#1ASSURANTⓇ Investor Presentation Second Quarter 2023 ASSURANTⓇ © 2023 Assurant, Inc. All rights reserved. 1#2Cautionary Statement Some of the statements in this presentation, including our business and financial plans and any statements regarding our anticipated future financial performance, business prospects, growth and operating strategies and similar matters, including performance outlook, financial objectives, business drivers, our ability to gain market share, and the strength, diversity, predictability and resiliency of enterprise and segment earnings, cash flows and other results, may constitute forward-looking statements within the meaning of the U.S. Private Securities Litigation Reform Act of 1995. Refer to Exhibit 1 in the Appendix for factors that could cause our actual results to differ materially from those currently estimated by management, including those projected in the company outlook and financial objectives, and information on where you can find a more detailed discussion of these factors in our SEC filings. Assurant uses non-GAAP financial measures to analyze the company's operating performance. Assurant's non-GAAP financial measures should not be considered in isolation or as a substitute for GAAP financial measures. Because Assurant's calculation of these measures may differ from similar measures used by other companies, investors should be careful when comparing Assurant's non-GAAP financial measures to those of other companies. Refer to Exhibit 2 in the Appendix for a reconciliation of non-GAAP financial measures to the most comparable GAAP financial measures. Assurant, Inc. is an insurance holding company and the ownership of its stock is subject to certain state and foreign insurance law requirements. Refer to Exhibit 3 for additional detail. ASSURANTⓇ © 2023 Assurant, Inc. All rights reserved. 2#3✰ ASSURANTⓇ ASSURANTⓇ O Our Vision To be the leading global business services company supporting the advancement of the connected world © 2023 Assurant, Inc. All rights reserved. 3#4Vision Propels Us Forward Towards Sustained Outperformance Track record of strong profitable growth ✰ ASSURANTⓇ Superior cash flow generation with disciplined deployment Leadership positions at scale ASSURANTⓇ Purpose-driven culture and commitment to sustainability Compelling valuation © 2023 Assurant, Inc. All rights reserved. 4#5B2B2C Model Aligned with Leaders and Long-term Winners 15 of Top 50 most valuable global brands 20+ year partnerships High client retention across all LOBS Net earned premiums, fees and other income(1) Client partnerships... • Connected Living $4.2B Mobile carriers Cable operators Retailers Credit card companies Auto Renters & Other $4.0B $0.5B • Auto dealers Property managers Affinity partners OEMs • Third-party administrators (TPAS) Homeowners $1.5B Banks • Mortgage servicers • P&C insurers, agents and brokers • Affinity partners ...with leading • 7 of top 10 global telecommunications • 4 of top 5 dealer groups global brands brands 4 of top 5 U.S. multifamily property management companies (1) Amounts reflect net earned premiums, fees and other income for the last twelve months ended June 30, 2023. Refer to Exhibit 4 in the Appendix for a list of sources. ⚫ 7 of top 10 mortgage servicers ASSURANTⓇ • 9 of top 10 P&C insurance agencies © 2023 Assurant, Inc. All rights reserved. 5#6Full-Year 2023 Outlook 2022 Baseline 2023 Outlook Adjusted EBITDA(1,2) $1.1 billion. High single-digit growth Adjusted EPS (1,2) $13.61 Segment Cash Generation (3) $550 million Growth rate to approximate Adjusted EBITDA ~65% of Adjusted EBITDA, including catastrophes (2,4) (1) Adjusted EBITDA and Adjusted earnings per diluted share (also referred to as Adjusted EPS) exclude reportable catastrophes. (2) Refer to Exhibit 2 in the Appendix for information regarding non-GAAP financial measures, including reconciliations to the most directly comparable GAAP measures. (3) Represents dividends paid to the holding company, inclusive of non-core operations. (4) 2023 segment cash generation includes a $140M expected annual catastrophe load. ASSURANTⓇ © 2023 Assurant, Inc. All rights reserved. 6#7Aligned Portfolio Focused on Advantaged Businesses Segment Adjusted EBITDA (1,2) 2022 Simplified and growing portfolio - - Assurant Segment Adjusted EBITDA CAGR of 7% since 2019(1,2) Capital-light businesses represent 77% of 2022 Segment Adjusted EBITDA (2,3) Relatively insulated from major macro- economic risks 11% 23% · Continue to optimize portfolio to limit catastrophe exposure 38% $1.2B 28% Global Lifestyle Global Housing Connected Living Automotive Renters & Other Homeowners (1) Segment Adjusted EBITDA excludes reportable catastrophes and Corporate and Other. CAGR is based on 2019 and 2022 as revised results, as further described in Exhibit 2 in the Appendix. (2) Refer to Exhibit 2 in the Appendix for information regarding non-GAAP financial measures, including reconciliations to the most directly comparable GAAP measures. (3) Capital-light businesses include all businesses other than Homeowners. ASSURANTⓇ © 2023 Assurant, Inc. All rights reserved. 