Non-GAAP Financial Measures In this report, the Company presents certain measures of its performance on a consolidated and segment basis that are not calculated in accordance with GAAP. We believe that these non-GAAP financial measures enhance the understanding for the Company and our investors of our performance by highlighting the results of operations and the underlying profitability drivers of our business. Segment-specific financial measures are calculated using only the portion of consolidated results attributable to that specific segment. Adjusted Consolidated Net Operating Income The Company believes that the non-GAAP financial measure of Adjusted Consolidated Net Operating Income provides investors with a valuable measure of its ongoing performance because it reveals underlying operational performance trends that otherwise might be less apparent if the items were not excluded. The most directly comparable GAAP financial measure is Net (Loss) Income attributable to Kemper Corporation. Adjusted Consolidated Net Operating Income is an after-tax, non-GAAP financial measure and is computed by excluding from Net (Loss) Income attributable to Kemper Corporation the after-tax impact of: (i) Change in Fair Value of Equity and Convertible Securities; (ii) Net Realized Investment Gains (Losses); (iii) Impairment Losses; (iv) Acquisition and Disposition Related Transaction, Integration, Restructuring and Other Costs; (v) Debt Extinguishment and Other Charges; (vi) Goodwill Impairment; (vii) Non-Core Operations; and (viii) Significant non-recurring or infrequent items that may not be indicative of ongoing operations Significant non-recurring items are excluded when (a) the nature of the charge or gain is such that it is reasonably unlikely to recur within two years, and (b) there has been no similar charge or gain within the prior two years. There were no applicable significant non-recurring items that the Company excluded from the calculation of Adjusted Consolidated Net Operating Income for the three and six months ended June 30, 2026 or 2025. Change in Fair Value of Equity and Convertible Securities, Net Realized Investment Gains (Losses) and Impairment Losses related to investments included in the Company’s results may vary significantly between periods and are generally driven by business decisions and external economic developments such as capital market conditions that impact the values of the Company’s investments, the timing of which is unrelated to the insurance underwriting process. Acquisition and Disposition Related Transaction Costs, Integration Costs, and Restructuring and Other Costs may vary significantly between periods and are generally driven by the timing of business decisions which are unrelated to the insurance underwriting process. In the second quarter of 2026, the Company completed the sale of Newins and recorded a gain in connection with the transaction. In the third quarter of 2025, a restructuring program was launched to achieve operational and organizational efficiencies. The Company will continue to evaluate additional efficiency opportunities through 2027. Debt Extinguishment and Other Charges relate to (i) loss from early extinguishment of debt, which is driven by the Company’s financing and refinancing decisions and capital needs, as well as external economic developments such as debt market conditions, the timing of which is unrelated to the insurance underwriting process; and (ii) other charges that are non-standard, not part of the ordinary course of business, and unrelated to the insurance underwriting process. Goodwill Impairments are excluded because they are infrequent and non-recurring charges. Non-Core Operations includes the results of our Preferred Insurance business which we expect to fully exit. These results are excluded because they are irrelevant to our ongoing operations and do not qualify for Discontinued Operations under GAAP. Significant non-recurring items are excluded because, by their nature, they are not indicative of the Company’s business or economic trends. 