CNA Financial Corporation Supplemental Financial Information September 30, 2025 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 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 Components of Net Investment Income 14 Net Investment Gains (Losses) 15 Other Claim & Claim Adjustment Expense Reserve Rollforward 16 Life & Group Policyholder Reserves 17 Definitions and Presentation 18 Page

Statements of Operations Periods ended September 30 Three Months Nine Months (In millions) 2025 2024 Change 2025 2024 Change Revenues: Net earned premiums $ 2,783 $ 2,593 7 % $ 8,103 $ 7,532 8 % Net investment income 638 626 2 1,904 1,853 3 Net investment (losses) gains (7) (10) (62) (42) Non-insurance warranty revenue 393 401 1,188 1,212 Other revenues 10 8 28 26 Total revenues 3,817 3,618 6 11,161 10,581 5 Claims, Benefits and Expenses: Insurance claims and policyholders’ benefits (re-measurement loss of $36, $48, $59 and $88) 2,032 2,019 6,144 5,708 Amortization of deferred acquisition costs 483 457 1,423 1,336 Non-insurance warranty expense 377 387 1,146 1,169 Other operating expenses 376 362 1,107 1,077 Interest expense 36 32 99 101 Total claims, benefits and expenses 3,304 3,257 (1) 9,919 9,391 (6) Income (loss) before income tax 513 361 1,242 1,190 Income tax (expense) benefit (110) (78) (266) (252) Net income (loss) $ 403 $ 283 42 % $ 976 $ 938 4 % 1

Components of Income (Loss), Per Share Data and Return on Equity Periods ended September 30 Three Months Nine Months (In millions, except per share data) 2025 2024 2025 2024 Components of Income (Loss) Core income (loss) $ 409 $ 293 $ 1,025 $ 974 Net investment gains (losses) (6) (7) (49) (33) Pension settlement transaction gains (losses) — (3) — (3) Net income (loss) $ 403 $ 283 $ 976 $ 938 Diluted Earnings (Loss) Per Common Share Core income (loss) $ 1.50 $ 1.08 $ 3.76 $ 3.57 Net investment gains (losses) (0.02) (0.03) (0.18) (0.12) Pension settlement transaction gains (losses) — (0.01) — (0.01) Diluted earnings (loss) per share $ 1.48 $ 1.04 $ 3.58 $ 3.44 Weighted Average Outstanding Common Stock and Common Stock Equivalents Basic 271.1 271.3 271.2 271.5 Diluted 272.3 272.7 272.4 272.7 Return on Equity Net income (loss) (1) 14.7 % 11.0 % 11.9 % 12.1 % Core income (loss) (2) 13.2 9.4 10.9 10.3 (1) 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. (2) 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) September 30, 2025 December 31, 2024 Total investments $ 50,536 $ 47,482 Reinsurance receivables, net of allowance for uncollectible receivables 6,445 6,051 Total assets 69,756 66,492 Insurance reserves 47,649 45,480 Claim and claim adjustment expenses 26,525 24,976 Unearned premiums 7,578 7,346 Future policy benefits 13,546 13,158 Debt 3,470 2,973 Total liabilities 58,434 55,979 Accumulated other comprehensive income (loss) (1) (1,211) (1,991) Total stockholders' equity 11,322 10,513 Book value per common share $ 41.83 $ 38.82 Book value per common share excluding AOCI $ 46.30 $ 46.16 Outstanding shares of common stock (in millions of shares) 270.7 270.8 Statutory capital and surplus - Combined Continental Casualty Companies (2) $ 11,535 $ 11,165 Three Months Ended September 30 2025 2024 Net cash flows provided (used) by operating activities $ 720 $ 748 Net cash flows provided (used) by investing activities (975) (553) Net cash flows provided (used) by financing activities 369 (120) Net cash flows provided (used) by operating, investing and financing activities $ 114 $ 75 Nine Months Ended September 30 2025 2024 Net cash flows provided (used) by operating activities $ 1,920 $ 1,868 Net cash flows provided (used) by investing activities (1,446) (762) Net cash flows provided (used) by financing activities (478) (998) Net cash flows provided (used) by operating, investing and financing activities $ (4) $ 108 (1) As of September 30, 2025 and December 31, 2024, AOCI included after-tax cumulative impacts of changes in discount rates used to measure long duration contracts of $86 million and $353 million. (2) Statutory capital and surplus as of September 30, 2025 is preliminary. 3

Property & Casualty - Results of Operations Periods ended September 30 Three Months Nine Months (In millions) 2025 2024 Change 2025 2024 Change Gross written premiums $ 3,591 $ 3,595 — % $ 11,683 $ 11,409 2 % Gross written premiums ex. 3rd party captives 2,890 2,825 2 9,385 8,964 5 Net written premiums 2,437 2,360 3 7,889 7,424 6 Net earned premiums 2,678 2,484 8 7,786 7,204 8 Insurance claims and policyholders' benefits 1,706 1,667 5,088 4,700 Amortization of deferred acquisition costs 483 457 1,423 1,336 Insurance related administrative expenses 295 292 891 850 Underwriting gain (loss) 194 68 185 384 318 21 Net investment income 396 372 6 1,172 1,090 8 Non-insurance warranty revenue 393 401 1,188 1,212 Other revenues 9 6 27 24 Non-insurance warranty expense 377 387 1,146 1,169 Other expenses 26 13 65 69 Interest expense — — — — Core income (loss) before income tax 589 447 1,560 1,406 Income tax (expense) benefit on core income (loss) (133) (101) (345) (308) Core income (loss) $ 456 $ 346 32 % $ 1,215 $ 1,098 11 % Other Performance Metrics Underwriting gain (loss) $ 194 $ 68 185 % $ 384 $ 318 21 % Effect of catastrophe losses 41 143 200 313 (Favorable) unfavorable net prior year loss reserve development (1) (5) 56 (24) (Favorable) unfavorable other development-related items (1) 1 3 8 11 Effect of (favorable) unfavorable development-related items — (2) 64 (13) Underlying underwriting gain (loss) $ 235 $ 209 12 % $ 648 $ 618 5 % Loss & LAE ratio 63.4 % 66.7 % 3.3 pts 65.0 % 64.9 % (0.1) pts Expense ratio 29.1 30.2 1.1 29.7 30.3 0.6 Dividend ratio 0.3 0.3 — 0.4 0.4 — Combined ratio 92.8 % 97.2 % 4.4 pts 95.1 % 95.6 % 0.5 pts Less: Effect of catastrophe impacts 1.5 5.8 4.3 2.6 4.3 1.7 Less: Effect of (favorable) unfavorable development-related items — (0.2) (0.2) 0.8 (0.2) (1.0) Underlying combined ratio 91.3 % 91.6 % 0.3 pts 91.7 % 91.5 % (0.2) pts Rate 3 % 3 % — pts 3 % 4 % (1) pts Renewal premium change 4 % 5 % (1) pts 5 % 5 % — pts Retention 81 % 85 % (4) pts 83 % 85 % (2) pts New business $ 549 $ 547 — % $ 1,759 $ 1,671 5 % (1) Other development-related items represents net prior year premium development, the effects of interest accretion on net prior year loss development and the change in allowance for uncollectible reinsurance. 4

