Earnings Document

Notices and Disclaimers

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 most recent annual report on Form 10-K on file 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.

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.

Non-GAAP Measures

This presentation, along with the presentation materials, may also reference or contain financial measures that are not in accordance with generally accepted accounting principles (GAAP). For reconciliations of non-GAAP measures to the most comparable GAAP measures and other information, please refer to CNA's press release and financial supplement that we have made available in connection with this presentation and our other filings with the Securities and Exchange Commission available at

www.cna.com

"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 © 2023 CNA. All rights reserved.

2

Third Quarter Overview

• Net income of $258 million versus net loss of $42 million in the prior year quarter; core income of $289 million versus $43 million in the prior year quarter.
• Core income up 56% to $291 million versus $186 million in the prior year quarter, excluding the results of the Life & Group annual reserve reviews.
• P&C core income up 35% to $351 million versus $260 million in the prior year quarter, reflects higher net investment income, record high pretax underlying underwriting income and lower catastrophe losses.
• Life & Group core loss of $29 million versus $192 million in the prior year quarter, reflects an unfavorable after- tax impact of $2 million in 2023 and $143 million in 2022 as a result of the annual reserve reviews. Results for the prior year quarter have been adjusted to reflect the application of the LDTI accounting standard.
• Net investment income up 31% to $553 million pretax, includes a $72 million increase from limited partnerships and common stock to $28 million and a $59 million increase from fixed income securities and other investments to $525 million.
• P&C combined ratio of 94.3%, compared with 95.8% in the prior year quarter, including 4.1 points of catastrophe loss impact compared with 5.5 points in the prior year quarter. P&C underlying combined ratio was 90.4% compared with 91.1%, in the prior year quarter. P&C underlying loss ratio was 60.0% and the expense ratio was 30.1%.
• P&C segments, excluding third party captives, generated gross written premium growth of 7% and net written premium growth of 6%. P&C renewal premium change of +6%, with written rate of +5% and exposure change of +1%.
• Book value per share of $31.61; book value per share excluding AOCI of $45.43, a 7% increase from year-end 2022 adjusting for $2.46 of dividends per share.
• Board of Directors declares regular quarterly cash dividend of $0.42 per share.

3

Financial Performance

Core income1 up 56% after excluding impact of Life & Group reserve assumption update in 2023 and 2022

• Excluding the impact of the L&G assumption updates, core income was $291 million and $186 million for the third quarter of 2023 and 2022 and $924 million and $714 million for 2023 and 2022 year to date.

• 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 reflect4 application of the new guidance.

Property & Casualty Operations

Continued strong profitability

5

Property & Casualty Production Metrics

Continue to manage rate/retention dynamic effectively

Retention

6

Specialty

Continued excellent all-in and underlying combined ratio

7

Specialty Production Metrics

Rate reductions moderated considerably in Financial Institutions and Management Liability

8

Commercial

Continued double-digit growth and record underlying combined ratio

9

Commercial Production Metrics

New business growth of 19% and rate of 8% which remains above long-run loss cost trend

Commercial Rate & Retention

10