Assurant : Q4 for Q4 2019 Investor Presentation 2019

Assurant Investor Overview

Fourth Quarter 2019

© 2020 Assurant, Inc. All rights reserved. 1

Cautionary Statement

Some of the statements included in this presentation, particularly those anticipating 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 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

We are a leading provider of lifestyle and housing solutions

Protecting	Inpartnership
major consumer	with leading
purchases …	brands that …
•	Home and Rental	•	Make
•	Car	•	Sell
•	Mobile Devices	•	Finance

• Appliances
• Funeral

Through innovative offerings…

• Device lifecycle management
• Premium tech support
• Integratedpoint-of- lease billing and tracking

Assurant is more than a traditional insurance company.

© 2020 Assurant, Inc. All rights reserved. 4

Transformed for Sustained Outperformance

2015

2016

2017

2018

2019

Portfolio		New		Returned to		Strategic TWG		Deepened Client
				Relationships &
Realignment		Organizational		Profitable		Acquisition		Strong Global
		Model		Growth				Lifestyle Growth

Embedded expense discipline to fund growth and innovation

Investments in technology, AI and data analytics to support better customer experience Deployed key talent across enterprise to support greater cross-selling and innovation

Repositioned for

continued

profitable growth..

• whiledeploying capital to drive

shareholder value

© 2020 Assurant, Inc. All rights reserved. 5

We Partner with Industry-leading Clients Through our Three Business Units

GLOBAL LIFESTYLE

Connecting and protecting consumer devices, appliances, cards and transactions.

• Connected Living
• Global Automotive
• Global Financial Services

Revenue(1)

Full-Year 2018 = $5.2 Billion(2)

Full-Year 2019 = $7.1 Billon

GLOBAL HOUSING

GLOBAL HOUSING

Helping customers protect their properties.

• Multifamily Housing
• Lender-PlacedInsurance
• Specialty

Revenue(1)

Full-Year 2018 = $2.1 Billion

Full-Year 2019 = $2.0 Billion

GLOBAL PRENEED

Helping ease the financial and emotional burden associated with end-of-life planning.

• Prearranged Funeral Funding
• Senior Lifestyle Planning Solutions

Revenue(1)

Full-Year 2018 = $190 Million

Full-Year 2019 = $201 Million

1. Revenue equals net earned premiums, fees and other income.
2. Beginning June 1, 2018, revenue includes TWG revenue, per the acquisition.

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Repositioned For Continued Profitable Growth

• Earnings expansion, outpacing market declines inlender-placed
• Double-digitgrowth in rest of portfolio driven by Connected Living, Multifamily Housing and Global Automotive

1. Net operating income excludes catastrophes, which throughout this presentation refers to reportable catastrophes as defined in Exhibit 2 in the Appendix.
2. Refer to Exhibit 2 in the Appendix for information regardingnon-GAAP financial measures, including reconciliations to the most directly comparable GAAP measures.
3. Beginning June 1, 2018, net operating income includes TWG earnings, per the acquisition.

Net Operating Income(1-3)

($M)

$574

$515

$418$413 $379

46%

54%

58%

69%

76%

54%	46%	42%	31%	24%
2015	2016	2017	2018	2019
		Lender-placed		Assurant, excl.
		insurance			Lender-placed

2015-2019(3)

8% CAGR Total Assurant

23% CAGR Assurant, excl. Lender-placed

© 2020 Assurant, Inc. All rights reserved. 7

2019 Investor Day Enterprise Financial Objectives to Deliver Strong Growth and Capital Return

2019 Annual Outlook(1,2)		2020-2021 Financial Objectives(2)

Operating EPS,	6-10% growth		12% average annual growth
excluding catastrophes

Supported by double-digit average annual

growth in net operating income and

Capital return to	$1.35 billion capital return through 2021
shareholders(3)

1. 2019 Outlook provided as part offull-year 2018 earnings on Feb. 12, 2019.
2. Refer to Exhibit 2 in the Appendix for information regardingnon-GAAP financial measures, including reconciliations to the most directly comparable GAAP measures.
3. Throughout the presentation, 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.

© 2020 Assurant, Inc. All rights reserved. 8

2019 Investor Day Objectives Supported by Segment Targets

Financial Objectives 2019-2021(1,2)

Segments

Earnings Expansion

Attractive Returns with Strong Cash Flow Generation

Ongoing Expense Discipline and Leverage

Enterprise Earnings Growth and Capital Return Driven by:

Global Lifestyle:At least 10% average annual growth in net operating income

Global Housing:17-20% Operating ROE, including average catastrophe load

Global Preneed:13% Operating ROE

Corporate:Maintain corporate segment loss at ~$85 million

1. Refer to Exhibit 2 in the Appendix for information regardingnon-GAAP financial measures, including reconciliations to the most directly comparable GAAP measures.
2. Segment financial objectives provided at March 2019 Investor Day.