Specialty - Results of Operations Periods ended September 30 Three Months Nine Months (In millions) 2025 2024 Change 2025 2024 Change Gross written premiums $ 1,700 $ 1,743 (2) % $ 5,064 $ 5,153 (2) % Gross written premiums ex. 3rd party captives 1,009 982 3 2,952 2,846 4 Net written premiums 867 862 1 2,601 2,511 4 Net earned premiums 881 848 4 2,573 2,493 3 Insurance claims and policyholders' benefits 536 511 1,569 1,485 Amortization of deferred acquisition costs 197 188 581 546 Insurance related administrative expenses 88 90 268 267 Underwriting gain (loss) 60 59 2 155 195 (21) Net investment income 162 157 3 483 461 5 Non-insurance warranty revenue 393 401 1,188 1,212 Other revenues 1 1 1 1 Non-insurance warranty expense 377 387 1,146 1,169 Other expenses 16 13 41 41 Interest expense — — — — Core income (loss) before income tax 223 218 640 659 Income tax (expense) benefit on core income (loss) (47) (47) (137) (142) Core income (loss) $ 176 $ 171 3 % $ 503 $ 517 (3) % Other Performance Metrics Underwriting gain (loss) $ 60 $ 59 2 % $ 155 $ 195 (21) % Effect of catastrophe losses — — — — (Favorable) unfavorable net prior year loss reserve development — — 10 (8) (Favorable) unfavorable other development-related items (1) — — — — Effect of (favorable) unfavorable development-related items — — 10 (8) Underlying underwriting gain (loss) $ 60 $ 59 2 % $ 165 $ 187 (12) % Loss & LAE ratio 60.6 % 60.1 % (0.5) pts 60.7 % 59.3 % (1.4) pts Expense ratio 32.5 32.7 0.2 33.0 32.5 (0.5) Dividend ratio 0.2 0.2 — 0.3 0.3 — Combined ratio 93.3 % 93.0 % (0.3) pts 94.0 % 92.1 % (1.9) pts Less: Effect of catastrophe impacts — — — — — — Less: Effect of (favorable) unfavorable development-related items — — — 0.4 (0.3) (0.7) Underlying combined ratio 93.3 % 93.0 % (0.3) pts 93.6 % 92.4 % (1.2) pts Rate 3 % — % 3 pts 3 % 1 % 2 pts Renewal premium change 4 % 2 % 2 pts 4 % 2 % 2 pts Retention 86 % 89 % (3) pts 87 % 89 % (2) pts New business $ 131 $ 129 2 % $ 365 $ 341 7 % (1) Other development-related items represents net prior year premium development, the effects of interest accretion on net prior year loss development and the change in allowance for uncollectible reinsurance. 5

Commercial - Results of Operations Periods ended September 30 Three Months Nine Months (In millions) 2025 2024 Change 2025 2024 Change Gross written premiums $ 1,569 $ 1,547 1 % $ 5,487 $ 5,160 6 % Gross written premiums ex. 3rd party captives 1,559 1,538 1 5,301 5,022 6 Net written premiums 1,251 1,221 2 4,312 4,017 7 Net earned premiums 1,453 1,325 10 4,235 3,774 12 Insurance claims and policyholders' benefits 967 961 2,929 2,647 Amortization of deferred acquisition costs 215 209 645 608 Insurance related administrative expenses 165 158 498 454 Underwriting gain (loss) 106 (3) N/M 163 65 151 Net investment income 192 183 5 575 534 8 Other revenues 8 5 26 23 Other expenses 11 8 36 33 Core income (loss) before income tax 295 177 728 589 Income tax (expense) benefit on core income (loss) (62) (38) (153) (125) Core income (loss) $ 233 $ 139 68 % $ 575 $ 464 24 % Other Performance Metrics Underwriting gain (loss) $ 106 $ (3) N/M % $ 163 $ 65 151 % Effect of catastrophe losses 39 127 182 285 (Favorable) unfavorable net prior year loss reserve development (1) (3) 46 (11) (Favorable) unfavorable other development-related items (1) 1 3 8 11 Effect of (favorable) unfavorable development-related items — — 54 — Underlying underwriting gain (loss) $ 145 $ 124 17 % $ 399 $ 350 14 % Loss & LAE ratio 66.1 % 72.0 % 5.9 pts 68.7 % 69.7 % 1.0 pts Expense ratio 26.1 27.7 1.6 26.9 28.1 1.2 Dividend ratio 0.5 0.5 — 0.5 0.5 — Combined ratio 92.7 % 100.2 % 7.5 pts 96.1 % 98.3 % 2.2 pts Less: Effect of catastrophe impacts 2.7 9.6 6.9 4.3 7.5 3.2 Less: Effect of (favorable) unfavorable development-related items — (0.1) (0.1) 1.3 — (1.3) Underlying combined ratio 90.0 % 90.7 % 0.7 pts 90.5 % 90.8 % 0.3 pts Rate 5 % 6 % (1) pts 5 % 6 % (1) pts Renewal premium change 6 % 8 % (2) pts 7 % 8 % (1) pts Retention 79 % 84 % (5) pts 82 % 84 % (2) pts New business $ 324 $ 345 (6) % $ 1,114 $ 1,117 — % (1) Other development-related items represents net prior year premium development, the effects of interest accretion on net prior year loss development and the change in allowance for uncollectible reinsurance. 6

International - Results of Operations Periods ended September 30 Three Months Nine Months (In millions) 2025 2024 Change 2025 2024 Change Gross written premiums $ 322 $ 305 6 % $ 1,132 $ 1,096 3 % Net written premiums 319 277 15 976 896 9 Net earned premiums 344 311 11 978 937 4 Insurance claims and policyholders' benefits 203 195 590 568 Amortization of deferred acquisition costs 71 60 197 182 Insurance related administrative expenses 42 44 125 129 Underwriting gain (loss) 28 12 133 66 58 14 Net investment income 42 32 31 114 95 20 Other revenues — — — — Other expenses (1) (8) (12) (5) Core income (loss) before income tax 71 52 192 158 Income tax (expense) benefit on core income (loss) (24) (16) (55) (41) Core income (loss) $ 47 $ 36 31 % $ 137 $ 117 17 % Other Performance Metrics Underwriting gain (loss) $ 28 $ 12 133 % $ 66 $ 58 14 % Effect of catastrophe losses 2 16 18 28 (Favorable) unfavorable net prior year loss reserve development — (2) — (5) (Favorable) unfavorable other development-related items (1) — — — — Effect of (favorable) unfavorable development-related items — (2) — (5) Underlying underwriting gain (loss) $ 30 $ 26 15 % $ 84 $ 81 4 % Loss & LAE ratio 59.1 % 62.5 % 3.4 pts 60.3 % 60.6 % 0.3 pts Expense ratio 32.7 33.6 0.9 32.9 33.1 0.2 Dividend ratio — — — — — — Combined ratio 91.8 % 96.1 % 4.3 pts 93.2 % 93.7 % 0.5 pts Less: Effect of catastrophe impacts 0.6 5.1 4.5 1.8 3.0 1.2 Less: Effect of (favorable) unfavorable development-related items — (0.7) (0.7) — (0.5) (0.5) Underlying combined ratio 91.2 % 91.7 % 0.5 pts 91.4 % 91.2 % (0.2) pts Rate (6) % (2) % (4) pts (4) % — % (4) pts Renewal premium change (3) % 1 % (4) pts (1) % 2 % (3) pts Retention 83 % 82 % 1 pts 85 % 81 % 4 pts New business $ 94 $ 73 29 % $ 280 $ 213 31 % (1) Other development-related items represents net prior year premium development, the effects of interest accretion on net prior year loss development and the change in allowance for uncollectible reinsurance. 7

Life & Group - Results of Operations Periods ended September 30 Three Months Nine Months (In millions) 2025 2024 2025 2024 Net earned premiums $ 106 $ 110 $ 318 $ 329 Net investment income 226 240 687 710 Other revenues — — — — Total operating revenues 332 350 1,005 1,039 Insurance claims and policyholders' benefits 336 336 949 973 Insurance related administrative expenses 29 30 90 88 Other expenses — 1 1 2 Total claims, benefits and expenses 365 367 1,040 1,063 Core income (loss) before income tax (33) (17) (35) (24) Income tax (expense) benefit on core income (loss) 11 8 20 19 Core income (loss) $ (22) $ (9) $ (15) $ (5) 8

