and ability to satisfy our obligations as they become due. If the Company were to experience any such uncertainties the Company believes it has alternative sources of liquidity available which are sufficient to cover any short-term needs as a result of any such uncertainties encountered. Management believes the current actions being executed to implement the planned strategic shift coupled with additional available sources of available liquidity, will be sufficient to enable the Company to meet its obligations for the foreseeable future.

VSRM Transaction (Tables)

VSRM Transaction (Tables)	12 Months Ended
	Dec. 31, 2023
Business Combinations [Abstract]
Schedule of Condensed Assets and Liabilities Incorporated Into Consolidated Balance Sheet from VSRM Acquisition	A condensed schedule of assets and liabilities incorporated into the consolidated balance sheet from the VSRM acquisition is provided below: Cash $ 3,921 Trade receivables 4,604 Customer relationship intangible assets 37,122 Other assets 574 Total assets $ 46,221 Trade and other payables 7,624 Deferred tax liability 9,407 Note payable to Affiliate 6,000 Senior debt 2,917 Total Liabilities $ 25,948 Fair value of net assets acquired $ 20,273
Schedule of Calculation of Revaluation Gain Related to Company's Equity Method Investment in VSRM as a Result of VSRM Transaction	The following table presents the calculation of the $ 8.8 million revaluation gain related to the Company's equity method investment in VSRM as a result of the VSRM Transaction: Carrying value of equity method investment in VSRM $ 1,773 Fair value of investment in VSRM 10,583 Gain on step acquisition $ 8,810
Schedule of Reconciles the Net Assets Disposed	The following table reconciles the net assets disposed of from this transaction: Cash at closing $ 32,759 Net liabilities transferred 1,499 Hold back 75 Stock of acquirer 3,822 Total purchase price $ 38,155 Cash $ 271 Premiums transferred to buyer 4,326 Intangible assets 38,154 Trade payables and accrued liabilities assumed by buyer ( 5,838 ) Net assets disposed of 36,913 Gross gain 1,242 Broker fee transaction costs ( 1,242 ) Net gain $ — The net gain on revaluation of the investment in VSRM and the disposal of the Security and Alarm Business line are summarized below: Gross gains $ 10,052 Broker fee ( 1,242 ) Net gain $ 8,810
Schedule of Assets And Liabilites Deconsolidated as a Result of This Transaction	The following table provides the assets and liabilities deconsolidated as a result of this transaction: Cash $ 497 Receivable from VSRM 934 Trade receivables 239 Intangible asset 196 Other assets 514 Total assets $ 2,380 Payable to Affiliates 286 Trade payables 193 Note payable 1,000 Other liabilities 901 Total Liabilities $ 2,380

Investments (Tables)

Investments (Tables)	12 Months Ended
	Dec. 31, 2023
Investments, Debt and Equity Securities [Abstract]
Schedule of Available-for-sale Securities	The cost or amortized cost, gross unrealized gain or loss, and estimated fair value of the investments in securities classified as available-for-sale at December 31, 2023 and 2022 were as follows (dollars in thousands): December 31, 2023 Cost or Gross Unrealized Amortized Gains Losses Estimated Debt securities: U.S. Government $ 5,405 $ 3 $ ( 161 ) $ 5,247 State and local government 24,274 — ( 3,810 ) 20,464 Corporate debt 34,002 — ( 3,507 ) 30,495 Asset-backed securities 38,289 47 ( 584 ) 37,752 Mortgage-backed securities 26,768 — ( 4,641 ) 22,127 Commercial mortgage-backed securities 3,404 — ( 160 ) 3,244 Collateralized mortgage obligations 3,228 — ( 444 ) 2,784 Total debt securities available for sale $ 135,370 $ 50 $ ( 13,307 ) $ 122,113 December 31, 2022 Cost or Gross Unrealized Amortized Gains Losses Estimated Debt securities: U.S. Government $ 7,833 $ — $ ( 335 ) $ 7,498 State and local government 25,487 1 ( 4,672 ) 20,816 Corporate debt 35,347 — ( 4,788 ) 30,559 Asset-backed securities 21,742 — ( 1,246 ) 20,496 Mortgage-backed securities 29,194 — ( 5,157 ) 24,037 Commercial mortgage-backed securities 3,414 — ( 186 ) 3,228 Collateralized mortgage obligations 4,102 — ( 535 ) 3,567 Total debt securities available for sale $ 127,119 $ 1 $ ( 16,919 ) $ 110,201
Schedule Of Unrealized Loss On Investments	The following table summarizes the aggregate fair value and gross unrealized losses, by security type, of the available-for-sale securities in unrealized loss positions. The table segregates the holdings based on the length of time that individual securities have been in a continuous unrealized loss position (dollars in thousands): December 31, 2023 Less than 12 months 12 months or More Total No. Fair Value of Gross No. Fair Value of Gross No. Fair Value of Gross Debt securities: U.S. Government 1 $ 649 $ ( 7 ) 9 $ 3,400 $ ( 154 ) 10 $ 4,049 $ ( 161 ) State and local government 3 1,193 ( 7 ) 113 19,096 ( 3,803 ) 116 20,289 ( 3,810 ) Corporate debt - - - 66 30,495 ( 3,507 ) 66 30,495 ( 3,507 ) Asset-backed securities 1 1,090 ( 1 ) 21 16,270 ( 583 ) 22 17,360 ( 584 ) Mortgage-backed securities 4 11 ( 1 ) 64 22,116 ( 4,640 ) 68 22,127 ( 4,641 ) Commercial mortgage - - - 4 3,225 ( 160 ) 4 3,225 ( 160 ) Collateralized mortgage - - - 32 2,803 ( 444 ) 32 2,803 ( 444 ) Total debt securities 9 2,943 ( 16 ) 309 97,405 ( 13,291 ) 318 100,348 ( 13,307 ) December 31, 2022 Less than 12 months 12 months or More Total No. Fair Value of Gross No. Fair Value of Gross No. Fair Value of Gross Debt securities: U.S. Government 8 $ 3,534 $ ( 135 ) 5 $ 3,964 $ ( 200 ) 13 $ 7,498 $ ( 335 ) State and local government 77 12,966 ( 2,318 ) 45 7,147 ( 2,354 ) 122 20,113 ( 4,672 ) Corporate debt 27 10,069 ( 1,373 ) 42 20,890 ( 3,415 ) 69 30,959 ( 4,788 ) Asset-backed securities 6 3,188 ( 76 ) 20 17,308 ( 1,170 ) 26 20,496 ( 1,246 ) Mortgage-backed securities 57 4,006 ( 573 ) 12 20,031 ( 4,584 ) 69 24,037 ( 5,157 ) Commercial mortgage 4 3,205 ( 186 ) — — — 4 3,205 ( 186 ) Collateralized mortgage 26 1,789 ( 196 ) 9 1,802 ( 339 ) 35 3,591 ( 535 ) Total debt securities 205 $ 38,757 $ ( 4,857 ) 133 $ 71,142 $ ( 12,062 ) 338 $ 109,899 $ ( 16,919 )
Schedule of Investment Income	The Company’s sources of net investment income are as follows (dollars in thousands): December 31, 2023 2022 Debt securities $ 4,121 $ 2,517 Equity securities 36 52 Cash, cash equivalents, and short-term investments 1,603 776 Total investment income 5,760 3,345 Investment expenses ( 234 ) ( 302 ) Net investment income $ 5,526 $ 3,043
Schedule of Gross Realized Gains and Losses on Securities	The following table summarizes the gross realized gains and losses from sales or maturities of available-for-sale debt securities and equity securities, as follows (dollars in thousands): December 31, 2023 2022 Debt securities: Gross realized gains $ — $ 6 Gross realized losses ( 20 ) ( 155 ) Total debt securities ( 20 ) ( 149 ) Equity securities: Gross realized gains — 375 Gross realized losses — ( 1,731 ) Total equity securities — ( 1,356 ) Total net realized investment gains $ ( 20 ) $ ( 1,505 )
Summary of Amortized Cost and Fair Value of Securities	The table below summarizes the amortized cost and fair value of available-for-sale debt securities by contractual maturity at December 31, 2023. Actual maturities may differ from contractual maturities because certain borrowers have the right to call or prepay obligations with or without call or prepayment penalties (dollars in thousands): Amortized Estimated Due in one year or less $ 3,212 $ 3,175 Due after one year through five years 30,996 28,983 Due after five years through ten years 18,768 15,904 Due after ten years 10,705 8,144 Securities with contractual maturities 63,681 56,206 Asset-backed securities 38,289 37,752 Mortgage-backed securities 26,768 22,127 Commercial mortgage-backed securities 3,404 3,244 Collateralized mortgage obligations 3,228 2,784 Total debt securities $ 135,370 $ 122,113

Fair Value Measurements (Tables

Fair Value Measurements (Tables)	12 Months Ended
	Dec. 31, 2023
Fair Value Disclosures [Abstract]
Summary of Assets and Liabilities Measured at Fair Value	The following tables present the Company’s assets and liabilities measured at fair value, classified by the valuation hierarchy as of December 31, 2023 and 2022 (dollars in thousands): December 31, 2023 Fair Value Measurements Using Total Level 1 Level 2 Level 3 Assets: Debt Securities: U.S. Government $ 5,247 $ — $ 5,247 $ — State and local government 20,464 — 20,464 — Corporate debt 30,495 — 30,495 — Asset-backed securities 37,752 — 37,752 — Mortgage-backed securities 22,127 — 22,127 — Commercial mortgage-backed securities 3,244 — 3,244 — Collateralized mortgage obligations 2,784 — 2,784 — Total debt securities 122,113 — 122,113 — Equity Securities 896 139 757 — Short-term investments 20,838 20,838 — — Total marketable investments measured at fair value $ 143,847 $ 20,977 $ 122,870 $ — Investments measured at NAV: Investment in limited partnership 1,458 Total assets measured at fair value $ 145,305 Liabilities: Senior Unsecured Notes * $ 11,791 $ — $ 11,791 $ — Senior Secured Notes * 9,965 — — 9,965 Total Liabilities (non-recurring fair value measure) $ 21,756 $ — $ 11,791 $ 9,965 * Carried at face value of debt net of unamortized debt issuance costs on the consolidated balance sheet December 31, 2022 Fair Value Measurements Using Total Level 1 Level 2 Level 3 Assets: Debt Securities: U.S. Government $ 7,498 $ — $ 7,498 $ — State and local government 20,816 — 20,816 — Corporate debt 30,559 — 30,559 — Asset-backed securities 20,496 — 20,496 — Mortgage-backed securities 24,037 — 24,037 — Commercial mortgage-backed securities 3,228 — 3,228 — Collateralized mortgage obligations 3,567 — 3,567 — Total debt securities 110,201 — 110,201 — Equity Securities 917 160 757 — Short-term investments 25,929 25,929 — — Total marketable investments measured at fair value $ 137,047 $ 26,089 $ 110,958 $ — Investments measured at NAV: Investment in limited partnership 350 Total assets measured at fair value $ 137,397 Liabilities: Senior Unsecured Notes * $ 22,430 $ — $ 22,430 $ — Subordinated Notes * 11,300 — — 11,300 Total Liabilities (non-recurring fair value measure) $ 33,730 $ — $ 22,430 $ 11,300 * Carried at face value of debt net of unamortized debt issuance costs on the consolidated balance sheet

Deferred Policy Acquisition C_2

Deferred Policy Acquisition Costs (Tables)	12 Months Ended
	Dec. 31, 2023
Deferred Policy Acquisition Costs Disclosures [Abstract]
Summary of Deferred Policy Acquisition Costs	The activity in deferred policy acquisition costs, net of reinsurance transactions, is as follows (dollars in thousands): December 31, 2023 2022 Balance at beginning of period $ 10,290 $ 12,267 Deferred policy acquisition costs 16,887 20,202 Amortization of policy acquisition costs ( 16,589 ) ( 22,179 ) Impact from renewal rights sale ( 4,303 ) — Net change ( 4,005 ) ( 1,977 ) Balance at end of period $ 6,285 $ 10,290

