(In millions, except number of shares and per share amounts) The following discussion and analysis of our financial condition and results of operations should be read in conjunction with Management’s Discussion and Analysis of Financial Condition and Results of Operations (“MD&A”) and the annual audited consolidated financial statements for the year ended December 31, 2025 and accompanying notes included in our Annual Report on Form 10-K for the year ended December 31, 2025 (the “2025 Annual Report”) filed with the U.S. Securities and Exchange Commission (the “SEC”) and the unaudited consolidated financial statements for the three and six months ended June 30, 2026 and accompanying notes (the “Consolidated Financial Statements”) included elsewhere in this Quarterly Report on Form 10-Q (this “Report”). The following discussion and analysis covers the three and six months ended June 30, 2026 (“Second Quarter 2026” and “Six Months 2026”) and the three and six months ended June 30, 2025 (“Second Quarter 2025” and “Six Months 2025”). Some of the statements in this Report, including our business and financial plans and any statements regarding our 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. 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 Report 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: (i)the impact of general economic, financial market and political conditions and conditions in the markets in which we operate, including inflation, geopolitical conflict in the Middle East, tariff policies in the United States and abroad, global supply chain impacts and recessionary pressures; (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 if they disintermediate us, or if those parties face financial, reputational or regulatory issues; (iii)significant competitive pressures, changes in customer preferences and disruption, including the impact of artificial intelligence; (iv)the failure to execute our strategy, including through organic growth and the continuing service of key executives, senior leaders, highly-skilled personnel and a high-performing workforce; (v)the failure to find suitable acquisitions at attractive prices, integrate acquired businesses or divest of non-strategic businesses effectively; (vi)our inability to recover should we experience a business continuity event; (vii)the failure to manage vendors and other third parties on whom we rely to conduct business and provide services to our clients; (viii)risks related to our international operations; (ix)declines in the value and availability of mobile devices, and regulatory compliance or other risks in our mobile business; (x)our inability to develop and maintain distribution sources or attract and retain sales representatives and executives with key client relationships; (xi)risks associated with joint ventures, franchises and investments in which we share ownership and management with third parties; (xii)the impact of catastrophe and non-catastrophe losses, including as a result of climate change and the current inflationary environment; (xiii)negative publicity relating to our business, practices, industry or clients; 30 (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 technology systems and infrastructure, or the failure to integrate those of acquired businesses; (xxvii)breaches of our 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; (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 “Critical Factors Affecting Results” below and in Item 7 of our 2025 Annual Report, and “Item 1A—Risk Factors” below and in our 2025 Annual Report. Segment Information As of June 30, 2026, we had two reportable operating segments which are defined based on the manner in which the Company’s chief operating decision maker, our CEO, reviews the business to assess performance and allocate resources, and which align to the nature of the products and services offered: •Global Lifestyle: includes mobile device solutions (including extended service contracts, insurance policies and related services), extended service contracts and related services for consumer electronics and appliances, and financial services and other insurance products (referred to as “Connected Living”); and vehicle protection services, commercial equipment protection and other related services (referred to as “Global Automotive”); and •Global Housing: includes lender-placed homeowners, manufactured housing and flood insurance, as well as voluntary manufactured housing, condominium and homeowners insurance (referred to as “Homeowners”); and renters insurance and other products (referred to as “Renters and Other”). In addition, we report the Corporate and Other segment, which includes corporate employee-related expenses, activities of the holding company and investments in our home warranty business. We define Adjusted EBITDA, our segment measure of profitability, as net income, excluding net realized gains (losses) on investments and fair value changes to equity securities, interest expense, benefit (provision) for income taxes, depreciation expense, amortization of purchased intangible assets, as well as other highly variable or unusual items. 