Cautionary Statement

Some of the statements included in this presentation, particularly those with respect to the proposed HYLA Mobile acquisition and process to explore strategic alternatives for our Global Preneed segment, including our financing plans and any statements regarding our anticipated future financial performance, business prospects, growth and operating strategies and other similar matters, including performance outlook, financial objectives and drivers, are 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 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. 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.

© 2020 Assurant, Inc. All rights reserved. 2

Investment Highlights

Multiple Levers To Drive Long-Term Shareholder Value

Profitable growth in attractive markets where we have leadership positions

Specialty risk businesses with superior returns and cash flows

Capital-light businesses with continued growth in the connected world

More diversified earnings with lower catastrophe exposure and a countercyclical hedge Track record of disciplined capital deployment

© 2020 Assurant, Inc. All rights reserved. 3

Further Aligning Strategic Focus on Market-leading Lifestyle and Housing Businesses

HYLA Mobile Acquisition

HYLA Mobile is a leading provider of smartphone software and trade-in and upgrade services

Scales our trade-in and upgrade offerings, adds new capabilities and provides a complementary client base, including the largest mobile carriers, retailers and OEMs in North America and Japan

HYLA has delivered double-digit growth during the past three years by leveraging a unique software-as-a-service (SaaS) approach and patented technology to drive device trade-in and upgrade programs, processing and disposition

Combined businesses will further sustainability practices by extending the life of mobile devices, servicing more than 30 trade-in or upgrade programs globally and 14 million devices annually

Exploring Strategic Alternatives for Global Preneed

On October 28, 2020, Assurant announced that it has started exploring a range of strategic alternatives, including the possible sale of the business

Allows us to put an even sharper focus on growth opportunities across our lifestyle and housing solutions that are driving the highest returns at a time when the world is connecting at an accelerating pace

© 2020 Assurant, Inc. All rights reserved. 5

Portfolio of Market-Leading Businesses with Attractive Growth Prospects

1. On October 28, 2020, the company announced that it is exploring a range of strategic alternatives for Global Preneed, including the possible sale of the business.

© 2020 Assurant, Inc. All rights reserved. 9

Connected Living

• Continued share gains through alignment

© 2020 Assurant, Inc. All rights reserved. 20

Continue to Expand Offerings and Profit Pools

Beyond Insurance

Since 2015:

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Global Automotive

Multifamily Housing

Vertically Integrated Capabilities Address Unique Customer Needs

Drives differentiation and value to clients and end-consumers

© 2020 Assurant, Inc. All rights reserved. 28

Integrated Solutions Across Resident Lifecycle

Lender-placed Insurance

Exhibit 1: Safe Harbor Statement

Some of the statements included in this presentation and its exhibits, particularly those with respect to the proposed HYLA Mobile acquisition and process to explore strategic alternatives for Global Preneed, including the company's financing plans and any statements regarding the company's anticipated future financial performance, business prospects, growth and operating strategies and similar matters, may constitute forward-looking statements within the meaning of the U.S. Private Securities Litigation Reform Act of 1995. The company does not have a definitive timetable to complete its review of strategic alternatives for Global Preneed and there can be no assurance that any such process will result in a transaction.

You can identify forward-looking statements by the use of words such as "outlook," "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 or its exhibits 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 impact of the COVID-19 pandemic, including the scope and duration of the outbreak, government actions and restrictive measures taken in response, and its effect on the global economic and financial markets; (ii) 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 those parties facing financial, reputational or regulatory issues; (iii) significant competitive pressures, changes in customer preferences and disruption; (iv) the failure to find suitable acquisitions, integrate completed acquisitions, or grow organically, and risks associated with joint ventures and franchise ownership and operations; (v) the impact of general economic, financial market and political conditions, including unfavorable conditions in the capital and credit markets and in the markets in which we operate, including as a result of COVID-19; (vi) risks related to our international operations, including the United Kingdom's withdrawal from the European Union, or fluctuations in exchange rates; (vii) the impact of catastrophic and non-catastrophe losses, including as a result of climate change; (viii) our inability to recover should we experience a business continuity event, including as a result of COVID-19; (ix) our inability to develop and maintain distribution sources or attract and retain sales representatives and executives with key client relationships; (x) the failure to manage vendors and other third parties on whom we rely to conduct business and provide services to our clients; (xi) declines in the value of mobile devices, the risk of guaranteed buybacks or export compliance risk in our mobile business; (xii) negative publicity relating to our products and services or the markets in which we operate; (xiii) the failure to implement our strategy and to attract and retain key personnel, including senior management; (xiv) employee misconduct; (xv) the adequacy of reserves established for claims and our inability to accurately predict and price for claims; (xvi) a decline in financial strength ratings or corporate senior debt ratings; (xvii) an impairment of goodwill or other intangible assets; (xviii) the failure to maintain effective internal control over financial reporting; (xix) a decrease in the value of our investment portfolio, including due to market, credit and liquidity risks, changes in interest rates and COVID-19; (xx) the impact of U.S. tax reform legislation and impairment of deferred tax assets; (xxi) the unavailability or inadequacy of reinsurance coverage and the credit risk of reinsurers, including those to whom we have sold business through reinsurance; (xxii) the credit risk of some of our agents, third-party administrators and clients;