Unpaid Losses and Loss Adjust_2

Unpaid Losses and Loss Adjustment Expenses (Tables)	12 Months Ended
	Dec. 31, 2023
Insurance Loss Reserves [Abstract]
Schedule of the Changes in the Reserves for Losses and Loss Adjustment Expense	The table below provides the changes in the reserves for losses and LAE, net of recoverables from reinsurers, for the periods indicated (dollars in thousands): December 31, 2023 2022 Gross reserves - beginning of period $ 165,539 $ 139,085 Less: reinsurance recoverables on unpaid losses 82,651 40,344 Net reserves - beginning of period 82,888 98,741 Add: incurred losses and loss adjustment expenses, net Current period 64,580 57,156 Prior period 17,833 24,284 Total net incurred losses and loss adjustment 82,413 81,440 Deduct: loss and loss adjustment expense payments, Current period 27,001 20,894 Prior period 34,495 76,399 Total net loss and loss adjustment expense 61,496 97,293 Net reserves - end of period 103,805 82,888 Plus: reinsurance recoverables on unpaid losses 70,807 82,651 Gross reserves - end of period $ 174,612 $ 165,539
Short-duration Insurance Contracts, Claims Development	The following tables represent cumulative incurred loss and allocated loss adjustment expenses ("ALAE"), net of reinsurance, by accident year and cumulative paid loss and ALAE, net of reinsurance, by accident year, for the years ended December 31, 2014 to 2023, as well as total IBNR and the cumulative number of reported claims for the year ended December 31, 2023 , by reportable segment and accident year (dollars in thousands). The tables do not include reinsurance recoverables from the LPT. The 2023 and 2022 columns in the commercial lines incurred and paid loss tables below do not include reinsurance recoverables on reserves of $ 10.9 million and $ 25.9 million and reinsurance recoverables on paid losses of $ 3.8 million and $ 3.9 million, respectively, related to the LPT. Commercial Lines Incurred loss and allocated loss adjustment expenses, net of reinsurance Total Cumulative Accident Year 2014* 2015* 2016* 2017* 2018* 2019* 2020* 2021* 2022* 2023 2023 2023 2014 19,709 19,907 22,711 26,367 28,145 28,766 29,045 29,175 29,011 29,093 — 1,755 2015 22,442 26,633 31,861 34,478 36,372 37,795 38,824 39,093 39,311 — 2,363 2016 32,396 34,935 40,440 44,355 46,089 46,993 48,677 49,162 19 3,559 2017 44,251 44,495 49,749 51,883 55,589 56,649 59,149 234 5,835 2018 42,624 42,432 49,741 55,261 60,102 61,881 568 6,128 2019 41,286 42,129 46,329 55,263 59,028 1,611 6,337 2020 33,867 35,328 39,193 43,918 3,012 3,866 2021 40,388 42,266 48,650 5,557 2,947 2022 41,708 49,751 10,142 2,323 2023 39,456 20,752 1,644 Total $ 479,399 $ 41,895 Commercial lines Cumulative paid loss and allocated loss adjustment expenses, net of reinsurance Accident Year 2014* 2015* 2016* 2017* 2018* 2019* 2020* 2021* 2022* 2023 2014 8,715 13,977 17,458 22,446 25,609 27,544 28,389 28,648 28,608 28,688 2015 10,470 17,817 22,549 30,475 34,497 35,833 37,563 38,685 39,116 2016 10,255 19,135 27,785 37,967 41,945 43,644 46,957 48,557 2017 12,448 23,020 34,205 42,308 47,148 52,800 57,304 2018 10,375 19,799 31,633 41,577 50,508 57,114 2019 10,078 20,462 28,958 39,893 50,369 2020 10,217 17,332 24,225 33,354 2021 12,870 21,313 30,478 2022 12,839 22,892 2023 8,486 Total $ 376,358 Net Unpaid losses and ALAE, years 2014 through 2023 $ 103,041 Unpaid losses and ALAE, prior to 2014* 160 Unpaid Losses, LPT ( 10,928 ) Unpaid losses and ALAE, net of reinsurance $ 92,273 * Presented as unaudited required supplementary information. Personal Lines Incurred loss and allocated loss adjustment expenses, net of reinsurance Total Cumulative Accident For the years ended December 31, Year 2014* 2015* 2016* 2017* 2018* 2019* 2020* 2021* 2022* 2023 2023 2023 2014 17,951 17,471 17,735 17,880 17,929 18,082 18,095 18,097 18,052 18,028 — 3,737 2015 10,877 13,445 14,721 15,285 15,364 15,427 15,427 15,448 15,456 — 2,154 2016 11,619 13,418 14,949 15,550 15,655 15,634 15,679 15,681 — 1,815 2017 14,058 13,550 14,493 14,793 14,911 14,957 14,955 — 2,914 2018 5,893 6,378 6,283 6,382 6,298 6,336 — 803 2019 3,099 2,712 2,898 2,862 2,867 — 341 2020 2,339 2,590 2,636 2,619 — 324 2021 4,409 4,332 4,240 — 48 2022 9,404 8,122 — 714 2023 19,444 1,156 1,584 Total $ 107,748 $ 1,156 Personal lines Cumulative paid loss and allocated loss adjustment expenses, net of reinsurance Accident For the years ended December 31, Year 2014* 2015* 2016* 2017* 2018* 2019* 2020* 2021* 2022* 2023 2014 12,819 16,515 17,260 17,746 17,855 18,047 18,068 18,070 18,025 18,027 2015 7,771 11,873 13,844 15,159 15,250 15,290 15,416 15,444 15,452 2016 7,119 11,238 14,442 15,110 15,351 15,452 15,679 15,681 2017 8,320 12,944 14,004 14,526 14,866 14,957 14,955 2018 4,296 5,618 6,100 6,242 6,244 6,333 2019 2,119 2,604 2,692 2,850 2,859 2020 1,307 2,455 2,605 2,619 2021 3,022 3,980 4,081 2022 5,397 7,923 2023 16,170 Total $ 104,100 Net Unpaid losses and ALAE, years 2014 through 2023 $ 3,648 Unpaid losses and ALAE, prior to 2014* — Unpaid losses and ALAE, net of reinsurance $ 3,648 * Presented as unaudited required supplementary information. Total Lines Incurred loss and allocated loss adjustment expenses, net of reinsurance Total Cumulative number of reported claims Accident For the years ended December 31, Year 2014* 2015* 2016* 2017* 2018* 2019* 2020* 2021* 2022* 2023 2023 2023 2014 37,660 37,378 40,446 44,247 46,074 46,848 47,140 47,272 47,063 47,121 — 5,492 2015 33,319 40,078 46,581 49,763 51,736 53,222 54,251 54,541 54,767 — 4,517 2016 44,015 48,353 55,389 59,905 61,744 62,627 64,356 64,843 19 5,374 2017 58,309 58,045 64,242 66,676 70,500 71,606 74,104 234 8,749 2018 48,517 48,810 56,024 61,643 66,400 68,217 568 6,931 2019 44,385 44,841 49,227 58,125 61,895 1,611 6,678 2020 36,206 37,918 41,829 46,537 3,012 4,190 2021 44,797 46,598 52,890 5,557 2,995 2022 51,112 57,873 10,142 3,037 2023 58,900 21,908 3,228 Total 587,147 43,051 Total lines Cumulative paid loss and allocated loss adjustment expenses, net of reinsurance Accident For the years ended December 31, Year 2014* 2015* 2016* 2017* 2018* 2019* 2020* 2021* 2022* 2023 2014 21,534 30,492 34,718 40,192 43,464 45,591 46,457 46,718 46,633 46,715 2015 18,241 29,690 36,393 45,634 49,747 51,123 52,979 54,129 54,568 2016 17,374 30,373 42,227 53,077 57,296 59,096 62,636 64,238 2017 20,768 35,964 48,209 56,834 62,014 67,757 72,259 2018 14,671 25,417 37,733 47,819 56,752 63,447 2019 12,197 23,066 31,650 42,743 53,228 2020 11,524 19,787 26,830 35,973 2021 15,892 25,293 34,559 2022 18,236 30,815 2023 — 24,656 Total $ 480,458 Net Unpaid losses and ALAE, years 2014 through 2023 $ 106,689 Unpaid losses and ALAE, prior to 2014* 160 Unpaid losses, LPT ( 10,928 ) Unpaid losses and ALAE, net of reinsurance $ 95,921 * Presented as unaudited required supplementary information.
Short-duration Insurance Contracts, Reconciliation of Loss Development to Liability	The following table reconciles the loss development information to the consolidated balance sheet for the year ended December 31, 2023, by reportable segment (dollars in thousands). December 31, Net unpaid losses claims and ALAE Commercial Lines $ 92,273 Personal Lines 3,648 Total unpaid losses and LAE, net of reinsurance 95,921 Reinsurance recoverable on losses and LAE Commercial Lines 68,981 Personal Lines 1,826 Total reinsurance recoverable on unpaid losses and LAE 70,807 ULAE expense 7,884 Total gross unpaid losses and LAE $ 174,612
Loss Duration Schedule	The following table represents the average annual percentage payout of incurred losses by age, net of reinsurance, for each reportable segment. Average annual percentage payout of incurred losses by age, net of reinsurance Year 1 Year 2 Year 3 Year 4 Year 5 Year 6 Year 7 Year 8 Year 9 Year Commercial Lines 27.3 % 21.6 % 18.6 % 12.8 % 9.2 % 4.9 % 2.9 % 1.5 % 0.7 % 0.5 % Personal Lines 83.1 % 11.3 % 5.3 % 0.3 % 0.0 % 0.0 % 0.0 % 0.0 % 0.0 % 0.0 % Total Lines 29.2 % 21.3 % 18.2 % 12.4 % 8.9 % 4.7 % 2.8 % 1.4 % 0.7 % 0.4 %

Reinsurance (Tables)

Reinsurance (Tables)	12 Months Ended
	Dec. 31, 2023
Reinsurance Disclosures [Abstract]
Summary of the Effects of Reinsurance	The following table presents the effects of reinsurance and assumed reinsurance transactions on written premiums, earned premiums and losses and LAE (dollars in thousands). In 2023, ceded written and earned premium amounts included $ 91,000 of reinsurance reinstatement costs related to catastrophe losses. In 2022, ceded written and earned premium amounts included $ 1.6 million of reinsurance reinstatement costs relating to Hurricane Ian. Year Ended December 31, 2023 2022 Written premiums: Direct $ 100,214 $ 95,832 Assumed 43,620 42,187 Ceded ( 75,146 ) ( 46,787 ) Net written premiums $ 68,688 $ 91,232 Earned premiums: Direct $ 96,595 $ 97,843 Assumed 49,977 37,558 Ceded ( 62,637 ) ( 38,690 ) Net earned premiums $ 83,935 $ 96,711 Loss and loss adjustment expenses: Direct $ 75,175 $ 73,000 Assumed 45,662 43,487 Ceded ( 38,424 ) ( 35,047 ) Net loss and LAE $ 82,413 $ 81,440

Debt (Tables)

Debt (Tables)	12 Months Ended
	Dec. 31, 2023
Debt Disclosure [Abstract]
Schedule of Outstanding Senior Debt	A summary of the Company's outstanding debt is as follows (dollars in thousands): As of December 31, 2023 As of December 31, 2022 Gross Debt Unamortized Net Debt Gross Debt Unamortized Net Debt Public Notes $ 17,887 $ 1,679 $ 16,208 $ 24,381 $ 195 $ 24,186 Senior Secured Notes 9,750 897 8,853 — — — Subordinated notes — — — 10,500 810 9,690 Total $ 27,637 $ 2,576 $ 25,061 $ 34,881 $ 1,005 $ 33,876
Summary of Scheduled Principal Payments of Company's Debt	The following table shows the scheduled principal payments of the Company's debt as of December 31, 2023 (dollars in thousands): Year Senior unsecured notes Senior secured notes 2024 1,000 — 2025 1,000 — 2026 1,000 — 2027 1,000 — 2028 5,750 17,887 Total $ 9,750 $ 17,887

Income Taxes (Tables)

Income Taxes (Tables)	12 Months Ended
	Dec. 31, 2023
Income Tax Disclosure [Abstract]
Schedule of Income Tax Expense (Benefit)	The income tax expense (benefit) is comprised of the following (dollars in thousands): Year Ended December 31, 2023 2022 Current tax expense (benefit) $ 26 $ ( 45 ) Deferred tax expense (benefit) ( 17 ) ( 9,396 ) Total income tax expense (benefit) $ 9 $ ( 9,441 )
Summary of Income Tax Expense (Benefit) Reconciliation	The income tax expense (benefit) differed from the amounts computed by applying the statutory U.S. federal income tax rate of 21 % in 2023 and 2022 to pretax income as a result of the following (dollars in thousands): Year Ended December 31, 2023 2022 Income (loss) before income taxes $ ( 25,644 ) $ ( 20,490 ) Statutory U.S. federal income tax rate ( 5,385 ) ( 4,303 ) State income taxes, net of federal benefit ( 1,503 ) ( 5,984 ) Tax‑exempt investment income and dividend received deduction ( 13 ) ( 22 ) Nondeductible meals and entertainment 73 79 Valuation allowance on deferred tax assets 7,254 3,715 Equity-earnings from Affiliate — 195 Net gain from sale of agency assets — ( 2,848 ) Utilization of state NOLs — ( 386 ) Deferred corrections ( 476 ) — PPP Loan forgiveness — — Other 59 113 Income tax expense (benefit) $ 9 $ ( 9,441 ) Effective tax rate — 46.1 %
Schedule of Deferred Tax Assets and Liabilities	The tax effects of temporary differences that give rise to significant portions of the deferred tax assets and deferred tax liabilities are presented below (dollars in thousands): December 31, 2023 2022 Deferred tax assets: Discounted unpaid losses and loss adjustment expenses $ 1,749 $ 1,217 Unearned premiums 1,648 2,324 Net operating loss carryforwards 16,960 12,152 Net unrealized losses on investments 2,780 3,687 State net operating loss carryforwards 6,523 5,097 Other 112 403 Gross deferred tax assets 29,772 24,880 Less valuation allowance ( 28,013 ) ( 21,663 ) Total deferred tax assets, net of allowance 1,759 3,217 Deferred tax liabilities: Investment basis difference 208 23 Tax rate change transition discounting 92 137 Equity investment in Affiliate — 691 Deferred policy acquisition costs 1,320 2,161 Intangible assets 115 115 Property and equipment 24 41 Other — 49 Total deferred tax liabilities 1,759 3,217 Net deferred tax liability $ — $ —

Statutory Financial Data, Ris_2

Statutory Financial Data, Risk-Based Capital and Dividend Restrictions (Tables)	12 Months Ended
	Dec. 31, 2023
Insurance [Abstract]
Summary of Statutory Basis Information	Summarized 2023 and 2022 statutory basis information for the non-captive Insurance Company Subsidiaries, which differs from generally accepted accounting principles, is as follows (dollars in thousands). CIC WPIC 2023 Statutory capital and surplus $ 32,117 $ 7,494 RBC authorized control level 19,050 5,268 Statutory net income (loss) ( 14,014 ) ( 9,841 ) RBC % 169 % 142 % CIC WPIC 2022 Statutory capital and surplus $ 47,827 $ 20,651 RBC authorized control level 15,541 5,098 Statutory net income (loss) ( 6,846 ) ( 4,171 ) RBC % 308 % 405 %

Accumulated Other Comprehensi_2

Accumulated Other Comprehensive Income (Loss) (Tables)	12 Months Ended
	Dec. 31, 2023
Equity [Abstract]
Schedule of Accumulated Other Comprehensive Income (Loss)	The following table presents changes in accumulated other comprehensive income (loss) for unrealized gains and losses on available-for-sale securities (dollars in thousands): Year Ended 2023 2022 Balance at beginning of period $ ( 18,203 ) $ ( 2,110 ) Other comprehensive income (loss) before reclassifications 3,624 ( 16,024 ) Less: amounts reclassified from accumulated other comprehensive income (loss) ( 51 ) 69 Net current period other comprehensive income (loss) 3,675 ( 16,093 ) Balance at end of period $ ( 14,528 ) $ ( 18,203 )

Earnings Per Share (Tables)

Earnings Per Share (Tables)	12 Months Ended
	Dec. 31, 2023
Earnings Per Share [Abstract]
Schedule of Earnings Per Share	The following table presents the calculation of basic and diluted earnings (loss) per common share, as follows (dollars in thousands, except share and per share amounts): Year Ended 2023 2022 Net income (loss) $ ( 25,904 ) $ ( 10,681 ) Preferred stock dividends 19 - Net income (loss) allocable to common shareholders $ ( 25,923 ) $ ( 10,681 ) Weighted average common shares, basic and diluted* 12,220,511 10,692,090 Earnings (loss) per share, basic and diluted $ ( 2.12 ) $ ( 1.00 ) * The preferred shares that may be convertible into a total of 4,000,000 common shares were anti-dilutive and thus did not impact the diluted earnings per share calculation. There were no unvested restricted stock units as of December 31, 2023. The non-vested shares of the restricted stock units and stock options were anti-dilutive as of December 31, 2022. Therefore, the non-vested shares are excluded from earnings (loss) per share for the years ended December 31, 2022 .