7#8Second 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#9Second Quarter 2023 Segment Results Global Lifestyle Adjusted EBITDA $197 million (11)% YoY (10)% YoY constant currency(1) Decline driven by lower Global Automotive and Connected Living results, including the absence of a $12.9 million gain from the sale of a real estate joint venture partnership in the prior year period. Excluding the real estate joint venture partnership gain, underlying Global Lifestyle results declined $11.1 million, or 5%, mainly from ongoing elevated claims costs in Global Automotive and weaker results in Asia Pacific and Europe within Connected Living. This was partially offset by higher investment income across Global Lifestyle and modest growth in extended service contracts and mobile device protection results in North America. Global Housing Adjusted EBITDA (2) $168 million • +107% YoY Adjusted EBITDA increased 153 percent compared to the second quarter 2022, primarily due to significant growth in Homeowners from higher lender-placed net earned premiums and lower non-catastrophe loss experience, including a $40.0 million year-over-year decrease in prior period reserve development. Second quarter 2023 included $13.4 million of reportable catastrophes, compared to $20.3 million in the prior year period. Excluding reportable catastrophes, Adjusted EBITDA (2) increased 107 percent primarily due to the factors noted above. Information listed as of June 30, 2023. (1) Refer to Exhibit 2 in the Appendix for information regarding non-GAAP financial measures, including reconciliations to the most directly comparable GAAP measures. (2) 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. ASSURANTⓇ © 2023 Assurant, Inc. All rights reserved. 9#10Strong Cash Generation Provides Significant Flexibility . Robust cash flow with over $5.8B in . segment dividends over the past 10 years(1) $495M holding company liquidity available as of June 30, 2023 Balanced portfolio creates diversified source of cash flows • Homeowners generates strong cash flows and provides capital to support growth $900 $800 $700 $600 $500 $400 $300 $200 $100 • Growth in less capital-intensive businesses expected to generate more predictable cash flows over time $- Segment Dividend History ($ in millions) (2) (2,4) (5) (2,3) (2,3) 2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 (1) Consists of dividends or returns of capital from operating subsidiaries to the holding company, net of infusions of liquid assets, and excluding acquisitions and divestitures. (2) 2015-2018 exclude dividends and infusions relating to Assurant Health and Assurant Employee Benefits. (3) 2016-2017 exclude $1.5 billion proceeds received from sale of Assurant Employee Benefits and Assurant Health wind-down. (4) 2018 includes $237M in proceeds received from a reduction in deferred tax liabilities from U.S. tax reform. Also includes $148M in dividends from The Warranty Group. (5) 2020 includes a portion of the cash received from the tax benefit related to the federal Coronavirus Aid, Relief, and Economic Security Act, or "CARES" Act. ASSURANTⓇ © 2023 Assurant, Inc. All rights reserved. 10#11Balanced Capital Allocation to Drive Shareholder Value Acquisitions & Organic Investments Disciplined investment approach to drive business growth and maximize returns Share Repurchases(1) Common Stock Dividends(1) Maintain a high level of capital stewardship Consistent with historical practice, increasing each year Repurchased 68% of shares since IPO (2) (1) Capital return includes share repurchases and common stock dividends, subject to Board approval and other factors, including those referenced in Exhibit 1 in the Appendix. (2) As of June 30, 2023. ASSURANTⓇ © 2023 Assurant, Inc. All rights reserved. 11#12Capital Management is Supported by a Strong Foundation Debt Management Target to maintain leverage ratio of <30% Continued disciplined income-oriented approach Investment Portfolio Ratings Risk Management Investment grade fixed assets comprising majority of portfolio Commitment to maintain investment grade ratings Robust data, systems and processes Deep regulatory and compliance expertise ASSURANTⓇ © 2023 Assurant, Inc. All rights reserved. 