44 Non-GAAP Financial Measures (Continued) Underlying Losses and Loss Adjustment Expenses (“LAE”) and Underlying Combined Ratio The following discussion uses the non-GAAP financial measures of (i) Underlying Losses and LAE and (ii) Underlying Combined Ratio. Underlying Losses and LAE (also referred to in the discussion as “Current Year Non-catastrophe Losses and LAE”) exclude the impact of catastrophe losses and loss and LAE reserve development from prior years from the Company’s Incurred Losses and LAE, which is the most directly comparable GAAP financial measure. The Underlying Combined Ratio is computed by adding the Current Year Non-catastrophe Losses and LAE Ratio with the Insurance Expense Ratio. The most directly comparable GAAP financial measure is the Combined Ratio, which is computed by adding Total Incurred Losses and LAE Ratio, including the impact of catastrophe losses and loss and LAE reserve development from prior years, with the Insurance Expense Ratio. The Company believes Underlying Losses and LAE and the Underlying Combined Ratio are useful to investors and uses these financial measures to reveal the trends in the Company’s Property & Casualty Insurance segment that may be obscured by catastrophe losses and prior-year reserve development. These catastrophe losses may cause the Company’s loss trends to vary significantly between periods as a result of their incidence of occurrence and magnitude and can have a significant impact on incurred losses and LAE and the Combined Ratio. Prior-year reserve developments are caused by unexpected loss development on historical reserves. Because reserve development relates to the re-estimation of losses from earlier periods, it has minimal bearing on the performance of the Company’s insurance products in the current period. The Company believes it is useful for investors to evaluate these components separately and in the aggregate when reviewing the Company’s underwriting performance. The preceding non-GAAP financial measures should not be considered a substitute for the comparable GAAP financial measures, as they do not fully recognize the overall profitability of the Company’s businesses. Summary of Results A reconciliation of Net (Loss) Income attributable to Kemper Corporation to Adjusted Consolidated Net Operating Income (a non-GAAP financial measure) for the three and six months ended June 30, 2026 and 2025 is presented below. Three Months Ended Six Months Ended (Dollars in Millions) Jun 30, 2026 Jun 30, 2025 Change Jun 30, 2026 Jun 30, 2025 Change Net (Loss) Income attributable to Kemper Corporation $ (464.8) $ 72.6 $ (537.4) $ (466.5) $ 172.3 $ (638.8) Less: Change in Fair Value of Equity and Convertible Securities (1.4) (0.4) (1.0) (2.4) (0.3) (2.1) Net Realized Investment Gains (Losses) 0.5 (0.1) 0.6 0.8 0.6 0.2 Impairment Losses (18.8) (2.8) (16.0) (20.1) (2.6) (17.5) Acquisition and Disposition Related Transaction, Integration, Restructuring and Other Costs (11.6) (3.8) (7.8) (16.6) (8.0) (8.6) Debt Extinguishment and Other Charges — — — — 0.4 (0.4) Goodwill Impairment (460.0) — (460.0) (460.0) — (460.0) Non-Core Operations 0.2 (4.4) 4.6 (7.0) (8.3) 1.3 Adjusted Consolidated Net Operating Income $ 26.3 $ 84.1 $ (57.8) $ 38.8 $ 190.5 $ (151.7) Components of Adjusted Consolidated Net Operating Income: Segment Adjusted Net Operating Income: Specialty Property & Casualty Insurance $ 15.8 $ 79.0 $ (63.2) $ 15.9 $ 176.9 $ (161.0) Life Insurance 18.3 12.6 5.7 36.3 29.8 6.5 Total Segment Adjusted Net Operating Income 34.1 91.6 (57.5) 52.2 206.7 (154.5) Corporate and Other Adjusted Net Operating Loss (9.0) (10.3) 1.3 (17.3) (21.7) 4.4 Less: Net Loss attributable to Noncontrolling Interest (1.2) (2.8) 1.6 (3.9) (5.5) 1.6 Adjusted Consolidated Net Operating Income $ 26.3 $ 84.1 $ (57.8) $ 38.8 $ 190.5 $ (151.7) 45 Summary of Results (Continued) Net (Loss) Income attributable to Kemper Corporation Three Months Ended June 30, 2026 Compared to the Same Period in 2025 Net Loss attributable to Kemper Corporation was $464.8 million, or $(7.90) per unrestricted common share, for the three months ended June 30, 2026, compared to Net Income attributable to Kemper Corporation of $72.6 million, or $1.13 per unrestricted common share, for the same period in 2025. Net (Loss) Income attributable to Kemper Corporation decreased by $537.4 million due primarily to a $460.0 million goodwill impairment related to the Specialty Property & Casualty Insurance segment, lower Adjusted Consolidated Net Operating Income and higher impairment losses. Adjusted Consolidated Net Operating Income decreased by $57.8 million for the three months ended June 30, 2026, compared to the same period in 2025, due primarily to a deterioration in Specialty Personal