Segment Information (Tables)

Segment Information (Tables)	12 Months Ended
	Dec. 31, 2023
Segment Reporting [Abstract]
Schedule of Information by Reportable Segment	The following table summarizes our net earned premiums: Net Earned Premium 2023 2022 Commercial 71 % 84 % Personal 29 % 16 % Total 100 % 100 % The wholesale agency business sells insurance products on behalf of the Company’s commercial and personal lines businesses as well as to third-party insurers. Certain acquisition costs incurred by the commercial and personal lines businesses are reflected as commission revenue for the wholesale agency business and are eliminated in the Eliminations category. In addition to the reportable segments, the Company maintains a Corporate and Other category to reconcile segment results to the consolidated totals. The Corporate and Other category includes: (i) corporate operating expenses such as salaries and related benefits of the Company’s executive management team, some finance and information technology personnel, and other corporate headquarters expenses, (ii) interest expense on the Company’s debt obligations; (iii) depreciation and amortization on property and equipment, and (iv) all investment income activity. All investment income activity is reported within net investment income, net realized investment gains, and change in fair value of equity securities on the consolidated statements of operations. The Company’s assets on the consolidated balance sheet are not allocated to the reportable segments. The following tables present information by reportable segment (dollars in thousands): Year Ended December 31, 2023 Commercial Personal Under-writing Wholesale Agency Corp-orate Elim-inations Total Gross written premiums $ 107,078 $ 36,756 $ 143,834 $ — $ — $ — $ 143,834 Net written premiums $ 36,580 $ 32,108 $ 68,688 $ — $ — $ — $ 68,688 Net earned premiums $ 59,221 $ 24,714 $ 83,935 $ — $ — $ — $ 83,935 Agency commission income — — — 5,680 — — 5,680 Other income 217 96 313 1,379 239 ( 1,237 ) 694 Segment revenue 59,438 24,810 84,248 7,059 239 ( 1,237 ) 90,309 Loss and loss adjustment expenses, net 62,828 19,585 82,413 — — — 82,413 Policy acquisition costs 9,134 6,663 15,797 6,401 — ( 1,306 ) 20,892 Operating expenses 11,988 3,444 15,432 1,153 1,306 — 17,891 Segment expenses 83,950 29,692 113,642 7,554 1,306 ( 1,306 ) 121,196 Segment underwriting gain (loss) ( 24,512 ) ( 4,882 ) ( 29,394 ) ( 495 ) ( 1,067 ) 69 ( 30,887 ) Net investment income 5,526 5,526 Net realized investment gains (losses) ( 20 ) ( 20 ) Change in fair value of equity securities 608 608 Gain on sale of renewal rights 2,335 2,335 Other gains — — Interest expense ( 3,206 ) ( 3,206 ) Income (loss) before income taxes $ ( 24,512 ) $ ( 4,882 ) $ ( 29,394 ) $ ( 495 ) $ 4,176 $ 69 $ ( 25,644 ) Selected Balance Sheet Data: Deferred policy acquisition costs $ 2,047 $ 4,357 $ ( 119 ) $ 6,285 Unearned premiums 45,494 19,656 65,150 Unpaid losses and loss adjustment expenses 169,039 5,573 174,612 Year Ended December 31, 2022 Commercial Personal Under-writing Wholesale Agency Corp-orate Elim-inations Total Gross written premiums $ 116,868 $ 21,151 $ 138,019 $ — $ — $ — $ 138,019 Net written premiums $ 72,318 $ 18,914 $ 91,232 $ — $ — $ — $ 91,232 Net earned premiums $ 80,823 $ 15,888 $ 96,711 $ — $ — $ — $ 96,711 Agency commission income — — — 1,414 — — 1,414 Other income 245 82 327 4,298 271 ( 3,542 ) 1,354 Segment revenue 81,068 15,970 97,038 5,712 271 ( 3,542 ) 99,479 Loss and loss adjustment expenses, net 70,762 10,678 81,440 — — — 81,440 Policy acquisition costs 17,682 4,604 22,286 3,653 — ( 3,760 ) 22,179 Operating expenses 13,069 1,936 15,005 2,612 1,192 ( 20 ) 18,789 Loss portfolio transfer risk fee 5,400 — 5,400 — — — 5,400 Segment expenses 106,913 17,218 124,131 6,265 1,192 ( 3,780 ) 127,808 Segment underwriting gain (loss) ( 25,845 ) ( 1,248 ) ( 27,093 ) ( 553 ) ( 921 ) $ 238 ( 28,329 ) Net investment income 32 3,011 3,043 Net realized investment gains (losses) ( 1,505 ) ( 1,505 ) Change in fair value of equity securities 403 403 Gain from VSRM Transaction 8,810 8,810 Other gains ( 1 ) 60 59 Interest expense ( 42 ) ( 2,929 ) ( 2,971 ) Income (loss) before income taxes $ ( 25,845 ) $ ( 1,248 ) $ ( 27,093 ) $ ( 564 ) $ 6,929 $ 238 $ ( 20,490 ) Selected Balance Sheet Data: Deferred policy acquisition costs $ 7,683 $ 2,796 $ ( 189 ) $ 10,290 Unearned premiums 56,565 11,322 67,887 Unpaid losses and loss adjustment expenses 159,558 5,981 165,539

Summary of Significant Accoun_3

Summary of Significant Accounting Policies - Narrative (Details)			1 Months Ended	12 Months Ended
	Dec. 20, 2023 USD ($)	Sep. 29, 2023 USD ($)	Sep. 30, 2023 USD ($)	Dec. 31, 2023 USD ($) Class_business State	Dec. 31, 2022 USD ($)
New Accounting Pronouncements or Change in Accounting Principle [Line Items]
Non Controlling Interest				50%
Number of types of business | Class_business				3
Number of states in which entity operates | State				50
Discount rate				9.50%
Unrecognized tax benefits				$ 0	$ 0
Income tax penalties and interest accrued				0	0
Net unrealized losses in debt securities				13,300,000
Consolidated net loss				(25,923,000)	(10,681,000)
Cash used from operation activities				13,600,000
Total shareholders' equity				2,889,000	18,950,000
Share issuance value				$ 6,000,000	5,000,000
Percentage of existing commercial lines book of business				25%
Accounting Standards Update 2016-02
New Accounting Pronouncements or Change in Accounting Principle [Line Items]
Right-of-use asset				$ 960,000	$ 1,300,000
Operating Lease, Right-of-Use Asset, Statement of Financial Position [Extensible Enumeration]				Other assets	Other assets
Lease liability				$ 1,000,000	$ 1,300,000
Operating Lease, Liability, Statement of Financial Position [Extensible Enumeration]				Other liabilities	Other liabilities
Minimum
New Accounting Pronouncements or Change in Accounting Principle [Line Items]
Lease term				5 years
Maximum
New Accounting Pronouncements or Change in Accounting Principle [Line Items]
Lease term				10 years
6.75% Public Senior Unsecured notes (Old Public Notes)
New Accounting Pronouncements or Change in Accounting Principle [Line Items]
Face amount of debt				$ 6,500,000
Senior Secured Notes
New Accounting Pronouncements or Change in Accounting Principle [Line Items]
Annual principal payment			$ 1,000,000
Senior Secured Notes | Privately Placed 12.5% Senior Secured Notes
New Accounting Pronouncements or Change in Accounting Principle [Line Items]
Face amount of debt				9,800,000
Maturity date			Sep. 30, 2028
Quarterly payment of principal				$ 250,000
Interest rate			12.50%	12.50%
Subordinated notes | Private Placement Subordinated Note
New Accounting Pronouncements or Change in Accounting Principle [Line Items]
Principal on subordinated notes paid down		$ 500,000
Restructuring of existing subordinated notes to senior secured notes			$ 10,000,000
Senior Unsecured Notes | 9.75% Public Senior Unsecured Notes (New Public Notes)
New Accounting Pronouncements or Change in Accounting Principle [Line Items]
Face amount of debt			$ 17,900,000	$ 17,900,000
Maturity date			Sep. 30, 2028
Interest rate			9.75%	9.75%
Senior Unsecured Notes | 6.75% Public Senior Unsecured notes (Old Public Notes)
New Accounting Pronouncements or Change in Accounting Principle [Line Items]
Repayment of debt			$ 24,400,000
Face amount of debt				$ 11,200,000
Maturity date				Sep. 30, 2023
Interest rate			6.75%	6.75%
Series A Preferred Stock
New Accounting Pronouncements or Change in Accounting Principle [Line Items]
Share issuance value	$ 6,000,000

Sale of Renewal Rights - Additi

Sale of Renewal Rights - Additional Information (Details)	1 Months Ended	12 Months Ended
	Sep. 30, 2023 USD ($)	Dec. 31, 2023 USD ($) Claim	Dec. 31, 2022 USD ($)
Collaborative Arrangement and Arrangement Other than Collaborative [Line Items]
Proceeds from sale of renewal rights		$ 2,335,000	$ 32,759,000	[1]
Gross earned premiums		96,595,000	97,843,000
Ceded Premiums Written		75,146,000	46,787,000
Renewal Rights
Collaborative Arrangement and Arrangement Other than Collaborative [Line Items]
Proceeds from sale of renewal rights	$ 2,500,000
Gross earned premiums		55,900,000	$ 41,000,000
Ceded Premiums Written	30,900,000
Commission ceded, net	$ 8,400,000
Percentage of unearned premium	100%
Net cash owned by the buyer retained under funds withheld provision		24,100,000
Expense incurred for policies ceded		$ 135,000
Number of claims staff transferred employment to buyer | Claim		5
New public debt purchased	$ 5,000,000
[1] See Note 3 ~ VSRM Transaction

VSRM Transaction - Narrative (D

VSRM Transaction - Narrative (Details) - USD ($)				1 Months Ended	3 Months Ended	12 Months Ended
	Oct. 14, 2022	Oct. 13, 2022	Oct. 12, 2022	Dec. 31, 2022	Dec. 31, 2022	Dec. 31, 2023	Dec. 31, 2022
Business Acquisition [Line Items]
Asset acquisition debt not transferred		$ 8,900,000
Asset acquisition tax liability not transferred		9,400,000
Asset purchase agreement purchase price	$ 38,200,000
Operating loss carry forwards, net of tax		9,400,000
Gain or loss on sale of business						$ 2,335,000	$ 0
VSRM
Business Acquisition [Line Items]
Ownership percentage	50%
Accounts receivable	$ 4,300,000
Current liabilities	5,800,000
Cash	271,000
Asset purchase agreement purchase price paid in cash	32,800,000
Asset purchase agreement purchase price paid in the form of the buyer's stock	3,800,000
Cash held back by buyer	(75,000)
Fair value of equity interest prior to acquisition			$ 10,600,000
VSRM | Promissory Note
Business Acquisition [Line Items]
Payments to acquire interest in venture	$ 9,700,000
CIC
Business Acquisition [Line Items]
Promissory note assumed as part of contribution of business						1,000,000
Domestic
Business Acquisition [Line Items]
Net operating loss carryforwards		12,500,000
State
Business Acquisition [Line Items]
Net operating loss carryforwards		$ 14,800,000				120,300,000
Sycamore Specialty Underwriters | VSRM
Business Acquisition [Line Items]
Net asset transferred, fair value				$ 0
Promissory note assumed as part of contribution of business				1,000,000
Receivable from VSRM						934,000
Existing related payable retained						$ 934,000
Sycamore Specialty Underwriters | VSRM | Vice President [Member]
Business Acquisition [Line Items]
Purchase price amount				1,000	$ 1,000		$ 1,000
Gain or loss on sale of business				$ 0
Asset Purchase Agreement
Business Acquisition [Line Items]
Non-operating gains, net of taxes generated					$ 8,800,000
Venture
Business Acquisition [Line Items]
Percentage of ownership interest purchased	50%	50%	50%
Payments to acquire interest in venture		$ 9,700,000
Settled the note with cash received from sale of Security & Alarm Business		5,900,000
Form of stock from the buyer of the Security & Alarm Business		3,800,000
Revaluation gain on step acquisition		$ 8,810,000
Ownership percentage		100%
Accounts receivable		$ 4,604,000
Cash		3,921,000
Venture | Promissory Note
Business Acquisition [Line Items]
Payments to acquire interest in venture		$ 9,700,000
Sycamore Specialty Underwriters | VSRM | Vice President [Member]
Business Acquisition [Line Items]
Percentage of ownership interest purchased				50%	50%		50%

VSRM Transaction - Schedule of

VSRM Transaction - Schedule of Condensed Assets and Liabilities Incorporated Into The Consolidated Balance Sheet from The VSRM Acquisition (Details) - Venture $ in Thousands	Oct. 13, 2022 USD ($)
Business Acquisition [Line Items]
Cash	$ 3,921
Trade receivables	4,604
Customer relationship intangible assets	37,122
Other assets	574
Total assets	46,221
Trade and other payables	7,624
Deferred tax liability	9,407
Note payable to Affiliate	6,000
Senior debt	2,917
Total Liabilities	25,948
Fair value of net assets acquired	$ 20,273

VSRM Transaction - Schedule o_2

VSRM Transaction - Schedule of Calculation of Revaluation Gain Related to Company's Equity Method Investment in VSRM as a Result of VSRM Transaction (Details) - Venture $ in Thousands	Oct. 13, 2022 USD ($)
Business Acquisition [Line Items]
Carrying value of equity method investment in VSRM	$ 1,773
Fair value of investment in VSRM	10,583
Gain on step acquisition	$ 8,810

VSRM Transaction - Schedule o_3

VSRM Transaction - Schedule of Calculation of Gain on VSRM Transaction (Parenthetical) (Details)	Oct. 14, 2022	Oct. 13, 2022	Oct. 12, 2022
Venture
Business Acquisition [Line Items]
Percentage of ownership interest purchased	50%	50%	50%

VSRM Transaction - Schedule o_4

VSRM Transaction - Schedule of Reconciles the Net Assets Disposed (Details) $ in Thousands	Oct. 14, 2022 USD ($)
Business Acquisition [Line Items]
Purchase price	$ 38,200
Venture
Business Acquisition [Line Items]
Cash at closing	32,759
Net liabilities transferred	1,499
Hold back	75
Stock of acquirer	3,822
Purchase price	38,155
Cash	271
Premiums transferred to buyer	4,326
Intangible assets	38,154
Trade payables and accrued liabilities assumed by buyer	(5,838)
Net assets disposed of	36,913
Gross gain	1,242
Broker fee transaction costs	$ (1,242)

VSRM Transaction - Net Gain on

VSRM Transaction - Net Gain on Revaluation of the Investment in VSRM and the Disposal of the Security and Alarm Business Line (Details) - USD ($) $ in Thousands		12 Months Ended
	Oct. 14, 2022	Dec. 31, 2023	Dec. 31, 2022
Business Acquisition [Line Items]
Net gain		$ 0	$ 8,810
Venture
Business Acquisition [Line Items]
Gross gains	$ 10,052
Broker fee	(1,242)
Net gain	$ 8,810

VSRM Transaction - Schedule o_5

VSRM Transaction - Schedule of Assets And Liabilities Deconsolidated as a Result of This Transaction (Details) - VSRM - Sycamore Specialty Underwriters	Dec. 31, 2023 USD ($)
Business Acquisition [Line Items]
Cash	$ 497,000
Receivable from VSRM	934,000
Trade receivables	239,000
Intangible asset	196,000
Other assets	514,000
Total assets	2,380,000
Payable to Affiliates	286,000
Trade payables	193,000
Note payable	1,000,000
Other liabilities	901,000
Total Liabilities	$ 2,380,000