1. the inability of our subsidiaries to pay sufficient dividends to the holding company and limitations on our ability to declare and pay dividends, including as a result of COVID- 19; (xxiv) changes in the method for determining LIBOR or the replacement of LIBOR; (xxv) the failure to effectively maintain and modernize our information technology systems and infrastructure, or the failure to integrate those of acquired businesses; (xxvi) breaches of our information systems or those of third parties with whom we do business, or the failure to protect data in such systems, including due to cyber-attacks and as a result of working remotely during the COVID-19 pandemic; (xxvii) 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 and data protection; (xxviii) the impact from litigation and regulatory actions, including those arising from COVID-19; (xxix) reductions or deferrals in the insurance premiums we charge, including as a result of COVID-19; and

1. changes in insurance and other regulation, including to mitigate the impact of COVID-19.

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 (the "SEC"), including but not limited to the risk factors identified in our most recent Annual Report on Form 10-K and Quarterly Reports on Form 10-Q, each as filed with the SEC.

© 2020 Assurant, Inc. All rights reserved. 34

Exhibit 2: Non-GAAP Financial Measures

Assurant uses the following non-GAAP financial measures to analyze the company's operating performance. 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. Net operating income equals net income attributable to common stockholders, excluding the Global Preneed goodwill impairment, net realized gains (losses) on investments (which includes unrealized gains (losses) on equity securities and changes in fair value of direct investments in collateralized loan obligations), COVID-19 direct and incremental expenses, the CARES Act tax benefit, foreign exchange gains (losses) from remeasurement of monetary assets and liabilities, the net charge related to Iké, as well as other highly variable or unusual items other than reportable catastrophes. Net operating income, excluding reportable catastrophes, excludes reportable catastrophes, which represent catastrophe losses net of reinsurance and client profit sharing adjustments and including reinstatement and other premiums. The company believes net operating income, excluding reportable catastrophes, provides investors a valuable measure of the performance of the company's ongoing business because it excludes items that do not represent the ongoing operations of the company and because it excludes reportable catastrophes, which can be volatile. The comparable GAAP measure is net income attributable to common stockholders.

(1) Global Lifestyle excludes reportable catastrophes. Additional details are included in the Financial Supplement.

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

© 2020 Assurant, Inc. All rights reserved. 35

Exhibit 2: Non-GAAP Financial Measures (Continued)

Assurant uses the following non-GAAP financial measures to analyze the company's operating performance. 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) Global Lifestyle excludes reportable catastrophes. Additional details are included in the Financial Supplement.

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

© 2020 Assurant, Inc. All rights reserved. 36

Exhibit 2: Non-GAAP Financial Measures (Continued)

Assurant uses the following non-GAAP financial measures to analyze the company's operating performance. 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 net operating income per diluted share, excluding reportable catastrophes, as another important measure of the company's stockholder value. Net operating income per diluted share equals net operating income (defined in prior slide) divided by weighted average diluted shares outstanding, excluding any dilutive effect from the assumed conversion of the mandatory convertible preferred stock prior to the acquisition date. The company believes this metric provides investors a valuable measure of stockholder value because it excludes items that do not represent the ongoing operations of the company. In addition, it excludes the effect of the mandatory convertible preferred stock, which was used to finance the TWG acquisition, prior to the acquisition date. The comparable GAAP measure is net income attributable to common stockholders per diluted share, defined as net income attributable to common stockholders plus any dilutive preferred stock dividends divided by weighted average diluted shares outstanding.

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

© 2020 Assurant, Inc. All rights reserved. 37

Exhibit 2: Non-GAAP Financial Measures (Continued)

Assurant uses the following non-GAAP financial measures to analyze the company's operating performance. 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.

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

© 2020 Assurant, Inc. All rights reserved. 38

Exhibit 2: Non-GAAP Financial Measures (Continued)

Assurant uses the following non-GAAP financial measures to analyze the company's operating performance. 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. Corporate and Other net operating loss equals Corporate and Other segment net loss attributable to common stockholders, excluding the Global Preneed goodwill impairment, interest expense, net realized gains (losses) on investments (which includes unrealized gains (losses) on equity securities and changes in fair value of direct investments in collateralized loan obligations), COVID-19 direct and incremental expenses, the CARES Act tax benefit, foreign exchange gains (losses) from remeasurement of monetary assets and liabilities, the net charge related to Iké, as well as other highly variable or unusual items other than reportable catastrophes. The company believes Corporate and Other net operating loss provides investors a valuable measure of the performance of the company's corporate segment because it excludes highly variable items that do not represent the ongoing results of the company's corporate segment. The comparable GAAP measure is Corporate and
   Other segment net loss attributable to common stockholders.

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

© 2020 Assurant, Inc. All rights reserved. 39