CNA Financial Corporation

Supplemental Financial Information

June 30, 2023

This report is for informational purposes only and includes consolidated financial statements and financial exhibits that are unaudited. This report should be read in conjunction with documents filed with the U.S. Securities and Exchange Commission, including the most recent Annual Report on Form 10-K and Quarterly Reports on Form 10-Q.

Table of Contents

	Page
Consolidated Results
Statements of Operations	1
Components of Income (Loss), Per Share Data and Return on Equity	2
Selected Balance Sheet Data and Statements of Cash Flows Data	3
Results of Operations
Property & Casualty	4
Specialty	5
Commercial	6
International	7
Life & Group	8
Corporate & Other	9
Investment Information
Investment Summary - Consolidated	10
Investment Summary - Property & Casualty and Corporate & Other	11
Investment Summary - Life & Group	12
Investments - Fixed Maturity Securities by Credit Rating	13
Investments - Commercial Real Estate Exposure	14
Components of Net Investment Income	15
Net Investment Gains (Losses)	16
Other
Claim & Claim Adjustment Expense Reserve Rollforward	17
Life & Group Reserves Rollforward	18
Definitions and Presentation	19

Statements of Operations

Periods ended June 30	Three Months						Six Months
(In millions)	2023		2022 (1)		Change		2023		2022 (1)		Change
Revenues:
Net earned premiums	$	2,347	$	2,155	9	%	$	4,595	$	4,214	9	%
Net investment income	575		432		33		1,100		880		25
Net investment (losses) gains	(32)		(59)				(67)		(70)
Non-insurance warranty revenue	407		392				814		774
Other revenues	7		6				14		13
Total revenues	3,304		2,926		13		6,456		5,811		11
Claims, Benefits and Expenses:
Insurance claims and policyholders' benefits (re-measurement gain (loss) of $(33), $1, $(34) and $6)	1,779		1,601				3,432		3,079
Amortization of deferred acquisition costs	403		374				782		718
Non-insurance warranty expense	384		367				768		721
Other operating expenses	346		329				683		655
Interest	31		28				59		56
Total claims, benefits and expenses	2,943		2,699		(9)		5,724		5,229		(9)
Income (loss) before income tax	361		227				732		582
Income tax (expense) benefit	(78)		(37)				(152)		(97)
Net income (loss)	$	283	$	190	49	%	$	580	$	485	20	%

(1) As of January 1, 2023, the Company adopted Accounting Standards Update (ASU) 2018-12, Financial Services-Insurance (Topic 944): Targeted Improvements to the Accounting for Long-Duration Contracts (LDTI), using the modified retrospective method applied as of the transition date of January 1, 2021. Prior period amounts have been adjusted to reflect application of the new guidance.

1

Components of Income (Loss), Per Share Data and Return on Equity

Periods ended June 30	Three Months						Six Months
(In millions, except per share data)	2023			2022 (1)			2023			2022 (1)
Components of Income (Loss)
Core income (loss)	$	308		$	230		$	633		$	528
Net investment gains (losses)	(25)			(40)			(53)			(43)
Net income (loss)	$	283		$	190		$	580		$	485
Diluted Earnings (Loss) Per Common Share
Core income (loss)	$	1.13		$	0.84		$	2.33		$	1.94
Net investment gains (losses)	(0.09)			(0.15)			(0.20)			(0.16)
Diluted earnings (loss) per share	$	1.04		$	0.69		$	2.13		$	1.78
Weighted Average Outstanding Common Stock and Common Stock Equivalents
Basic	271.2			271.7			271.2			271.8
Diluted	272.0			272.6			272.1			272.7
Return on Equity
Net income (loss) (2)	13.0		%	8.1		%	13.4		%	9.7		%
Core income (loss) (3)	10.2			7.6			10.4			8.6

(1) As of January 1, 2023, the Company adopted LDTI using the modified retrospective method applied as of the transition date of January 1, 2021. Prior period amounts have been adjusted to reflect application of the new guidance.

(2) Annualized net income (loss) divided by the average stockholders' equity including accumulated other comprehensive income (loss) (AOCI) for the period. Average equity including AOCI is calculated using a simple average of the beginning and ending balances for the period.

(3) Annualized core income (loss) divided by the average stockholders' equity excluding AOCI for the period. Average equity excluding AOCI is calculated using a simple average of the beginning and ending balances for the period.

2

Selected Balance Sheet Data and Statements of Cash Flows Data

(In millions, except per share data)	June 30, 2023		December 31, 2022 (1)
Total investments	$	44,435	$	43,177
Reinsurance receivables, net of allowance for uncollectible receivables	5,581		5,416
Total assets	63,088		61,000
Insurance reserves:
Claim and claim adjustment expenses (2)	22,802		22,120
Unearned premiums	6,978		6,374
Future policy benefits (2)	13,666		13,480
Debt	3,176		2,781
Total liabilities	54,362		52,452
Accumulated other comprehensive income (loss) (3)	(3,425)		(3,598)
Total stockholders' equity	8,726		8,548
Book value per common share	$	32.22	$	31.55
Book value per common share excluding AOCI	$	44.86	$	44.83
Outstanding shares of common stock (in millions of shares)	270.9		270.9
Statutory capital and surplus - Combined Continental Casualty Companies (4)	$	10,520	$	10,572