Sale of Certain Agency Busine_2

Sale of Certain Agency Business - Narrative (Details) $ in Thousands		1 Months Ended		12 Months Ended
	Oct. 20, 2022 USD ($)	Dec. 31, 2021 USD ($)	Jun. 30, 2021 USD ($) Interger	Dec. 31, 2023 USD ($)	Dec. 31, 2022 USD ($)
Other gains (losses)				$ 0	$ 59
Venture Holdings, Inc
Number of promissory notes | Interger			2
Repayments of Debt	$ 5,000	$ 3,000
Venture Holdings, Inc | Promissory Notes One
Remaining balance paid by promissory note	$ 6,000		$ 3,000
Venture Holdings, Inc | Promissory Notes Two
Remaining balance paid by promissory note			$ 6,000
Sycamore Specialty Underwriters | Promissory Notes One
Promissory note assumed as part of contribution of business				$ 1,000

Investments - Available-for-sal

Investments - Available-for-sale Securities (Details) - USD ($) $ in Thousands	Dec. 31, 2023	Dec. 31, 2022
Debt Securities, Available-for-sale [Line Items]
Debt securities, Cost or Amortized Cost	$ 135,370	$ 127,119
Debt securities, Gross Unrealized Gain	50	1
Debt securities, Gross Unrealized Losses	(13,307)	(16,919)
Debt securities, Estimated Fair Value	122,113	110,201
U.S. Government
Debt Securities, Available-for-sale [Line Items]
Debt securities, Cost or Amortized Cost	5,405	7,833
Debt securities, Gross Unrealized Gain	3	0
Debt securities, Gross Unrealized Losses	(161)	(335)
Debt securities, Estimated Fair Value	5,247	7,498
State and local government
Debt Securities, Available-for-sale [Line Items]
Debt securities, Cost or Amortized Cost	24,274	25,487
Debt securities, Gross Unrealized Gain	0	1
Debt securities, Gross Unrealized Losses	(3,810)	(4,672)
Debt securities, Estimated Fair Value	20,464	20,816
Corporate debt
Debt Securities, Available-for-sale [Line Items]
Debt securities, Cost or Amortized Cost	34,002	35,347
Debt securities, Gross Unrealized Gain	0	0
Debt securities, Gross Unrealized Losses	(3,507)	(4,788)
Debt securities, Estimated Fair Value	30,495	30,559
Asset-backed securities
Debt Securities, Available-for-sale [Line Items]
Debt securities, Cost or Amortized Cost	38,289	21,742
Debt securities, Gross Unrealized Gain	47	0
Debt securities, Gross Unrealized Losses	(584)	(1,246)
Debt securities, Estimated Fair Value	37,752	20,496
Mortgage-backed securities
Debt Securities, Available-for-sale [Line Items]
Debt securities, Cost or Amortized Cost	26,768	29,194
Debt securities, Gross Unrealized Gain	0	0
Debt securities, Gross Unrealized Losses	(4,641)	(5,157)
Debt securities, Estimated Fair Value	22,127	24,037
Commercial mortgage-backed securities
Debt Securities, Available-for-sale [Line Items]
Debt securities, Cost or Amortized Cost	3,404	3,414
Debt securities, Gross Unrealized Gain	0	0
Debt securities, Gross Unrealized Losses	(160)	(186)
Debt securities, Estimated Fair Value	3,244	3,228
Collateralized mortgage obligations
Debt Securities, Available-for-sale [Line Items]
Debt securities, Cost or Amortized Cost	3,228	4,102
Debt securities, Gross Unrealized Gain	0	0
Debt securities, Gross Unrealized Losses	(444)	(535)
Debt securities, Estimated Fair Value	$ 2,784	$ 3,567

Investments - Available-for-s_2

Investments - Available-for-sale Securities in Unrealized Loss Positions (Details) $ in Thousands	Dec. 31, 2023 USD ($) Security	Dec. 31, 2022 USD ($) Security
Debt Securities, Available-for-sale, Continuous Unrealized Loss Position, Number of Positions [Abstract]
Debt securities, less than 12 months, number of issues | Security	9	205
Debt securities, 12 months or More, number of issues | Security	309	133
Debt securities, number of issues | Security	318	338
Debt Securities, Available-for-sale, Unrealized Loss Position [Abstract]
Debt securities, less than 12 months, fair value	$ 2,943	$ 38,757
Debt securities, 12 months or More, fair value	97,405	71,142
Debt securities, fair value	100,348	109,899
Debt Securities, Available-for-sale, Unrealized Loss Position, Accumulated Loss [Abstract]
Debt securities, less than 12 months, unrealized losses	(16)	(4,857)
Debt securities, 12 months or More, unrealized losses	(13,291)	(12,062)
Debt securities, total unrealized losses	$ (13,307)	$ (16,919)
U.S. Government
Debt Securities, Available-for-sale, Continuous Unrealized Loss Position, Number of Positions [Abstract]
Debt securities, less than 12 months, number of issues | Security	1	8
Debt securities, 12 months or More, number of issues | Security	9	5
Debt securities, number of issues | Security	10	13
Debt Securities, Available-for-sale, Unrealized Loss Position [Abstract]
Debt securities, less than 12 months, fair value	$ 649	$ 3,534
Debt securities, 12 months or More, fair value	3,400	3,964
Debt securities, fair value	4,049	7,498
Debt Securities, Available-for-sale, Unrealized Loss Position, Accumulated Loss [Abstract]
Debt securities, less than 12 months, unrealized losses	(7)	(135)
Debt securities, 12 months or More, unrealized losses	(154)	(200)
Debt securities, total unrealized losses	$ (161)	$ (335)
State and local government
Debt Securities, Available-for-sale, Continuous Unrealized Loss Position, Number of Positions [Abstract]
Debt securities, less than 12 months, number of issues | Security	3	77
Debt securities, 12 months or More, number of issues | Security	113	45
Debt securities, number of issues | Security	116	122
Debt Securities, Available-for-sale, Unrealized Loss Position [Abstract]
Debt securities, less than 12 months, fair value	$ 1,193	$ 12,966
Debt securities, 12 months or More, fair value	19,096	7,147
Debt securities, fair value	20,289	20,113
Debt Securities, Available-for-sale, Unrealized Loss Position, Accumulated Loss [Abstract]
Debt securities, less than 12 months, unrealized losses	(7)	(2,318)
Debt securities, 12 months or More, unrealized losses	(3,803)	(2,354)
Debt securities, total unrealized losses	$ (3,810)	$ (4,672)
Corporate debt
Debt Securities, Available-for-sale, Continuous Unrealized Loss Position, Number of Positions [Abstract]
Debt securities, less than 12 months, number of issues | Security	0	27
Debt securities, 12 months or More, number of issues | Security	66	42
Debt securities, number of issues | Security	66	69
Debt Securities, Available-for-sale, Unrealized Loss Position [Abstract]
Debt securities, less than 12 months, fair value	$ 0	$ 10,069
Debt securities, 12 months or More, fair value	30,495	20,890
Debt securities, fair value	30,495	30,959
Debt Securities, Available-for-sale, Unrealized Loss Position, Accumulated Loss [Abstract]
Debt securities, less than 12 months, unrealized losses	0	(1,373)
Debt securities, 12 months or More, unrealized losses	(3,507)	(3,415)
Debt securities, total unrealized losses	$ (3,507)	$ (4,788)
Asset-backed securities
Debt Securities, Available-for-sale, Continuous Unrealized Loss Position, Number of Positions [Abstract]
Debt securities, less than 12 months, number of issues | Security	1	6
Debt securities, 12 months or More, number of issues | Security	21	20
Debt securities, number of issues | Security	22	26
Debt Securities, Available-for-sale, Unrealized Loss Position [Abstract]
Debt securities, less than 12 months, fair value	$ 1,090	$ 3,188
Debt securities, 12 months or More, fair value	16,270	17,308
Debt securities, fair value	17,360	20,496
Debt Securities, Available-for-sale, Unrealized Loss Position, Accumulated Loss [Abstract]
Debt securities, less than 12 months, unrealized losses	(1)	(76)
Debt securities, 12 months or More, unrealized losses	(583)	(1,170)
Debt securities, total unrealized losses	$ (584)	$ (1,246)
Mortgage-backed securities
Debt Securities, Available-for-sale, Continuous Unrealized Loss Position, Number of Positions [Abstract]
Debt securities, less than 12 months, number of issues | Security	4	57
Debt securities, 12 months or More, number of issues | Security	64	12
Debt securities, number of issues | Security	68	69
Debt Securities, Available-for-sale, Unrealized Loss Position [Abstract]
Debt securities, less than 12 months, fair value	$ 11	$ 4,006
Debt securities, 12 months or More, fair value	22,116	20,031
Debt securities, fair value	22,127	24,037
Debt Securities, Available-for-sale, Unrealized Loss Position, Accumulated Loss [Abstract]
Debt securities, less than 12 months, unrealized losses	(1)	(573)
Debt securities, 12 months or More, unrealized losses	(4,640)	(4,584)
Debt securities, total unrealized losses	$ (4,641)	$ (5,157)
Commercial mortgage-backed securities
Debt Securities, Available-for-sale, Continuous Unrealized Loss Position, Number of Positions [Abstract]
Debt securities, less than 12 months, number of issues | Security	0	4
Debt securities, 12 months or More, number of issues | Security	4	0
Debt securities, number of issues | Security	4	4
Debt Securities, Available-for-sale, Unrealized Loss Position [Abstract]
Debt securities, less than 12 months, fair value	$ 0	$ 3,205
Debt securities, 12 months or More, fair value	3,225	0
Debt securities, fair value	3,225	3,205
Debt Securities, Available-for-sale, Unrealized Loss Position, Accumulated Loss [Abstract]
Debt securities, less than 12 months, unrealized losses	0	(186)
Debt securities, 12 months or More, unrealized losses	(160)	0
Debt securities, total unrealized losses	$ (160)	$ (186)
Collateralized mortgage obligations
Debt Securities, Available-for-sale, Continuous Unrealized Loss Position, Number of Positions [Abstract]
Debt securities, less than 12 months, number of issues | Security	0	26
Debt securities, 12 months or More, number of issues | Security	32	9
Debt securities, number of issues | Security	32	35
Debt Securities, Available-for-sale, Unrealized Loss Position [Abstract]
Debt securities, less than 12 months, fair value	$ 0	$ 1,789
Debt securities, 12 months or More, fair value	2,803	1,802
Debt securities, fair value	2,803	3,591
Debt Securities, Available-for-sale, Unrealized Loss Position, Accumulated Loss [Abstract]
Debt securities, less than 12 months, unrealized losses	0	(196)
Debt securities, 12 months or More, unrealized losses	(444)	(339)
Debt securities, total unrealized losses	$ (444)	$ (535)

Investments - Net Investment In

Investments - Net Investment Income (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2023	Dec. 31, 2022
Net Investment Income [Line Items]
Investment income	$ 5,760	$ 3,345
Investment expenses	(234)	(302)
Net investment income	5,526	3,043
Debt securities
Net Investment Income [Line Items]
Investment income	4,121	2,517
Equity securities
Net Investment Income [Line Items]
Investment income	36	52
Cash, cash equivalents and short-term investments
Net Investment Income [Line Items]
Investment income	$ 1,603	$ 776

Investments - Gross Realized Ga

Investments - Gross Realized Gains and Losses (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2023	Dec. 31, 2022
Debt securities:
Gross realized gains	$ 0	$ 6
Gross realized losses	(20)	(155)
Total debt securities	(20)	(149)
Equity securities:
Gross realized gains	0	375
Gross realized losses	0	(1,731)
Total equity securities	0	(1,356)
Total net realized investment gains	$ (20)	$ (1,505)

Investments - Narrative (Detail

Investments - Narrative (Details) - USD ($)	12 Months Ended
	Dec. 31, 2023	Dec. 31, 2022
Investments, Debt and Equity Securities [Abstract]
Gross unrealized gain (loss) on available for sale securities	$ 13,300,000
Proceeds from sale of available-for-sale debt securities	11,900,000	$ 32,000,000
Gross realized gains from sales of available-for-sale debt securities	0	5,000
Gross realized losses from sales of available-for-sale debt securities	18,000	155,000
Gross unrealized gains	505,000	0
Gross unrealized losses	535,000	638,000
Amount payable for securities purchased	0	0
Amount receivable for securities sold	0	650,000
Other than temporary impairments losses, investments	0
Investments	1,400,000	1,800,000
Deposits held in trust accounts	8,200,000	8,000,000
Deposits, held in trust for collateral requirements	123,500,000	$ 95,700,000
Collateral of gross unearned premiums and gross loss reserves	111,300,000
Unearned premiums run off	$ 0

Investments - Available-for-s_3

Investments - Available-for-sale Fixed Maturity Securities by Contractual Maturity (Details) - USD ($) $ in Thousands	Dec. 31, 2023	Dec. 31, 2022
Amortized Cost
Due in one year or less	$ 3,212
Due after one year through five years	30,996
Due after five years through ten years	18,768
Due after ten years	10,705
Securities with contractual maturities	63,681
Total debt securities	135,370	$ 127,119
Estimated Fair Value
Due in one year or less	3,175
Due after one year through five years	28,983
Due after five years through ten years	15,904
Due after ten years	8,144
Securities with contractual maturities	56,206
Total debt securities	122,113	110,201
Asset-backed securities
Amortized Cost
Total debt securities	38,289	21,742
Estimated Fair Value
Total debt securities	37,752	20,496
Mortgage-backed securities
Amortized Cost
Total debt securities	26,768	29,194
Estimated Fair Value
Total debt securities	22,127	24,037
Commercial mortgage-backed securities
Amortized Cost
Total debt securities	3,404	3,414
Estimated Fair Value
Total debt securities	3,244	3,228
Collateralized mortgage obligations
Amortized Cost
Total debt securities	3,228	4,102
Estimated Fair Value
Total debt securities	$ 2,784	$ 3,567