© 2020 Assurant, Inc. All rights reserved. 9

2020 Outlook Aligns with Investor Day Enterprise Financial Objectives

2019 Results		2020 Annual Outlook(1,2)

Operating EPS,	$9.21		10-14% growth
excluding catastrophes	(6% growth)		(off of $9.21)

Net operating income,	$574 million
excluding catastrophes	(11% growth)

Capital return to	$426 million
shareholders(3)	($275 million in share repurchases,
	$151 common dividends)

1. 2020 outlook provided as part offull-year 2019 earnings on Feb. 11, 2020.
2. Refer to Exhibit 2 in the Appendix for information regardingnon-GAAP financial measures, including reconciliations to the most directly comparable GAAP measures.
3. Throughout the presentation, 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.

© 2020 Assurant, Inc. All rights reserved. 10

Long-Term Drivers of Outperformance

MARKET-	INNOVATIVE
LEADING
OFFERINGS
POSITIONS

MACRO &

CONSUMER

TRENDS

LEADING BRANDS	BROAD,
DIFFERENTIATED
& DISTRIBUTION
CAPABILITIES
PARTNERS

GREATER

DIVERSIFICATION

DISCIPLINED

CAPITAL

DEPLOYMENT

STRONG

EARNINGS &

CASH FLOW

© 2020 Assurant, Inc. All rights reserved. 11

Portfolio of Market-leading Businesses with Attractive Growth Prospects

Mobile

Auto

Multifamily

Lender-placed

Preneed

Housing

Insurance

Favorable

Refurbed

devices,

Stable

overall

Household

Mortgage

Favorable

Industry

Internet of

Things

car sales in U.S.

formation

originations

demographics driven

Trends

and 5G upgrades

growing again

by baby boomers

Attachment

Higher device

Mix of new and

Policy penetration

U.S. economic

Improved point-of-

used cars and

and

Rate Drivers

prices

and persistency

sale technology

global expansion

housing cycle

Assurant

Industry

Combined

PMC and affinity

Partnering with

Alignment with

consolidation;

strength of

Positioning

channel growth

industry leaders

industry leader

global growth

Assurant and TWG

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Partnerships with Leading Global Brands and Broad Distribution Channels

HOUSING	AUTO	MOBILE

	Mortgage
Small PMCs	Servicers

8 of theTop 10	9 of theTop 10	6 of theTop 10
largest mortgage	global auto	global connected
servicers in the U.S.	manufacturers	living brands
MULTIFAMILY HOUSING	PRENEED

LARGE PMCs

BANKS

Dealers,

Agents,

NationalE-tailers

Accounts

AUTO TPA	RETAILERS

9 of theTop 10	The largestfuneral home
largest multifamily housing	and cemetery service provider
property management	in the U.S. and Canada
companies (PMCs) in the U.S.

OEMs	MOBILE
	CARRIERS
Automotive,	Cable
Mobile Device

Refer to Exhibit 3 in the Appendix for list of sources. Information listed as of December 31, 2019, unless otherwise noted.

© 2020 Assurant, Inc. All rights reserved. 13

Robust and Diversified Cash Flow Creates Significant Flexibility to Drive Shareholder Value

1. • Robust cash flow with over$5.7B in segment dividendsover the past 10 years(1)
   • ~100% of segment earningsexpected to be distributed to Holding Company
   • More balanced portfolio createsdiversified source of cash flows
   • • Risk businesses generate strong cash flows and provide capital to support growth
     • Growth in less capital intensive businesses generates more predictable cash flows over time
2. Consists of dividends from operating subsidiaries to the holding company, net of infusions, and excluding acquisitions and divestitures.

Conversion Percentage of

Segment Earnings(2)

(3) (3) (4)

$5.7B Total Dividends

1. Conversion percentage equals dividends from operating subsidiaries, net of infusions, to the holding company, divided by segment operating earnings. Segment operating earnings exclude Corporate and Other losses, interest expense and preferred dividends.2015-2018 exclude dividends and infusions relating to Assurant Health and Assurant Employee Benefits.
2. 2016-2017exclude $1.5 billion proceeds received from sale of Assurant Employee Benefits and Assurant Health wind-down.
3. 2018 includes $237 million in proceeds received from a reduction in deferred tax liabilities from U.S. tax reform. Also includes $148 million in dividends from The Warranty Group.