Corporate & Other - Results of Operations Periods ended September 30 Three Months Nine Months (In millions) 2025 2024 2025 2024 Net earned premiums $ (1) $ (1) $ (1) $ (1) Net investment income 16 14 45 53 Other revenues 1 2 1 2 Total operating revenues 16 15 45 54 Insurance claims and policyholders' benefits (10) 16 107 35 Insurance related administrative expenses — (1) 1 (1) Interest expense 36 32 99 101 Other expenses 26 23 59 65 Total claims, benefits and expenses 52 70 266 200 Core income (loss) before income tax (36) (55) (221) (146) Income tax (expense) benefit on core income (loss) 11 11 46 27 Core income (loss) $ (25) $ (44) $ (175) $ (119) 9

Investment Summary - Consolidated September 30, 2025 June 30, 2025 December 31, 2024 (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 $ 25,476 $ (110) $ 25,704 $ (503) $ 24,944 $ (882) States, municipalities and political subdivisions: Tax-exempt 4,463 (38) 3,515 (169) 3,167 (48) Taxable 3,913 (426) 3,860 (500) 3,637 (544) Total states, municipalities and political subdivisions 8,376 (464) 7,375 (669) 6,804 (592) Asset-backed: RMBS 3,701 (340) 3,545 (402) 3,244 (481) CMBS 1,593 (69) 1,648 (90) 1,681 (131) Other ABS 3,610 (162) 3,576 (188) 3,541 (215) Total asset-backed 8,904 (571) 8,769 (680) 8,466 (827) U.S. Treasury and obligations of government-sponsored enterprises 223 (3) 226 (5) 220 — Foreign government 723 (13) 725 (19) 677 (24) Redeemable preferred stock — — — — — — Total fixed maturity securities 43,702 (1,161) 42,799 (1,876) 41,111 (2,325) Equities: Common stock 197 — 223 — 180 — Non-redeemable preferred stock 529 — 504 — 479 — Total equities 726 — 727 — 659 — Limited partnership investments: Hedge funds 366 — 371 — 359 — Private equity funds 2,347 — 2,296 — 2,161 — Total limited partnership investments 2,713 — 2,667 — 2,520 — Other invested assets 97 — 88 — 85 — Mortgage loans 1,055 — 1,040 — 1,019 — Short-term investments 2,243 — 1,727 (1) 2,088 — Total investments $ 50,536 $ (1,161) $ 49,048 $ (1,877) $ 47,482 $ (2,325) Net receivable/(payable) on investment activity $ (41) $ (220) $ 16 Effective duration (in years) 6.3 6.3 6.2 Weighted average rating (1) A A A RMBS - Residential mortgage-backed securities CMBS - Commercial mortgage-backed securities Other ABS - Other asset-backed securities (1) Obligations of the U.S. Government, U.S. Government agencies and U.S. Government-sponsored enterprises were classified as AAA for purposes of calculating the weighted average rating. 10

Investment Summary - Property & Casualty and Corporate & Other September 30, 2025 June 30, 2025 December 31, 2024 (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 $ 14,421 $ (155) $ 14,852 $ (307) $ 14,755 $ (538) States, municipalities and political subdivisions: Tax-exempt 2,316 (150) 1,437 (228) 983 (189) Taxable 2,547 (358) 2,510 (407) 2,157 (446) Total states, municipalities and political subdivisions 4,863 (508) 3,947 (635) 3,140 (635) Asset-backed: RMBS 3,699 (340) 3,543 (402) 3,242 (481) CMBS 1,571 (67) 1,626 (88) 1,659 (128) Other ABS 3,056 (64) 3,019 (82) 2,979 (105) Total asset-backed 8,326 (471) 8,188 (572) 7,880 (714) U.S. Treasury and obligations of government-sponsored enterprises 214 (3) 217 (5) 211 — Foreign government 675 (5) 679 (9) 631 (14) Redeemable preferred stock — — — — — — Total fixed maturity securities 28,499 (1,142) 27,883 (1,528) 26,617 (1,901) Equities: Common stock 197 — 223 — 180 — Non-redeemable preferred stock 192 — 158 — 115 — Total equities 389 — 381 — 295 — Limited partnership investments: Hedge funds 325 — 329 — 275 — Private equity funds 2,082 — 2,038 — 1,653 — Total limited partnership investments 2,407 — 2,367 — 1,928 — Other invested assets 97 — 88 — 85 — Mortgage loans 884 — 867 — 844 — Short-term investments 2,108 — 1,636 (1) 2,040 — Total investments $ 34,384 $ (1,142) $ 33,222 $ (1,529) $ 31,809 $ (1,901) Net receivable/(payable) on investment activity $ (45) $ (205) $ 7 Effective duration (in years) 4.6 4.5 4.3 Weighted average rating (1) A A A (1) Obligations of the U.S. Government, U.S. Government agencies and U.S. Government-sponsored enterprises were classified as AAA for purposes of calculating the weighted average rating. 11

Investment Summary - Life & Group September 30, 2025 June 30, 2025 December 31, 2024 (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 $ 11,055 $ 45 $ 10,852 $ (196) $ 10,189 $ (344) States, municipalities and political subdivisions: Tax-exempt 2,147 112 2,078 59 2,184 141 Taxable 1,366 (68) 1,350 (93) 1,480 (98) Total states, municipalities and political subdivisions 3,513 44 3,428 (34) 3,664 43 Asset-backed: RMBS 2 — 2 — 2 — CMBS 22 (2) 22 (2) 22 (3) Other ABS 554 (98) 557 (106) 562 (110) Total asset-backed 578 (100) 581 (108) 586 (113) U.S. Treasury and obligations of government-sponsored enterprises 9 — 9 — 9 — Foreign government 48 (8) 46 (10) 46 (10) Redeemable preferred stock — — — — — — Total fixed maturity securities 15,203 (19) 14,916 (348) 14,494 (424) Equities: Common stock — — — — — — Non-redeemable preferred stock 337 — 346 — 364 — Total equities 337 — 346 — 364 — Limited partnership investments: Hedge funds 41 — 42 — 84 — Private equity funds 265 — 258 — 508 — Total limited partnership investments 306 — 300 — 592 — Other invested assets — — — — — — Mortgage loans 171 — 173 — 175 — Short-term investments 135 — 91 — 48 — Total investments $ 16,152 $ (19) $ 15,826 $ (348) $ 15,673 $ (424) Net receivable/(payable) on investment activity $ 4 $ (15) $ 9 Effective duration (in years) 9.8 9.8 9.8 Weighted average rating (1) A- A- A- (1) Obligations of the U.S. Government, U.S. Government agencies and U.S. Government-sponsored enterprises were classified as AAA for purposes of calculating the weighted average rating. 12