12#13High Quality and Diversified Investment Portfolio Other 6% Preferred Equity 2% Fixed Maturity Securities by Credit Quality • • · Total investments and cash and cash equivalents of $9.4 billion Fixed maturity investments, cash and short-term investments represent 88% of the portfolio 94% of fixed maturity investments are investment grade Average duration of approximately 5 years(2) Commercial Mortgages 3% U.S. Govt/ Agency 1% Foreign Govt 5% Cash and Short-term 18% Municipals 1% Information listed as of June 30, 2023. (1) Expressed as a percentage of total investments and cash and cash equivalents. (2) Average duration includes fixed maturities, preferred stock, and commercial mortgages. ASSURANTⓇ Investment Portfolio Breakdown (1) Corporate 46% RMBS 5% CMBS 4% ABS 9% AAA / AA / A 57% Baa 37% Ba and Lower 6% © 2023 Assurant, Inc. All rights reserved. 13#14Purpose-Driven Culture and Commitment to Sustainability Great Place To Work.Ⓡ Certified FEB 2022-FEB 2023 Great Place to Work across 13 markets, including U.S. Talent Key Goals Ensure workforce and leadership reflect the diversity of our consumers and communities • Sustain strong engagement through career growth, fair and equitable total rewards and wellbeing • Double 2020 new diverse supplier spend by 2025 USA TM Electric vehicle product rolled out in 12 countries Integrating CDP environmental Products Climate commitment into DISCLOSURE INSIGHT ACTION business operations • Reinforce value of offerings to support connected lifestyle Accelerate the rollout of sustainability offerings Help consumers invest in products to enhance their wellbeing Track emissions globally; implemented Scope 1 and 2 emissions 40% reduction target by 2030 • Improve energy efficiency • Optimize global real estate footprint • Integrate ESG commitment into investment portfolio Refer to Exhibit 4 in the Appendix for a list of sources. Information listed as of June 30, 2023, unless otherwise noted. ASSURANTⓇ © 2023 Assurant, Inc. All rights reserved. 14#15Assurant's Pledge to be a Purpose-driven Company Continuing to integrate ESG and sustainability within our long-term strategy and business operations Recent Assurant accomplishments: • Responsible Employer 2022 Global Workforce Composition: 53% racial and/or ethnic groups (U.S. only) 62% of the 13 Independent directors are racially, ethnically or gender diverse (as of April 2023) 60% women (global) • 30% of the Management Committee is racially, ethnically or gender diverse (as of April 2023) 44% managerial roles filled by racial and/or ethnic groups; 43% by women (U.S. only) Ongoing pay equity reviews confirmed no evidence of systemic or material pay equity issues • • Impact on Society Continue to integrate ESG considerations into monitoring and decision making for our $9 billion investment portfolio Scope 1 and 2 reductions; began Scope 3 reporting including investment portfolio Ongoing TCFD enhancements Processed 29 million mobile devices for repair or resale, and recycled 2 million • • Donated $4 million to charitable partners Earned a "B" rating by CDP for the fifth consecutive year for environmental practices and disclosures • 2022 Sustainability Report includes inaugural SASB Index Customer Commitment Integrity and Ethics Successfully completed total of 222 information security audits No material information security breaches • 15,000+ employees completed mandatory privacy and ethics training Information listed as of 2022, unless otherwise noted. ✰ ASSURANTⓇ • • Net Promoter Scores (NPS) improved year over year Continued to increase investment in training, tools and emerging digital technologies ° Continue to rollout Voice of the Customer Platform to ensure we have appropriate insights to tailor product and service offerings and provide value to the end consumer © 2023 Assurant, Inc. All rights reserved. 15#16Delivering Long-Term Shareholder Value Strong profitable growth ✰ ASSURANTⓇ Superior cash flow generation with disciplined deployment Leadership positions at scale ASSURANTⓇ Purpose-driven culture and commitment to sustainability Compelling valuation © 2023 Assurant, Inc. All rights reserved. 16#17ASSURANTⓇ Appendix © 2022 Assurant, Inc. All rights reserved. 17#18Exhibit 1: Safe Harbor Statement Some of the statements in this presentation, including our business and financial plans and any statements regarding the company's anticipated future financial performance, business prospects, growth and operating strategies and similar matters, including financial objectives and the strength, diversity, predictability and resiliency of enterprise and segment earnings, cash flows and other results, may constitute forward-looking statements within the meaning of the U.S. Private Securities Litigation Reform Act of 1995. You can identify forward-looking statements by the use of words such as "outlook," "objective," "will," "may," "can,” “anticipates," "expects," "estimates," "projects," "intends," "plans," "believes," "targets," "forecasts," "potential," "approximately," and the negative version of those words and other words and terms with a similar meaning. Any forward-looking