Automobile’s Underlying loss and LAE ratio driven by higher claim severity and frequency on bodily injury coverages in California and lower business volumes. Income from Non-Core Operations increased by $4.6 million for the three months ended June 30, 2026 compared to the same period in 2025, primarily due to lower losses driven by the continued run-off of the business. Separately, on August 1, 2025, certain Non-Core Operations subsidiaries entered into a renewal rights agreement with a third party and certain of its affiliates (collectively, the “Third Party”) whereby the Third Party will offer replacement policies for certain policies written by these subsidiaries in New York in accordance with the state’s non-renewal rules. During the second quarter of 2026, these subsidiaries and the Third Party began execution of the agreement, based on having received regulatory approval from the New York Department of Financial Services during the first quarter of 2026. Corporate and Other Adjusted Net Operating Loss decreased by $1.3 million for the three months ended June 30, 2026 compared to the same period in 2025, primarily driven by higher net investment income. Six Months Ended June 30, 2026 Compared to the Same Period in 2025 Net Loss attributable to Kemper Corporation was $466.5 million, or $(7.93) per unrestricted common share, for the six months ended June 30, 2026, compared to Net Income attributable to Kemper Corporation of $172.3 million, or $2.69 per unrestricted common share, for the same period in 2025. Net (Loss) Income attributable to Kemper Corporation decreased by $638.8 million due primarily to a $460.0 million goodwill impairment related to the Specialty Property & Casualty Insurance segment, lower Adjusted Consolidated Net Operating Income and higher impairment losses. Adjusted Consolidated Net Operating Income decreased by $151.7 million for the six months ended June 30, 2026, compared to the same period in 2025, due primarily to a deterioration in Specialty Personal Automobile’s Underlying loss and LAE ratio driven by higher claim severity and frequency on bodily injury coverages in California, lower business volumes, and a Florida Statutory Profit Limit Refund (as further discussed below). Following the enactment of Florida insurance reform in 2023, the Company has experienced lower loss costs within its personal auto business, resulting in favorable loss reserve development and improved expected profitability for recent accident years. As of December 31, 2025, the Company concluded that it is probable Florida personal auto underwriting profit for the three most recent accident years ended December 31, 2025 will exceed the profit limitation established under Florida statute, and recorded a reduction to earned premiums representing its estimate of profits expected to be returned to policyholders. During the first quarter of 2026, the Company increased its estimate of profits expected to be returned to policyholders for the three most recent accident years ended December 31, 2025 by $11.0 million given favorable development through March 31, 2026. During the first quarter of 2026, the Company also concluded that it is probable underwriting profit for the subsequent three-year accident period (2024 through 2026) will exceed the applicable profit limitation and recorded a reduction to earned premiums of $17.0 million representing its estimate of profits expected to be returned to policyholders for that period. These actions resulted in a total reduction to earned premiums of $28.0 million for the first quarter of 2026. During the second quarter of 2026, the Company increased its estimate of profits expected to be returned to policyholders for accident years 2024 through 2026 and recorded a $2.0 million reduction to earned premiums. The estimate for accident years 2024 through 2026 remains subject to changes based on future development through March 31, 2027. The statute requires that excess profits for accident years 2023 through 2025 be returned to policyholders active as of December 31, 2025, and the Company expects to do so. The loss from Non-Core Operations decreased by $1.3 million for the six months ended June 30, 2026 compared to the same period in 2025, primarily due to lower catastrophe losses, partially offset by higher adverse prior year development. 