Three Months Ended June 30	2023		2022
Net cash flows provided (used) by operating activities	$	501	$	608
Net cash flows provided (used) by investing activities	(909)		(302)
Net cash flows provided (used) by financing activities	280		(98)
Net cash flows provided (used) by operating, investing and financing activities	$	(128)	$	208

Six Months Ended June 30	2023		2022
Net cash flows provided (used) by operating activities	$	937	$	1,253
Net cash flows provided (used) by investing activities	(858)		(431)
Net cash flows provided (used) by financing activities	(200)		(786)
Net cash flows provided (used) by operating, investing and financing activities	$	(121)	$	36

(1) As of January 1, 2023, the Company adopted LDTI using the modified retrospective method applied as of the transition date of January 1, 2021. Prior period amounts have been adjusted to reflect application of the new guidance.

(2) In conjunction with the adoption of LDTI, at January 1, 2023, $3.0 billion of the long term care reserves for policyholders currently receiving benefits within the Life & Group segment were classified from Claim and claim adjustment expense to Future policy benefits. This change was applied retrospectively as of January 1, 2021.

(3) As of June 30, 2023 and December 31, 2022, AOCI included after-tax cumulative impacts of changes in discount rates used to measure long duration contracts of $(181) million and $(41) million.

(4) Statutory capital and surplus as of June 30, 2023 is preliminary.

3

Property & Casualty - Results of Operations

Periods ended June 30	Three Months								Six Months
(In millions)	2023			2022			Change		2023			2022			Change
Gross written premiums	$	3,909		$	3,715		5	%	$	7,529		$	7,132		6	%
Gross written premiums ex. 3rd party captives	2,986			2,676			12		5,710			5,130			11
Net written premiums	2,513			2,296			9		4,760			4,319			10
Net earned premiums	2,234			2,037			10		4,367			3,977			10
Net investment income	332			227			46		633			462			37
Non-insurance warranty revenue	407			392					814			774
Other revenues	7			5					14			13
Total operating revenues	2,980			2,661			12		5,828			5,226			12
Insurance claims and policyholders' benefits	1,406			1,233					2,755			2,415
Amortization of deferred acquisition costs	403			374					782			718
Non-insurance warranty expense	384			367					768			721
Other insurance related expenses	287			245					562			503
Other expenses	17			36					38			57
Total claims, benefits and expenses	2,497			2,255			(11)		4,905			4,414			(11)
Core income (loss) before income tax	483			406					923			812
Income tax (expense) benefit on core income (loss)	(109)			(89)					(203)			(174)
Core income (loss)	$	374		$	317		18	%	$	720		$	638		13	%
Other Performance Metrics
Underwriting gain (loss)	$	138		$	185		(25)	%	$	268		$	341		(21)	%
Loss & LAE ratio	62.6		%	60.2		%	(2.4)	pts	62.8		%	60.4		%	(2.4)	pts
Expense ratio	30.9			30.5			(0.4)		30.8			30.7			(0.1)
Dividend ratio	0.3			0.3			—		0.3			0.3			—
Combined ratio	93.8		%	91.0		%	(2.8)	pts	93.9		%	91.4		%	(2.5)	pts
Combined ratio excluding catastrophes and development	91.1		%	90.8		%	(0.3)	pts	91.0		%	91.0		%	—	pts
Net accident year catastrophe losses incurred	$	68		$	37				$	120		$	57
Effect on loss & LAE ratio	3.1		%	1.8		%	(1.3)	pts	2.7		%	1.4		%	(1.3)	pts
Net prior year development and other: (favorable) / unfavorable	$	(6)		$	(31)				$	9		$	(41)
Effect on loss & LAE ratio	(0.4)		%	(1.6)		%	(1.2)	pts	0.2		%	(1.0)		%	(1.2)	pts
Rate	5		%	6		%	(1)	pts	5		%	6		%	(1)	pts
Renewal premium change	7		%	8		%	(1)	pts	7		%	9		%	(2)	pts
Retention	86		%	86		%	—	pts	86		%	84		%	2	pts
New business	$	555		$	500		11	%	$	1,058		$	951		11	%