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Capital Deployment Strategy Creates Balance Between

Shareholder Returns and Growth Balanced Capital

Deployment Strategy

Capital Management Principles		12% 11%
•	Invest in business to drive sustained innovation and growth		2004 -
•	Select tuck-in acquisitions	33%	2019	44%

•Target to maintain investment grade rating

•Return excess capital to shareholders(1)

-Repurchased 63% of shares since IPO				Common		Share		M&A		Capital
			Stock		Repurchases			Infusions
-2019-2021 objective: expect to return $1.35B to shareholders				Dividends
via share repurchases and common stock dividends				Capital Deployment Mix
oIn 2019, returned$426 million to shareholders

25%

	2019-	50%
	2021
25%
Acquisitions/		Share Repurchases		Common Stock
Organic Growth
		Dividends

(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.

© 2020 Assurant, Inc. All rights reserved. 15

Long-Term Strategy to Deliver Sustained Outperformance

MARKET-	INNOVATIVE
LEADING
OFFERINGS
POSITIONS

Assurant In 2021

• Even stronger portfolio of businesses with leadership positions and attractive growth prospects

• Deeper partnerships with leading brands to sustain innovation, drive better customer experience

LEADING BRANDS	BROAD,
DIFFERENTIATED
& DISTRIBUTION
CAPABILITIES
PARTNERS

• Broader offerings beyond insurance to meet evolving consumer needs
• Leader in innovation for the connected world - across devices, cars and home
• Continue to advance thinking and implement best practices in governance and social responsibility approach

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Financial Update

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Fourth Quarter 2019 Results

Q4 2019 Net Operating Income ex. CATs(1,2)($M)

200.0	16.1	(21.6)(1)
175.0	72.0	(20.1)
150.0		( 4.7 )	139.5
125.0
100.0	97.8
75.0
50.0
25.0
-

1. Refer to Exhibit 2 for a reconciliation ofnon-GAAP financial measures to the most comparable GAAP financial measures.
2. Reportable catastrophes include catastrophe losses, net of reinsurance and client profit sharing adjustments, as well as reinstatement and other premiums.

Total Assurant

• Net operating income, excluding CATs,decreased due to the absence of a client recoverable in prior-year period, higher non-CAT loss experience in Global Housing and IT-related severance
• Earnings per share, excluding CATs(1),decreased 2% driven primarily by the factors noted above

Global Lifestyle

• Securedlong-term extension with a major mobile client in Japan
• Excluding aprior-year period recoverable and IT-related severance, earnings increased driven by continued mobile subscriber growth in Asia Pacific and North America
• Results partially offset by higher expenses in Auto and continued investments in mobile

Global Housing

• Earnings declined primarily due to highernon-CAT loss experience in sharing economy offerings and the previously disclosed reduction in loans tracked from a financially insolvent client
• Higher premium rates inlender-placed helped offset the decline
• Small commercial business inrun-off; results improved in quarter

Global Preneed

• Earnings down slightly from lower investment income; growth in U.S. and more profitable sales mix mostly offset the decline

© 2020 Assurant, Inc. All rights reserved. 18

Full-Year 2019 Results

Full-Year 2019 Net Operating Income ex. CATs(1,2)($M)

800.0	52.2	(85.6)(1)
700.0	299.6	(82.9)
600.0		(18.7)	574.0
500.0
400.0	409.4
300.0
200.0
100.0
-

Total Assurant

• Net operating income, excluding CATs,increased 11% primarily due to strong growth in mobile and TWG contributions in Global Lifestyle
• Earnings per share, excluding CATs(1),increased 6% driven by strong underlying earnings growth, partially offset by the shares issued last year for TWG
• Added or renewed more than 60 valuable client partnerships across Lifestyle and Housing segments and launched several new product offerings

Global Lifestyle

• Record year for segment as earnings increased 37% led by Connected Living
• Now protect over 53 million mobile subscribers, up 15% since 2018
• Global Auto growth from strength across distribution channels and the scale and expertise acquired with TWG

Global Housing

• Earnings declined primarily from lower results inlender-placed and higher losses in specialty housing portfolio
• Renewed 16 clients inlender-placed, representing 60% of tracked loans
• Grew renters' policies in multifamily housing to 2.2 million, up 10%

1. Refer to Exhibit 2 for a reconciliation ofnon-GAAP financial measures to the most comparable GAAP financial measures.
2. Reportable catastrophes include catastrophe losses, net of reinsurance and client profit sharing adjustments, as well as reinstatement and other premiums.