Fair Value Measurements - Finan

Fair Value Measurements - Financial Instruments (Details) - USD ($) $ in Thousands	Dec. 31, 2023	Dec. 31, 2022
Assets:
Total debt securities	$ 122,113	$ 110,201
Equity Securities	896	917
Short-term investments	20,838	25,929
Total marketable investments measured at fair value	143,847	137,047
Total assets measured at fair value	145,305	137,397
Liabilities:
Total Liabilities (non-recurring fair value measure)	21,756	33,730
U.S. Government
Assets:
Total debt securities	5,247	7,498
State and local government
Assets:
Total debt securities	20,464	20,816
Corporate debt
Assets:
Total debt securities	30,495	30,559
Asset-backed securities
Assets:
Total debt securities	37,752	20,496
Mortgage-backed securities
Assets:
Total debt securities	22,127	24,037
Commercial mortgage-backed securities
Assets:
Total debt securities	3,244	3,228
Collateralized mortgage obligations
Assets:
Total debt securities	2,784	3,567
Senior Unsecured Notes
Liabilities:
Debt	11,791	22,430
Senior Secured Notes
Liabilities:
Debt	9,965
Subordinated notes
Liabilities:
Debt		11,300
Partnership interest
Assets:
Investments measured at NAV	1,458	350
Level 1
Assets:
Total debt securities	0	0
Equity Securities	139	160
Short-term investments	20,838	25,929
Total marketable investments measured at fair value	20,977	26,089
Liabilities:
Total Liabilities (non-recurring fair value measure)	0	0
Level 1 | U.S. Government
Assets:
Total debt securities	0	0
Level 1 | State and local government
Assets:
Total debt securities	0	0
Level 1 | Corporate debt
Assets:
Total debt securities	0	0
Level 1 | Asset-backed securities
Assets:
Total debt securities	0	0
Level 1 | Mortgage-backed securities
Assets:
Total debt securities	0	0
Level 1 | Commercial mortgage-backed securities
Assets:
Total debt securities	0	0
Level 1 | Collateralized mortgage obligations
Assets:
Total debt securities	0	0
Level 1 | Senior Unsecured Notes
Liabilities:
Debt	0	0
Level 1 | Senior Secured Notes
Liabilities:
Debt	0
Level 1 | Subordinated notes
Liabilities:
Debt		0
Level 2
Assets:
Total debt securities	122,113	110,201
Equity Securities	757	757
Short-term investments	0	0
Total marketable investments measured at fair value	122,870	110,958
Liabilities:
Total Liabilities (non-recurring fair value measure)	11,791	22,430
Level 2 | U.S. Government
Assets:
Total debt securities	5,247	7,498
Level 2 | State and local government
Assets:
Total debt securities	20,464	20,816
Level 2 | Corporate debt
Assets:
Total debt securities	30,495	30,559
Level 2 | Asset-backed securities
Assets:
Total debt securities	37,752	20,496
Level 2 | Mortgage-backed securities
Assets:
Total debt securities	22,127	24,037
Level 2 | Commercial mortgage-backed securities
Assets:
Total debt securities	3,244	3,228
Level 2 | Collateralized mortgage obligations
Assets:
Total debt securities	2,784	3,567
Level 2 | Senior Unsecured Notes
Liabilities:
Debt	11,791	22,430
Level 2 | Senior Secured Notes
Liabilities:
Debt	0
Level 2 | Subordinated notes
Liabilities:
Debt		0
Level 3
Assets:
Total debt securities	0	0
Equity Securities	0	0
Short-term investments	0	0
Total marketable investments measured at fair value	0	0
Liabilities:
Total Liabilities (non-recurring fair value measure)	9,965	11,300
Level 3 | U.S. Government
Assets:
Total debt securities	0	0
Level 3 | State and local government
Assets:
Total debt securities	0	0
Level 3 | Corporate debt
Assets:
Total debt securities	0	0
Level 3 | Asset-backed securities
Assets:
Total debt securities	0	0
Level 3 | Mortgage-backed securities
Assets:
Total debt securities	0	0
Level 3 | Commercial mortgage-backed securities
Assets:
Total debt securities	0	0
Level 3 | Collateralized mortgage obligations
Assets:
Total debt securities	0	0
Level 3 | Senior Unsecured Notes
Liabilities:
Debt	0	0
Level 3 | Senior Secured Notes
Liabilities:
Debt	$ 9,965
Level 3 | Subordinated notes
Liabilities:
Debt		$ 11,300

Fair Value Measurements - Narra

Fair Value Measurements - Narrative (Details) - USD ($)	12 Months Ended
	Dec. 31, 2023	Dec. 31, 2022
Fair Value, Concentration of Risk, Financial Statement Captions [Line Items]
Transfers into level 3	$ 0	$ 0
Transfers out of Level 3	$ 0	$ 0
Level 1
Fair Value, Concentration of Risk, Financial Statement Captions [Line Items]
Marketable investment percentage	15%	18%
Level 2
Fair Value, Concentration of Risk, Financial Statement Captions [Line Items]
Marketable investment percentage	85%	82%

Deferred Policy Acquisition C_3

Deferred Policy Acquisition Costs - Activity in Deferred Policy Acquisition Costs (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2023	Dec. 31, 2022
Movement Analysis of Deferred Policy Acquisition Costs [Roll Forward]
Balance at beginning of period	$ 10,290	$ 12,267
Deferred policy acquisition costs	16,887	20,202
Amortization of policy acquisition costs	(16,589)	(22,179)
Impact from renewal rights sale	(4,303)
Net change	(4,005)	(1,977)
Balance at end of period	$ 6,285	$ 10,290

Unpaid Losses and Loss Adjust_3

Unpaid Losses and Loss Adjustment Expenses - Changes in the Liability for Unpaid Losses and Loss Adjustment Expenses (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2023	Dec. 31, 2022
Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]
Gross reserves - beginning of period	$ 165,539	$ 139,085
Less: reinsurance recoverables on unpaid losses	82,651	40,344
Net reserves - beginning of period	82,888	98,741
Add: incurred losses and loss adjustment expenses, net of reinsurance
Current period	64,580	57,156
Prior period	17,833	24,284
Total net incurred losses and LAE	82,413	81,440
Deduct: loss and loss adjustment expense payments, net of reinsurance
Current period	27,001	20,894
Prior period	34,495	76,399
Total net loss and loss adjustment expense payments	61,496	97,293
Net reserves - end of period	103,805	82,888
Plus: reinsurance recoverables on unpaid losses	70,807	82,651
Gross reserves - end of period	$ 174,612	$ 165,539

Unpaid Losses and Loss Adjust_4

Unpaid Losses and Loss Adjustment Expenses - Narrative (Details) - USD ($)	12 Months Ended
	Dec. 31, 2023	Dec. 31, 2022	Nov. 01, 2022	Dec. 31, 2021
Liability for Claims and Claims Adjustment Expense [Line Items]
Prior year adjustments	$ 17,833,000	$ 24,284,000
Losses and loss adjustment expenses, net	82,413,000	81,440,000
Unpaid losses and loss adjustment expenses	174,612,000	165,539,000		$ 139,085,000
Reinsurance recoverables on unpaid losses	70,807,000	82,651,000		$ 40,344,000
Reinsurance recoverables on paid losses	12,619,000	6,653,000
Loss Portfolio Transfer (“LPT”) Reinsurance Agreement
Liability for Claims and Claims Adjustment Expense [Line Items]
Reinsurance recoverables on unpaid losses	10,900,000	25,900,000
Reinsurance recoverables on paid losses	3,800,000	3,900,000
Accident Year 2022
Liability for Claims and Claims Adjustment Expense [Line Items]
Prior year adjustments	5,900,000
Accident Year 2021
Liability for Claims and Claims Adjustment Expense [Line Items]
Prior year adjustments	6,800,000	1,800,000
Accident Year 2020
Liability for Claims and Claims Adjustment Expense [Line Items]
Prior year adjustments	4,900,000	4,000,000
Accident Year 2019
Liability for Claims and Claims Adjustment Expense [Line Items]
Prior year adjustments	$ 218,000	9,600,000
Accident Year 2018
Liability for Claims and Claims Adjustment Expense [Line Items]
Prior year adjustments		5,200,000
Accident Year 2017
Liability for Claims and Claims Adjustment Expense [Line Items]
Prior year adjustments		$ 3,700,000
Minimum | Loss Portfolio Transfer (“LPT”) Reinsurance Agreement
Liability for Claims and Claims Adjustment Expense [Line Items]
Reinsurance recoverables on paid losses			$ 46,300,000
Commercial Line
Liability for Claims and Claims Adjustment Expense [Line Items]
Percentage of additional loss emergence of adverse development	58%
Reinsurance recoverables on unpaid losses	$ 68,981,000
Personal Line
Liability for Claims and Claims Adjustment Expense [Line Items]
Reinsurance recoverables on unpaid losses	$ 1,826,000

Unpaid Losses and Loss Adjust_5

Unpaid Losses and Loss Adjustment Expenses - Loss Development (Details)	Dec. 31, 2023 USD ($) Claim	Dec. 31, 2022 USD ($)	Dec. 31, 2021 USD ($)	Dec. 31, 2020 USD ($)	Dec. 31, 2019 USD ($)	Dec. 31, 2018 USD ($)	Dec. 31, 2017 USD ($)	Dec. 31, 2016 USD ($)	Dec. 31, 2015 USD ($)	Dec. 31, 2014 USD ($)
Claims Development [Line Items]
Incurred	$ 587,147,000
Total IBNR	43,051,000
Cumulative Paid	480,458
Net Unpaid losses and ALAE, years 2014 through 2023	106,689,000
Unpaid losses and ALAE, prior to 2014	160,000
Unpaid Losses, LPT	10,928,000
Unpaid losses and ALAE, net of reinsurance	95,921,000
Commercial Lines
Claims Development [Line Items]
Incurred	479,399,000
Total IBNR	41,895,000
Cumulative Paid	376,358,000
Net Unpaid losses and ALAE, years 2014 through 2023	103,041,000
Unpaid losses and ALAE, prior to 2014	160,000
Unpaid Losses, LPT	(10,928,000)
Unpaid losses and ALAE, net of reinsurance	92,273,000
Personal Lines
Claims Development [Line Items]
Incurred	107,748,000
Total IBNR	1,156,000
Cumulative Paid	104,100
Net Unpaid losses and ALAE, years 2014 through 2023	3,648,000
Unpaid losses and ALAE, prior to 2014	0
Unpaid losses and ALAE, net of reinsurance	3,648,000
Accident Year 2014
Claims Development [Line Items]
Incurred	47,121,000	$ 47,063,000	$ 47,272,000	$ 47,140,000	$ 46,848,000	$ 46,074,000	$ 44,247,000	$ 40,446,000	$ 37,378,000	$ 37,660,000
Total IBNR	$ 0
Cumulative number of reported claims | Claim	5,492
Cumulative Paid	$ 46,715	46,633,000	46,718,000	46,457,000	45,591,000	43,464,000	40,192,000	34,718,000	30,492,000	21,534,000
Accident Year 2014 | Commercial Lines
Claims Development [Line Items]
Incurred	29,093,000	29,011,000	29,175,000	29,045,000	28,766,000	28,145,000	26,367,000	22,711,000	19,907,000	19,709,000
Total IBNR	$ 0
Cumulative number of reported claims | Claim	1,755
Cumulative Paid	$ 28,688,000	28,608,000	28,648,000	28,389,000	27,544,000	25,609,000	22,446,000	17,458,000	13,977,000	8,715,000
Accident Year 2014 | Personal Lines
Claims Development [Line Items]
Incurred	18,028,000	18,052,000	18,097,000	18,095,000	18,082,000	17,929,000	17,880,000	17,735,000	17,471,000	17,951,000
Total IBNR	$ 0
Cumulative number of reported claims | Claim	3,737
Cumulative Paid	$ 18,027	18,025,000	18,070,000	18,068,000	18,047,000	17,855,000	17,746,000	17,260,000	16,515,000	$ 12,819,000
Accident Year 2015
Claims Development [Line Items]
Incurred	54,767,000	54,541,000	54,251,000	53,222,000	51,736,000	49,763,000	46,581,000	40,078,000	33,319,000
Total IBNR	$ 0
Cumulative number of reported claims | Claim	4,517
Cumulative Paid	$ 54,568	54,129,000	52,979,000	51,123,000	49,747,000	45,634,000	36,393,000	29,690,000	18,241,000
Accident Year 2015 | Commercial Lines
Claims Development [Line Items]
Incurred	39,311,000	39,093,000	38,824,000	37,795,000	36,372,000	34,478,000	31,861,000	26,633,000	22,442,000
Total IBNR	$ 0
Cumulative number of reported claims | Claim	2,363
Cumulative Paid	$ 39,116,000	38,685,000	37,563,000	35,833,000	34,497,000	30,475,000	22,549,000	17,817,000	10,470,000
Accident Year 2015 | Personal Lines
Claims Development [Line Items]
Incurred	15,456,000	15,448,000	15,427,000	15,427,000	15,364,000	15,285,000	14,721,000	13,445,000	10,877,000
Total IBNR	$ 0
Cumulative number of reported claims | Claim	2,154
Cumulative Paid	$ 15,452	15,444,000	15,416,000	15,290,000	15,250,000	15,159,000	13,844,000	11,873,000	$ 7,771,000
Accident Year 2016
Claims Development [Line Items]
Incurred	64,843,000	64,356,000	62,627,000	61,744,000	59,905,000	55,389,000	48,353,000	44,015,000
Total IBNR	$ 19,000
Cumulative number of reported claims | Claim	5,374
Cumulative Paid	$ 64,238	62,636,000	59,096,000	57,296,000	53,077,000	42,227,000	30,373,000	17,374,000
Accident Year 2016 | Commercial Lines
Claims Development [Line Items]
Incurred	49,162,000	48,677,000	46,993,000	46,089,000	44,355,000	40,440,000	34,935,000	32,396,000
Total IBNR	$ 19,000
Cumulative number of reported claims | Claim	3,559
Cumulative Paid	$ 48,557,000	46,957,000	43,644,000	41,945,000	37,967,000	27,785,000	19,135,000	10,255,000
Accident Year 2016 | Personal Lines
Claims Development [Line Items]
Incurred	15,681,000	15,679,000	15,634,000	15,655,000	15,550,000	14,949,000	13,418,000	11,619,000
Total IBNR	$ 0
Cumulative number of reported claims | Claim	1,815
Cumulative Paid	$ 15,681	15,679,000	15,452,000	15,351,000	15,110,000	14,442,000	11,238,000	$ 7,119,000
Accident Year 2017
Claims Development [Line Items]
Incurred	74,104,000	71,606,000	70,500,000	66,676,000	64,242,000	58,045,000	58,309,000
Total IBNR	$ 234,000
Cumulative number of reported claims | Claim	8,749
Cumulative Paid	$ 72,259	67,757,000	62,014,000	56,834,000	48,209,000	35,964,000	20,768,000
Accident Year 2017 | Commercial Lines
Claims Development [Line Items]
Incurred	59,149,000	56,649,000	55,589,000	51,883,000	49,749,000	44,495,000	44,251,000
Total IBNR	$ 234,000
Cumulative number of reported claims | Claim	5,835
Cumulative Paid	$ 57,304,000	52,800,000	47,148,000	42,308,000	34,205,000	23,020,000	12,448,000
Accident Year 2017 | Personal Lines
Claims Development [Line Items]
Incurred	14,955,000	14,957,000	14,911,000	14,793,000	14,493,000	13,550,000	14,058,000
Total IBNR	$ 0
Cumulative number of reported claims | Claim	2,914
Cumulative Paid	$ 14,955	14,957,000	14,866,000	14,526,000	14,004,000	12,944,000	$ 8,320,000
Accident Year 2018
Claims Development [Line Items]
Incurred	68,217,000	66,400,000	61,643,000	56,024,000	48,810,000	48,517,000
Total IBNR	$ 568,000
Cumulative number of reported claims | Claim	6,931
Cumulative Paid	$ 63,447	56,752,000	47,819,000	37,733,000	25,417,000	14,671,000
Accident Year 2018 | Commercial Lines
Claims Development [Line Items]
Incurred	61,881,000	60,102,000	55,261,000	49,741,000	42,432,000	42,624,000
Total IBNR	$ 568,000
Cumulative number of reported claims | Claim	6,128
Cumulative Paid	$ 57,114,000	50,508,000	41,577,000	31,633,000	19,799,000	10,375,000
Accident Year 2018 | Personal Lines
Claims Development [Line Items]
Incurred	6,336,000	6,298,000	6,382,000	6,283,000	6,378,000	5,893,000
Total IBNR	$ 0
Cumulative number of reported claims | Claim	803
Cumulative Paid	$ 6,333	6,244,000	6,242,000	6,100,000	5,618,000	$ 4,296,000
Accident Year 2019
Claims Development [Line Items]
Incurred	61,895,000	58,125,000	49,227,000	44,841,000	44,385,000
Total IBNR	$ 1,611,000
Cumulative number of reported claims | Claim	6,678
Cumulative Paid	$ 53,228	42,743,000	31,650,000	23,066,000	12,197,000
Accident Year 2019 | Commercial Lines
Claims Development [Line Items]
Incurred	59,028,000	55,263,000	46,329,000	42,129,000	41,286,000
Total IBNR	$ 1,611,000
Cumulative number of reported claims | Claim	6,337
Cumulative Paid	$ 50,369,000	39,893,000	28,958,000	20,462,000	10,078,000
Accident Year 2019 | Personal Lines
Claims Development [Line Items]
Incurred	2,867,000	2,862,000	2,898,000	2,712,000	3,099,000
Total IBNR	$ 0
Cumulative number of reported claims | Claim	341
Cumulative Paid	$ 2,859	2,850,000	2,692,000	2,604,000	$ 2,119,000
Accident Year 2020
Claims Development [Line Items]
Incurred	46,537,000	41,829,000	37,918,000	36,206,000
Total IBNR	$ 3,012,000
Cumulative number of reported claims | Claim	4,190
Cumulative Paid	$ 35,973	26,830,000	19,787,000	11,524,000
Accident Year 2020 | Commercial Lines
Claims Development [Line Items]
Incurred	43,918,000	39,193,000	35,328,000	33,867,000
Total IBNR	$ 3,012,000
Cumulative number of reported claims | Claim	3,866
Cumulative Paid	$ 33,354,000	24,225,000	17,332,000	10,217,000
Accident Year 2020 | Personal Lines
Claims Development [Line Items]
Incurred	2,619,000	2,636,000	2,590,000	2,339,000
Total IBNR	$ 0
Cumulative number of reported claims | Claim	324
Cumulative Paid	$ 2,619	2,605,000	2,455,000	$ 1,307,000
Accident Year 2021
Claims Development [Line Items]
Incurred	52,890,000	46,598,000	44,797,000
Total IBNR	$ 5,557,000
Cumulative number of reported claims | Claim	2,995
Cumulative Paid	$ 34,559	25,293,000	15,892,000
Accident Year 2021 | Commercial Lines
Claims Development [Line Items]
Incurred	48,650,000	42,266,000	40,388,000
Total IBNR	$ 5,557,000
Cumulative number of reported claims | Claim	2,947
Cumulative Paid	$ 30,478,000	21,313,000	12,870,000
Accident Year 2021 | Personal Lines
Claims Development [Line Items]
Incurred	4,240,000	4,332,000	4,409,000
Total IBNR	$ 0
Cumulative number of reported claims | Claim	48
Cumulative Paid	$ 4,081	3,980,000	$ 3,022,000
Accident Year 2022
Claims Development [Line Items]
Incurred	57,873,000	51,112,000
Total IBNR	$ 10,142,000
Cumulative number of reported claims | Claim	3,037
Cumulative Paid	$ 30,815	18,236,000
Accident Year 2022 | Commercial Lines
Claims Development [Line Items]
Incurred	49,751,000	41,708,000
Total IBNR	$ 10,142,000
Cumulative number of reported claims | Claim	2,323
Cumulative Paid	$ 22,892,000	12,839,000
Accident Year 2022 | Personal Lines
Claims Development [Line Items]
Incurred	8,122,000	9,404,000
Total IBNR	$ 0
Cumulative number of reported claims | Claim	714
Cumulative Paid	$ 7,923	$ 5,397,000
Accident Year 2023
Claims Development [Line Items]
Incurred	58,900,000
Total IBNR	$ 21,908,000
Cumulative number of reported claims | Claim	3,228
Cumulative Paid	$ 24,656
Accident Year 2023 | Commercial Lines
Claims Development [Line Items]
Incurred	39,456,000
Total IBNR	$ 20,752,000
Cumulative number of reported claims | Claim	1,644
Cumulative Paid	$ 8,486,000
Accident Year 2023 | Personal Lines
Claims Development [Line Items]
Incurred	19,444,000
Total IBNR	$ 1,156,000
Cumulative number of reported claims | Claim	1,584
Cumulative Paid	$ 16,170