46 Summary of Results (Continued) Corporate and Other Adjusted Net Operating Loss decreased by $4.4 million for the six months ended June 30, 2026 compared to the same period in 2025, primarily driven by lower interest expense due to the redemption of $450 million of 4.350% senior notes in the first quarter of 2025 and higher net investment income. Revenues Three Months Ended June 30, 2026 Compared to the Same Period in 2025 Total Revenues decreased by $132.9 million to $1,092.7 million for the three months ended June 30, 2026, compared to $1,225.6 million for the same period in 2025. The decrease was primarily driven by lower earned premiums and higher impairment losses, partially offset by higher net investment income. Earned Premiums decreased by $119.2 million to $1,011.6 million for the three months ended June 30, 2026, compared to $1,130.8 for the same period in 2025, primarily driven by a $114.2 million decrease from the Specialty Property & Casualty Insurance segment, mainly attributable to lower personal automobile volumes, and further impacted by a $7.2 million reduction from the Preferred Insurance business, reported as Non-Core Operations, due primarily to lower volumes resulting from the exit and run-off of the business. These decreases were partially offset by higher commercial automobile volumes within the Specialty Property & Casualty Insurance segment. Net Investment Income increased by $9.5 million to $105.4 million for the three months ended June 30, 2026, compared to $95.9 million for the same period in 2025, primarily driven by increased earnings on alternative investments and higher levels and yields of fixed maturity securities, partially offset by lower average Short-term invested assets. Impairment Losses increased by $20.1 million for the three months ended June 30, 2026, compared to the same period in 2025, primarily driven by a $21.0 million credit loss allowance recognized on the Reciprocal Exchange surplus notes. Six Months Ended June 30, 2026 Compared to the Same Period in 2025 Total Revenues decreased by $218.7 million to $2,199.9 million for the six months ended June 30, 2026, compared to $2,418.6 million for the same period in 2025. The decrease was primarily driven by lower earned premiums and higher impairment losses, partially offset by higher net investment income. Earned Premiums decreased by $207.8 million to $2,010.9 million for the six months ended June 30, 2026, compared to $2,218.7 for the same period in 2025, primarily driven by a $191.2 million decrease from the Specialty Property & Casualty Insurance segment, mainly attributable to lower personal automobile volumes, a $30.0 million Florida Statutory Profit Limit Refund in the first half of 2026, and further impacted by a $19.9 million reduction from the Preferred Insurance business, reported as Non-Core Operations, due primarily to lower volumes resulting from the exit and run-off of the business. These decreases were partially offset by higher commercial automobile volumes within the Specialty Property & Casualty Insurance segment. Net Investment Income increased by $15.4 million to $212.5 million for the six months ended June 30, 2026, compared to $197.1 million for the same period in 2025, primarily driven by increased earnings on alternative investments and higher levels and yields of fixed maturity securities, partially offset by lower average Short-term invested assets. Impairment Losses increased by $22.1 million for the six months ended June 30, 2026, compared to the same period in 2025, primarily driven by a $21.0 million credit loss allowance recognized on the Reciprocal Exchange surplus notes. 47 Specialty Property & Casualty Insurance Selected financial information for the Specialty Property & Casualty Insurance segment is presented below. Three Months Ended Six Months Ended (Dollars in Millions) Jun 30, 2026 Jun 30, 2025 Jun 30, 2026 Jun 30, 2025 Net Premiums Written $ 854.7 $ 1,001.5 $ 1,779.7 $ 2,070.3 Earned Premiums $ 896.6 $ 1,010.8 $ 1,781.8 $ 1,973.0 Net Investment Income 53.7 49.6 109.0 100.1 Other Income 1.3 2.7 4.0 4.0 Total Revenues 951.6 1,063.1 1,894.8 2,077.1 Incurred Losses and LAE related to: Current Year: Non-catastrophe Losses and LAE 732.7 730.1 1,475.5 1,412.4 Catastrophe Losses and LAE 6.1 5.3 7.4 9.1 Prior Years: Non-catastrophe Losses and LAE 9.1 13.6 12.3 14.1 Catastrophe Losses and LAE 0.1 0.4 0.5 0.6 Total Incurred Losses and LAE 748.0 749.4 1,495.7 1,436.2 Insurance Expenses 184.3 