Investments - Fixed Maturity Securities by Credit Rating September 30, 2025 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 $ — $ — $ 8 $ (1) $ 813 $ (8) $ 8,266 $ (13) $ 14,895 $ (85) $ 1,494 $ (3) $ 25,476 $ (110) States, municipalities and political subdivisions — — 2,133 (29) 4,887 (328) 1,133 (56) 205 (44) 18 (7) 8,376 (464) Asset-backed: RMBS 3,038 (248) 648 (95) 8 — — — — — 7 3 3,701 (340) CMBS — — 666 1 565 (31) 211 (13) 104 (11) 47 (15) 1,593 (69) Other ABS — — 484 (12) 291 (70) 1,456 (31) 1,187 (34) 192 (15) 3,610 (162) Total asset-backed 3,038 (248) 1,798 (106) 864 (101) 1,667 (44) 1,291 (45) 246 (27) 8,904 (571) U.S. Treasury and obligations of government-sponsored enterprises 223 (3) — — — — — — — — — — 223 (3) Foreign government — — 189 — 319 (1) 96 (8) 119 (4) — — 723 (13) Redeemable preferred stock — — — — — — — — — — — — — — Total fixed maturity securities $ 3,261 $ (251) $ 4,128 $ (136) $ 6,883 $ (438) $ 11,162 $ (121) $ 16,510 $ (178) $ 1,758 $ (37) $ 43,702 $ (1,161) Percentage of total fixed maturity securities 7 % 9 % 16 % 26 % 38 % 4 % 100 % 13

Components of Net Investment Income Consolidated Periods ended September 30 Three Months Nine Months (In millions) 2025 2024 2025 2024 Taxable fixed income securities $ 506 $ 490 $ 1,510 $ 1,446 Tax-exempt fixed income securities 44 35 114 109 Total fixed income securities 550 525 1,624 1,555 Common stock 3 13 20 31 Limited partnerships - hedge funds 14 13 46 35 Limited partnerships - private equity funds 54 54 159 160 Total limited partnership and common stock investments 71 80 225 226 Other, net of investment expense 17 21 55 72 Net investment income $ 638 $ 626 $ 1,904 $ 1,853 Effective income yield for fixed income securities portfolio 4.8 % 4.8 % 4.8 % 4.8 % Limited partnership and common stock return for the period 2.5 3.1 8.3 9.4 Property & Casualty and Corporate & Other Periods ended September 30 Three Months Nine Months (In millions) 2025 2024 2025 2024 Taxable fixed income securities $ 308 $ 301 $ 922 $ 893 Tax-exempt fixed income securities 19 8 38 27 Total fixed income securities 327 309 960 920 Common stock 3 13 20 31 Limited partnerships - hedge funds 12 10 40 22 Limited partnerships - private equity funds 48 30 128 89 Total limited partnership and common stock investments 63 53 188 142 Other, net of investment expense 22 24 69 81 Net investment income $ 412 $ 386 $ 1,217 $ 1,143 Effective income yield for fixed income securities portfolio 4.4 % 4.3 % 4.4 % 4.3 % Life & Group Periods ended September 30 Three Months Nine Months (In millions) 2025 2024 2025 2024 Taxable fixed income securities $ 198 $ 189 $ 588 $ 553 Tax-exempt fixed income securities 25 27 76 82 Total fixed income securities 223 216 664 635 Common stock — — — — Limited partnerships - hedge funds 2 3 6 13 Limited partnerships - private equity funds 6 24 31 71 Total limited partnership and common stock investments 8 27 37 84 Other, net of investment expense (5) (3) (14) (9) Net investment income $ 226 $ 240 $ 687 $ 710 Effective income yield for fixed income securities portfolio 5.7 % 5.7 % 5.7 % 5.6 % 14

Net Investment Gains (Losses) Periods ended September 30 Consolidated Three Months Nine Months (In millions) 2025 2024 2025 2024 Fixed maturity securities: Corporate and other bonds $ (6) $ (17) $ (55) $ (38) States, municipalities and political subdivisions 1 (1) — (3) Asset-backed (5) (4) (12) (25) Total fixed maturity securities (10) (22) (67) (66) Non-redeemable preferred stock 4 13 10 25 Derivatives, short-term and other (1) (1) — (1) Mortgage loans — — (5) — Net investment gains (losses) (7) (10) (62) (42) Income tax benefit (expense) on net investment gains (losses) 1 3 13 9 Net investment gains (losses), after tax $ (6) $ (7) $ (49) $ (33) 15

Claim & Claim Adjustment Expense Reserve Rollforward Three months ended September 30, 2025 (In millions) Specialty Commercial International P&C Operations Life & Group Corporate & Other Total Operations Claim & claim adjustment expense reserves, beginning of period Gross $ 7,704 $ 11,888 $ 3,256 $ 22,848 $ 611 $ 2,744 $ 26,203 Ceded 1,631 1,490 490 3,611 79 2,240 5,930 Net 6,073 10,398 2,766 19,237 532 504 20,273 Net incurred claim & claim adjustment expenses 534 960 204 1,698 11 4 1,713 Net claim & claim adjustment expense payments (486) (770) (127) (1,383) (11) (21) (1,415) Foreign currency translation adjustment and other — — (40) (40) 6 — (34) Claim & claim adjustment expense reserves, end of period Net 6,121 10,588 2,803 19,512 538 487 20,537 Ceded 1,648 1,565 512 3,725 77 2,186 5,988 Gross $ 7,769 $ 12,153 $ 3,315 $ 23,237 $ 615 $ 2,673 $ 26,525 Nine months ended September 30, 2025 (In millions) Specialty Commercial International P&C Operations Life & Group Corporate & Other Total Operations Claim & claim adjustment expense reserves, beginning of period Gross $ 7,426 $ 11,336 $ 2,920 $ 21,682 $ 622 $ 2,672 $ 24,976 Ceded 1,447 1,397 504 3,348 81 2,284 5,713 Net 5,979 9,939 2,416 18,334 541 388 19,263 Net incurred claim & claim adjustment expenses 1,562 2,907 590 5,059 25 147 5,231 Net claim & claim adjustment expense payments (1,421) (2,259) (361) (4,041) (33) (48) (4,122) Foreign currency translation adjustment and other 1 1 158 160 5 — 165 Claim & claim adjustment expense reserves, end of period Net 6,121 10,588 2,803 19,512 538 487 20,537 Ceded 1,648 1,565 512 3,725 77 2,186 5,988 Gross $ 7,769 $ 12,153 $ 3,315 $ 23,237 $ 615 $ 2,673 $ 26,525 16

Life & Group Policyholder Reserves Three months ended September 30, 2025 (In millions) Claim and claim adjustment expenses Future policy benefits Total Beginning of Period $ 532 $ 13,329 $ 13,861 Incurred claims and policyholders' benefits (1) 11 324 335 Benefit and expense payments (11) (296) (307) Change in discount rate assumptions and other (AOCI) 6 189 195 End of Period $ 538 $ 13,546 $ 14,084 Nine months ended September 30, 2025 (In millions) Claim and claim adjustment expenses Future policy benefits Total Beginning of Period $ 541 $ 13,158 $ 13,699 Incurred claims and policyholders' benefits (1) 25 920 945 Benefit and expense payments (33) (870) (903) Change in discount rate assumptions and other (AOCI) 5 338 343 End of Period $ 538 $ 13,546 $ 14,084 (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. 17

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 and gains or losses resulting from pension settlement transactions. Net investment gains or losses are excluded from the calculation of core income (loss) because they are generally driven by economic factors that are not necessarily reflective of our primary operations. The calculation of core income (loss) excludes gains or losses resulting from pension settlement transactions as they result from decisions regarding our defined benefit pension plans which are unrelated to 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 P to the Consolidated Financial Statements within the December 31, 2024 Form 10-K for further discussion regarding how the Company manages its business. • In evaluating the results of the Specialty, Commercial and International segments, management uses the loss ratio, the underlying loss ratio, the expense ratio, the dividend ratio, the combined ratio and the underlying 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 underlying loss ratio excludes the impact of catastrophe losses and development-related items from the loss ratio. Development-related items represents net prior year loss reserve and premium development, and includes the effects of interest accretion and change in allowance for uncollectible reinsurance. 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 ratio, the expense ratio and the dividend ratio. The underlying combined ratio is the sum of the underlying loss ratio, the expense ratio and the dividend ratio. The underlying loss ratio and the underlying combined ratio are deemed to be non-GAAP financial measures, and management believes some investors may find these ratios useful to evaluate our underwriting performance since they remove the impact of catastrophe losses, which are unpredictable as to timing and amount, and development-related items as they are not indicative of our current year underwriting performance. 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. 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. 18