Unpaid Losses and Loss Adjust_6

Unpaid Losses and Loss Adjustment Expenses - Reconciliation of Loss to the Liability for Claims (Details) - USD ($) $ in Thousands	Dec. 31, 2023	Dec. 31, 2022	Dec. 31, 2021
Short-duration Insurance Contracts, Reconciliation of Claims Development to Liability [Line Items]
Unpaid losses and ALAE, net of reinsurance	$ 95,921
Reinsurance recoverables on unpaid losses	70,807	$ 82,651	$ 40,344
ULAE expense	7,884
Total gross unpaid losses and LAE	174,612	$ 165,539	$ 139,085
Commercial Lines
Short-duration Insurance Contracts, Reconciliation of Claims Development to Liability [Line Items]
Unpaid losses and ALAE, net of reinsurance	92,273
Reinsurance recoverables on unpaid losses	68,981
Personal Lines
Short-duration Insurance Contracts, Reconciliation of Claims Development to Liability [Line Items]
Unpaid losses and ALAE, net of reinsurance	3,648
Reinsurance recoverables on unpaid losses	$ 1,826

Unpaid Losses and Loss Adjust_7

Unpaid Losses and Loss Adjustment Expenses - Loss Duration (Details)	Dec. 31, 2023
Short-duration Insurance Contracts, Historical Claims Duration [Line Items]
Year 1	29.20%
Year 2	21.30%
Year 3	18.20%
Year 4	12.40%
Year 5	8.90%
Year 6	4.70%
Year 7	2.80%
Year 8	1.40%
Year 9	0.70%
Year 10, and onwards	0.40%
Commercial Lines
Short-duration Insurance Contracts, Historical Claims Duration [Line Items]
Year 1	27.30%
Year 2	21.60%
Year 3	18.60%
Year 4	12.80%
Year 5	9.20%
Year 6	4.90%
Year 7	2.90%
Year 8	1.50%
Year 9	0.70%
Year 10, and onwards	0.50%
Personal Lines
Short-duration Insurance Contracts, Historical Claims Duration [Line Items]
Year 1	83.10%
Year 2	11.30%
Year 3	5.30%
Year 4	0.30%
Year 5	0%
Year 6	0%
Year 7	0%
Year 8	0%
Year 9	0%
Year 10, and onwards	0%

Reinsurance - Narrative (Detail

Reinsurance - Narrative (Details) - USD ($)			1 Months Ended	12 Months Ended			24 Months Ended	48 Months Ended	60 Months Ended
	Nov. 01, 2022	Jan. 01, 2022	Sep. 30, 2023	Dec. 31, 2023	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2023	Dec. 31, 2023	Dec. 31, 2023	Jun. 30, 2022
Effects Of Reinsurance [Line Items]
Reinsurance recoverables on paid losses				$ 12,619,000	$ 6,653,000		$ 12,619,000	$ 12,619,000	$ 12,619,000
Stated net reserves retained				103,805,000	82,888,000	$ 98,741,000	103,805,000	103,805,000	103,805,000
Losses and loss adjustment expenses, net				82,413,000	81,440,000
Reinsurance recoverables on unpaid losses				70,807,000	82,651,000	$ 40,344,000	70,807,000	70,807,000	70,807,000
Prior period				17,833,000	24,284,000
Prepaid reinsurance premiums				28,908,000	16,399,000		28,908,000	28,908,000	28,908,000
Assumed premiums written				43,620,000	42,187,000
Ceded premium written				75,146,000	46,787,000
Ceded premiums earned				62,637,000	38,690,000
Hurricane
Effects Of Reinsurance [Line Items]
Ceded premium written					1,600,000
Ceded premiums earned					1,600,000
Catastrophe Losses
Effects Of Reinsurance [Line Items]
Ceded premium written				91,000
Ceded premiums earned				91,000
Accident Year 2019
Effects Of Reinsurance [Line Items]
Prior period				218,000	9,600,000
Loss Portfolio Transfer (“LPT”) Reinsurance Agreement
Effects Of Reinsurance [Line Items]
Reinsurance recoverables on paid losses				3,800,000	3,900,000		3,800,000	3,800,000	3,800,000
Reinsurance recoverables on unpaid losses				10,900,000	25,900,000		10,900,000	10,900,000	10,900,000
100% Quota Share Reinsurance Agreement
Effects Of Reinsurance [Line Items]
Ceded premium written			$ 30,900,000
Minimum | Loss Portfolio Transfer (“LPT”) Reinsurance Agreement
Effects Of Reinsurance [Line Items]
Reinsurance recoverables on paid losses	$ 46,300,000
Minimum | 100% Quota Share Reinsurance Agreement
Effects Of Reinsurance [Line Items]
Percentage of commission ceded, net			22%
Maximum | 100% Quota Share Reinsurance Agreement
Effects Of Reinsurance [Line Items]
Percentage of commission ceded, net			27%
100% Cede of Commercial Liability Risks In Excess of $400,000
Effects Of Reinsurance [Line Items]
Amount retained (excess of)				400,000	340,000
Ceded Commercial Property Risks In Excess of $200,000
Effects Of Reinsurance [Line Items]
Amount retained (excess of)				400,000
Ceded Commercial Property Risks In Excess of $400,000
Effects Of Reinsurance [Line Items]
Amount retained (excess of)					300,000
Ceded Homeowners Specific Risks In Excess of $300,000
Effects Of Reinsurance [Line Items]
Amount retained (excess of)				300,000	300,000
Liability Risk
Effects Of Reinsurance [Line Items]
Percentage of ceding commission		40%				40%
Workers Compensation and Casualty Clash
Effects Of Reinsurance [Line Items]
Amount retained (excess of)							1,000,000
Amount reinsured							$ 29,000,000
Commercial Auto Physical Damage Risk
Effects Of Reinsurance [Line Items]
Amount retained (excess of)				400,000
Liability Reinsurance Policy
Effects Of Reinsurance [Line Items]
Amount retained (excess of)									400,000
Amount reinsured									$ 600,000
Property Reinsurance Policy | Homeowners Lines
Effects Of Reinsurance [Line Items]
Amount reinsured								1,700,000
Property Reinsurance Policy | Commercial Lines
Effects Of Reinsurance [Line Items]
Amount retained (excess of)				400,000	300,000
Amount reinsured				7,600,000	7,700,000
Property Reinsurance Policy | Property, Liability and Casualty Insurance Product Line
Effects Of Reinsurance [Line Items]
Amount retained (excess of)				3,000,000	2,000,000
Insured property value				$ 27,000,000	$ 28,000,000
Termination date				Jun. 01, 2024	Jun. 01, 2023
Property Reinsurance Policy | Maximum | Homeowners Lines
Effects Of Reinsurance [Line Items]
Amount retained (excess of)								$ 300,000
Quota Share Reinsurance Agreement | Cannabis Program Net Written Premiums
Effects Of Reinsurance [Line Items]
Reinsurance retention policy, reinsured percentage				50%
Quota Share Reinsurance Agreement | Minimum | Commercial Lines
Effects Of Reinsurance [Line Items]
Reinsurance retention policy, reinsured percentage				90%
Quota Share Reinsurance Agreement | Maximum | Commercial Lines
Effects Of Reinsurance [Line Items]
Reinsurance retention policy, reinsured percentage				100%
Quota Share Reinsurance Agreement, Other Arrangements | Maximum | Other insurance product line
Effects Of Reinsurance [Line Items]
Reinsurance retention policy, reinsured percentage				100%
Insurance Fronting Arrangement
Effects Of Reinsurance [Line Items]
Assumed premiums written				$ 43,600,000	$ 42,200,000
Fleming Reinsurance Ltd | Loss Portfolio Transfer (“LPT”) Reinsurance Agreement
Effects Of Reinsurance [Line Items]
Stated net reserves retained										$ 40,800,000
Losses and loss adjustment expenses, net	5,500,000
One-time risk fee retained										5,400,000
Amount reinsured	40,800,000
Fleming Reinsurance Ltd | Loss Portfolio Transfer (“LPT”) Reinsurance Agreement | Accident Year 2019
Effects Of Reinsurance [Line Items]
Reinsurance recoverables on paid losses										66,300,000
Stated net reserves retained										$ 40,800,000
Prior period	20,000,000
Fleming Reinsurance Ltd | Maximum | Loss Portfolio Transfer (“LPT”) Reinsurance Agreement
Effects Of Reinsurance [Line Items]
Reinsurance recoverables on paid losses	$ 66,300,000
Corridor | Agreement between CIC and WPIC and Fleming Re
Effects Of Reinsurance [Line Items]
Losses and loss adjustment expenses, net				5,500,000	5,500,000
Layer | Minimum | Agreement between CIC and WPIC and Fleming Re
Effects Of Reinsurance [Line Items]
Losses and loss adjustment expenses, net				9,100,000	644,000
Layer | Maximum | Agreement between CIC and WPIC and Fleming Re
Effects Of Reinsurance [Line Items]
Losses and loss adjustment expenses, net				$ 20,000,000	$ 20,000,000

Reinsurance - Effects of Reinsu

Reinsurance - Effects of Reinsurance and Assumption Transactions (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2023	Dec. 31, 2022
Written premiums:
Direct	$ 100,214	$ 95,832
Assumed	43,620	42,187
Ceded	(75,146)	(46,787)
Net written premiums	68,688	91,232
Earned premiums:
Direct	96,595	97,843
Assumed	49,977	37,558
Ceded	(62,637)	(38,690)
Net earned premiums	83,935	96,711
Loss and loss adjustment expenses:
Direct	75,175	73,000
Assumed	45,662	43,487
Ceded	(38,424)	(35,047)
Total net incurred losses and LAE	$ 82,413	$ 81,440

Debt - Narrative (Details)