4

Specialty - Results of Operations

Periods ended June 30	Three Months								Six Months
(In millions)	2023			2022			Change		2023			2022			Change
Gross written premiums	$	1,769		$	1,904		(7)	%	$	3,549		$	3,750		(5)	%
Gross written premiums ex. 3rd party captives	961			973			(1)		1,847			1,858			(1)
Net written premiums	825			832			(1)		1,613			1,603			1
Net earned premiums	812			794			2		1,609			1,566			3
Net investment income	142			100			42		271			203			33
Non-insurance warranty revenue	407			392					814			774
Other revenues	—			—					—			1
Total operating revenues	1,361			1,286			6		2,694			2,544			6
Insurance claims and policyholders' benefits	476			458					942			904
Amortization of deferred acquisition costs	168			162					333			319
Non-insurance warranty expense	384			367					768			721
Other insurance related expenses	94			81					180			162
Other expenses	12			12					26			25
Total claims, benefits and expenses	1,134			1,080			(5)		2,249			2,131			(6)
Core income (loss) before income tax	227			206					445			413
Income tax (expense) benefit on core income (loss)	(50)			(45)					(97)			(89)
Core income (loss)	$	177		$	161		10	%	$	348		$	324		7	%
Other Performance Metrics
Underwriting gain (loss)	$	74		$	93		(20)	%	$	154		$	181		(15)	%
Loss & LAE ratio	58.3		%	57.5		%	(0.8)	pts	58.3		%	57.5		%	(0.8)	pts
Expense ratio	32.4			30.4			(2.0)		31.9			30.7			(1.2)
Dividend ratio	0.2			0.2			—		0.2			0.2			—
Combined ratio	90.9		%	88.1		%	(2.8)	pts	90.4		%	88.4		%	(2.0)	pts
Combined ratio excluding catastrophes and development	91.2		%	89.2		%	(2.0)	pts	90.6		%	89.6		%	(1.0)	pts
Net accident year catastrophe losses incurred	$	—		$	1				$	—		$	1
Effect on loss & LAE ratio	—		%	0.1		%	0.1	pts	—		%	0.1		%	0.1	pts
Net prior year development and other: (favorable) / unfavorable	$	(2)		$	(10)				$	(2)		$	(20)
Effect on loss & LAE ratio	(0.3)		%	(1.2)		%	(0.9)	pts	(0.2)		%	(1.3)		%	(1.1)	pts
Rate	(1)		%	7		%	(8)	pts	—		%	8		%	(8)	pts
Renewal premium change	—		%	9		%	(9)	pts	2		%	9		%	(7)	pts
Retention	89		%	85		%	4	pts	89		%	85		%	4	pts
New business	$	120		$	132		(9)	%	$	228		$	277		(18)	%

5

Commercial - Results of Operations

Periods ended June 30	Three Months								Six Months
(In millions)	2023			2022			Change		2023			2022			Change
Gross written premiums	$	1,719		$	1,429		20	%	$	3,161		$	2,637		20	%
Gross written premiums ex. 3rd party captives	1,604			1,321			21		3,044			2,527			20
Net written premiums	1,329			1,134			17		2,517			2,135			18
Net earned premiums	1,120			974			15		2,166			1,878			15
Net investment income	165			113			46		314			231			36
Other revenues	6			4					13			12
Total operating revenues	1,291			1,091			18		2,493			2,121			18
Insurance claims and policyholders' benefits	745			615					1,439			1,193
Amortization of deferred acquisition costs	175			156					344			304
Other insurance related expenses	158			134					300			264
Other expenses	10			11					16			18
Total claims, benefits and expenses	1,088			916			(19)		2,099			1,779			(18)
Core income (loss) before income tax	203			175					394			342
Income tax (expense) benefit on core income (loss)	(44)			(37)					(84)			(72)
Core income (loss)	$	159		$	138		15	%	$	310		$	270		15	%
Other Performance Metrics
Underwriting gain (loss)	$	42		$	69		(39)	%	$	83		$	117		(29)	%
Loss & LAE ratio	66.2		%	62.7		%	(3.5)	pts	65.9		%	63.0		%	(2.9)	pts
Expense ratio	29.6			30.0			0.4		29.8			30.3			0.5
Dividend ratio	0.5			0.5			—		0.5			0.5			—
Combined ratio	96.3		%	93.2		%	(3.1)	pts	96.2		%	93.8		%	(2.4)	pts
Combined ratio excluding catastrophes and development	91.6		%	92.0		%	0.4	pts	91.8		%	92.3		%	0.5	pts
Net accident year catastrophe losses incurred	$	59		$	29				$	103		$	45
Effect on loss & LAE ratio	5.2		%	3.0		%	(2.2)	pts	4.7		%	2.4		%	(2.3)	pts
Net prior year development and other: (favorable) / unfavorable	$	(4)		$	(16)				$	(4)		$	(16)
Effect on loss & LAE ratio	(0.5)		%	(1.8)		%	(1.3)	pts	(0.3)		%	(0.9)		%	(0.6)	pts
Rate	8		%	5		%	3	pts	8		%	5		%	3	pts
Renewal premium change	11		%	7		%	4	pts	10		%	8		%	2	pts
Retention	85		%	87		%	(2)	pts	85		%	86		%	(1)	pts
New business	$	343		$	280		23	%	$	653		$	508		29	%

