The following table presents the Company's investments related to insurance operations and other Tiptree investing activities, measured at fair value as of the following periods:


	As of September 30, 2023
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Available for sale securities, at fair value, net of allowance for credit losses	$	669,566	$	—	$	31,672	$	701,238
Loans, at fair value	13,888		62,087		—		75,975
Equity securities	26,291		—		37,165		63,456
Other investments	86,290		4,081		2,464		92,835
Total investments	$	796,035	$	66,168	$	71,301	$	933,504


	As of December 31, 2022
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Available for sale securities, at fair value, net of allowance for credit losses	$	611,980	$	—	$	—	$	611,980
Loans, at fair value	14,312		50,531		—		64,843
Equity securities	72,992		—		12,784		85,776
Other investments	66,163		4,038		2,824		73,025
Total investments	$	765,447	$	54,569	$	15,608	$	835,624

A majority of the Company’s investments in Available for Sale Securities, at fair value, net of allowance for credit losses (AFS securities) as of September 30, 2023 and December 31, 2022 are held by subsidiaries in the insurance segment. The following tables present the Company's investments in AFS securities:


	As of September 30, 2023
	Amortized cost		Allowance for Credit Losses(1)		Gross unrealized gains		Gross unrealized losses		Fair value
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	487,001	$	—	$	448	$	(40,654)	$	446,795
Obligations of state and political subdivisions	49,889		(1)		—		(4,780)		45,108
Corporate securities	191,425		(331)		—		(13,299)		177,795
Asset backed securities	32,054		(14)		—		(3,832)		28,208
Certificates of deposit	1,724		—		—		—		1,724
Obligations of foreign governments	1,806		—		—		(199)		1,608
Total	$	763,899	$	(346)	$	448	$	(62,764)	$	701,238


	As of December 31, 2022
	Amortized cost		Allowance for Credit Losses(1)		Gross unrealized gains		Gross unrealized losses		Fair value
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	417,278	$	—	$	844	$	(36,062)	$	382,060
Obligations of state and political subdivisions	54,390		(3)		4		(4,937)		49,454
Corporate securities	176,187		(183)		1		(14,006)		161,999
Asset backed securities	19,596		(1)		—		(4,246)		15,349
Certificates of deposit	756		—		—		—		756
Obligations of foreign governments	2,629		(3)		—		(264)		2,362
Total	$	670,836	$	(190)	$	849	$	(59,515)	$	611,980

(1) Represents the amount of impairment that has resulted from credit-related factors, and therefore was recognized in net realized and unrealized gains (losses) as a credit loss on AFS securities. Amount excludes unrealized losses relating to non-credit factors.

The amortized cost and fair values of AFS securities, by contractual maturity date, are shown below. Expected maturities may differ from contractual maturities because borrowers may have the right to call or prepay obligations with or without call or prepayment penalties.


	As of
	September 30, 2023				December 31, 2022
	Amortized Cost		Fair Value		Amortized Cost		Fair Value
Due in one year or less	$	243,795	$	242,412	$	52,265	$	51,315
Due after one year through five years	239,551		220,569		300,767		280,965
Due after five years through ten years	38,350		34,686		54,419		49,465
Due after ten years	210,149		175,363		243,789		214,887
Asset backed securities	32,054		28,208		19,596		15,348
Total	$	763,899	$	701,238	$	670,836	$	611,980

The following tables present the gross unrealized losses on AFS securities by length of time that individual AFS securities have been in a continuous unrealized loss position for less than twelve months, and twelve months or greater and do not have an allowance for credit losses:


	As of September 30, 2023
	Less Than or Equal to One Year					More Than One Year
	Fair value		Gross unrealized losses		# of Securities(1)	Fair value		Gross unrealized losses		# of Securities(1)
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	205,524	$	(12,178)	448	$	136,938	$	(28,476)	464
Obligations of state and political subdivisions	1,304		(91)		29	43,802		(4,689)		158
Corporate securities	167,158		(12,649)		1,053	10,637		(650)		52
Asset backed securities	2,102		(317)		29	26,107		(3,515)		153

Obligations of foreign governments	—		—		1	1,607		(199)		7
Total	$	376,088	$	(25,235)	1,560	$	219,091	$	(37,529)	834