statements contained in this presentation are based upon our historical performance and on current plans, estimates and expectations. The inclusion of this forward-looking information should not be regarded as a representation by us or any other person that our future plans, estimates or expectations will be achieved. Our actual results might differ materially from those projected in the forward- looking statements. We undertake no obligation to update or review any forward-looking statement, whether as a result of new information, future events or other developments. The following factors could cause our actual results to differ materially from those currently estimated by management, including those projected in the company outlook: i. the loss of significant clients, distributors or other parties with whom we do business, or if we are unable to renew contracts with them on favorable terms, or if they disintermediate us, or if those parties face financial, reputational or regulatory issues; ii. significant competitive pressures, changes in customer preferences and disruption; iii. the failure to execute our strategy, including through the continuing service of key executives, senior leaders, highly-skilled personnel and a high-performing workforce; iv. the failure to find suitable acquisitions at attractive prices, integrate acquired businesses or divest of non-strategic businesses effectively or identify new areas for organic growth; v. our inability to recover should we experience a business continuity event; vi. the failure to manage vendors and other third parties on whom we rely to conduct business and provide services to our clients; vii. risks related to our international operations; viii. declines in the value and availability of mobile devices, and export compliance or other risks in our mobile business; ix. our inability to develop and maintain distribution sources or attract and retain sales representatives and executives with key client relationships; x. risks associated with joint ventures, franchises and investments in which we share ownership and management with third parties; xi. the impact of catastrophe and non-catastrophe losses, including as a result of the current inflationary environment and climate change; xii. negative publicity relating to our business, industry or clients; xiii. the impact of general economic, financial market and political conditions and conditions in the markets in which we operate, including the current inflationary environment; xiv. the adequacy of reserves established for claims and our inability to accurately predict and price for claims and other costs; xv. a decline in financial strength ratings of our insurance subsidiaries or in our corporate senior debt ratings; xvi. fluctuations in exchange rates, including in the current environment; xvii. an impairment of goodwill or other intangible assets; xviii. the failure to maintain effective internal control over financial reporting; xix. unfavorable conditions in the capital and credit markets; xx. a decrease in the value of our investment portfolio, including due to market, credit and liquidity risks, and changes in interest rates; xxi. an impairment in the value of our deferred tax assets; xxii. the unavailability or inadequacy of reinsurance coverage and the credit risk of reinsurers, including those to whom we have sold business through reinsurance; xxiii. the credit risk of some of our agents, third-party administrators and clients; xxiv. the inability of our subsidiaries to pay sufficient dividends to the holding company and limitations on our ability to declare and pay dividends or repurchase shares; xxv. limitations in the analytical models we use to assist in our decision-making; xxvi. the failure to effectively maintain and modernize our information technology systems and infrastructure, or the failure to integrate those of acquired businesses; xxvii. breaches of our information technology systems or those of third parties with whom we do business, or the failure to protect the security of data in such systems, including due to cyberattacks and as a result of working remotely; xxviii. the costs of complying with, or the failure to comply with, extensive laws and regulations to which we are subject, including those related to privacy, data security, data protection and tax; xxix. the impact of litigation and regulatory actions; xxx. reductions or deferrals in the insurance premiums we charge; xxxi. changes in insurance, tax and other regulations, including the Inflation Reduction Act of 2022; xxxii. volatility in our common stock price and trading volume; and xxxiii. employee misconduct. For additional information on factors that could affect our actual results, please refer to the factors identified in the reports we file with the U.S. Securities and Exchange Commission, including the risk factors identified in our most recent Annual Report on Form 10-K and Quarterly Reports on Form 10-Q. ✰ ASSURANT ® © 2023 Assurant, Inc. All rights reserved. 