6

International - Results of Operations

Periods ended June 30	Three Months								Six Months
(In millions)	2023			2022			Change		2023			2022			Change
Gross written premiums	$	421		$	382		10	%	$	819		$	745		10	%
Net written premiums	359			330			9		630			581			8
Net earned premiums	302			269			12		592			533			11
Net investment income	25			14			79		48			28			71
Other revenues	1			1					1			—
Total operating revenues	328			284			15		641			561			14
Insurance claims and policyholders' benefits	185			160					374			318
Amortization of deferred acquisition costs	60			56					105			95
Other insurance related expenses	35			30					82			77
Other expenses	(5)			13					(4)			14
Total claims, benefits and expenses	275			259			(6)		557			504			(11)
Core income (loss) before income tax	53			25					84			57
Income tax (expense) benefit on core income (loss)	(15)			(7)					(22)			(13)
Core income (loss)	$	38		$	18		111	%	$	62		$	44		41	%
Other Performance Metrics
Underwriting gain (loss)	$	22		$	23		(4)	%	$	31		$	43		(28)	%
Loss & LAE ratio	61.0		%	59.5		%	(1.5)	pts	63.1		%	59.6		%	(3.5)	pts
Expense ratio	31.2			32.1			0.9		31.5			32.4			0.9
Dividend ratio	—			—			—		—			—			—
Combined ratio	92.2		%	91.6		%	(0.6)	pts	94.6		%	92.0		%	(2.6)	pts
Combined ratio excluding catastrophes and development	89.1		%	90.6		%	1.5	pts	89.2		%	91.0		%	1.8	pts
Net accident year catastrophe losses incurred	$	9		$	7				$	17		$	11
Effect on loss & LAE ratio	3.1		%	2.8		%	(0.3)	pts	2.9		%	2.0		%	(0.9)	pts
Net prior year development and other: (favorable) / unfavorable	$	—		$	(5)				$	15		$	(5)
Effect on loss & LAE ratio	—		%	(1.8)		%	(1.8)	pts	2.5		%	(1.0)		%	(3.5)	pts
Rate	4		%	6		%	(2)	pts	4		%	8		%	(4)	pts
Renewal premium change	7		%	10		%	(3)	pts	7		%	10		%	(3)	pts
Retention	83		%	84		%	(1)	pts	83		%	79		%	4	pts
New business	$	92		$	88		5	%	$	177		$	166		7	%

7

Life & Group - Results of Operations

Periods ended June 30	Three Months				Six Months
(In millions)	2023		2022 (1)		2023		2022 (1)
Net earned premiums	$	113	$	118	$	228	$	238
Net investment income	229		201		443		413
Other revenues	—		1		—		—
Total operating revenues	342		320		671		651
Insurance claims and policyholders' benefits	344		311		655		615
Other insurance related expenses	31		29		60		60
Other expenses	—		2		1		5
Total claims, benefits and expenses	375		342		716		680
Core income (loss) before income tax	(33)		(22)		(45)		(29)
Income tax (expense) benefit on core income (loss)	13		13		22		25
Core income (loss)	$	(20)	$	(9)	$	(23)	$	(4)

(1) As of January 1, 2023, the Company adopted LDTI using the modified retrospective method applied as of the transition date of January 1, 2021. Prior period amounts have been adjusted to reflect application of the new guidance.

8

Corporate & Other - Results of Operations

Periods ended June 30	Three Months				Six Months
(In millions)	2023		2022		2023		2022
Net earned premiums	$	—	$	—	$	—	$	(1)
Net investment income	14		4		24		5
Other revenues	—		—		—		—
Total operating revenues	14		4		24		4
Insurance claims and policyholders' benefits	29		57		22		49
Other insurance related expenses	—		1		1		3
Other expenses	42		44		80		83
Total claims, benefits and expenses	71		102		103		135
Core income (loss) before income tax	(57)		(98)		(79)		(131)
Income tax (expense) benefit on core income (loss)	11		20		15		25
Core income (loss)	$	(46)	$	(78)	$	(64)	$	(106)

9

Investment Summary - Consolidated

	June 30, 2023				March 31, 2023				December 31, 2022
(In millions)	Carrying Value		Net Unrealized Gains (Losses)		Carrying Value		Net Unrealized Gains (Losses)		Carrying Value		Net Unrealized Gains (Losses)
Fixed maturity securities:
Corporate and other bonds	$	22,611	$	(1,570)	$	22,915	$	(1,238)	$	21,429	$	(1,708)
States, municipalities and political subdivisions:
Tax-exempt	4,225		1		4,383		71		4,633		(45)
Taxable	3,585		(453)		3,618		(402)		3,684		(556)
Total states, municipalities and political subdivisions	7,810		(452)		8,001		(331)		8,317		(601)
Asset-backed:
RMBS	2,693		(440)		2,659		(407)		2,631		(442)
CMBS	1,583		(253)		1,631		(237)		1,635		(251)
Other ABS	3,248		(321)		3,165		(298)		2,927		(359)
Total asset-backed	7,524		(1,014)		7,455		(942)		7,193		(1,052)
U.S. Treasury and obligations of government-sponsored enterprises	127		(3)		124		(2)		110		(1)
Foreign government	651		(49)		609		(38)		575		(42)
Redeemable preferred stock	5		—		3		—		3		—
Total fixed maturity securities	38,728		(3,088)		39,107		(2,551)		37,627		(3,404)
Equities:
Common stock	205		—		206		—		185		—
Non-redeemable preferred stock	478		—		476		—		489		—
Total equities	683		—		682		—		674		—
Limited partnership investments:
Hedge funds	331		—		434		—		456		—
Private equity funds	1,689		—		1,548		—		1,470		—
Total limited partnership investments	2,020		—		1,982		—		1,926		—
Other invested assets	71		—		79		—		78		—
Mortgage loans	1,009		—		1,006		—		1,040		—
Short term investments	1,924		(1)		1,167		—		1,832		1
Total investments	$	44,435	$	(3,089)	$	44,023	$	(2,551)	$	43,177	$	(3,403)
Net receivable/(payable) on investment activity	$	41			$	(1)			$	8
Effective duration (in years)	6.5				6.8				6.6
Weighted average rating	A				A				A