31 Executive Summary Summary of Financial Results Consolidated net income increased $63.3 million, or 27%, to $298.6 million for Second Quarter 2026 from $235.3 million for Second Quarter 2025, primarily driven by higher Global Lifestyle and Global Housing earnings, and lower reportable catastrophes, partially offset by the impact of a higher effective tax rate and higher Corporate and Other expenses. Global Lifestyle Adjusted EBITDA increased $43.0 million, or 21%, to $244.4 million for Second Quarter 2026 from $201.4 million for Second Quarter 2025, driven by earnings growth across Connected Living and Global Automotive. Connected Living increased 29%, including $10.2 million of favorable non-run rate benefits in Second Quarter 2026. Excluding this, earnings grew 22%, primarily driven by global mobile growth, including global supply chain and device protection programs, as well as higher contributions from financial services. Global Automotive results increased from growth within global partnerships. Global Lifestyle net earned premiums, fees and other income increased $222.1 million, or 9%, to $2.57 billion for Second Quarter 2026 from $2.35 billion for Second Quarter 2025, driven primarily by Connected Living growth from global supply chain volumes and device protection programs, as well as higher contributions from extended service contracts and financial services programs. Global Housing Adjusted EBITDA increased $60.4 million, or 28%, to $274.8 million for Second Quarter 2026 from $214.4 million for Second Quarter 2025. Results included $17.6 million of lower pre-tax reportable catastrophes. Excluding reportable catastrophes, Adjusted EBITDA increased $42.8 million, or 18%, mainly driven by favorable non-catastrophe loss experience, primarily from lower than typical claims frequency. In Homeowners, results also benefitted from lower catastrophe reinsurance costs and growth in specialty products and lender-placed insurance. Global Housing growth was partially offset by $11.6 million of lower favorable prior period reserve development. Global Housing net earned premiums, fees and other income increased $50.1 million, or 7%, to $747.8 million for Second Quarter 2026 from $697.7 million for Second Quarter 2025, primarily driven by Homeowners due to growth in specialty products and lender-placed insurance, and lower catastrophe reinsurance costs. Corporate and Other Adjusted EBITDA decreased $10.2 million, or 34%, to $(40.0) million for Second Quarter 2026 from $(29.8) million for Second Quarter 2025, mainly driven by higher employee-related expenses and organic investments to support our home warranty business. This increase was partially offset by higher investment income from higher asset balances. Critical Factors Affecting Results Our results depend on, among other things, the appropriateness of our product pricing, underwriting, the accuracy of our reserving methodology for future policyholder benefits and claims, the frequency and severity of reportable and non-reportable catastrophes, returns on and values of invested assets, our investment income, and our ability to enhance operational efficiencies and manage our expenses. Our results also depend on our ability to profitably grow our businesses, including our Connected Living, Global Automotive, and Renters and Other businesses, and the performance of our Homeowners business, which will be impacted by our ability to provide a superior customer experience, including from our investments in technology and digital initiatives. Factors affecting these items, including conditions in the financial markets, the global economy, political conditions and the markets in which we operate, fluctuations in exchange rates, interest rates and inflation, and tariffs and global supply chain disruptions may have a material adverse effect on our results of operations or financial condition. For more information on these and other factors that could affect our results, see “Item 1A—Risk Factors” below and in our 2025 Annual Report, and “Item 7—Management’s Discussion and Analysis of Financial Condition and Results of Operations—Critical Factors Affecting Results” in our 2025 Annual Report. Our results may also be impacted by our ability to capitalize on opportunities for further growth, including within adjacent markets such as home warranty. Our mobile business is subject to volatility in device trade-in volumes and margins based on the actual and anticipated timing of the release of new devices, carrier promotional programs and sales prices for used devices, as well as to changes in consumer preferences and client forecasts and demands. Our Homeowners revenue is impacted by changes in the housing market, as well as the voluntary insurance market. In addition, across many of our businesses, we must respond to competitive pressures, including the threat of disruption and competition for talent. For more information on these and other factors that could affect our results, see “Item 1A—Risk Factors—Business, Strategic and Operational Risks—Significant competitive pressures, changes in customer preferences and disruption could adversely affect our results of operations”, “—Our mobile business is subject to the risk of declines in the value and availability of mobile devices, and to regulatory compliance and other risks” and “—The success of our business depends on the execution of our strategy, including through the continuing service of key executives, senior leaders, highly-skilled personnel and a high-performing workforce” in our 2025 Annual Report. 32 Critical Accounting Policies and Estimates Our 2025 Annual Report describes the accounting policies and estimates that are critical to the understanding of our results of operations, financial condition and liquidity. The accounting policies and estimation process described in the 2025 Annual Report were consistently applied to the unaudited interim Consolidated Financial Statements for Second Quarter 2026. Recent Accounting Pronouncements For a discussion of recent accounting pronouncements, see Note 3 to the Consolidated Financial Statements included elsewhere in this Report. 