18#19Exhibit 2: Non-GAAP Financial Measures Assurant uses the following non-GAAP financial measures to analyze the company's operating performance. Assurant's non-GAAP financial measures should not be considered in isolation or as a substitute for GAAP financial measures. Because Assurant's calculation of these measures may differ from similar measures used by other companies, investors should be careful when comparing Assurant's non-GAAP financial measures to those of other companies. (1) Assurant uses Segment Adjusted EBITDA, excluding reportable catastrophes, as an important measure of Global Lifestyle and Global Housing's combined operating performance. Assurant defines Segment Adjusted EBITDA, excluding reportable catastrophes, as Adjusted EBITDA for Global Lifestyle plus Adjusted EBITDA for Global Housing, which in each case is the company's GAAP segment measure of profitability, excluding in each case reportable catastrophes (which represent individual catastrophic events that generate losses in excess of $5.0 million, pre-tax, net of reinsurance and client profit sharing adjustments and including reinstatement and other premiums). The as reported results have been revised for the following adjustments: The company believes this metric provides investors with an important measure of Global Lifestyle and Global Housing's combined operating performance because it excludes reportable catastrophes, which can be volatile. The comparable GAAP measure is Global Lifestyle Adjusted EBITDA and Global Housing Adjusted EBITDA. (UNAUDITED) Twelve Months 2022 Twelve Months 2019 Segment Segment ($ in millions) Global Lifestyle Adjusted EBITDA $ Reportable catastrophes Global Adjusted Housing EBITDA 809.4 $ 246.0 $ 1,055.4 0.7 171.4 172.1 Global Lifestyle Global Housing Adjusted EBITDA (0.1) S 603.6 $ 368.8 38.0 S 972.4 37.9 Adjusted EBITDA, excluding reportable catastrophes S 810.1 $ 417.4 $ 1,227.5 S 603.5 $ 406.8 $ 1,010.3 (UNAUDITED) ($ in millions) Adjusted EBITDA Reportable catastrophes Adjusted EBITDA, excluding reportable catastrophes 2Q 2023 Global Lifestyle 2Q 2022 Global Global Global Housing Lifestyle Housing $ 197.0 $ 154.6 $ 221.0 $ 61.0 13.4 20.3 $ 197.0 $ 168.0 $ 221.0 $ 81.3 ✰ ASSURANTⓇ © 2023 Assurant, Inc. All rights reserved. 19#20Exhibit 2: Non-GAAP Financial Measures (Continued) (2) Assurant uses Adjusted EBITDA, excluding reportable catastrophes, as an important measure of the company's operating performance. Assurant defines Adjusted EBITDA, excluding reportable catastrophes, as net income, excluding net realized losses (gains) on investments and fair value changes to equity securities, non-core operations, restructuring costs related to strategic exit activities, Assurant Health runoff operations, interest expense, provision (benefit) for income taxes, depreciation expense, amortization of purchased intangible assets, and reportable catastrophes (defined above), as well as other highly variable or unusual items. The company believes this metric provides investors with an important measure of the company's operating performance because it excludes items and reportable catastrophes that do not represent the ongoing operations of the company or can be volatile, and therefore (i) enhances management's and investors' ability to analyze the ongoing operations of its businesses and (ii) facilitates comparisons of its operating performance over multiple periods, including because the amortization expense associated with purchased intangible assets may fluctuate from period to period based on the timing, size, nature and number of acquisitions. Although the company excludes amortization of purchased intangible assets from Adjusted EBITDA, revenue generated from such intangible assets is included within the revenue in determining Adjusted EBITDA. The comparable GAAP measure is net income. ($ in millions) GAAP net income from continuing operations Less: Interest expense Provision for income taxes Depreciation expense Twelve Months Ended December 31, 2022 $ 276.6 108.3 73.3 86.3 69.7 Amortization of purchased intangible assets Adjustments, pre-tax: Net realized losses (gains) on investments and fair value changes to equity securities COVID-19 direct and incremental expenses 179.7 4.7 0.9 79.5 53.1 Loss on extinguishment of debt Non-core operations Restructuring costs Other Adjustments: Assurant Health runoff operations Acquisition integration expenses Foreign exchange related losses Gain related to benefit plan activity Merger and acquisition transaction and other related expenses Total other adjustments 0.6 14.9 13.4 (18.2) 13.4 24.1 ✰ ASSURANTⓇ (Income) loss attributable to non-controlling interests Adjusted EBITDA Reportable catastrophes Adjusted EBITDA, excluding reportable catastrophes 956.2 172.1 $ 1,128.3 Additional details about the components of Other adjustments and other key financial metrics are included in the Financial Supplement located on Assurant's Investor Relations website http://ir.assurant.com/investor/default.aspx © 2023 Assurant, Inc. All rights reserved. 