RMBS - Residential mortgage-backed securities

CMBS - Commercial mortgage-backed securities

Other ABS - Other asset-backed securities

10

Investment Summary - Property & Casualty and Corporate & Other

	June 30, 2023				March 31, 2023				December 31, 2022
(In millions)	Carrying Value		Net Unrealized Gains (Losses)		Carrying Value		Net Unrealized Gains (Losses)		Carrying Value		Net Unrealized Gains (Losses)
Fixed maturity securities:
Corporate and other bonds	$	13,715	$	(1,248)	$	13,881	$	(1,056)	$	13,165	$	(1,260)
States, municipalities and political subdivisions:
Tax-exempt	1,190		(190)		1,200		(175)		1,197		(211)
Taxable	1,954		(431)		1,955		(405)		1,986		(486)
Total states, municipalities and political subdivisions	3,144		(621)		3,155		(580)		3,183		(697)
Asset-backed:
RMBS	2,691		(440)		2,645		(407)		2,617		(442)
CMBS	1,554		(250)		1,602		(234)		1,606		(248)
Other ABS	2,648		(245)		2,564		(235)		2,374		(276)
Total asset-backed	6,893		(935)		6,811		(876)		6,597		(966)
U.S. Treasury and obligations of government-sponsored enterprises	126		(3)		123		(2)		109		(1)
Foreign government	623		(41)		580		(30)		546		(34)
Redeemable preferred stock	5		—		3		—		3		—
Total fixed maturity securities	24,506		(2,848)		24,553		(2,544)		23,603		(2,958)
Equities:
Common stock	205		—		206		—		185		—
Non-redeemable preferred stock	62		—		62		—		73		—
Total equities	267		—		268		—		258		—
Limited partnership investments:
Hedge funds	183		—		240		—		252		—
Private equity funds	935		—		857		—		814		—
Total limited partnership investments	1,118		—		1,097		—		1,066		—
Other invested assets	71		—		79		—		78		—
Mortgage loans	808		—		797		—		830		—
Short term investments	1,875		(1)		1,148		—		1,772		1
Total investments	$	28,645	$	(2,849)	$	27,942	$	(2,544)	$	27,607	$	(2,957)
Net receivable/(payable) on investment activity	$	37			$	(4)			$	(3)
Effective duration (in years)	4.6				4.8				4.7
Weighted average rating	A				A				A

11

Investment Summary - Life & Group

	June 30, 2023				March 31, 2023				December 31, 2022
(In millions)	Carrying Value		Net Unrealized Gains (Losses)		Carrying Value		Net Unrealized Gains (Losses)		Carrying Value		Net Unrealized Gains (Losses)
Fixed maturity securities:
Corporate and other bonds	$	8,896	$	(322)	$	9,034	$	(182)	$	8,264	$	(448)
States, municipalities and political subdivisions:
Tax-exempt	3,035		191		3,183		246		3,436		166
Taxable	1,631		(22)		1,663		3		1,698		(70)
Total states, municipalities and political subdivisions	4,666		169		4,846		249		5,134		96
Asset-backed:
RMBS	2		—		14		—		14		—
CMBS	29		(3)		29		(3)		29		(3)
Other ABS	600		(76)		601		(63)		553		(83)
Total asset-backed	631		(79)		644		(66)		596		(86)
U.S. Treasury and obligations of government-sponsored enterprises	1		—		1		—		1		—
Foreign government	28		(8)		29		(8)		29		(8)
Redeemable preferred stock	—		—		—		—		—		—
Total fixed maturity securities	14,222		(240)		14,554		(7)		14,024		(446)
Equities:
Common stock	—		—		—		—		—		—
Non-redeemable preferred stock	416		—		414		—		416		—
Total equities	416		—		414		—		416		—
Limited partnership investments:
Hedge funds	148		—		194		—		204		—
Private equity funds	754		—		691		—		656		—
Total limited partnership investments	902		—		885		—		860		—
Other invested assets	—		—		—		—		—		—
Mortgage loans	201		—		209		—		210		—
Short term investments	49		—		19		—		60		—
Total investments	$	15,790	$	(240)	$	16,081	$	(7)	$	15,570	$	(446)
Net receivable/(payable) on investment activity	$	4			$	3			$	11
Effective duration (in years)	9.9				10.1				9.9
Weighted average rating	A-				A-				A