33 Results of Operations Assurant Consolidated The table below presents information regarding our consolidated results of operations for the periods indicated: For the Three Months Ended June 30, For the Six Months Ended June 30, 2026 2025 2026 2025 Revenues: Net earned premiums $ 2,767.4 $ 2,587.7 $ 5,549.3 $ 5,150.0 Fees and other income 554.6 463.7 1,054.4 866.6 Net investment income 142.4 128.7 302.0 253.5 Net realized losses on investments and fair value changes to equity securities (10.2) (21.7) (31.4) (37.7) Total revenues 3,454.2 3,158.4 6,874.3 6,232.4 Benefits, losses and expenses: Policyholder benefits 748.3 721.5 1,517.4 1,501.2 Underwriting, selling, general and administrative expenses 2,300.6 2,121.2 4,587.7 4,205.0 Interest expense 28.4 26.7 56.7 53.5 Total benefits, losses and expenses 3,077.3 2,869.4 6,161.8 5,759.7 Income before provision for income taxes 376.9 289.0 712.5 472.7 Provision for income taxes 78.3 53.7 139.8 90.8 Net income $ 298.6 $ 235.3 $ 572.7 $ 381.9 For the Three Months Ended June 30, 2026 Compared to the Three Months Ended June 30, 2025 Net income increased $63.3 million, or 27%, to $298.6 million for Second Quarter 2026 from $235.3 million for Second Quarter 2025, primarily due to higher earnings in Global Lifestyle and Global Housing, $13.8 million of lower after-tax reportable catastrophes and lower net realized losses on investments. The increase in net income was partially offset by a higher annualized effective tax rate, mainly driven by higher transferrable tax credits reported in the prior year, higher Corporate and Other expenses and $7.0 million of higher after-tax depreciation expense, mainly due to higher software assets placed into service. For the Six Months Ended June 30, 2026 Compared to the Six Months Ended June 30, 2025 Net income increased $190.8 million, or 50%, to $572.7 million for Six Months 2026 from $381.9 million for Six Months 2025, primarily driven by $118.6 million of lower after-tax reportable catastrophes and higher earnings in Global Lifestyle and Global Housing. The increase in net income was partially offset by $13.4 million of higher after-tax depreciation expense, mainly due to higher software assets placed into service, and higher Corporate and Other expenses. 34 Global Lifestyle The table below presents information regarding the Global Lifestyle segment’s results of operations for the periods indicated: For the Three Months Ended June 30, For the Six Months Ended June 30, 2026 2025 2026 2025 Revenues Net earned premiums $ 2,065.6 $ 1,935.9 $ 4,159.9 $ 3,881.5 Fees and other income 507.3 414.9 964.0 775.9 Net investment income 97.3 87.7 206.2 171.7 Total revenues 2,670.2 2,438.5 5,330.1 4,829.1 Benefits, losses and expenses Policyholder benefits 512.5 461.5 1,016.2 903.9 Selling and underwriting expenses 1,267.7 1,230.2 2,594.9 2,496.0 Cost of sales 302.6 231.4 567.6 416.2 General expenses 343.0 314.0 670.3 613.8 Total benefits, losses and expenses 2,425.8 2,237.1 4,849.0 4,429.9 Global Lifestyle Adjusted EBITDA $ 244.4 $ 201.4 $ 481.1 $ 399.2 Net earned premiums, fees and other income: Connected Living $ 1,554.5 $ 1,326.4 $ 3,034.7 $ 2,559.8 Global Automotive 1,018.4 1,024.4 2,089.2 2,097.6 Total $ 2,572.9 $ 2,350.8 $ 5,123.9 $ 4,657.4 Net earned premiums, fees and other income: Domestic $ 1,904.6 $ 1,796.2 $ 3,841.0 $ 3,591.4 International 668.3 554.6 1,282.9 1,066.0 Total $ 2,572.9 $ 2,350.8 $ 5,123.9 $ 4,657.4 For the Three Months Ended June 30, 2026 Compared to the Three Months Ended June 30, 2025 Adjusted EBITDA increased $43.0 million, or 21%, to $244.4 million for Second Quarter 2026 from $201.4 million for Second Quarter 2025, primarily driven by Connected Living growth from higher contributions from global supply chain programs and financial services, $10.2 million of non-run rate items in Second Quarter 2026, as well as subscriber growth in device protection programs. In addition, Global Automotive results also drove the increase due to higher global partnership contributions. Total revenues increased $231.7 million, or 10%, to $2.67 billion for Second Quarter 2026 from $2.44 billion for Second Quarter 2025. Net earned premiums increased $129.7 million, or 7%, primarily driven by Connected Living growth from device protection programs, extended service contracts, including a recently launched U.S. program, and financial services, including a card benefits program. Fees and other income increased $92.4 million, or 22%, primarily driven by higher volumes in domestic supply chain programs within Connected Living. Net investment income increased $9.6 million, or 11%, primarily driven by fixed maturity securities due to higher asset balances and yields. Total benefits, losses and expenses increased $188.7 million, or 8%, to $2.43 billion for Second Quarter 2026 from $2.24 billion for Second Quarter 2025. Cost of sales increased $71.2 million, or 31%, mainly driven by higher volumes in domestic supply chain programs. Policyholder benefits increased $51.0 million, or 11%, primarily due to Connected Living, mainly driven by growth in extended service contracts, including a recently launched U.S. program. Selling and underwriting expenses increased $37.5 million, or 3%, primarily due to an increase in commission expenses in Connected Living, mainly related to the growth from device protection programs in line with the increase in net earned premiums, partially offset by a decline in Global Automotive. General expenses increased $29.0 million, or 9%, primarily due to higher employee-related expenses to support growth initiatives. 