Global Preneed

• Underlying earnings grew excluding accounting adjustment in third quarter 2019
• Creating a more profitable sales mix and continue to generate strong cash flows

© 2020 Assurant, Inc. All rights reserved. 19

Appendix

© 2020 Assurant, Inc. All rights reserved. 20

Exhibit 1: Safe Harbor Statement

Some of the statements included in this presentation and its exhibits, particularly those anticipating future financial performance, business prospects, growth and operating strategies and similar matters, are forward-looking statements within the meaning of the U.S. Private Securities Litigation Reform Act of 1995. You can identify these 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, 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; significant competitive pressures, changes in customer preferences and disruption;

the failure to find suitable acquisitions, integrate completed acquisitions, or grow organically, and risks associated with joint ventures and franchise ownership and operations; the impact of general economic, financial market and political conditions, including unfavorable conditions in the capital and credit markets, and conditions in the markets in which we operate; risks related to our international operations, including the United Kingdom's withdrawal from the European Union, or fluctuations in exchange rates;

the impact of catastrophic and non-catastrophe losses, including as a result of climate change; our inability to recover should we experience a business continuity event;

our inability to develop and maintain distribution sources or attract and retain sales representatives and executives with key client relationships; the failure to manage vendors and other third parties on whom we rely to conduct business and provide services to our clients; declines in the value of mobile devices, the risk of guaranteed buybacks or export compliance risk in our mobile business; negative publicity relating to our products and services or the markets in which we operate; the failure to implement our strategy and to attract and retain key personnel, including senior management; employee misconduct; the adequacy of reserves established for claims and our inability to accurately predict and price for claims; a decline in financial strength ratings or corporate senior debt ratings; an impairment of goodwill or other intangible assets; the failure to maintain effective internal control over financial reporting; a decrease in the value of our investment portfolio including due to market, credit and liquidity risks and changes in interest rates; the impact of U.S. tax reform legislation and impairment of deferred tax assets; the unavailability or inadequacy of reinsurance coverage and the credit risk of reinsurers, including those to whom we have sold business through reinsurance; the credit risk of some of our agents, third-party administrators and clients; the inability of our subsidiaries to pay sufficient dividends to the holding company and limitations on our ability to declare and pay dividends; changes in the method for determining LIBOR or the replacement of LIBOR; the failure to effectively maintain and modernize our information technology systems and infrastructure, or the failure to integrate those of acquired businesses; 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; 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; the impact from litigation and regulatory actions; reductions in the insurance premiums we charge; and changes in insurance and other regulation.

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 as filed with the SEC.

© 2020 Assurant, Inc. All rights reserved. 21

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 net charge related to Iké, Assurant Health runoff operations, net realized gains (losses) on investments, amortization of deferred gains (including Assurant Employee Benefits), net charges relating to the acquisition of The Warranty Group ("TWG"), foreign exchange gains (losses) from remeasurement of monetary assets and liabilities, loss on sale of Mortgage Solutions and other highly variable or unusual items. 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.

Additional details about the components of net TWG acquisition related charges and 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. 22

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 net TWG acquisition related charges and 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. 23

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 net charge related to Iké, Assurant Health runoff operations, net TWG acquisition related charges, foreign exchange gains (losses) from remeasurement of monetary assets and liabilities, amortization of deferred gains on disposal of businesses, net realized gains (losses) on investments, interest expense, loss on sale of Mortgage Solutions and other highly variable or unusual items. 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 & Other segment net loss attributable to common stockholders.

Additional details about the components of net TWG acquisition related charges and 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

1. The company outlook for net operating income per diluted share, excluding reportable catastrophe losses, and Corporate and Other net operating loss each constituteforward-looking information and the company believes that it cannot reconcile such forward-looking information to the most comparable GAAP measure without unreasonable efforts. Many of the 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. The company is able to reasonably quantify a range for amortization of deferred gains based on certain assumptions relating to future reinsured premium on disposed business during the forecast period. Amortization of deferred gains on disposal of businesses is expected to be approximately $8-9 million after-tax. The company is also able to quantify a range of interest expense and preferred stock dividends, as disclosed in the outlook. The interest expense estimate assumes no additional debt is incurred or extinguished in the forecast period and excludes after-tax interest expenses included in debt extinguishment and other related costs. Preferred stock dividends are subject to Board approval.

© 2020 Assurant, Inc. All rights reserved. 24

Exhibit 3: Data Sources

Global Housing

Global Lifestyle

8 of the top 10 largest mortgage servicers in the US

9 of the top 10 Largest multifamily housing PMCs in the U.S.

Source:Internal Management

information

Source:2019 NMHC 50 Largest Apartment Managers

9 of the top 10 global auto manufacturers

6 of the top 10 global connected living brands

Source:2019 Best Global Brands

by Interbrand

Source:2019 Best Global Brands

by Interbrand

Multifamily housing market represents renter-occupied housing units as sourced by U.S. Census data with renters insurance penetration and premium growth estimates according to the Insurance Information Institute.

7 of the top 10 U.S. Third Party Administrators

Source:Internal Management

Information

Mobile (in Connected Living) market represents global smartphone shipments as sourced by IDC data.

Automotive market represents global new and used auto sales as sourced from

BMI Research, NADA and Mannheim.

Global Preneed

The largest funeral home and	Source:Internal Management
cemetery service provider in	information
the U.S. & Canada

Note: All data listed as of December 31, 2019 unless otherwise noted.

© 2020 Assurant, Inc. All rights reserved. 25