214.8 380.5 419.9 Segment Adjusted Operating Income 19.3 98.9 18.6 221.0 Income Tax Expense 3.5 19.9 2.7 44.1 Total Segment Adjusted Net Operating Income $ 15.8 $ 79.0 $ 15.9 $ 176.9 Ratios Based On Earned Premiums Current Year Non-catastrophe Losses and LAE Ratio 81.7 % 72.3 % 82.8 % 71.6 % Current Year Catastrophe Losses and LAE Ratio 0.7 0.5 0.4 0.5 Prior Years Non-catastrophe Losses and LAE Ratio 1.0 1.3 0.7 0.7 Prior Years Catastrophe Losses and LAE Ratio — — — — Total Incurred Loss and LAE Ratio 83.4 74.1 83.9 72.8 Insurance Expense Ratio 20.6 21.3 21.4 21.3 Combined Ratio 104.0 % 95.4 % 105.3 % 94.1 % Underlying Combined Ratio Current Year Non-catastrophe Losses and LAE Ratio 81.7 % 72.3 % 82.8 % 71.6 % Insurance Expense Ratio 20.6 21.3 21.4 21.3 Underlying Combined Ratio 102.3 % 93.6 % 104.2 % 92.9 % Non-GAAP Measure Reconciliation Combined Ratio 104.0 % 95.4 % 105.3 % 94.1 % Less: Current Year Catastrophe Losses and LAE Ratio 0.7 0.5 0.4 0.5 Prior Years Non-catastrophe Losses and LAE Ratio 1.0 1.3 0.7 0.7 Prior Years Catastrophe Losses and LAE Ratio — — — — Underlying Combined Ratio 102.3 % 93.6 % 104.2 % 92.9 % 48 Specialty Property & Casualty Insurance (Continued) Insurance Reserves (Dollars in Millions) Jun 30, 2026 Dec 31, 2025 Insurance Reserves: Personal Automobile $ 1,893.9 $ 1,826.8 Commercial Automobile 1,063.7 942.6 Total Insurance Reserves $ 2,957.6 $ 2,769.4 Insurance Reserves: Loss and Allocated LAE Reserves: Case and Allocated LAE $ 1,063.5 $ 960.4 Incurred But Not Reported 1,699.3 1,610.9 Total Loss and LAE Reserves 2,762.8 2,571.3 Unallocated LAE Reserves 194.8 198.1 Total Insurance Reserves1 $ 2,957.6 $ 2,769.4 1 Includes $31.1 million and $29.4 million attributable to Kemper Reciprocal as of June 30, 2026 and December 31, 2025, respectively, which is reported as a consolidated VIE. See MD&A, “Critical Accounting Estimates,” of the 2025 Annual Report for additional information pertaining to the Company’s process of estimating property and casualty insurance reserves for losses and LAE, development of property and casualty insurance losses and LAE from prior accident years, also referred to as “reserve development” in the discussion of segment results, estimated variability of property and casualty insurance reserves for losses and LAE, and a discussion of some of the variables that may impact development of property and casualty insurance losses and LAE and the estimated variability of property and casualty insurance reserves for losses and LAE. Overall Three Months Ended June 30, 2026 Compared to the Same Period in 2025 The Specialty Property & Casualty Insurance segment reported Total Segment Adjusted Net Operating Income of $15.8 million for the three months ended June 30, 2026, compared to $79.0 million for the same period in 2025. Segment adjusted net operating results decreased by $63.2 million, which included a $60.6 million decrease from personal automobile insurance and a $2.6 million decrease from commercial automobile insurance. The decrease in personal automobile Adjusted Net Operating Income was primarily driven by higher underlying losses resulting from higher claim severity and frequency in California and lower business volumes. The decrease in commercial automobile insurance Adjusted Net Operating Income was primarily driven by higher underlying losses resulting from higher claim severity and frequency, partially offset by higher business volumes. Earned Premiums in the Specialty Property & Casualty Insurance segment decreased by $114.2 million for the three months ended June 30, 2026, compared to the same period in 2025, primarily due to lower personal automobile volumes, partially offset by higher commercial automobile volumes. Net Investment Income increased by $4.1 million for the three months ended June 30, 2026 compared to the same period in 2025, due primarily to higher levels and yields from fixed maturity securities and increased earnings on alternative investments, partially offset by lower average short-term investments. 