35 For the Six Months Ended June 30, 2026 Compared to the Six Months Ended June 30, 2025 Adjusted EBITDA increased $81.9 million, or 21%, to $481.1 million for Six Months 2026 from $399.2 million for Six Months 2025, primarily driven by subscriber growth in device protection programs, higher contributions from global supply chain programs and higher net investment income in Global Automotive, including a $10.2 million gain on the sale of real estate joint venture in the first quarter of 2026. Total revenues increased $501.0 million, or 10%, to $5.33 billion for Six Months 2026 from $4.83 billion for Six Months 2025. Net earned premiums increased $278.4 million, or 7%, primarily driven by growth in Connected Living from device protection programs, extended service contracts, including a recently launched U.S. program, and financial services, including a card benefits program. Fees and other income increased $188.1 million, or 24%, primarily driven by higher volumes in domestic supply chain programs within Connected Living. Net investment income increased $34.5 million, or 20%, primarily driven by fixed maturity securities due to higher asset balances and yields and the aforementioned gain on the sale of a real estate joint venture in the first quarter of 2026. Total benefits, losses and expenses increased $419.1 million, or 9%, to $4.85 billion for Six Months 2026 from $4.43 billion for Six Months 2025. Cost of sales increased $151.4 million, or 36%, mainly driven by higher volumes in domestic supply chain programs. Policyholder benefits increased $112.3 million, or 12%, primarily due to Connected Living, mainly from growth in extended service contracts, including a recently launched U.S. program, and higher losses within financial services. Selling and underwriting expenses increased $98.9 million, or 4%, primarily due to an increase in commission expenses in Connected Living, mainly related to the growth from device protection programs in line with the increase in net earned premiums, partially offset by a decline in Global Automotive. General expenses increased $56.5 million, or 9%, primarily due to higher employee-related expenses to support growth initiatives. 36 Global Housing The table below presents information regarding the Global Housing segment’s results of operations for the periods indicated: For the Three Months Ended June 30, For the Six Months Ended June 30, 2026 2025 2026 2025 Revenues Net earned premiums $ 700.5 $ 650.2 $ 1,386.5 $ 1,265.5 Fees and other income 47.3 47.5 90.4 89.0 Net investment income 35.6 34.4 76.3 68.1 Total revenues 783.4 732.1 1,553.2 1,422.6 Benefits, losses and expenses Policyholder benefits 235.4 258.7 499.3 591.7 Selling and underwriting expenses 60.4 52.4 120.3 91.9 General expenses 212.8 206.6 422.1 412.2 Total benefits, losses and expenses 508.6 517.7 1,041.7 1,095.8 Global Housing Adjusted EBITDA $ 274.8 $ 214.4 $ 511.5 $ 326.8 Impact of reportable catastrophes $ 12.2 $ 29.8 $ 36.6 $ 186.5 Net earned premiums, fees and other income Homeowners $ 600.4 $ 552.8 $ 1,180.5 $ 1,075.7 Renters and Other 147.4 144.9 296.4 278.8 Total $ 747.8 $ 697.7 $ 1,476.9 $ 1,354.5 For the Three Months Ended June 30, 2026 Compared to the Three Months Ended June 30, 2025 Adjusted EBITDA increased $60.4 million, or 28%, to $274.8 million for Second Quarter 2026 from $214.4 million for Second Quarter 2025, mainly driven by favorable non-catastrophe loss experience, primarily from lower than typical claims frequency, $17.6 million of lower pre-tax reportable catastrophes, lower catastrophe reinsurance costs and growth in various specialty products and lender-placed insurance, as well as modest growth in Renters and Other. This increase was partially offset by $11.6 million of lower favorable year-over-year non-catastrophe prior period reserve development and higher costs associated with growth. Total revenues increased $51.3 million, or 7%, to $783.4 million for Second Quarter 2026 from $732.1 million for Second Quarter 2025. Net earned premiums increased $50.3 million, or 8%, primarily driven by growth in various specialty products, lower catastrophe reinsurance premiums, higher average premiums in Homeowners, as well as growth in the private flood business. Net investment income increased $1.2 million, or 3%, primarily due to higher asset balances and yields. Fees and other income decreased $0.2 million. Total benefits, losses and expenses decreased $9.1 million, or 2%, to $508.6 million for Second Quarter 2026 from $517.7 million for Second Quarter 2025. Policyholder benefits decreased $23.3 million, or 9%, primarily due to lower frequency for non-catastrophe losses and lower reportable catastrophe losses, partially offset by exposure growth for non-catastrophe losses and $11.6 million of lower favorable year-over-year non-catastrophe prior period reserve development. Second Quarter 2026 had $22.3 million of favorable non-catastrophe prior period reserve development compared to $33.9 million in Second Quarter 2025. Selling and underwriting expenses increased $8.0 million, or 15%, primarily driven by lower National Flood Insurance Program commission income and higher commissions related to growth across various products. General expenses increased $6.2 million, or 3%, primarily due to higher costs associated with net earned premium growth. For the Six Months Ended June 30, 2026 Compared to the Six Months Ended June 30, 2025 Adjusted EBITDA increased $184.7 million, or 57%, to $511.5 million for Six Months 2026 from $326.8 million for Six Months 2025, mainly due to $149.9 million of lower pre-tax reportable catastrophes primarily related to the California wildfires, growth across both Homeowners and Renters and Other, and higher net investment income. This increase in Adjusted 37 EBITDA was partially offset by unfavorable non-catastrophe loss experience, due to $21.5 million of lower favorable year-over-year non-catastrophe prior year reserve development and higher costs associated with growth. Total revenues increased $130.6 million, or 9%, to $1.55 billion for Six Months 2026 from $1.42 billion for Six Months 2025. Net earned premiums increased $121.0 million, or 10%, primarily driven by Homeowners from growth across various specialty products, higher lender-placed policies in-force and average insured values, as well as growth in Renters and Other, primarily from the prior year acquisition of a block