20#21Exhibit 2: Non-GAAP Financial Measures (Continued) ($ in millions) GAAP net income 2023 2022 2Q 2Q $ 156.3 $ 52.2 Less: Interest expense Provision for income taxes Depreciation expense Amortization of purchased intangible assets 27.2 27.2 48.0 17.7 25.4 21.8 18.7 17.0 Adjustments, pre-tax: Net realized losses on investments and fair value changes to equity 20.0 76.4 securities Non-core operations 30.2 36.7 Restructuring costs (1.3) 0.2 0.5 Assurant Health runoff operations Other Adjustments: COVID-19 direct and incremental expenses (Gain) loss on extinguishment of debt Acquisition integration expenses Foreign exchange related losses Gain related to benefit plan activity Merger and acquisition transaction and other related expenses Total other adjustments Adjusted EBITDA Reportable catastrophes Adjusted EBITDA, excluding reportable catastrophes 1.1 0.9 0.1 3.0 4.6 7.1 (6.0) (4.9) (0.1) 0.2 (1.4) 7.4 323.1 257.1 13.4 20.3 $ 336.5 $ 277.4 Additional details about the components of Other adjustments and other key financial metrics are included in the Financial Supplement located on Assurant's Investor Relations website http://ir.assurant.com/investor/default.aspx ✰ ASSURANTⓇ © 2023 Assurant, Inc. All rights reserved. 21#22Exhibit 2: Non-GAAP Financial Measures (Continued) (3) Assurant uses Adjusted earnings per diluted share as an important measure of the company's stockholder value. Assurant defines Adjusted earnings per diluted share as net income, excluding net realized losses (gains) on investments and fair value changes to equity securities, amortization of purchased intangible assets, non- core operations, restructuring costs related to strategic exit activities, Assurant Health runoff operations, as well as other highly variable or unusual items, divided by the weighted average diluted shares outstanding. The company believes this metric provides investors with an important measure of stockholder value because it excludes items that do not represent the ongoing operations of the company, and therefore (i) enhances management's and investors' ability to analyze the ongoing operations of its businesses and (ii) facilitates comparisons of its operating performance over multiple periods, including because the amortization expense associated with purchased intangible assets may fluctuate from period to period based on the timing, size, nature and number of acquisitions. Although the company excludes amortization of purchased intangible assets from Adjusted earnings, revenue generated from such intangible assets is included within the revenue in determining Adjusted earnings. The comparable GAAP measure is net income per diluted share, defined as net income, divided by the weighted average diluted shares outstanding. Assurant uses Adjusted earnings, excluding reportable catastrophes, per diluted share (each as defined above) as another important measure of the company's stockholder value. The company believes this metric provides investors with an important measure of stockholder value for the reasons noted above and because it excludes reportable catastrophes, which can be volatile. The comparable GAAP measure is net income per diluted share (defined above). ($ per share) GAAP net income from continuing operations per diluted share Adjustments per diluted share, pre-tax: Net realized losses (gains) on investments and fair value changes to equity securities Amortization of purchased intangible assets COVID-19 direct and incremental expenses Loss on extinguishment of debt Non-core operations Restructuring costs Other Adjustments: Assurant Health runoff operations Acquisition integration expenses Foreign exchange related losses Gain related to benefit plan activity Merger and acquisition transaction and other related expenses Twelve Months Ended December 31, 2022 $ 5.05 3.28 1.27 0.08 0.02 1.45 0.97 0.01 0.27 0.25 (0.33) 0.25 (1.44) 11.13 3.14 (0.66) Adjusted earnings, excluding reportable catastrophes, per diluted share $ 13.61 (Benefit) provision for income taxes Adjusted earnings, per diluted share Reportable catastrophes, pre-tax Tax impact of reportable catastrophes Information on the share counts used in the per share calculations are included in the Financial Supplement located on Assurant's Investor Relations website http://ir.assurant.com/investor/default.aspx ✰ ASSURANTⓇ © 2023 Assurant, Inc. All rights reserved. 