49 Specialty Property & Casualty Insurance (Continued) Incurred Loss and LAE were $748.0 million or 83.4% of earned premiums for the three months ended June 30, 2026 compared to $749.4 million or 74.1% of earned premiums, for the same period in 2025. Incurred losses and LAE as a percentage of earned premiums increased primarily due to a deterioration in the underlying loss and LAE ratio. Underlying losses and LAE as a percentage of earned premiums were 81.7% for the three months ended June 30, 2026, a deterioration of 9.4 percentage points, compared to the same period in 2025, due to higher claim severity and frequency primarily related to bodily injury coverages in California. Underlying losses and LAE exclude the impact of catastrophes and loss and LAE reserve development. Adverse loss and LAE reserve development (including catastrophe reserve development) was $9.2 million for the three months ended June 30, 2026, compared to adverse development of $14.0 million for the same period in 2025, an improvement of $4.8 million, due primarily to favorable development on personal injury protection and collision coverages in personal automobile, partially offset by adverse loss patterns in bodily injury and higher losses associated with litigation matters. Catastrophe losses and LAE (excluding reserve development) were $6.1 million for the three months ended June 30, 2026 compared to $5.3 million for the same period in 2025, a deterioration of $0.8 million due to increased severity of catastrophe events in 2026. Insurance Expenses were $184.3 million, or 20.6% of earned premiums, for the three months ended June 30, 2026, compared to $214.8 million, or 21.3% of earned premiums for the same period in 2025. Insurance Expenses decreased $30.5 million due to lower expenses associated with decreased business volumes. The Specialty Property & Casualty Insurance segment’s three months ended June 30, 2026 effective tax rate was 18.9% compared to 20.3% for the same period in 2025. The effective income tax rate for the second quarters of 2026 and 2025 differs from the federal statutory income tax rate due to investments in Company-Owned Life Insurance, tax-exempt investment income and nondeductible stock and executive compensation. The difference in effective tax rates between the second quarters of 2026 and 2025 is primarily due to changes in pretax income. Six Months Ended June 30, 2026 Compared to the Same Period in 2025 The Specialty Property & Casualty Insurance segment reported Total Segment Adjusted Net Operating Income of $15.9 million for the six months ended June 30, 2026, compared to Total Segment Adjusted Net Operating Income of $176.9 million for the same period in 2025. Segment adjusted net operating results decreased by $161.0 million, which included a $161.5 million decrease from personal automobile insurance and a $0.5 million increase from commercial automobile insurance. The decrease in personal automobile Adjusted Net Operating Income was primarily driven by higher underlying losses resulting from higher claim severity and frequency in California, lower business volumes, as well as a $30.0 million Florida Statutory Profit Limit Refund in the first half of 2026. The increase in commercial automobile insurance Adjusted Net Operating Income was primarily driven by higher earned premium per exposure, partially offset by higher underlying losses. Earned Premiums in the Specialty Property & Casualty Insurance segment decreased by $191.2 million for the six months ended June 30, 2026, compared to the same period in 2025, due to lower personal automobile volumes and a $30.0 million Florida Statutory Profit Limit Refund in the first half of 2026, partially offset by higher commercial automobile volumes. Net Investment Income increased by $8.9 million for the six months ended June 30, 2026 compared to the same period in 2025, due primarily to higher levels and yields of fixed maturity securities and increased earnings on alternative investments, partially offset by lower average short-term investments. Incurred Loss and LAE were $1,495.7 million or 83.9% of earned premiums for the six months ended June 30, 2026 compared to $1,436.2 million or 72.8% of earned premiums, for the same period in 2025. Incurred losses and LAE as a percentage of earned premiums increased primarily due to a deterioration in the underlying loss and LAE ratio. Underlying losses and LAE as a percentage of earned premiums were 82.8% for the six months ended June 30, 2026, a deterioration of 11.2 percentage points, compared to the same period in 2025 due to higher claim severity and frequency primarily related to bodily injury coverages in California, partially offset by higher average earned premium per exposure (3.0% increase year over year). Underlying