of renters policies. Net investment income increased $8.2 million, or 12%, primarily due to a gain on the sale of a real estate joint venture as well as higher asset balances and yields. Fees and other income increased $1.4 million, or 2%, primarily driven by continued growth in service fees within Homeowners. Total benefits, losses and expenses decreased $54.1 million, or 5%, to $1.04 billion for Six Months 2026 from $1.10 billion for Six Months 2025. Policyholder benefits decreased $92.4 million, or 16%, primarily due to lower reportable catastrophe losses, partially offset by higher non-catastrophe losses from exposure growth, as well as $21.5 million of lower favorable year-over-year non-catastrophe prior year reserve development. Six Months 2026 had $41.9 million of favorable non-catastrophe prior year reserve development compared to $63.4 million in Six Months 2025. Selling and underwriting expenses increased $28.4 million, or 31%, primarily driven by lower National Flood Insurance Program commission income and higher Renters and Other commissions related to the prior year acquisition of a block of renters policies. General expenses increased $9.9 million, or 2%, primarily due to higher costs associated with net earned premium growth. 38 Corporate and Other The tables below present information regarding the Corporate and Other’s segment results of operations for the periods indicated: For the Three Months Ended June 30, For the Six Months Ended June 30, 2026 2025 2026 2025 Revenues Net earned premiums $ — $ — $ — $ — Fees and other income — 1.3 — 1.7 Net investment income 8.8 5.6 18.1 11.4 Total revenues 8.8 6.9 18.1 13.1 Benefits, losses and expenses Policyholder benefits — — — — General expenses 48.8 36.7 90.0 70.9 Total benefits, losses and expenses 48.8 36.7 90.0 70.9 Corporate and Other Adjusted EBITDA $ (40.0) $ (29.8) $ (71.9) $ (57.8) For the Three Months Ended June 30, 2026 Compared to the Three Months Ended June 30, 2025 Adjusted EBITDA decreased $10.2 million, or 34%, to $(40.0) million for Second Quarter 2026 from $(29.8) million for Second Quarter 2025, primarily due to higher general expenses, partially offset by higher net investment income, each as explained below. Total revenues increased $1.9 million, or 28%, to $8.8 million for Second Quarter 2026 from $6.9 million for Second Quarter 2025, driven by an increase in net investment income of $3.2 million, or 57%, mostly due to higher asset balances and yields on fixed maturity securities and higher cash levels, partially offset by a decrease in fees and other income of $1.3 million, mostly due to the absence of proceeds on the sale of Internet Protocol addresses from Second Quarter 2025. Total benefits, losses and expenses increased $12.1 million, or 33%, to $48.8 million for Second Quarter 2026 from $36.7 million for Second Quarter 2025, driven by an increase in general expenses of $12.1 million, due to higher employee-related expenses and higher investments in our home warranty business. For the Six Months Ended June 30, 2026 Compared to the Six Months Ended June 30, 2025 Adjusted EBITDA decreased $14.1 million, or 24%, to $(71.9) million for Six Months 2026 from $(57.8) million for Six Months 2025. The change in results was primarily due to higher general expenses, partially offset by higher net investment income, each as explained below. Total revenues increased $5.0 million, or 38%, to $18.1 million for Six Months 2026 from $13.1 million for Six Months 2025, driven by an increase in net investment income of $6.7 million, or 59%, mainly due to higher asset balances and yields on fixed maturity securities and higher cash levels, partially offset by a decrease in fees and other income of $1.7 million, mostly due to the absence of proceeds on the sale of Internet Protocol addresses from Six Months 2025. Total benefits, losses and expenses increased $19.1 million, or 27%, to $90.0 million for Six Months 2026 from $70.9 million for Six Months 2025, driven by an increase in general expenses of $19.1 million, due to higher investments in our home warranty business and higher employee-related expenses. 39 Investments We had total investments of $10.46 billion and $10.06 billion as of June 30, 2026 and December 31, 2025, respectively. Net unrealized losses on our fixed maturity securities portfolio increased $87.9 million during Six Months 2026, from a $55.7 million unrealized loss at December 31, 2025 to a $143.6 million unrealized loss as of June 30, 2026, primarily due to an increase in Treasury rates. The following table shows the credit quality of our fixed maturity securities portfolio as of the dates indicated: Fair value as of Fixed Maturity Securities by Credit Quality June 30, 2026 December 31, 2025 Aaa / Aa / A $ 4,959.3 55.2 % $ 4,710.9 54.9 % Baa 3,379.5 37.6 % 3,257.9 38.0 % Ba 558.8 6.2 % 527.6 6.2 % B and lower 91.9 1.0 % 81.3 0.9 % Total $ 8,989.5 100.0 % $ 8,577.7 100.0 % The following table shows the major categories of net investment income for the periods indicated: Three Months Ended June 30, Six Months Ended June 30, 2026 2025 2026 2025 Fixed maturity securities $ 124.5 $ 107.4 $ 243.9 $ 208.3 Equity securities 3.8 3.1 6.6 6.0 Commercial mortgage loans on real estate 4.2 4.8 8.7 9.8 Short-term investments 4.4 4.9 9.1 9.9 Other investments (2.1) (0.9) 16.2 (1.9) Cash and cash equivalents 12.1 13.7 26.4 29.7 Total investment income 146.9 133.0 310.9 261.8 Investment expenses (4.5) (4.3) (8.9) (8.3) Net investment income $ 142.4 $ 128.7 $ 302.0 $ 253.5 Net investment income increased $13.7 million, or 11%, to $142.4 million for Second Quarter 2026 from $128.7 million for Second Quarter 2025, primarily driven by increased income from fixed maturity securities related to higher yields and asset balances, partially offset by lower income from short-term investments