12

Investments - Fixed Maturity Securities by Credit Rating

June 30, 2023	U.S. Government, Government agencies and Government-sponsored enterprises					AAA					AA					A					BBB					Non-investment grade					Total
(In millions)	Fair Value			Net Unrealized Gains (Losses)		Fair Value			Net Unrealized Gains (Losses)		Fair Value			Net Unrealized Gains (Losses)		Fair Value			Net Unrealized Gains (Losses)		Fair Value			Net Unrealized Gains (Losses)		Fair Value			Net Unrealized Gains (Losses)		Fair Value			Net Unrealized Gains (Losses)
Corporate and other bonds	$	3		$	—	$	30		$	(3)	$	533		$	(42)	$	6,351		$	(321)	$	14,270		$	(1,057)	$	1,424		$	(147)	$	22,611		$	(1,570)
States, municipalities and political subdivisions	—			—		1,190			(28)		4,651			(368)		1,671			1		297			(57)		1			—		7,810			(452)
Asset-backed:
RMBS	2,400			(330)		273			(113)		—			—		4			—		—			—		16			3		2,693			(440)
CMBS	—			—		425			(35)		620			(107)		209			(35)		256			(56)		73			(20)		1,583			(253)
Other ABS	—			—		395			(17)		221			(46)		1,263			(95)		1,207			(138)		162			(25)		3,248			(321)
Total asset-backed	2,400			(330)		1,093			(165)		841			(153)		1,476			(130)		1,463			(194)		251			(42)		7,524			(1,014)
U.S. Treasury and obligations of government-sponsored enterprises	127			(3)		—			—		—			—		—			—		—			—		—			—		127			(3)
Foreign government	—			—		179			(9)		360			(25)		81			(13)		31			(2)		—			—		651			(49)
Redeemable preferred stock	—			—		—			—		—			—		—			—		—			—		5			—		5			—
Total fixed maturity securities	$	2,530		$	(333)	$	2,492		$	(205)	$	6,385		$	(588)	$	9,579		$	(463)	$	16,061		$	(1,310)	$	1,681		$	(189)	$	38,728		$	(3,088)
Percentage of total fixed maturity securities	7		%			6		%			17		%			25		%			41		%			4		%			100		%

13

Investments - Commercial Real Estate Exposure

Fixed Income and Direct Mortgage Loans

	June 30, 2023						June 30, 2023
(In millions)	Estimated Fair Value		Net Unrealized Gains (Losses)			(In millions)	Estimated Fair Value		Net Unrealized Gains (Losses)
Commercial mortgage-backed:						Corporate and other bonds - REITs:
Single asset, single borrower:						Retail	$	455	$	(48)
Office	$	289	$	(77)		Office	255		(30)
Retail	278		(38)			Industrial	86		(5)
Lodging	218		(20)			Other (1)	416		(39)
Industrial	90		(6)			Total corporate and other bonds - REITs (2)	$	1,212	$	(122)
Multifamily	51		(4)
Total single asset, single borrower	926		(145)
Conduits (multi property, multi borrower pools)	657		(108)
Total commercial mortgage-backed	$	1,583	$	(253)
	June 30, 2023						June 30, 2023
(In millions)	Estimated Fair Value		Net Unrealized Gains (Losses)			(In millions)	Estimated Fair Value		Net Unrealized Gains (Losses)
Commercial mortgage-backed:						Corporate and other bonds - REITs:
AAA	$	425	$	(35)		AA	$	11	$	(1)
AA	620		(107)			A	249		(13)
A	209		(35)			BBB	936		(106)
BBB	256		(56)			Non-investment grade	16		(2)
Non-investment grade	73		(20)			Total corporate and other bonds - REITs (2)	$	1,212	$	(122)
Total commercial mortgage-backed	$	1,583	$	(253)
	June 30, 2023
(In millions)	Carrying Value		Percentage of Total
Mortgage loans:
Retail	$	470	44		%
Office	255		25		%
Industrial	131		13		%
Other	183		18		%
Total mortgage loans	$	1,039	100		%	(1) Other includes a diversified mix of property type strategies including self-storage, healthcare and apartments.
Less: Allowance for expected credit losses	(30)
Total mortgage loans - net of allowance	$	1,009				(2) REITs - Real estate investment trusts

14

Components of Net Investment Income

Periods ended June 30	Consolidated
	Three Months						Six Months
(In millions)	2023			2022			2023			2022
Taxable fixed income securities	$	444		$	385		$	874		$	753
Tax-exempt fixed income securities	46			66			95			139
Total fixed income securities	490			451			969			892
Common stock	13			(21)			16			(31)
Limited partnerships - hedge funds	7			(35)			21			(45)
Limited partnerships - private equity funds	48			41			59			69
Total limited partnership and common stock investments	68			(15)			96			(7)
Other, net of investment expense	17			(4)			35			(5)
Net investment income	$	575		$	432		$	1,100		$	880
Effective income yield for fixed income securities portfolio	4.6		%	4.3		%	4.6		%	4.3		%
Limited partnership and common stock return	3.1			(0.7)			4.5			(0.3)

	Property & Casualty and Corporate & Other
Periods ended June 30
	Three Months						Six Months
(In millions)	2023			2022			2023			2022
Taxable fixed income securities	$	272		$	237		$	533		$	462
Tax-exempt fixed income securities	11			12			22			23
Total fixed income securities	283			249			555			485
Common stock	13			(21)			16			(31)
Limited partnerships - hedge funds	3			(20)			11			(25)
Limited partnerships - private equity funds	27			23			33			38
Total limited partnership and common stock investments	43			(18)			60			(18)
Other, net of investment expense	20			—			42			—
Net investment income	$	346		$	231		$	657		$	467
Effective income yield for fixed income securities portfolio	4.2		%	3.7		%	4.1		%	3.7		%

