Investor Presentaiton

Second Quarter 2023 Results Adjusted EBITDA (1) $337 million +21% YoY Segment Net Earned Premiums, Fees and Other Income(2) $2.65 billion +7% YOY +22% YoY constant currency Adjusted EPS(1) +7% YoY constant currency $4.09 +26% YoY Capital Deployment $60 million Repurchases & Common stock dividends Liquidity $495 million Cash at holding company "Overall, we are pleased with our second quarter results which were driven by significant top-line growth and improving loss experience in Global Housing. While Global Lifestyle results were down year-over-year from ongoing elevated claims in Global Automotive and lower contributions in Japan, we have seen continued strength in our U.S. Connected Living business and made significant progress in the first half of this year stabilizing international results which were impacted by headwinds in the second half of 2022," said Assurant President and CEO Keith Demmings. "Given our strong year-to-date performance and momentum expected in the second-half of the year, we are increasing our 2023 outlook as we now expect Adjusted EBITDA and Adjusted earnings per share, both excluding catastrophes, to increase high single-digits. In addition, we resumed share repurchases in the second quarter and expect to continue share repurchase activity for the remainder of the year as we generate strong cash flows through our differentiated business model," Demmings added. Information listed is for the period ended June 30, 2023, other than liquidity, which is as of June 30, 2023. (1) Excludes reportable catastrophes. Refer to Exhibit 2 in the Appendix for information regarding non-GAAP financial measures, including reconciliations to the most directly comparable GAAP measures. (2) Segment net earned premiums, fees and other income refers to the net earned premiums, fees and other income of the Global Lifestyle and Global Housing segments. Refer to Exhibit 2 in the Appendix for information regarding non-GAAP financial measures, including reconciliations to the most directly comparable GAAP measures. ✰ ASSURANTⓇ © 2023 Assurant, Inc. All rights reserved. 8

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