and cash and cash equivalents due to lower yields. Net realized losses on investments and fair value changes to equity securities decreased $11.5 million, or 53%, to $10.2 million for Second Quarter 2026 from $21.7 million for Second Quarter 2025, primarily driven by reduced sales of fixed maturity and equity securities. Net investment income increased $48.5 million, or 19%, to $302.0 million for Six Months 2026 from $253.5 million for Six Months 2025, primarily driven by increased income from fixed maturity securities related to higher yields and asset balances and a gain on the sale of a real estate joint venture in the first quarter of 2026. The increase in net investment income was partially offset by lower income from short-term investments and cash and cash equivalents due to lower yields. Net realized losses on investments and fair value changes to equity securities decreased $6.3 million, or 17%, to $31.4 million for Six Months 2026 from $37.7 million for Six Months 2025, primarily driven by reduced sales of fixed maturity and equity securities. As of June 30, 2026, we owned $14.3 million of securities guaranteed by financial guarantee insurance companies. Included in this amount was $13.5 million of municipal securities, which had a credit rating of A+ with the guarantee, but would have had a credit rating of AA- without the guarantee. For more information on our investments, see Notes 7 and 8 to the Consolidated Financial Statements included elsewhere in this Report. Catastrophe Reinsurance Program Effective April 2026, coverage was placed with various reinsurers that are all rated A- or better by A.M. Best. 2026 reinsurance premiums for the total program are estimated to be $181.7 million pre-tax, compared to $210.0 million pre-tax for 2025. The estimate for 2026 premiums reflects our exposure changes, expected Florida Hurricane Catastrophe Fund (“FHCF”) 40 program impacts and favorable underlying rates from improved reinsurance market conditions. Actual reinsurance premiums will vary if exposure changes significantly from estimates or if reinstatement premiums are required due to catastrophe events. The U.S. per-occurrence catastrophe coverage includes a main reinsurance program providing $1.59 billion of coverage in excess of a $160.0 million retention for a first event. Layers 1 through 5 of the program allow for one automatic reinstatement, with layer 1 not having reinstatement premium liability. When combined with the FHCF, the U.S. program protects against gross Florida losses of up to approximately $1.80 billion, in excess of retention. Liquidity and Capital Resources The following section discusses our ability to generate cash flows from each of our subsidiaries, borrow funds at competitive rates and raise new capital to meet our operating and growth needs. Management believes that we will have sufficient liquidity to satisfy our needs over the next twelve months, including the ability to pay interest on our debt and dividends on our common stock. In January 2025, we entered into an agreement to sell our Miami, Florida property for a purchase price of $126.0 million, subject to certain adjustments and to the buyer receiving the requisite development approvals. If the transaction is consummated pursuant to the terms of the agreement, we expect to record a gain above the current carrying value of $46.0 million as of June 30, 2026, less estimated costs to sell. We do not anticipate that any such gain will impact our capital deployment priorities. There can be no assurance that the transaction will be consummated. Regulatory Requirements Assurant, Inc. is a holding company and, as such, has limited direct operations of its own. Our assets consist primarily of the capital stock of our subsidiaries. Accordingly, our future cash flows depend upon the availability of dividends and other statutorily permissible payments from our subsidiaries. Our subsidiaries’ ability to pay such dividends and make such other payments is regulated by the states and territories in which our subsidiaries are domiciled. These dividend regulations vary by jurisdiction and by type of insurance provided by the applicable subsidiary, but generally require our insurance subsidiaries to maintain minimum solvency requirements and limit the amount of dividends they can pay to the holding company. See “Item 1—Business—Regulation—U.S. Insurance Regulation” and “Item 1A—Risk Factors—Legal and Regulatory Risks—Changes in insurance regulation may reduce our profitability and limit our growth” in our 2025 Annual Report. Along with solvency regulations, the primary driver in determining the amount of capital used for dividends from insurance subsidiaries is the level of capital needed to maintain desired financial strength ratings from A.M. Best Company (“A.M. Best”). For the year ending December 31, 2026, the maximum amount of dividends our regulated U.S. domiciled insurance subsidiaries could pay us, under applicable laws and regulations without prior regulatory approval, is approximately $791.9 million. Our international and non-insurance subsidiaries provide additional sources of dividends. Regulators or rating agencies could become more conservative in their methodology and criteria, increasing capital requirements for our insurance subsidiaries or the enterprise. For further information on our ratings and the risks of ratings downgrades, see “Item 1—Business—Ratings” and “Item 1A—Risk Factors—Financial Risks—A decline in the financial strength ratings of our insurance subsidiaries could adversely affect our results of operations and financial condition” in our 2025 Annual Report. Holding Company As of June 30, 2026, we had approximately $911.5 million in holding company liquidity, $686.5 million above our minimum level of $225.0 million. The minimum level of