losses and LAE exclude the impact of catastrophes and loss and LAE reserve development. Adverse loss and LAE reserve development (including catastrophe reserve development) was $12.8 million for the six months ended June 30, 2026, compared to adverse development of $14.7 million for the same period in 2025, an improvement of $1.9 million due primarily to development on personal injury protection and collision coverages in personal automobile, partially offset by loss patterns in bodily injury and higher losses associated with litigation matters. Catastrophe losses and LAE (excluding reserve development) were $7.4 million for the six months ended June 30, 2026 compared to $9.1 million for the same period in 2025, a decrease of $1.7 million due to fewer catastrophe events in 2026. 50 Specialty Property & Casualty Insurance (Continued) Insurance Expenses were $380.5 million, or 21.4% of earned premiums, for the six months ended June 30, 2026, compared to $419.9 million, or 21.3% of earned premiums for the same period in 2025. Insurance Expenses decreased $39.4 million due to lower expenses associated with decreased business volumes. The Specialty Property & Casualty Insurance segment’s six months ended June 30, 2026 effective tax rate was 15.5% compared to 20.3% for the same period in 2025. The effective income tax rate for the six months ended June 30, 2026 and 2025 differs from the federal statutory income tax rate due to investments in Company-Owned Life Insurance, tax-exempt investment income and nondeductible stock and executive compensation. The difference in effective tax rates between the six months ended 2026 and 2025 is primarily due to changes in pretax income. Specialty Personal Automobile Insurance Selected financial information for the specialty personal automobile insurance product line is presented below. Three Months Ended Six Months Ended (Dollars in Millions) Jun 30, 2026 Jun 30, 2025 Jun 30, 2026 Jun 30, 2025 Net Premiums Written $ 590.7 $ 767.0 $ 1,241.1 $ 1,590.9 Earned Premiums $ 647.4 $ 789.3 $ 1,294.4 $ 1,543.0 Incurred Losses and LAE related to: Current Year: Non-catastrophe Losses and LAE $ 543.1 $ 571.7 $ 1,111.2 $ 1,100.1 Catastrophe Losses and LAE 5.1 4.3 6.2 7.0 Prior Years: Non-catastrophe Losses and LAE (8.6) (5.0) (11.5) (9.7) Catastrophe Losses and LAE — 0.3 0.4 0.4 Total Incurred Losses and LAE $ 539.6 $ 571.3 $ 1,106.3 $ 1,097.8 Ratios Based On Earned Premiums Current Year Non-catastrophe Losses and LAE Ratio 83.8 % 72.5 % 85.9 % 71.2 % Current Year Catastrophe Losses and LAE Ratio 0.8 0.5 0.5 0.5 Prior Years Non-catastrophe Losses and LAE Ratio (1.3) (0.6) (0.9) (0.6) Prior Years Catastrophe Losses and LAE Ratio — — — — Total Incurred Loss and LAE Ratio 83.3 72.4 85.5 71.1 Insurance Expense Ratio 21.7 22.0 22.5 22.1 Combined Ratio 105.0 % 94.4 % 108.0 % 93.2 % Underlying Combined Ratio Current Year Non-catastrophe Losses and LAE Ratio 83.8 % 72.5 % 85.9 % 71.2 % Insurance Expense Ratio 21.7 22.0 22.5 22.1 Underlying Combined Ratio 105.5 % 94.5 % 108.4 % 93.3 % Non-GAAP Measure Reconciliation Combined Ratio 105.0 % 94.4 % 108.0 % 93.2 % Less: Current Year Catastrophe Losses and LAE Ratio 0.8 0.5 0.5 0.5 Prior Years Non-catastrophe Losses and LAE Ratio (1.3) (0.6) (0.9) (0.6) Prior Years Catastrophe Losses and LAE Ratio — — — — Underlying Combined Ratio 105.5 % 94.5 % 108.4 % 93.3 % 51 Specialty Property & Casualty Insurance (Continued) Three Months Ended June 30, 2026 Compared to the Same Period in 2025 Earned Premiums on personal automobile insurance decreased by $141.9 million for the three months ended June 30, 2026, compared to the same period in 2025, primarily due to lower volumes. Incurred losses and LAE were $539.6 million, or 83.3% of earned premiums for the three months ended June 30, 2026, compared to $571.3 million, or 72.4% of earned premiums, for the same period in 2025. Incurred losses and LAE as a percentage of earned premiums increased due to a deterioration in the underlying loss and LAE ratio. Underlying losses and LAE as a percentage of related earned premiums were 83.8% for the three months ended June 30, 2026, compared to 72.5% for the same period in 2025, a deterioration of 11.3 percentage points. The deterioration was driven by higher claim severity and frequency, primarily related to bodily injury coverages in California. Prior year favorable loss and LAE reserve development was $8.6 million