Debt - Narrative (Details) - USD ($)		12 Months Ended
	Sep. 29, 2023	Dec. 31, 2023	Dec. 31, 2022	Sep. 30, 2023
6.75% Public Senior Unsecured notes (Old Public Notes)
Debt Instrument [Line Items]
Face amount of debt		$ 6,500,000
Senior Unsecured Notes
Debt Instrument [Line Items]
Amount of new notes for which existing notes exchanged		5,000,000
Senior Unsecured Notes | 9.75% Public Senior Unsecured Notes (New Public Notes)
Debt Instrument [Line Items]
Face amount of debt		$ 17,900,000		$ 17,900,000
Maturity date				Sep. 30, 2028
Interest rate		9.75%		9.75%
Interest rate, payment terms		interest rate of 9.75% per annum, payable quarterly at the end of March, June, September and December
Debt issuance costs		$ 1,700,000
Senior Unsecured Notes | 6.75% Public Senior Unsecured notes (Old Public Notes)
Debt Instrument [Line Items]
Face amount of debt		$ 11,200,000
Maturity date		Sep. 30, 2023
Interest rate		6.75%		6.75%
Repayments of Debt		$ 24,400,000
Notes paid off		13,200,000
Non-cash exchange of existing notes for new notes		11,200,000
Senior Secured Notes
Debt Instrument [Line Items]
Call premium		1,800,000
Senior Secured Notes | Privately Placed 12.5% Senior Secured Notes
Debt Instrument [Line Items]
Face amount of debt		$ 9,800,000
Maturity date				Sep. 30, 2028
Interest rate		12.50%		12.50%
Quarterly payment of principal		$ 250,000
Interest rate, payment terms		Interest is payable quarterly at the end of March, June, September, and December
Call premium percentage		22%
Restructuring costs incurred		$ 173,000
Debt issuance costs		897,000
Concession made to the lender		0
Line of credit
Debt Instrument [Line Items]
Borrowing capacity			$ 10,000,000
Line of credit | LIBOR
Debt Instrument [Line Items]
Variable interest rate			2.75%
Subordinated notes | Subordinated notes
Debt Instrument [Line Items]
Restructuring of existing subordinated notes to senior secured notes				$ 10,000,000
Principal on subordinated notes paid down	$ 500,000
Subordinated notes | 6.75% Public Senior Unsecured notes (Old Public Notes)
Debt Instrument [Line Items]
Amount of existing notes exchanged for new notes		5,000,000
Offering to New Note | Senior Unsecured Notes August 2023
Debt Instrument [Line Items]
Face amount of debt		6,700,000
Exchange Offering
Debt Instrument [Line Items]
Face amount of debt		$ 6,200,000

Debt - Outstanding Senior Debt

Debt - Outstanding Senior Debt (Details) - FHLB of Indianapolis - USD ($) $ in Thousands	Dec. 31, 2023	Dec. 31, 2022
Debt Instrument [Line Items]
Gross Debt	$ 27,637	$ 34,881
Unamortized Debt Issuance Costs	2,576	1,005
Net Debt	25,061	33,876
Public Notes
Debt Instrument [Line Items]
Gross Debt	17,887	24,381
Unamortized Debt Issuance Costs	1,679	195
Net Debt	16,208	24,186
Senior Secured Notes
Debt Instrument [Line Items]
Gross Debt	9,750
Unamortized Debt Issuance Costs	897
Net Debt	$ 8,853
Subordinated notes
Debt Instrument [Line Items]
Gross Debt		10,500
Unamortized Debt Issuance Costs		810
Net Debt		$ 9,690

Debt - Scheduled Principal Paym

Debt - Scheduled Principal Payments of Company's Debt (Details) - USD ($) $ in Thousands	Dec. 31, 2023	Dec. 31, 2022
Debt Instrument [Line Items]
Total	$ 25,061	$ 33,876
Senior Unsecured Notes
Debt Instrument [Line Items]
2024	1,000
2025	1,000
2026	1,000
2027	1,000
2028	5,750
Total	9,750
Senior Secured Notes
Debt Instrument [Line Items]
2028	17,887
Total	$ 17,887

Income Taxes - Narrative (Detai

Income Taxes - Narrative (Details) - USD ($)	12 Months Ended
	Dec. 31, 2023	Dec. 31, 2022	Oct. 13, 2022
Operating Loss Carryforwards [Line Items]
Current income tax receivable	$ 65,000	$ 58,000
Effective income tax rate	21%	21%
Valuation allowance	$ 28,013,000	$ 21,663,000
Domestic Tax Authority | Internal Revenue Service (IRS)
Operating Loss Carryforwards [Line Items]
Net operating loss carryforwards	80,800,000
Net operating loss carryforwards, subject to expiration	78,200,000
Net operating loss carryforwards, not subject to expiration	10,300,000
Net operating loss carryforwards subject to limitations	19,500,000
State Tax Authority
Operating Loss Carryforwards [Line Items]
Net operating loss carryforwards	$ 120,300,000		$ 14,800,000
State Tax Authority | Minimum
Operating Loss Carryforwards [Line Items]
Income tax statute of limitations period	3 years
State Tax Authority | Maximum
Operating Loss Carryforwards [Line Items]
Income tax statute of limitations period	4 years

Income Taxes - Income Tax Expen

Income Taxes - Income Tax Expense (Benefit) (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2023	Dec. 31, 2022
Income Tax Disclosure [Abstract]
Current tax expense (benefit)	$ 26	$ (45)
Deferred tax expense (benefit)	(17)	(9,396)
Total income tax expense (benefit)	$ 9	$ (9,441)

Income Taxes - Effective Income

Income Taxes - Effective Income Tax Reconciliation (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2023	Dec. 31, 2022
Income Tax Disclosure [Abstract]
Income (loss) before income taxes	$ (25,644)	$ (20,490)
Statutory U.S. federal income tax rate	(5,385)	(4,303)
State income taxes, net of federal benefit	(1,503)	(5,984)
Tax‑exempt investment income and dividend received deduction	(13)	(22)
Nondeductible meals and entertainment	73	79
Valuation allowance on deferred tax assets	7,254	3,715
Equity-earnings from Affiliate	0	195
Net gain from sale of agency assets	0	(2,848)
Utilization of state NOLs	0	(386)
Deferred corrections	(476)	0
PPP Loan forgiveness	0	0
Other	59	113
Total income tax expense (benefit)	$ 9	$ (9,441)
Effective tax rate	0%	46.10%

Income Taxes - Components of De

Income Taxes - Components of Deferred Tax Assets and Liabilities (Details) - USD ($)	Dec. 31, 2023	Dec. 31, 2022
Deferred tax assets:
Discounted unpaid losses and loss adjustment expenses	$ 1,749,000	$ 1,217,000
Unearned premiums	1,648,000	2,324,000
Net operating loss carryforwards	16,960,000	12,152,000
Net unrealized losses on investments	2,780,000	3,687,000
State net operating loss carryforwards	6,523,000	5,097,000
Other	112,000	403,000
Gross deferred tax assets	29,772,000	24,880,000
Less valuation allowance	(28,013,000)	(21,663,000)
Total deferred tax assets, net of allowance	1,759,000	3,217,000
Deferred tax liabilities:
Investment basis difference	208,000	23,000
Tax rate change transition discounting	92,000	137,000
Equity investment in Affiliate	0	691,000
Deferred policy acquisition costs	1,320,000	2,161,000
Intangible assets	115,000	115,000
Property and equipment	24,000	41,000
Other	0	49,000
Total deferred tax liabilities	1,759,000	3,217,000
Net deferred tax liability	$ 0	$ 0

Statutory Financial Data, Ris_3

Statutory Financial Data, Risk-Based Capital and Dividend Restrictions - Summary of Statutory Basis Information (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2023	Dec. 31, 2022
CIC
Statutory Accounting Practices [Line Items]
Statutory capital and surplus	$ 32,117	$ 47,827
RBC authorized control level	19,050	15,541
Statutory net income (loss)	$ (14,014)	$ (6,846)
RBC %	169%	308%
WPIC
Statutory Accounting Practices [Line Items]
Statutory capital and surplus	$ 7,494	$ 20,651
RBC authorized control level	5,268	5,098
Statutory net income (loss)	$ (9,841)	$ (4,171)
RBC %	142%	405%

Statutory Financial Data, Ris_4

Statutory Financial Data, Risk-Based Capital and Dividend Restrictions - Narrative (Details)	12 Months Ended
	Dec. 31, 2023
Insurance [Abstract]
Dividend restriction percentage of statutory surplus of preceding year	10%

Shareholders' Equity - Narrativ

Shareholders' Equity - Narrative (Details)			12 Months Ended
	Dec. 20, 2023 USD ($) Vote $ / shares shares	Aug. 10, 2022 USD ($) $ / shares shares	Dec. 31, 2023 USD ($) Vote $ / shares shares	Dec. 31, 2022 USD ($) $ / shares shares
Equity Class Of Treasury Stock [Line Items]
Preferred stock, par value (in dollars per share) | $ / shares			$ 0	$ 0
Preferred stock, shares issued			1,000	0
Preferred stock, shares outstanding			1,000	0
Additional paid in capital due to stock repurchase | $				$ 10,000
Cash returned from stock repurchase program | $				$ 14,000
Common stock, shares issued (in shares)			12,222,881	12,215,849
Common stock, shares outstanding (in shares)			12,222,881	12,215,849
Common stock voting rights, number of votes per share | Vote			1
Restricted Stock Units (RSUs)
Equity Class Of Treasury Stock [Line Items]
Shares repurchased (in shares)			1,968	1,968
Shares repurchased | $			$ 3,000	$ 4,000
Preferred Stock
Equity Class Of Treasury Stock [Line Items]
Preferred stock dividend rate			8%
Preferred stock equated to an annualized rate			10.50%
Preferred shares dividend basis point			2%
Preferred stock redemption description			The Company has the option to redeem the Preferred Stock at the end of any fiscal quarter, in whole or in part, at a price equal to issue price, plus the amount that would result in a 20.0%, compounded annually, annualized return to the holder (inclusive of the dividends paid), on the portion being redeemed.
Preferred stock redemption percentage			20%
Conversion of preferred stock in to common stock			4,000
Preferred stock, shares issued			1,000	0
Preferred stock, shares outstanding			1,000	0
Preferred Stock | Series A Preferred Stock
Equity Class Of Treasury Stock [Line Items]
Preferred stock voting rights, number of votes per share | Vote	0
Common stocks
Equity Class Of Treasury Stock [Line Items]
Common stock, shares issued (in shares)			12,222,881	12,215,849
Common stock, shares outstanding (in shares)			12,222,881	12,215,849
Private placement | Preferred Stock | Series A Preferred Stock
Equity Class Of Treasury Stock [Line Items]
Shares issued | $	$ 6,000,000
Shares issued (in shares)	1,000
Preferred stock, par value (in dollars per share) | $ / shares	$ 0
Offering price per share (in dollars per share) | $ / shares	$ 6,000
Maturity date	Jun. 30, 2026
Private placement | Common stocks
Equity Class Of Treasury Stock [Line Items]
Shares issued | $		$ 5,000,000
Shares issued (in shares)		2,500,000
Offering price per share (in dollars per share) | $ / shares		$ 2

Accumulated Other Comprehensi_3

Accumulated Other Comprehensive Income (Loss) - Accumulated Other Comprehensive Income (Loss) (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2023	Dec. 31, 2022
AOCI Attributable to Parent, Net of Tax [Roll Forward]
Balance at beginning of period	$ 18,950	$ 40,503
Other comprehensive income (loss)	3,675	(16,093)
Balance at end of period	2,889	18,950
Accumulated Other Comprehensive Income (Loss)
AOCI Attributable to Parent, Net of Tax [Roll Forward]
Balance at beginning of period	(18,203)	(2,110)
Other comprehensive income (loss) before reclassifications	3,624	(16,024)
Less: amounts reclassified from accumulated other comprehensive income (loss)	(51)	69
Other comprehensive income (loss)	3,675	(16,093)
Balance at end of period	$ (14,528)	$ (18,203)

Earnings Per Share - Basic and

Earnings Per Share - Basic and Diluted Income (Loss) Per Common Share (Details) - USD ($) $ / shares in Units, $ in Thousands		12 Months Ended
		Dec. 31, 2023	Dec. 31, 2022
Earnings Per Share [Abstract]
Net income (loss)		$ (25,904)	$ (10,681)
Preferred stock dividends		19
Net income (loss) allocable to common shareholders		$ (25,923)	$ (10,681)
Weighted average common shares outstanding, basic	[1]	12,220,511	10,692,090
Weighted average common shares outstanding, diluted	[1]	12,220,511	10,692,090
Earnings (loss) per share, basic		$ (2.12)	$ (1)
Earnings (loss) per share, diluted		$ (2.12)	$ (1)
[1] The preferred shares that may be convertible into a total of 4,000,000 common shares were anti-dilutive and thus did not impact the diluted earnings per share calculation. There were no unvested restricted stock units as of December 31, 2023. The non-vested shares of the restricted stock units and stock options were anti-dilutive as of December 31, 2022. Therefore, the non-vested shares are excluded from earnings (loss) per share for the years ended December 31, 2022 .

Earnings Per Share - Basic an_2

Earnings Per Share - Basic and Diluted Income (Loss) Per Common Share (Parenthetical) (Details)	12 Months Ended
	Dec. 31, 2023 shares
Earnings Per Share [Abstract]
Total of convertible preferred shares, antidilutive securities excluded from computation of earnings per share	4,000,000
Unvested restricted stock units	0

Stock-based Compensation - Narr

Stock-based Compensation - Narrative (Details) - USD ($)		6 Months Ended	12 Months Ended
	Mar. 08, 2022	Jun. 30, 2020	Dec. 31, 2023	Dec. 31, 2022	Dec. 31, 2018	Dec. 31, 2016
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share-based compensation nonvested shares			0
Employee Stock Option
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Options issued to purchase shares of common stock	630,000	280,000
Vesting period	5 years	5 years
Strike price	$ 4.53	$ 3.81
Expiration date	Mar. 08, 2032	Jun. 30, 2030
Estimated grant date fair value of options issued to purchase shares of common stock	$ 612,000	$ 290,000
Stock options volatility rate	65.04%
Options exercisable term	5 years
Risk free interest rate of options	1.80%
Risk free interest rate term of options	5 years
Market value of stock	$ 2.4
Employee Stock Option | Stock Options Granted on June 30, 2020 [Member]
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share-based compensation expense			$ 51,000	$ 53,000
Share-based compensation expense not yet recognized			$ 78,000
Share-based compensation nonvested shares			100,000
Employee Stock Option | Stock Options Granted on March 8, 2022 [Member]
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share-based compensation expense			$ 122,000	102,000
Share-based compensation expense not yet recognized			$ 387,000
Share-based compensation nonvested shares			504,000
Restricted Stock Units (RSUs)
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share-based compensation expense			$ 17,000	$ 56,000
Restricted Stock Units (RSUs) | 2015 Omnibus Incentive Plan
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Shares granted in period (in shares)					70,000	111,281
Shares granted in period					$ 404,000	$ 909,000
Share-based compensation nonvested shares			0

Related Party Transactions - Na

Related Party Transactions - Narrative (Details) - USD ($)	Oct. 13, 2022	Dec. 31, 2023
Venture
Related Party Transaction [Line Items]
Total consideration	$ 9,700,000
Waterford Bank
Related Party Transaction [Line Items]
Common stock owned		$ 528,000

Employee Benefit Plans (Details

Employee Benefit Plans (Details) - USD ($)	12 Months Ended
	Dec. 31, 2023	Dec. 31, 2022
Retirement Benefits [Abstract]
Minimum employee contribution amount, percentage of gross compensation	1%
Maximum employee contribution amount, percentage of gross compensation	100%
Employee matching contribution, percentage of employee gross compensation	4%
Plan expense	$ 411,000	$ 457,000