holding company liquidity, which can be used for unforeseen capital needs at our subsidiaries or liquidity needs at the holding company, is an internal minimum level we seek to maintain, calibrated based on approximately one year of pre-tax corporate operating losses and interest expenses. We use the term “holding company liquidity” to represent the portion of cash and other liquid marketable securities held at Assurant, Inc. (out of a total of $1.04 billion as of June 30, 2026) which we are not otherwise holding for a specific purpose as of the balance sheet date. We can use such assets for stock repurchases, stockholder dividends, acquisitions and other corporate purposes. Dividends or returns of capital paid by our subsidiaries, net of infusions of liquid assets and excluding amounts used for or as a result of acquisitions or received from dispositions, were $372.9 million and $925.1 million for Six Months 2026 and Twelve Months 2025, respectively. We use these cash inflows primarily to pay holding company operating expenses, to make interest payments on indebtedness, to make dividend payments to our common stockholders, to fund investments and acquisitions, and to repurchase our common stock. From time to time, we may also seek to purchase outstanding debt in open market repurchases or privately negotiated transactions. Dividends and Repurchases During Six Months 2026, we made common stock repurchases and paid dividends to our common stockholders of $292.0 million. We paid dividends of $0.88 per common share on June 29, 2026 to stockholders of record as of June 8, 2026. Any determination to declare and pay future dividends is at the sole discretion of the Board of Directors (the “Board”) and depends 41 upon various factors, including: our subsidiaries’ payments of dividends and other statutorily permissible payments to us; our results of operations and cash flows; our financial condition and capital requirements; general business conditions and growth prospects; any legal, tax, regulatory and contractual restrictions on the payment of dividends; and any other factors the Board deems relevant. Payments of dividends on shares of common stock will be restricted if an event of default has occurred or if the proposed common stock dividend payment would cause an event of default under the Credit Facility (as defined below); or if we defer the payment of interest on our 7.00% Fixed-to-Floating Rate Subordinated Notes due March 2048 or our 5.25% Subordinated Notes due January 2061 (refer to “—Senior and Subordinated Notes” below). During Six Months 2026, we repurchased 866,226 shares of our outstanding common stock at a cost of $200.1 million, exclusive of commissions. In November 2025, the Board authorized a share repurchase program for up to $700.0 million of our outstanding common stock. As of June 30, 2026, $574.5 million aggregate cost at purchase remained unused under the November 2025 repurchase authorization. The timing and the amount of future repurchases will depend on various factors, including those listed above. Assurant Subsidiaries The primary sources of funds for our subsidiaries consist of premiums and fees collected, proceeds from the sales and maturity of investments and net investment income. Cash is primarily used to pay insurance claims, agent commissions, operating expenses and taxes. We generally invest our subsidiaries’ funds in order to generate investment income. We conduct periodic asset liability studies to measure the duration of our insurance liabilities, to develop optimal asset portfolio maturity structures for our significant lines of business and ultimately to assess that cash flows are sufficient to meet the timing of cash needs. These studies are conducted in accordance with formal company-wide Asset Liability Management guidelines. To complete a study for a particular line of business, models are developed to project asset and liability cash flows and balance sheet items under a varied set of plausible economic scenarios. These models consider many factors including the current investment portfolio, the required capital for the related assets and liabilities, our tax position and projected cash flows from both existing and projected new business. For risks related to modeling, see “Item 1A – Risk Factors – Financial Risks –Actual results may differ materially from the analytical models we use to assist in our decision-making in key areas such as pricing, catastrophe risks, reserving and capital management.” in our 2025 Annual Report. Alternative asset portfolio asset allocations are analyzed for significant lines of business. An investment portfolio maturity structure is then selected from these profiles given our return hurdle and risk appetite. Scenario testing of significant liability assumptions and new business projections is also performed. Our liabilities generally do not include policyholder optionality, which means that the timing of payments is generally insensitive to the interest rate environment. In addition, our investment portfolio is largely comprised of highly liquid public fixed maturity securities with a sufficient component of such securities invested that are near maturity which may be sold with minimal risk of loss to meet cash needs. Generally, our subsidiaries’ premiums, fees and investment income, along with planned asset sales and maturities, provide sufficient cash to pay claims and expenses. However, there may be instances when unexpected cash needs arise in excess of that available from usual operating sources. In such instances, we have several options to raise needed funds, including selling assets from the subsidiaries’ investment portfolios, using holding company cash (if available), issuing commercial paper, or drawing funds from the Credit Facility. 