Periods ended June 30	Life & Group
	Three Months						Six Months
(In millions)	2023			2022			2023			2022
Taxable fixed income securities	$	172		$	148		$	341		$	291
Tax-exempt fixed income securities	35			54			73			116
Total fixed income securities	207			202			414			407
Common stock	—			—			—			—
Limited partnerships - hedge funds	4			(15)			10			(20)
Limited partnerships - private equity funds	21			18			26			31
Total limited partnership and common stock investments	25			3			36			11
Other, net of investment expense	(3)			(4)			(7)			(5)
Net investment income	$	229		$	201		$	443		$	413
Effective income yield for fixed income securities portfolio	5.5		%	5.4		%	5.5		%	5.4		%

15

Net Investment Gains (Losses)

Periods ended June 30	Consolidated
	Three Months				Six Months
(In millions)	2023		2022		2023		2022
Fixed maturity securities:
Corporate and other bonds	$	(12)	$	(30)	$	(35)	$	(27)
States, municipalities and political subdivisions	(3)		19		7		22
Asset-backed	(12)		(4)		(21)		(12)
Total fixed maturity securities	(27)		(15)		(49)		(17)
Non-redeemable preferred stock	3		(71)		(11)		(109)
Derivatives, short term and other	(2)		27		(1)		56
Mortgage loans	(6)		—		(6)		—
Net investment gains (losses)	(32)		(59)		(67)		(70)
Income tax benefit (expense) on net investment gains (losses)	7		19		14		27
Net investment gains (losses), after tax	$	(25)	$	(40)	$	(53)	$	(43)

16

Claim & Claim Adjustment Expense Reserve Rollforward

Three months ended June 30, 2023 (In millions)	Specialty		Commercial		International		P&C Operations		Life & Group (1)		Corporate & Other		Total Operations
Claim & claim adjustment expense reserves, beginning of period
Gross	$	6,976	$	9,528	$	2,502	$	19,006	$	704	$	2,699	$	22,409
Ceded	1,336		1,003		399		2,738		102		2,369		5,209
Net	5,640		8,525		2,103		16,268		602		330		17,200
Net incurred claim & claim adjustment expenses	474		742		185		1,401		10		44		1,455
Net claim & claim adjustment expense payments	(397)		(618)		(144)		(1,159)		(12)		(16)		(1,187)
Foreign currency translation adjustment and other	1		—		34		34		(12)		—		22
Claim & claim adjustment expense reserves, end of period
Net	5,718		8,648		2,178		16,544		588		358		17,490
Ceded	1,465		1,026		405		2,896		100		2,316		5,312
Gross	$	7,183	$	9,674	$	2,583	$	19,440	$	688	$	2,674	$	22,802

Six months ended June 30, 2023 (In millions)	Specialty		Commercial		International		P&C Operations		Life & Group (1)		Corporate & Other		Total Operations
Claim & claim adjustment expense reserves, beginning of period
Gross	$	6,878	$	9,395	$	2,403	$	18,676	$	695	$	2,749	$	22,120
Ceded	1,315		965		400		2,680		101		2,410		5,191
Net	5,563		8,430		2,003		15,996		594		339		16,929
Net incurred claim & claim adjustment expenses	939		1,429		374		2,742		18		45		2,805
Net claim & claim adjustment expense payments	(785)		(1,212)		(254)		(2,251)		(24)		(26)		(2,301)
Foreign currency translation adjustment and other	1		1		55		57		—		—		57
Claim & claim adjustment expense reserves, end of period
Net	5,718		8,648		2,178		16,544		588		358		17,490
Ceded	1,465		1,026		405		2,896		100		2,316		5,312
Gross	$	7,183	$	9,674	$	2,583	$	19,440	$	688	$	2,674	$	22,802

(1) In conjunction with the adoption of LDTI, at January 1, 2023, the Company reclassified $3.0 billion of the long term care reserves for policyholders currently receiving benefits from Claim and claim adjustment expense to Future policy benefits. This change was applied retrospectively as of January 1, 2021.

17

Life & Group Reserves Rollforward

Three months ended June 30, 2023 (In millions)	Claim and claim adjustment expenses		Future policy benefits		Total
Beginning of period	$	602	$	13,976	$	14,578
Incurred claims and policyholders' benefits (1)	10		338		348
Benefit and expense payments	(12)		(327)		(339)
Change in discount rate assumptions and other (AOCI)	(12)		(321)		(333)
End of Period	$	588	$	13,666	$	14,254

Six months ended June 30, 2023 (In millions)	Claim and claim adjustment expenses		Future policy benefits		Total
Beginning of period (2)	$	594	$	13,479	$	14,073
Incurred claims and policyholders' benefits (1)	18		638		656
Benefit and expense payments	(24)		(629)		(653)
Change in discount rate assumptions and other (AOCI)	—		178		178
End of Period	$	588	$	13,666	$	14,254

(1) Incurred claims and policyholders' benefits above does not agree to Net incurred claims and benefits as reflected in Note J to the Condensed Consolidated Financial Statements included under Part I, Item 1 of the Quarterly Report on Form 10-Q due to the timing of benefit and expense cash flows in determining Future Policy Benefit reserves, along with the allowable expenses in the reserve under LDTI guidance.