Commitments and Contingencies (

Commitments and Contingencies (Details) - Agreement to Design and Implement New Systems - USD ($)	Dec. 31, 2023	Dec. 31, 2022
Other Commitments [Line Items]
Minimum monthly payment	$ 30,000
Commitments expenses incurred	$ 1,900,000	$ 1,900,000

Segment Information - Narrative

Segment Information - Narrative (Details) - Business	12 Months Ended
	Dec. 31, 2023	Dec. 31, 2022
Segment Reporting Information [Line Items]
Number of businesses	3
Gross Written Premiums | Geographic Concentration Risk | Michigan, Texas, Oklahoma and California
Segment Reporting Information [Line Items]
Concentration risk	59.90%	52.80%

Segment Information - Summary o

Segment Information - Summary of Net Earned Premiums by Segment (Details) - Net Earned Premium - Operating Segments - Product Concentration	12 Months Ended
	Dec. 31, 2023	Dec. 31, 2022
Segment Reporting Information [Line Items]
Net Earned Premium	100%	100%
Commercial Lines
Segment Reporting Information [Line Items]
Net Earned Premium	71%	84%
Personal Lines
Segment Reporting Information [Line Items]
Net Earned Premium	29%	16%

Segment Information - Informati

Segment Information - Information by Reportable Segment (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2023	Dec. 31, 2022	Dec. 31, 2021
Segment Reporting Information [Line Items]
Gross written premiums	$ 143,834	$ 138,019
Net written premiums	68,688	91,232
Net earned premiums	83,935	96,711
Other income	694	1,354
Agency commission income	5,680	1,414
Segment revenue	90,309	99,479
Loss and loss adjustment expenses, net	82,413	81,440
Policy acquisition costs	20,892	22,179
Operating expenses	17,891	18,789
Loss portfolio transfer risk fee	0	5,400
Segment expenses	121,196	127,808
Segment underwriting gain (loss)	(30,887)	(28,329)
Net investment income	5,526	3,043
Net realized investment gains (losses)	(20)	(1,505)
Change in fair value of equity securities	608	403
Gain on sale of renewal rights	2,335	0
Gain from VSRM Transaction	0	8,810
Other gains	0	59
Interest expense	(3,206)	(2,971)
Income (loss) before income taxes	(25,644)	(20,490)
Deferred policy acquisition costs	6,285	10,290	$ 12,267
Unearned premiums	65,150	67,887
Unpaid losses and loss adjustment expenses	174,612	165,539	$ 139,085
Operating Segments | Commercial Lines
Segment Reporting Information [Line Items]
Gross written premiums	107,078	116,868
Net written premiums	36,580	72,318
Net earned premiums	59,221	80,823
Other income	217	245
Segment revenue	59,438	81,068
Loss and loss adjustment expenses, net	62,828	70,762
Policy acquisition costs	9,134	17,682
Operating expenses	11,988	13,069
Loss portfolio transfer risk fee		5,400
Segment expenses	83,950	106,913
Segment underwriting gain (loss)	(24,512)	(25,845)
Income (loss) before income taxes	(24,512)	(25,845)
Deferred policy acquisition costs	2,047	7,683
Unearned premiums	45,494	56,565
Unpaid losses and loss adjustment expenses	169,039	159,558
Operating Segments | Personal Lines
Segment Reporting Information [Line Items]
Gross written premiums	36,756	21,151
Net written premiums	32,108	18,914
Net earned premiums	24,714	15,888
Other income	96	82
Segment revenue	24,810	15,970
Loss and loss adjustment expenses, net	19,585	10,678
Policy acquisition costs	6,663	4,604
Operating expenses	3,444	1,936
Segment expenses	29,692	17,218
Segment underwriting gain (loss)	(4,882)	(1,248)
Income (loss) before income taxes	(4,882)	(1,248)
Deferred policy acquisition costs	4,357	2,796
Unearned premiums	19,656	11,322
Unpaid losses and loss adjustment expenses	5,573	5,981
Operating Segments | Underwriting
Segment Reporting Information [Line Items]
Gross written premiums	143,834	138,019
Net written premiums	68,688	91,232
Net earned premiums	83,935	96,711
Other income	313	327
Segment revenue	84,248	97,038
Loss and loss adjustment expenses, net	82,413	81,440
Policy acquisition costs	15,797	22,286
Operating expenses	15,432	15,005
Loss portfolio transfer risk fee		5,400
Segment expenses	113,642	124,131
Segment underwriting gain (loss)	(29,394)	(27,093)
Income (loss) before income taxes	(29,394)	(27,093)
Operating Segments | Wholesale Agency
Segment Reporting Information [Line Items]
Other income	1,379	4,298
Agency commission income	5,680	1,414
Segment revenue	7,059	5,712
Policy acquisition costs	6,401	3,653
Operating expenses	1,153	2,612
Segment expenses	7,554	6,265
Segment underwriting gain (loss)	(495)	(553)
Net investment income		32
Other gains		(1)
Interest expense		(42)
Income (loss) before income taxes	(495)	(564)
Corporate
Segment Reporting Information [Line Items]
Other income	239	271
Segment revenue	239	271
Operating expenses	1,306	1,192
Segment expenses	1,306	1,192
Segment underwriting gain (loss)	(1,067)	(921)
Net investment income	5,526	3,011
Net realized investment gains (losses)	(20)	(1,505)
Change in fair value of equity securities	608	403
Gain on sale of renewal rights	2,335
Gain from VSRM Transaction		8,810
Other gains		60
Interest expense	(3,206)	(2,929)
Income (loss) before income taxes	4,176	6,929
Eliminations
Segment Reporting Information [Line Items]
Other income	(1,237)	(3,542)
Segment revenue	(1,237)	(3,542)
Policy acquisition costs	(1,306)	(3,760)
Operating expenses		(20)
Segment expenses	(1,306)	(3,780)
Segment underwriting gain (loss)	69	238
Income (loss) before income taxes	69	238
Deferred policy acquisition costs	$ (119)	$ (189)

Schedule II - Condensed Finan_2

Schedule II - Condensed Financial Information of Registrant - Balance Sheets (Details) - USD ($) $ in Thousands	Dec. 31, 2023	Dec. 31, 2022	Dec. 31, 2021
Assets
Other assets	$ 6,339	$ 7,862
Total assets	311,804	312,350
Liabilities:
Debt	25,061	33,876
Total liabilities	308,915	293,400
Shareholders' equity:
Preferred stock, no par value (10,000,000 shares authorized; 1,000 and 0 issued and outstanding, respectively)	6,000	0
Common stock, no par value (100,000,000 shares authorized; 12,222,881 and 12,215,849 issued and outstanding, respectively)	98,100	97,913
Accumulated deficit	(86,683)	(60,760)
Accumulated other comprehensive income (loss)	(14,528)	(18,203)
Total shareholders' equity	2,889	18,950	$ 40,503
Total liabilities and shareholders' equity	311,804	312,350
Parent Company
Assets
Investment in subsidiaries	31,157	56,670
Cash	3,174	9,022
Other assets	1,457	2,434
Total assets	35,821	68,239
Liabilities:
Debt	29,061	33,876
Other liabilities	1,798	5,659
Total liabilities	34,295	49,289
Shareholders' equity:
Preferred stock, no par value (10,000,000 shares authorized; 1,000 and 0 issued and outstanding, respectively)	6,000	0
Common stock, no par value (100,000,000 shares authorized; 12,222,881 and 12,215,849 issued and outstanding, respectively)	98,100	97,913
Accumulated deficit	(86,683)	(60,760)
Accumulated other comprehensive income (loss)	(15,891)	(18,203)
Total shareholders' equity	1,526	18,950
Total liabilities and shareholders' equity	35,821	68,239
Parent Company | Subsidiaries
Liabilities:
Due to subsidiaries	3,436	9,754
Parent Company | Affiliate
Assets
Due from Affiliate	$ 33	$ 113

Schedule II - Condensed Finan_3

Schedule II - Condensed Financial Information of Registrant - Balance Sheets Stock Information (Details) - $ / shares	Dec. 31, 2023	Dec. 31, 2022
Condensed Balance Sheet Statements, Captions [Line Items]
Preferred stock, par value (in dollars per share)	$ 0	$ 0
Preferred stock, shares authorized (in shares)	10,000,000	10,000,000
Preferred stock, shares issued (in shares)	1,000	0
Preferred stock, shares outstanding (in shares)	1,000	0
Common stock, shares authorized (in shares)	100,000,000	100,000,000
Common stock, shares issued (in shares)	12,222,881	12,215,849
Common stock, shares outstanding (in shares)	12,222,881	12,215,849
Parent Company
Condensed Balance Sheet Statements, Captions [Line Items]
Preferred stock, par value (in dollars per share)	$ 0	$ 0
Preferred stock, shares authorized (in shares)	10,000,000	10,000,000
Preferred stock, shares issued (in shares)	1,000	0
Preferred stock, shares outstanding (in shares)	1,000	0
Common stock, par value (in dollars per share)	$ 0	$ 0
Common stock, shares authorized (in shares)	100,000,000	100,000,000
Common stock, shares issued (in shares)	12,222,881	12,215,849
Common stock, shares outstanding (in shares)	12,222,881	12,215,849

Schedule II - Condensed Finan_4

Schedule II - Condensed Financial Information of Registrant - Statements of Comprehensive Income (Loss) (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2023	Dec. 31, 2022
Revenue and Other Income
Revenue	$ 98,758	$ 104,889
Other income	694	1,354
Expenses
Operating expenses	17,891	18,789
Interest expense	3,206	2,971
Total expenses	124,402	125,379
Income tax expense (benefit)	9	(9,441)
Net income (loss)	(25,904)	(10,681)
Other Comprehensive Income
Other comprehensive income (loss)	3,675	(16,093)
Parent Company
Revenue and Other Income
Revenue	18,186	5,170
Other income	819	190
Expenses
Operating expenses	14,133	14,365
Interest expense	3,079	2,816
Total expenses	17,212	17,181
Income (loss) before equity in earnings (losses) of subsidiaries and income tax expense (benefit)	974	(12,011)
Income tax expense (benefit)	73	(4,078)
Income (loss) before equity earnings (losses) of subsidiaries	901	(7,933)
Equity earnings (losses) in subsidiaries	(26,805)	(2,748)
Net income (loss)	(25,904)	(10,681)
Other Comprehensive Income
Other comprehensive income (loss)	2,312	(16,093)
Total Comprehensive income (loss)	(23,592)	(26,774)
Parent Company | Management fees from subsidiaries
Revenue and Other Income
Revenue	$ 17,367	$ 4,980

Schedule II - Condensed Finan_5

Schedule II - Condensed Financial Information of Registrant - Statement of Cash Flows (Details) - USD ($) $ in Thousands		12 Months Ended
		Dec. 31, 2023	Dec. 31, 2022
Cash Flows from Operating Activities
Net income (loss)		$ (25,904)	$ (10,681)
Adjustments to reconcile net income (loss) to net cash used in operating activities:
Depreciation and amortization		545	417
Stock-based compensation expense		251	(368)
Deferred income tax expense		(17)	(9,396)
Other (gain) loss		0	(59)
Changes in operating assets and liabilities:
Other assets		250	(138)
Net cash provided by operating activities		(13,392)	(40,474)
Cash Flows From Investing Activities
Contributions to subsidiaries	[1]		(1,947)
Purchases of investments		(234,869)	(318,227)
Net cash provided by (used in) investing activities		(272)	56,503
Cash Flows From Financing Activities
Proceeds received from issuance of shares of preferred stock		6,000
Proceeds received from issuance of shares of common stock			5,000
Proceeds from issuance of long-term debt		6,727
Repurchase of common stock		(3)	10
Paydown of long-term debt		(13,971)	(2,917)
Debt issuance costs		(1,999)
Net cash provided by (used in) financing activities		(3,246)	2,093
Net increase (decrease) in cash		(16,910)	18,122
Cash at beginning of period		28,035	9,913
Cash at end of period		11,125	28,035
Supplemental Disclosure of Cash Flow Information:
Interest paid		3,077	2,979
Preferred stock dividends declared but not paid at end of period		19
Parent Company
Cash Flows from Operating Activities
Net income (loss)		(25,904)	(10,681)
Adjustments to reconcile net income (loss) to net cash used in operating activities:
Depreciation and amortization		545	436
Equity in undistributed (income) loss of subsidiaries		26,805	2,748
Stock-based compensation expense		190	211
Deferred income tax expense		(3,806)	3,884
Changes in operating assets and liabilities:
Due from subsidiaries		(6,318)	2,699
Due from Affiliate		80	107
Current income tax recoverable		0	0
Other assets		860	62
Other liabilities		(73)	(203)
Net cash provided by operating activities		(7,621)	(737)
Cash Flows From Investing Activities
Contributions to subsidiaries		1,019	4,000
Dividends received from subsidiaries		0	0
Purchases of investments		0	0
Purchases of property and equipment		0	0
Net cash provided by (used in) investing activities		1,019	4,000
Cash Flows From Financing Activities
Proceeds received from issuance of shares of preferred stock		6,000	0
Proceeds received from issuance of shares of common stock		0	5,000
Proceeds from issuance of long-term debt		10,727	0
Repurchase of common stock		(3)	10
Borrowings under debt arrangements		0	5,000
Repayment of lines of credit		0	(5,000)
Paydown of long-term debt		(13,971)	0
Debt issuance costs		(1,999)	0
Net cash provided by (used in) financing activities		754	5,010
Net increase (decrease) in cash		(5,848)	8,273
Cash at beginning of period		9,022	749
Cash at end of period		3,174	9,022
Supplemental Disclosure of Cash Flow Information:
Interest paid		2,949	2,979
Preferred stock dividends declared but not paid at end of period		$ 19	$ 0
[1] See Note 3 ~ VSRM Transaction

Schedule II - Condensed Finan_6

Schedule II - Condensed Financial Information of Registrant - Additional Information (Details) - USD ($) $ in Thousands	3 Months Ended	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2023	Dec. 31, 2022
Guarantee of debt
Condensed Cash Flow Statements Captions [Line Items]
Guarantee obligation		$ 10,000
Interest rate		4%
Fair value adjustment of surplus note		$ 6,800
Parent Company
Condensed Cash Flow Statements Captions [Line Items]
Dividends received from subsidiaries during period		0	$ 0
Parent Company | RCIC
Condensed Cash Flow Statements Captions [Line Items]
Dividends received from subsidiaries during period		$ 1,400
Parent Company | CIS
Condensed Cash Flow Statements Captions [Line Items]
Dividends received from subsidiaries during period	$ 10,800

Schedule V - Valuation and Qu_2

Schedule V - Valuation and Qualifying Accounts (Details) - Valuation for Deferred Tax Assets - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2023	Dec. 31, 2022
SEC Schedule, 12-09, Movement in Valuation Allowances and Reserves [Roll Forward]
Balance at Beginning of Period	$ 21,663	$ 14,594
Charged to Expense	7,254	3,715
Decrease to Other Comprehensive Income	(904)	3,354
Deductions from Allowance Account	0	0
Balance at End of Period	$ 28,013	$ 21,663