	As of December 31, 2022
	Less Than or Equal to One Year					More Than One Year
	Fair value		Gross unrealized losses		# of Securities(1)	Fair value		Gross unrealized losses		# of Securities(1)
U.S. Treasury securities and obligations of U.S. government authorities and agencies	$	164,593	$	(9,357)	354	$	186,591	$	(26,705)	385
Obligations of state and political subdivisions	25,507		(1,076)		97	20,219		(3,861)		78
Corporate securities	45,016		(1,446)		176	114,683		(12,560)		417
Asset backed securities	10,298		(3,642)		46	5,051		(604)		34

Obligations of foreign governments	309		(1)		1	2,054		(263)		8
Total	$	245,723	$	(15,522)	674	$	328,598	$	(43,993)	922

Management believes that it is more likely than not that the Company will be able to hold the fixed maturity AFS securities that were in an unrealized loss position as of September 30, 2023 until full recovery of their amortized cost basis.


	Obligations of state and political subdivisions		Corporate securities		Asset backed securities		Obligations of foreign governments		Total
Balance at December 31, 2021	$	—	$	(241)	$	—	$	(4)	$	(245)
(Increase) in allowance for credit losses	(3)		(109)		(1)		—		(113)

Gains from recoveries of amounts previously written off	—		70		—		2		72
Balance at September 30, 2022	$	(3)	$	(280)	$	(1)	$	(2)	$	(286)

Balance at December 31, 2022	$	(3)	$	(183)	$	(1)	$	(3)	$	(190)
(Increase) in allowance for credit losses	—		(287)		(14)		—		(301)



Gains from recoveries of amounts previously written off	2		139		1		3		145
Balance at September 30, 2023	$	(1)	$	(331)	$	(14)	$	—	$	(346)

The Company applies a discounted cash flow model, based on assumptions and model outputs provided by an investment management company, in determining its lifetime expected credit losses on AFS securities. This includes determining the present value of expected future cash flows discounted at the book yield of the security.


	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023	2022
Net gains from recoveries (credit losses) on AFS securities	$	(50)	$	35	(156)	(41)

Pursuant to certain reinsurance agreements and statutory licensing requirements, the Company has deposited invested assets in custody accounts or insurance department safekeeping accounts. The Company cannot remove or replace investments in regulatory deposit accounts without prior approval of the contractual party or regulatory authority, as applicable. The following table presents the Company's restricted investments included in the Company's AFS securities:


	As of
	September 30, 2023		December 31, 2022


Fair value of restricted investments in trust pursuant to reinsurance agreements	$	48,092	$	34,386
Fair value of restricted investments for special deposits required by state insurance departments	16,681		16,816
Total fair value of restricted investments	$	64,773	$	51,202


	Three Months Ended September 30,				Nine Months Ended September 30,

	2023		2022		2023		2022
Purchases of AFS securities	$	146,512	$	12,395	$	449,165	$	138,738

Proceeds from maturities, calls and prepayments of AFS securities	$	231,101	$	13,689	$	319,100	$	51,328



Gross proceeds from sales of AFS securities	$	2,578	$	—	$	42,536	$	16,970


	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023		2022
Gross realized gains	$	80	$	—	$	80	$	74
Gross realized (losses)	(78)		—		(3,034)		(184)
Total net realized gains (losses) from investment sales and redemptions	$	2	$	—	$	(2,954)	$	(110)

The following table presents the Company’s investments in loans measured at fair value and the Company’s investments in loans measured at fair value pledged as collateral:


	As of September 30, 2023								As of December 31, 2022
	Fair value		Unpaid principal balance (UPB)		Fair value exceeds / (below) UPB		Pledged as collateral		Fair value		Unpaid principal balance (UPB)		Fair value exceeds / (below) UPB		Pledged as collateral
Insurance:
Corporate loans (1)	$	13,888	$	17,118	$	(3,230)	$	—	$	14,312	$	16,032	$	(1,720)	$	—

Mortgage:
Mortgage loans held for sale (2)	62,087		61,392		695		61,376		50,531		49,361		1,170		50,113
Total loans, at fair value	$	75,975	$	78,510	$	(2,535)	$	61,376	$	64,843	$	65,393	$	(550)	$	50,113

(2) As of September 30, 2023, there were three mortgage loans held for sale that were 90 days or more past due. As of December 31, 2022, there were no mortgage loans held for sale that were 90 days or more past due.