(2) In conjunction with the adoption of LDTI, at January 1, 2023, the Company reclassified $3.0 billion of the long term care reserves for policyholders currently receiving benefits from Claim and claim adjustment expense to Future policy benefits. This change was applied retrospectively as of January 1, 2021.

18

Definitions and Presentation

•Collectively, CNA Financial Corporation (CNAF) and its subsidiaries are referred to as CNA or the Company.

•P&C Operations includes Specialty, Commercial and International.

•Life & Group segment includes the individual and group run-off long term care businesses as well as structured settlement obligations not funded by annuities related to certain property and casualty claimants.

•Corporate & Other segment primarily includes certain corporate expenses, including interest on corporate debt, and the results of certain property and casualty business in run-off, including CNA Re, asbestos and environmental pollution (A&EP), a legacy portfolio of excess workers' compensation (EWC) policies and certain legacy mass tort reserves.

•Management uses the core income (loss) financial measure to monitor the Company’s operations for the Specialty, Commercial and International segments. Core income (loss) is calculated by excluding from net income (loss) the after-tax effects of net investment gains or losses. The calculation of core income (loss) excludes net investment gains or losses because net investment gains or losses are generally driven by economic factors that are not necessarily reflective of our primary operations. Management monitors core income (loss) for each business segment to assess segment performance. Presentation of consolidated core income (loss) is deemed to be a non-GAAP financial measure and management believes some investors may find this measure useful to evaluate the Company's primary operations. Please refer to Note O to the Consolidated Financial Statements within the December 31, 2022 Form 10-K for further discussion regarding how the Company manages its business.

•This financial supplement may also reference or contain financial measures utilized to monitor the Company's investment portfolio that are not in accordance with GAAP. The Company's investment portfolio is monitored by management through analysis of various factors including unrealized gains and losses on securities, portfolio duration and exposure to market and credit risk.

•For reconciliations of non-GAAP measures to the most comparable GAAP measures and other information, please refer herein and/or to CNA's most recent 10-K on file with the Securities and Exchange Commission, as well as the press release, available at www.cna.com.

•In evaluating the results of the Specialty, Commercial and International segments, management uses the loss ratio, the expense ratio, the dividend ratio and the combined ratio. These ratios are calculated using financial results prepared in accordance with accounting principles generally accepted in the United States of America. The loss ratio is the percentage of net incurred claim and claim adjustment expenses to net earned premiums. The expense ratio is the percentage of insurance underwriting and acquisition expenses, including the amortization of deferred acquisition costs, to net earned premiums. The dividend ratio is the ratio of policyholders' dividends incurred to net earned premiums. The combined ratio is the sum of the loss, expense and dividend ratios. In addition, management also utilizes renewal premium change, rate, retention and new business in evaluating operating trends. Renewal premium change represents the estimated change in average premium on policies that renew, including rate and exposure changes. Rate represents the average change in price on policies that renew excluding exposure change. For certain products within Small Business, where quantifiable, rate includes the influence of new business as well. Exposure represents the measure of risk used in the pricing of the insurance product. The change in exposure represents the change in premium dollars on policies that renew as a result of the change in risk of the policy. Retention represents the percentage of premium dollars renewed, excluding rate and exposure changes, in comparison to the expiring premium dollars from policies available to renew. New business represents premiums from policies written with new customers and additional policies written with existing customers.

•Management uses underwriting gain (loss), calculated using GAAP financial results, to monitor insurance operations of our Specialty, Commercial and International segments. Underwriting gain (loss) is pretax and calculated as net earned premiums less total insurance expenses, which includes insurance claims and policyholders' benefits, amortization of deferred acquisition costs and other insurance related expenses.

19

•Gross written premiums ex. 3rd party captives represents gross written premiums excluding business which is ceded to third party captives, including business related to large warranty programs.

•Statutory capital and surplus represents the excess of an insurance company's admitted assets over its liabilities, including loss reserves, as determined in accordance with statutory accounting practices.

•Pretax net prior year development and other represents net prior year loss reserve and premium development, and includes the effects of interest accretion and change in allowance for uncollectible reinsurance and deductible amounts.

•Net investment income from fixed income securities, as presented, includes both fixed maturity securities and non-redeemable preferred stock.

•Accounting Standards Update: In August 2018, the FASB issued ASU 2018-12, Financial Services-Insurance (Topic 944): Targeted Improvements to the Accounting for Long-Duration Contracts. The updated accounting guidance requires changes to the measurement and disclosure of long-duration contracts. For the Company, this includes the run-off long term care business in the Life & Group segment. The Company adopted the new guidance effective January 1, 2023, using the modified retrospective method applied as of the transition date of January 1, 2021. All prior period amounts have been adjusted to reflect application of the new guidance. While the requirements of the new guidance represent a material change from legacy accounting, the new guidance does not impact capital and surplus under statutory accounting practices, cash flows or the underlying economics of the business. Additional information regarding the Company’s adoption of ASU 2018-12 and the impact to historical financial results is contained in the Company's Q1 2023 Financial Supplement, furnished on Form 8-K, on May 1, 2023 with the Securities and Exchange Commission.

•Certain immaterial differences are due to rounding.

•N/M = Not Meaningful

20