22#23Exhibit 2: Non-GAAP Financial Measures (Continued) ($ per share) GAAP net income per diluted share Adjustments per diluted share, pre-tax: Net realized losses on investments and fair value changes to equity securities Amortization of purchased intangible assets Non-core operations Restructuring costs Assurant Health runoff operations Other Adjustments: COVID-19 direct and incremental expenses Loss on extinguishment of debt Acquisition integration expenses Foreign exchange related losses Gain related to benefit plan activity Benefit for income taxes Adjusted earnings, per diluted share Reportable catastrophes, pre-tax Tax impact of reportable catastrophes Adjusted earnings, excluding reportable catastrophes, per diluted share 2023 2022 2Q 2Q $ 2.90 $ 0.95 0.37 1.39 0.35 0.31 0.56 0.67 (0.03) 0.01 0.02 0.02 0.05 0.09 0.13 (0.11) (0.09) (0.24) (0.51) 3.89 2.95 0.25 0.37 (0.05) (0.07) 4.09 $ 3.25 Information on the share counts used in the per share calculations are included in the Financial Supplement located on Assurant's Investor Relations website http://ir.assurant.com/investor/default.aspx ASSURANTⓇ © 2023 Assurant, Inc. All rights reserved. 23#24Exhibit 2: Non-GAAP Financial Measures (Continued) (4) The metrics included within the company's outlook each constitute forward-looking information and the company believes that it cannot, without unreasonable efforts, forecast certain information needed to reconcile such forward-looking information to the most comparable GAAP measure, the probable significance of which cannot be determined. The company is able to quantify a full-year estimate of interest expense, depreciation expense and amortization of purchased intangible assets, each on a pre-tax basis, which are expected to be approximately $110 million, $110 million and $76 million, respectively. Many of the other GAAP components cannot be reliably quantified due to the combination of variability and volatility of such components and may, depending on the size of the components, have a significant impact on the reconciliation. (5) Constant Currency: Represents a non-GAAP financial measure. Excludes the impact of changes in foreign currency exchange rates used in the translation of the income statement because they can be volatile. These amounts are calculated by translating the comparable prior period results at the weighted average foreign currency exchange rates used in the current period, and it excludes the impact of foreign exchange transaction gains (losses) associated with the remeasurement of non-functional currencies. The company believes this information allows investors to identify the significance of changes in foreign currency exchange rates in period-to-period comparisons. (UNAUDITED) Constant Currency 2Q 2023 Percentage change in Global Lifestyle and Global Housing net earned premiums, fees and other income: Including FX impact FX impact Excluding FX impact Percentage change in Global Lifestyle net earned premiums, fees and other income: Including FX impact FX impact Excluding FX impact Percentage change in GAAP net income, including FX impact Percentage change in Adjusted EBITDA, including FX impact Percentage change in Adjusted EBITDA, excluding reportable catastrophes: 6.7 % (0.7)% 7.4 % 4.8 % (0.8)% 5.6 % 199.4 % 25.7 % ✰ ASSURANTⓇ Including FX impact FX impact 21.3 % (1.0)% Excluding FX impact 22.3 % Percentage change in Global Lifestyle Adjusted EBITDA: Including FX impact (10.9)% FX impact Excluding FX impact (1.3)% (9.6)% © 2023 Assurant, Inc. All rights reserved. 24#25Exhibit 3: Regulatory Requirements As a reminder, Assurant, Inc. is an insurance holding company, with insurance subsidiaries domiciled in a number of states in the U.S. and international jurisdictions. The ownership of our stock is subject to certain state and foreign insurance law requirements. Those are typically triggered when ownership reaches 10% of voting securities but some jurisdictions may have different requirements. We encourage engagement with us prior to approaching ownership levels that may trigger these requirements. ✰ ASSURANTⓇ © 2023 Assurant, Inc. All rights reserved. 25#26Exhibit 4: Data Sources Assurant 15 of Top 50 most valuable global brands Source: World 100 Most Valuable Brands in 2022 by Visual Capitalist Global Lifestyle 7 of the top 10 global telecommunications brands 4 of the top 5 dealer groups Source: Telecoms 150 2022 Ranking by Brand Finance Source: Autonews Top 150 (2022), internal management estimates Global Housing 4 of the top 5 largest multifamily housing PMCs in the U.S. Source: 2022 NMHC 50 Largest Apartment Managers 9 of the top 10 P&C insurance agencies of the top 10 mortgage servicers Source: Internal Management information Source: Internal Management information ASSURANTⓇ © 2023 Assurant, Inc. All rights reserved. 26