• Management uses underwriting gain (loss) and underlying underwriting gain (loss), calculated using GAAP financial results, to monitor our insurance operations. Underwriting gain (loss) is deemed to be a non-GAAP financial measure and is calculated pretax 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. Net income (loss) is the most directly comparable GAAP measure. Management believes some investors may find this measure useful to evaluate the profitability, before tax, derived from our underwriting activities, which are managed separately from our investing activities. Underlying underwriting gain (loss) is also deemed to be a non-GAAP financial measure, and represents pretax underwriting gain (loss) excluding catastrophe losses and development-related items. Management believes some investors may find this measure useful to evaluate the profitability, before tax, derived from our underwriting activities, excluding the impact of catastrophe losses, which are unpredictable as to timing and amount, and development-related items as they are not indicative of our current year underwriting performance. • 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 filings with the Securities and Exchange Commission, available at www.cna.com. • 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. • Net investment income from fixed income securities, as presented, includes both fixed maturity securities and non-redeemable preferred stock. • Certain immaterial differences are due to rounding. • N/M = Not Meaningful 19

CNA Financial Corporation Third Quarter 2025 Results November 3, 2025

Forward Looking Statements The statements made in the course of this presentation and/or contained in the presentation materials may include statements that relate to anticipated future events (forward-looking statements) rather than actual present conditions or historical events. These statements are made pursuant to the safe harbor provisions of the Private Securities Litigation Reform Act of 1995 and generally include words such as “believes,” “expects,” “intends,” “anticipates,” “estimates” and similar expressions. Forward-looking statements, by their nature, are subject to a variety of inherent risks and uncertainties that could cause actual results to differ materially from the results projected. Many of these risks and uncertainties cannot be controlled by CNA. For a detailed description of these risks and uncertainties, please refer to CNA’s filings with the Securities and Exchange Commission available at www.cna.com. Any forward-looking statements and other financial information contained in this presentation speak only as of the date hereof. Further, CNA does not have any obligation to update or revise any forward-looking statement made in the course of this presentation and/or contained in the presentation materials even if CNA’s expectations or any related events, conditions or circumstances change. Reconciliation of GAAP Measures to Non-GAAP Measures This earnings presentation contains financial measures that are not in accordance with accounting principles generally accepted in the United States of America (GAAP). Management utilizes these financial measures to monitor the Company's insurance operations and investment portfolio. The Company believes the presentation of these measures provides investors with a better understanding of the significant factors that comprise the Company's operating performance. Reconciliations of these measures to the most comparable GAAP measures can be found in the Appendix to this presentation. For additional information, please refer to CNA's filings with the Securities and Exchange Commission, available at www.cna.com Available Information and Risk Factors CNA files annual, quarterly and current reports and other information with the SEC. The SEC filings are available on the CNA website (www.cna.com) and at the SEC's website (www.sec.gov). These filings describe some of the more material risks we face and how these risks could lead to events or circumstances that may have a material adverse effect on our business, financial condition, results of operations or cash flows. You should review these filings as they contain important information about CNA and its business. "CNA" is a registered trademark of CNA Financial Corporation. Certain CNA Financial Corporation subsidiaries use the "CNA" trademark in connection with insurance underwriting and claims activities. Copyright © 2025 CNA. All rights reserved. 2 Notices and Disclaimers

• Net income of $403 million versus $283 million in the prior year quarter; core income up 40% to a record $409 million versus $293 million in the prior year quarter. Year to date core income up 5% to a record $1,025 million. • P&C core income of $456 million versus $346 million, reflects lower catastrophe losses, improved underlying underwriting results and higher net investment income. • Life & Group core loss of $22 million versus $9 million in the prior year quarter. • Corporate & Other core loss of $25 million versus $44 million in the prior year quarter. • Net investment income up 2% to $638 million pretax, reflects a $21 million increase from fixed income securities and other investments to $567 million and a $9 million decrease from limited partnerships and common stock to $71 million. • P&C combined ratio of 92.8%, compared with 97.2% in the prior year quarter, including 1.5 points of catastrophe loss impact compared with 5.8 points in the prior year quarter. • Catastrophe losses of $41 million pretax versus $143 million in the prior year quarter. • P&C underlying combined ratio was 91.3%, compared with 91.6% in the prior year quarter. P&C underlying loss ratio was 61.9% and the expense ratio was 29.1%. • P&C segments, excluding third party captives, generated gross written premium growth of 2% and net written premium growth of 3%. P&C renewal premium change of +4%, with written rate of +3% and exposure change of +1%. • Book value per share of $41.83; book value per share excluding AOCI of $46.30, a 8% increase from year-end 2024 adjusting for $3.38 of dividends per share paid. • Board of Directors declares regular quarterly cash dividend of $0.46 per share. 3 Third Quarter Overview

4 (In millions, except ratios and per share data) Third Quarter Year to Date 2025 2024 Change 2025 2024 Change Revenues $3,817 $3,618 6 % $11,161 $10,581 5 % Core income 409 293 40 % 1,025 974 5 % Net income 403 283 42 % 976 938 4 % Diluted earnings per common share: Core income $1.50 $1.08 39 % $3.76 $3.57 5 % Net income 1.48 1.04 42 % 3.58 3.44 4 % Core ROE 13.2 % 9.4 % 3.8 pts 10.9 % 10.3 % 0.6 pts Lower catastrophe losses, record underlying results and higher investment income drive record core income results Financial Performance

5 (In millions, except ratios) Third Quarter Year to Date 2025 2024 2025 2024 GWP ex. 3rd party captives $2,890 $2,825 $9,385 $8,964 GWP change (% year over year) 2 % 5 % Net written premium $2,437 $2,360 $7,889 $7,424 NWP change (% year over year) 3 % 6 % Net earned premium $2,678 $2,484 $7,786 $7,204 NEP change (% year over year) 8 % 8 % Underwriting gain $194 $68 $384 $318 Loss ratio 63.4 % 66.7 % 65.0 % 64.9 % Less: Effect of catastrophes impacts 1.5 % 5.8 % 2.6 % 4.3 % Less: Effect of (favorable) unfavorable development-related items — % (0.2) % 0.8 % (0.2) % Underlying loss ratio 61.9 % 61.1 % 61.6 % 60.8 % Expense ratio 29.1 % 30.2 % 29.7 % 30.3 % Combined ratio 92.8 % 97.2 % 95.1 % 95.6 % Underlying combined ratio 91.3 % 91.6 % 91.7 % 91.5 % Property & Casualty Operations Excellent underwriting results driven by lower catastrophe losses and expense ratio

6 Property & Casualty Rate & Retention 2024 2025 Q1 Q2 Q3 Q4 Q1 Q2 Q3 4% 4% 3% 3% 4% 3% 3% 6% 5% 5% 4% 6% 5% 4% 85% 85% 85% 86% 86% 83% 81% Retention Renewal Premium Change Rate GWP ex. 3rd party captives ($M) $2,936 $3,203 $2,825 $3,230 $3,142 $3,353 $2,890 New Business ($M) $529 $595 $547 $591 $565 $645 $549 Specialty Rate 2% —% —% 1% 3% 3% 3% Retention 88% 90% 89% 89% 89% 86% 86% Commercial Rate 6% 7% 6% 6% 6% 5% 5% Retention 85% 84% 84% 84% 84% 81% 79% International Rate 1% —% (2)% (3)% (2)% (4)% (6)% Retention 82% 80% 82% 85% 85% 86% 83% Property & Casualty Operations Metrics Continued disciplined and nuanced execution across the portfolio

