CNA Financial Investor Presentation — February 2022

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2021 FOURTH QUARTER AND YEAR- END

EARNINGS CONFERENCE CALL

FEBRUARY 15, 2022Consolidated Financial Results –Highlights2021 FOURTH QUARTER EARNINGS CONFERENCE CALL

2Quarter Ended December 31, 2021 2020 Year Ended December 31, 2021 2020

Net income (loss) per diluted share 2.28$ (0.36)$ Net income (loss) per diluted share 3.16$ (4.50)$

Net realized investment gains per diluted share 0.59$ 0.94$ Net realized investment gains (losses) per diluted share 1.47$ (1.02)$

Adjusted operating income (loss) per diluted share 1.69$ (1.30)$ Adjusted operating income (loss) per diluted share 1.69$ (2.88)$

GAAP combined ratio 83.1% 123.1% GAAP combined ratio 100.3% 115.9%

Goodwill impairment - $ (0.60)$

Book value per share 35.05$ 32.93$

Return on equity 9.5% -13.0%Property and Casualty Business Highlights2021 FOURTH QUARTER EARNINGS CONFERENCE CALL

Combined ratio of 83.1% is the lowest quarterly combined ratio in over 14 years

Core loss ratio improved 24.5 pts in Q4 2021 as compared to Q4 2020.

Commercial auto loss ratio in Q4 2021 improved 68.1 percentage points as compared to Q4 2020 due to a

decrease in frequency and severity of auto liability claims, reduction in commercial auto exposure units and favorable prior accident year reserve development.

Prior accident year favorable reserve development $22.8M in Q4 2021 compared to unfavorable reserve development of $12.4M in Q4 2020

Favorable reserve development for the current quarter came primarily from our commercial auto line of business.

Catastrophe losses below prior year and historical average, adding 3.5 percentage points to the combined ratio in Q4 2021 compared to 7.9 percentage points in Q4 2020. Historical average for catastrophe losses in fourth quarter is 5.3 percentage points added to the combined ratio.