42 Senior and Subordinated Notes The following table shows the principal amount and carrying value of our outstanding debt, less unamortized discount and issuance costs as applicable, as of June 30, 2026 and December 31, 2025: June 30, 2026 December 31, 2025 Principal Amount Carrying Value Principal Amount Carrying Value 4.90% Senior Notes due March 2028 $ 300.0 $ 299.3 $ 300.0 $ 299.0 3.70% Senior Notes due February 2030 350.0 348.7 350.0 348.5 2.65% Senior Notes due January 2032 350.0 347.9 350.0 347.7 6.75% Senior Notes due February 2034 275.0 273.1 275.0 273.1 5.55% Senior Notes due February 2036 300.0 296.2 300.0 296.1 7.00% Fixed-to-Floating Rate Subordinated Notes due March 2048 400.0 398.7 400.0 398.3 5.25% Subordinated Notes due January 2061 250.0 244.2 250.0 244.2 Total debt $ 2,208.1 $ 2,206.9 In the next five years, we have two debt maturities in March 2028 and February 2030 when the 2028 Senior Notes and the 2030 Senior Notes, respectively, become due and payable. Credit Facility and Commercial Paper Program We have a $500.0 million five-year senior unsecured revolving credit facility (the “Credit Facility”) with certain lenders party thereto, JPMorgan Chase Bank, N.A., as administrative agent, and Wells Fargo Bank, National Association, as syndication agent. The Credit Facility provides for revolving loans and the issuance of multi-bank, syndicated letters of credit and letters of credit from a sole issuing bank in an aggregate amount of $500.0 million, which may be increased up to $750.0 million. The Credit Facility is available until June 2030, provided we are in compliance with all covenants. The Credit Facility has a sublimit for letters of credit issued thereunder of $50.0 million. The proceeds from these loans may be used for our commercial paper program or for general corporate purposes. We made no borrowings under the Credit Facility during Six Months 2026, and no loans were outstanding under the Credit Facility as of June 30, 2026. Our commercial paper program requires us to maintain liquidity facilities either in an available amount equal to any outstanding notes from the program or in an amount sufficient to maintain the ratings assigned to the notes issued from the program. Our commercial paper is rated AMB-1+ by A.M. Best, P-2 by Moody’s and A-2 by S&P. Our subsidiaries do not maintain commercial paper or other borrowing facilities. This program is backed up by the Credit Facility, of which $500.0 million was available as of June 30, 2026. We did not use the commercial paper program during Six Months 2026 and there were no amounts relating to the commercial paper program outstanding as of June 30, 2026. Cash Flows We monitor cash flows at the consolidated, holding company and subsidiary levels. Cash flow forecasts at the consolidated and subsidiary levels are provided on a monthly basis, and we use trend and variance analyses to project future cash needs making adjustments to the forecasts when needed. The table below shows our net cash flows for the periods indicated: For the Six Months Ended June 30, Net cash provided by (used in): 2026 2025 Operating activities $ 694.7 $ 657.9 Investing activities (506.4) (784.5) Financing activities (325.9) (223.0) Effect of exchange rate changes on cash and cash equivalents 2.2 28.6 Net change in cash $ (135.4) $ (321.0) We typically generate operating cash inflows from premiums collected from our insurance products, fees received for services and income received from our investments, while outflows consist of policy acquisition costs, benefits paid and 43 operating expenses. These net cash flows are then invested to support the obligations of our insurance products and required capital supporting these products. Our cash flows from operating activities are affected by the timing of premiums, fees, and investment income received and expenses paid. Net cash provided by operating activities was $694.7 million for Six Months 2026 compared to net cash provided by operating activities of $657.9 million for Six Months 2025. The change in net operating cash flows was largely attributable to growth in our Homeowners and Connected Living businesses and the timing of collections of premiums and fees in our mobile business in Connected Living. Net cash used in investing activities was $506.4 million for Six Months 2026 compared to net cash used in investing activities of $784.5 million for Six Months 2025. The change in net investing cash flows was primarily driven by higher sales of fixed maturity securities during Six Months 2026 and an increase in sales of short-term investments due to the timing of working capital needs. Net cash used in financing activities was $325.9 million for Six Months 2026 compared to net cash used in financing activities of $223.0 million for Six Months 2025. The change in net financing cash flows was primarily due to higher share repurchases during Six Months 2026. The table below shows our cash outflows for interest and dividends for the periods indicated: For the Six Months Ended June 30, 2026 2025 Interest paid on debt $ 56.5 $ 53.7 Common stock dividends 91.9 83.6 Total $ 148.4 $ 137.3 Letters of Credit In the normal course of business, letters of credit are issued for various purposes. These letters of credit are supported by commitments under which we are required to indemnify the financial institution issuing the letter of credit if the letter of credit is drawn. We had $1.4 million and $1.7 million of letters of credit outstanding as of June 30, 2026 and December 31, 2025, respectively. Limited Recourse Note In 2024, we entered into a financing arrangement pursuant to which we are able to issue a $100 million limited recourse note and, in return, obtain a $100 million asset-backed note from a Delaware master trust. As of June 30, 2026, no notes have been issued under this arrangement.