7 (In millions, except ratios) Third Quarter Year to Date 2025 2024 2025 2024 GWP ex. 3rd party captives $1,009 $982 $2,952 $2,846 GWP change (% year over year) 3 % 4 % Net written premium $867 $862 $2,601 $2,511 NWP change (% year over year) 1 % 4 % Net earned premium $881 $848 $2,573 $2,493 NEP change (% year over year) 4 % 3 % Underwriting gain $60 $59 $155 $195 Loss ratio 60.6 % 60.1 % 60.7 % 59.3 % Less: Effect of catastrophes impacts — % — % — % — % Less: Effect of unfavorable (favorable) development-related items — % — % 0.4 % (0.3) % Underlying loss ratio 60.6 % 60.1 % 60.3 % 59.6 % Expense ratio 32.5 % 32.7 % 33.0 % 32.5 % Combined ratio 93.3 % 93.0 % 94.0 % 92.1 % Underlying combined ratio 93.3 % 93.0 % 93.6 % 92.4 % Specialty Continued solid underwriting results

8 Specialty Rate & Retention 2024 2025 Q1 Q2 Q3 Q4 Q1 Q2 Q3 —% —% 3% 1% 2% 3% 4% 4% 4% 88% 90% 89% 89% 89% 86% 86% Retention Renewal Premium Change Rate GWP ex. 3rd party captives ($M) $880 $984 $982 $1,049 $930 $1,013 $1,009 New Business ($M) $94 $118 $129 $121 $112 $122 $131 FI & Mgmt Liability Rate (3)% (6)% (5)% (4)% (1)% 1% (1)% Retention 90% 92% 91% 89% 89% 84% 86% Affinity Professional E&O Rate 2% 3% 2% 3% 2% 3% 2% Retention 92% 92% 91% 93% 93% 92% 88% Medical Malpractice Rate 7% 9% 7% 9% 7% 8% 9% Retention 80% 85% 83% 84% 85% 85% 83% Surety Net Written Premiums $184 $175 $176 $157 $204 $182 $193 Warranty & Alt. Risks Revenues $461 $459 $452 $443 $445 $446 $439 2% 3%1% 3% Specialty Production Metrics Stable rate, renewal premium change and retention 3%

9 (In millions, except ratios) Third Quarter Year to Date 2025 2024 2025 2024 GWP ex. 3rd party captives $1,559 $1,538 $5,301 $5,022 GWP change (% year over year) 1 % 6 % Net written premium $1,251 $1,221 $4,312 $4,017 NWP change (% year over year) 2 % 7 % Net earned premium $1,453 $1,325 $4,235 $3,774 NEP change (% year over year) 10 % 12 % Underwriting gain (loss) $106 ($3) $163 $65 Loss ratio 66.1 % 72.0 % 68.7 % 69.7 % Less: Effect of catastrophes impacts 2.7 % 9.6 % 4.3 % 7.5 % Less: Effect of (favorable) unfavorable development-related items — % (0.1) % 1.3 % — % Underlying loss ratio 63.4 % 62.5 % 63.1 % 62.2 % Expense ratio 26.1 % 27.7 % 26.9 % 28.1 % Combined ratio 92.7 % 100.2 % 96.1 % 98.3 % Underlying combined ratio 90.0 % 90.7 % 90.5 % 90.8 % Commercial Excellent underwriting results driven by lower catastrophe losses and record underlying results

10 Commercial Rate & Retention 2024 2025 Q1 Q2 Q3 Q4 Q1 Q2 Q3 6% 7% 6% 6% 6% 5% 5% 8% 7% 8% 7% 7% 6% 6% 85% 84% 84% 84% 84% 81% 79% Retention Renewal Premium Change Rate GWP ex. 3rd party captives ($M) $1,682 $1,802 $1,538 $1,794 $1,839 $1,903 $1,559 New Business ($M) $367 $405 $345 $395 $370 $420 $324 Middle Market Rate 5% 5% 4% 4% 4% 4% 3% Retention 83% 84% 85% 84% 84% 81% 79% Construction Rate 8% 9% 9% 9% 9% 10% 8% Retention 86% 87% 84% 86% 82% 81% 73% National Accounts Rate 8% 7% 6% 6% 5% —% 2% Retention 87% 83% 85% 84% 88% 83% 86% Small Business Rate 3% 4% 4% 5% 5% 4% 5% Retention 81% 79% 80% 81% 82% 80% 76% Marine / Other Net Written Premium $104 $116 $95 $94 $111 $115 $112 Commercial Production Metrics Achieving strong rate and improved terms & conditions on liability coverages, while national accounts property rate remains soft

1 Excluding currency fluctuations, GWP grew 3% for the third quarter and 3% year to date. NWP grew 12% for the third quarter and 9% year to date. 11 (In millions, except ratios) Third Quarter Year to Date 2025 2024 2025 2024 Gross written premium $322 $305 $1,132 $1,096 GWP change (% year over year)1 6 % 3 % Net written premium $319 $277 $976 $896 NWP change (% year over year)1 15 % 9 % Net earned premium $344 $311 $978 $937 NEP change (% year over year) 11 % 4 % Underwriting gain $28 $12 $66 $58 Loss ratio 59.1 % 62.5 % 60.3 % 60.6 % Less: Effect of catastrophes impacts 0.6 % 5.1 % 1.8 % 3.0 % Less: Effect of unfavorable (favorable) development-related items — % (0.7) % — % (0.5) % Underlying loss ratio 58.5 % 58.1 % 58.5 % 58.1 % Expense ratio 32.7 % 33.6 % 32.9 % 33.1 % Combined ratio 91.8 % 96.1 % 93.2 % 93.7 % Combined ratio excl. catastrophes and development 91.2 % 91.7 % 91.4 % 91.2 % International Strong GWP growth with consistently profitable results

12 Life & Group Core loss reflects lower income from limited partnership investments (In millions) Third Quarter Year to Date 2025 2024 2025 2024 Net earned premiums $106 $110 $318 $329 Total claims, benefits and expenses 365 367 1,040 1,063 Net investment income 226 240 687 710 Core loss before income tax (33) (17) (35) (24) Income tax benefit 11 8 20 19 Core loss ($22) ($9) ($15) ($5) Core loss includes an unfavorable after-tax impact of $7 million in 2025 and $5 million in 2024 as a result of the annual assumption updates.