Equity securities consist mainly of publicly traded common and preferred stocks and fixed income exchange traded funds. Included within the equity securities balance are 17.0 million shares of Invesque as of September 30, 2023 and December 31, 2022, for which the Company has elected to apply the fair value option. The following table presents information on the cost and fair value of the Company’s equity securities related to Insurance and Tiptree Capital as of the following periods:


	As of September 30, 2023
	Insurance				Tiptree Capital - Other				Total
	Cost		Fair Value		Cost		Fair Value		Cost		Fair Value
Invesque	$	23,339	$	1,174	$	111,491	$	5,619	$	134,830	$	6,793
Fixed income exchange traded funds	1,339		1,291		—		—		1,339		1,291
Other equity securities	25,749		23,826		29,941		31,546		55,690		55,372
Total equity securities	$	50,427	$	26,291	$	141,432	$	37,165	$	191,859	$	63,456


	As of December 31, 2022
	Insurance				Tiptree Capital - Other				Total
	Cost		Fair Value		Cost		Fair Value		Cost		Fair Value
Invesque	$	23,339	$	2,670	$	111,491	$	12,784	$	134,830	$	15,454
Fixed income exchange traded funds	56,263		56,256		—		—		56,263		56,256
Other equity securities	15,773		14,066		—		—		15,773		14,066
Total equity securities	$	95,375	$	72,992	$	111,491	$	12,784	$	206,866	$	85,776


	As of September 30, 2023
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Corporate bonds, at fair value (1)	$	62,929	$	—	$	—	$	62,929

Debentures	23,234		—		—		23,234

Other	127		4,081		2,464		6,672
Total other investments	$	86,290	$	4,081	$	2,464	$	92,835


	As of December 31, 2022
			Tiptree Capital
	Insurance		Mortgage		Other		Total
Corporate bonds, at fair value (1)	$	42,080	$	—	$	—	$	42,080

Debentures	23,853		—		—		23,853

Other	230		4,038		2,824		7,092
Total other investments	$	66,163	$	4,038	$	2,824	$	73,025

Net investment income represents investment income and expense from investments related to insurance operations as disclosed within net investment income on the condensed consolidated statements of operations. The following table presents the components of net investment income by source of income:


	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023		2022
Interest:
AFS securities	$	5,255	$	3,094	$	16,863	$	7,955
Loans, at fair value	168		173		422		514
Other investments	1,758		1,382		5,837		4,240
Dividends from equity securities	39		212		1,339		883

Subtotal	7,220		4,861		24,461		13,592
Less: investment expenses	1,804		1,229		4,848		3,428
Net investment income	$	5,416	$	3,632	$	19,613	$	10,164

Other investment income represents revenue from non-insurance activities as disclosed within other revenue on the condensed consolidated statements of operations, see Note (15) Other Revenue and Other Expenses. The following tables present the components of other investment income by type:


	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023		2022

Interest income from Loans, at fair value (1)	$	826	$	766	$	2,213	$	4,652

Loan fee income (1)	4,193		3,998		12,186		14,494
Other	1,072		7,829		2,458		28,337
Other investment income	$	6,091	$	12,593	$	16,857	$	47,483

The following table presents the components of net realized and unrealized gains (losses) recorded on the condensed consolidated statements of operations. Net unrealized gains (losses) on AFS securities are included within other comprehensive income (loss) (“OCI”), net of tax, and, as such, are not included in this table. Net realized and unrealized gains (losses) on non-investment related financial assets and liabilities are included below:


	Three Months Ended September 30,				Nine Months Ended September 30,
	2023		2022		2023		2022
Net realized gains (losses)
Insurance:
Reclass of unrealized gains (losses) on AFS securities from OCI	$	2	$	—	$	(2,954)	$	(110)
Net gains from recoveries (credit losses) on AFS securities	(50)		35		(156)		(41)
Net realized gains (losses) on loans	(2,902)		(1,241)		(2,900)		(1,617)
Net realized gains (losses) on equity securities	(1,076)		(1,639)		(1,923)		(4,104)
Net realized gains (losses) on corporate bonds	(695)		(2,937)		(1,919)		(3,049)
Other	1,089		3,951		335		(2,612)
Tiptree Capital
Mortgage:
Net realized gains (losses) on loans	8,848		11,902		29,680		32,475
Other	1,971		663		2,107		13,376
Other:
Net realized gains (losses) on loans (1)	—		—		—		24,403
Net realized gains on vessel sales	—		14,099		—		21,217