2025 L&G Reserve Review Neutral impact to GAAP reserves following assumption updates for the 3rd straight year (In millions) Change to GAAP Liability for Future Policy Benefits (LFPB) from Changes in Underlying Cash Flow Assumptions 2025 Economic Assumptions ▪ Additional near-term cost of care inflation prudence reflected through earnings ▪ Effect of interest rate changes on carried LFPB reflected through AOCI under GAAP +$50 Morbidity ▪ Unfavorable incidence and claim closure updates, partially offset by favorable utilization revisions +$125 Persistency ▪ Slightly favorable impacts from mortality updates ($10) Premium Rate Actions ▪ Favorable impacts due to rate achievement greater than prior year's estimates ▪ Updates to future rate increase assumptions based on current filing plan ($170) Expense & Other ▪ Refinements to operational and overhead expectations $0 Increase/(Decrease) to GAAP LFPB from LTC Assumption Updates ($5) Net Premium Ratio Updates ▪ Favorable assumption adjustments deferred into future periods +$12 Increase/(Decrease) to GAAP LFPB $7 Structured Settlements ▪ Neutral impact to claim reserves +$2 Increase/(Decrease) to Total Life & Group GAAP Reserves $9 13

LTC Progress Focused on Active Management Proactive approach to managing block across all dimensions of the business 14 Material progress made recently • 31 rate increase approvals in 2025 with an average rate increase amount of 28% • Approximately 1,200 buyouts in 2025 with $51M of cash paid • Increased the fixed-income duration for the LTC portfolio to ~10 years, up ~1 year from 2021, taking advantage of the higher interest rate environment; asset and liability durations generally matched • Strategic investments in claims management, anti-fraud and wellness initiatives to improve financial outcomes Ability to Withstand Stresses • Prudent reserving assumptions informed by historical experience, including no morbidity improvement, 10 years of mortality improvement, negligible future premium risk and an ultimate 10-year treasury rate assumption of 3.00% • $1.5b of Statutory reserve margin as of September 30, 2025, following 2025 assumption updates Significantly improved runoff Long Term Care business compared to 2015 • Individual LTC block closed in 2004; Group LTC block closed to new accounts in 2004 and closed to new enrollees in 2016 • Total policy counts have reduced ~50% since 2015 • The larger Individual LTC reserves have peaked and are decreasing, while Group LTC reserves will peak at levels less than half of Individual LTC due to less rich benefits • Premium rates are 93% higher than original pricing & 84k policyholders have reduced coverage since 2017

Individual LTC Block Characteristics More mature, richer benefit ILTC reserves have reached inflection point 15 Commentary Block Characteristics • De-risking of the more mature ILTC block with richer policy benefits is well underway ◦ We believe the ILTC reserve balance is at peak levels and declining with significant policyholder experience utilized for assumption setting • Total ILTC policies have declined by 50% (~96,000 policies) since 2015 with stable open claim counts ◦ We expect approximately 65% of existing ILTC policies will run off over the next 10 years Individual Block Be ne fit s Average Age 83 years old Average Max Daily Benefit $333 % of policies with Lifetime Benefits 39% Average Benefit Period (non-lifetime) 3.8 years % of policies with Compound Inflation 44% % of policies with Simple Inflation 22% C la im s # of Open Claims 12.4k Average Age of New Claimant 86 years old 1 Reserves are discounted at locked-in discount rates. 2 ILTC metrics do not include CNA's 50% coinsurance business (26k healthy policies and 3k claims as of Q3 2025). 3 Healthy policies do not include 8k non-forfeiture limited benefit policies as of Q3 2025. Total Inforce ILTC Policies 2,3 Actual & Projected GAAP Reserves ($b) 1,2 177 166 155 144 133 124 115 107 97 89 83 14 14 14 14 15 14 13 13 13 13 12 Healthy Policies Open Claims 2015 2016 2017 2018 2019 2020 2021 2022 2023 2024 2025 Q3 50% Reduction $9.7 $3.7 2020 2022 2024 2026 2028 2030 2032 2034 2036 2038 2040 Projections Using 2025 AssumptionsActuals (In thousands)

Total Inforce GLTC Policies 2 Group LTC Block Characteristics Less rich benefits and peak reserves significantly below ILTC peak reserves 16 Commentary Block Characteristics • We believe the projected GAAP GLTC reserves will peak in the mid-2030’s at substantially lower levels than peak ILTC reserves ◦ GLTC's expected lower reserve trajectory primarily driven by less rich benefits compared to ILTC • Total GLTC policies have declined 48% (~111,000 insureds) since 2015 from our continued active management with claim counts remaining stable throughout ◦ We expect approximately 25% of existing GLTC policies will run off over the next 10 years Group Block Be ne fit s Average Age 70 years old Average Max Daily Benefit $220 % of policies with Lifetime Benefits 1% Average Benefit Period (non-lifetime) 4.5 years % of policies with Compound Inflation 13% % of policies with Simple Inflation 1% C la im s # of Open Claims 3.0k Average Age of New Claimant 78 years old 1 Reserves are discounted at locked-in discount rates. 2 Healthy policies do not include 85k non-forfeiture limited benefit policies as of Q3 2025. Actual & Projected GAAP Reserves ($b) 1,2 $2.8 $3.8 2020 2022 2024 2026 2028 2030 2032 2034 2036 2038 2040 Projections Using 2025 AssumptionsActuals 227 207 185 158 149 144 139 135 125 119 115 2 2 3 3 3 3 3 3 3 3 3 Healthy Policies Open Claims 2015 2016 2017 2018 2019 2020 2021 2022 2023 2024 2025 Q3 48% Reduction (In thousands)

Q3 2024 Q4 2024 Q1 2025 Q2 2025 Q3 2025 Total CNAF Limited Partnership & Common Stock Highlights Fixed Income Securities 4.8% 4.8% 4.8% 4.9% 4.8% Fixed Income Effective Yield (Pretax) Q3 2024 Q4 2024 Q1 2025 Q2 2025 Q3 2025 80 94 54 100 71 3.1% 3.5% 2.0% 3.6% 2.5% Limited Partnership & Common Stock Return (Pretax) Q3 2024 Q4 2024 Q1 2025 Q2 2025 Q3 2025 $M $M $M 17 Pretax Net Investment Income Strong contributions from fixed income and limited partnerships • Net investment income from fixed income is up 5% year-over-year • Fixed income benefited from strong operating cash flows and the continued impact of favorable reinvestment rates • Solid limited partnership and common stock results in the quarter; trailing twelve month return of 12% 525 529 530 544 550 626 644 604 662 638

6% 5% 3% 2% 2% 1% 18 Life & Group 9.8 yrs P&C and Corporate 4.6 yrs Total 6.3 yrs 1 AAA includes obligations of the U.S. Government, U.S. Government agencies and U.S. Government-sponsored enterprises. AA 16% A 26% BBB 38% Corporate & Other 50% Municipals 17% Other ABS 7% RMBS 7% AAA 1 16% Non-IG 4% LPs & Common Stock Short Term & Other CMBS Mortgage Loans Other Fixed Income Preferred Stock Effective Portfolio Duration • 88% of total invested assets are in fixed income securities • High-quality portfolio with an average credit rating of “A” • Duration well matched with insurance liabilities • Net unrealized loss improved from year-end driven by lower risk-free rates and tightening credit spreads Fixed Maturities by Rating Portfolio Composition Highlights High quality, diversified and liquid investment portfolio Investment Portfolio

Capital • Financial strength ratings from all four rating agencies have been affirmed since August 2024 • Moody’s and AM Best maintain positive outlooks; S&P and Fitch maintain stable outlooks • Statutory surplus remains very strong • Adjusting for dividends, book value per share ex. AOCI increased 8% Leverage • Debt maturity schedule is termed out to effectively manage refinancing • $500M debt issuance in Q3 in advance of upcoming maturity of $500M in the first quarter of 2026 Liquidity • Ample liquidity at both holding and operating company levels to meet obligations (In millions, except per share data) Sep 30, 2025 Dec 31, 2024 Debt $3,470 $2,973 Stockholders' equity 11,322 10,513 Total capital $14,792 $13,486 AOCI (1,211) (1,991) Capital ex. AOCI $16,003 $15,477 BVPS ex. AOCI $46.30 $46.16 Dividends per share (YTD) $3.38 $3.76 Debt-to-capital 23.5 % 22.0 % Debt-to-capital ex. AOCI 21.7 % 19.2 % Statutory surplus $11,535 $11,165 Holding company liquidity 1 $1,330 $1,207 19 1 Includes $250 million available under credit facility Financial Strength Conservative capital and debt profile support business objectives

Results for the Three Months Ended September 30 Results for the Nine Months Ended September 30 (In millions) 2025 2024 2025 2024 Net income $403 $283 $976 $938 Less: Net investment losses (6) (7) (49) (33) Less: Pension settlement transaction losses — (3) — (3) Core income $409 $293 $1,025 $974 Core income (loss) is calculated by excluding from net income (loss) the after-tax effects of net investment gains or losses and gains or losses resulting from pension settlement transactions. Net investment gains or losses are excluded from the calculation of core income (loss) because they are generally driven by economic factors that are not necessarily reflective of our primary operations. The calculation of core income (loss) excludes gains or losses resulting from pension settlement transactions as they result from decisions regarding our defined benefit pension plans which are unrelated to 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 our primary operations. Reconciliation of Net Income (Loss) per Diluted Share to Core Income (Loss) per Diluted Share Results for the Three Months Ended September 30 Results for the Nine Months Ended September 30 2025 2024 2025 2024 Net income per diluted share $1.48 $1.04 $3.58 $3.44 Less: Net investment losses (0.02) (0.03) (0.18) (0.12) Less: Pension settlement transaction losses — (0.01) — (0.01) Core income per diluted share $1.50 $1.08 $3.76 $3.57 Core income (loss) per diluted share provides management and investors with a valuable measure of the Company's operating performance for the same reasons applicable to its underlying measure, core income (loss). Core income (loss) per diluted share is core income (loss) on a per diluted share basis. 21 Reconciliation of Net Income (Loss) to Core Income (Loss) Reconciliation of GAAP Measures to Non-GAAP Measures

22 Results for the Three Months Ended September 30, 2025 (In millions) Specialty Commercial International Property & Casualty Net income $ 173 $ 229 $ 44 $ 446 Net investment losses, after tax 3 4 3 10 Core income $ 176 $ 233 $ 47 $ 456 Less: Net investment income 162 192 42 396 Non-insurance warranty revenue (expense) 16 — — 16 Other revenue (expense), including interest expense (15) (3) 1 (17) Income tax expense on core income (47) (62) (24) (133) Underwriting gain 60 106 28 194 Effect of catastrophe losses — 39 2 41 Effect of development-related items — — — — Underlying underwriting gain $ 60 $ 145 $ 30 $ 235 Reconciliation of Net Income (Loss) to Underwriting Gain (Loss) and Underlying Underwriting Gain (Loss) Underwriting gain (loss) is deemed to be a non-GAAP financial measure and is calculated pretax as net earned premiums less total insurance expenses, which includes insurance claims and policyholders' benefits, amortization of deferred acquisition costs and insurance related administrative expenses. Net income (loss) is the most directly comparable GAAP measure. Management believes some investors may find this measure useful to evaluate the profitability, before tax, derived from our underwriting activities which are managed separately from our investing activities. Underlying underwriting gain (loss) is also deemed to be a non-GAAP financial measure, and represents pretax underwriting results excluding catastrophe losses and development-related items. Management believes some investors may find this measure useful to evaluate the profitability, before tax, derived from our underwriting activities, excluding the impact of catastrophe losses, which are unpredictable as to timing and amount, and development-related items as they are not indicative of our current year underwriting performance. Reconciliation of GAAP Measures to Non-GAAP Measures

23 Results for the Three Months Ended September 30, 2024 (In millions) Specialty Commercial International Property & Casualty Net income $ 167 $ 132 $ 34 $ 333 Net investment losses, after tax 4 7 2 13 Core income $ 171 $ 139 $ 36 $ 346 Less: Net investment income 157 183 32 372 Non-insurance warranty revenue (expense) 14 — — 14 Other revenue (expense), including interest expense (12) (3) 8 (7) Income tax expense on core income (47) (38) (16) (101) Underwriting gain (loss) 59 (3) 12 68 Effect of catastrophe losses — 127 16 143 Effect of favorable development-related items — — (2) (2) Underlying underwriting gain $ 59 $ 124 $ 26 $ 209 Reconciliation of GAAP Measures to Non-GAAP Measures

24 Results for the Nine Months Ended September 30, 2025 (In millions) Specialty Commercial International Property & Casualty Net income $ 487 $ 552 $ 135 $ 1,174 Net investment losses, after tax 16 23 2 41 Core income $ 503 $ 575 $ 137 $ 1,215 Less: Net investment income 483 575 114 1,172 Non-insurance warranty revenue (expense) 42 — — 42 Other revenue (expense), including interest expense (40) (10) 12 (38) Income tax expense on core income (137) (153) (55) (345) Underwriting gain 155 163 66 384 Effect of catastrophe losses — 182 18 200 Effect of unfavorable development-related items 10 54 — 64 Underlying underwriting gain $ 165 $ 399 $ 84 $ 648 Reconciliation of GAAP Measures to Non-GAAP Measures

25 Results for the Nine Months Ended September 30, 2024 (In millions) Specialty Commercial International Property & Casualty Net income $ 498 $ 436 $ 116 $ 1,050 Net investment losses, after tax 19 28 1 48 Core income $ 517 $ 464 $ 117 $ 1,098 Less: Net investment income 461 534 95 1,090 Non-insurance warranty revenue (expense) 43 — — 43 Other revenue (expense), including interest expense (40) (10) 5 (45) Income tax expense on core income (142) (125) (41) (308) Underwriting gain 195 65 58 318 Effect of catastrophe losses — 285 28 313 Effect of favorable development-related items (8) — (5) (13) Underlying underwriting gain $ 187 $ 350 $ 81 $ 618 The underlying loss ratio excludes the impact of catastrophe losses and development-related items from the loss ratio. The underlying combined ratio is the sum of the underlying loss ratio, the expense ratio and the dividend ratio. The underlying loss ratio and the underlying combined ratio are deemed to be non-GAAP financial measures, and management believes some investors may find these ratios useful to evaluate our underwriting performance since they remove the impact of catastrophe losses, which are unpredictable as to timing and amount, and development-related items as they are not indicative of our current year underwriting performance. The components to reconcile the combined ratio and loss ratio to the underlying combined ratio and underlying loss ratio for Property & Casualty, Specialty, Commercial and International segments are set forth on pages 5, 7, 9 and 11, respectively. Components to reconcile the combined ratio and loss ratio to the underlying combined ratio and underlying loss ratio Reconciliation of GAAP Measures to Non-GAAP Measures

September 30, 2025 December 31, 2024 Book value per share $41.83 $38.82 Less: Per share impact of AOCI (4.47) (7.34) Book value per share excluding AOCI $46.30 $46.16 Book value per share excluding AOCI allows management and investors to analyze the amount of the Company's net worth primarily attributable to the Company's business operations. The Company believes this measurement is useful as it reduces the effect of items that can fluctuate significantly from period to period, primarily based on changes in interest rates. Calculation of Return on Equity and Core Return on Equity Results for the Three Months Ended September 30 Results for the Nine Months Ended September 30 ($ millions) 2025 2024 2025 2024 Annualized net income $1,615 $1,132 $1,302 $1,251 Average stockholders' equity including AOCI (a) 10,992 10,316 10,917 10,326 Return on equity 14.7 % 11.0 % 11.9 % 12.1 % Annualized core income $1,637 $1,176 $1,367 $1,299 Average stockholders' equity excluding AOCI (a) 12,390 12,508 12,518 12,580 Core return on equity 13.2 % 9.4 % 10.9 % 10.3 % Core return on equity provides management and investors with a measure of how effectively the Company is investing the portion of the Company's net worth that is primarily attributable to its business operations. a Average stockholders' equity is calculated using a simple average of the beginning and ending balances for the period. 26 Reconciliation of Book Value per Share to Book Value per Share Excluding AOCI Reconciliation of GAAP Measures to Non-GAAP Measures