for the three months ended June 30, 2026, compared to $4.7 million for the same period in 2025, an improvement of $3.9 million due primarily to development on personal injury protection and collision coverages, partially offset by loss patterns in bodily injury and higher losses associated with litigation matters. Catastrophe losses and LAE (excluding reserve development) were $5.1 million for the three months ended June 30, 2026, compared to $4.3 million for the same period in 2025, a deterioration of $0.8 million due to increased severity of catastrophe events in 2026. Six Months Ended June 30, 2026 Compared to the Same Period in 2025 Earned Premiums on personal automobile insurance decreased by $248.6 million for the six months ended June 30, 2026, compared to the same period in 2025, primarily due to lower volumes and a $30.0 million Florida Statutory Profit Limit Refund in the first half of 2026. Incurred losses and LAE were $1,106.3 million, or 85.5% of earned premiums for the six months ended June 30, 2026, compared to $1,097.8 million, or 71.1% of earned premiums, for the same period in 2025. Incurred losses and LAE as a percentage of earned premiums increased due to a deterioration in the underlying loss and LAE ratio. Underlying losses and LAE as a percentage of related earned premiums were 85.9% for the six months ended June 30, 2026, compared to 71.2% for the same period in 2025, a deterioration of 14.7 percentage points. The deterioration was driven by higher claim severity and frequency, primarily related to bodily injury coverages in California, and the Florida Statutory Profit Limit Refund in the first half of 2026. Favorable loss and LAE reserve development was $11.1 million for the six months ended June 30, 2026, compared to $9.3 million for the same period in 2025, an improvement of $1.8 million due primarily to development on personal injury protection and collision coverages, partially offset by loss patterns in bodily injury and higher losses associated with litigation matters. Catastrophe losses and LAE (excluding reserve development) were $6.2 million for the six months ended June 30, 2026, compared to $7.0 million for the same period in 2025, an improvement of $0.8 million due to fewer catastrophe events in 2026. 52 Specialty Property & Casualty Insurance (Continued) Commercial Automobile Insurance Selected financial information for the commercial automobile insurance product line is presented below. Three Months Ended Six Months Ended (Dollars in Millions) Jun 30, 2026 Jun 30, 2025 Jun 30, 2026 Jun 30, 2025 Net Premiums Written $ 264.0 $ 234.5 $ 538.6 $ 479.4 Earned Premiums $ 249.2 $ 221.5 $ 487.4 $ 430.0 Incurred Losses and LAE related to: Current Year: Non-catastrophe Losses and LAE $ 189.6 $ 158.4 $ 364.3 $ 312.3 Catastrophe Losses and LAE 1.0 1.0 1.2 2.1 Prior Years: Non-catastrophe Losses and LAE 17.7 18.6 23.8 23.8 Catastrophe Losses and LAE 0.1 0.1 0.1 0.2 Total Incurred Losses and LAE $ 208.4 $ 178.1 $ 389.4 $ 338.4 Ratios Based On Earned Premiums Current Year Non-catastrophe Losses and LAE Ratio 76.1 % 71.5 % 74.8 % 72.7 % Current Year Catastrophe Losses and LAE Ratio 0.4 0.5 0.2 0.5 Prior Years Non-catastrophe Losses and LAE Ratio 7.1 8.4 4.9 5.5 Prior Years Catastrophe Losses and LAE Ratio — — — — Total Incurred Loss and LAE Ratio 83.6 80.4 79.9 78.7 Insurance Expense Ratio 17.6 18.6 18.3 18.5 Combined Ratio 101.2 % 99.0 % 98.2 % 97.2 % Underlying Combined Ratio Current Year Non-catastrophe Losses and LAE Ratio 76.1 % 71.5 % 74.8 % 72.7 % Insurance Expense Ratio 17.6 18.6 18.3 18.5 Underlying Combined Ratio 93.7 % 90.1 % 93.1 % 91.2 % Non-GAAP Measure Reconciliation Combined Ratio 101.2 % 99.0 % 98.2 % 97.2 % Less: Current Year Catastrophe Losses and LAE Ratio 0.4 0.5 0.2 0.5 Prior Years Non-catastrophe Losses and LAE Ratio 7.1 8.4 4.9 5.5 Prior Years Catastrophe Losses and LAE Ratio — — — — Underlying Combined Ratio 93.7 % 90.1 % 93.1 % 91.2 % 53 Specialty Property & Casualty Insurance (Continued) Three Months Ended June 30, 2026 Compared to the Same Period in 2025 Earned Premiums on commercial automobile insurance increased by $27.7 million for the three months ended June 30, 2026, compared to the same period in 2025, due primarily to higher average earned premium per exposure, targeted mix shifts, and higher business volumes. Incurred losses and LAE were $208.4 million, or 83.6% of earned premiums in 2026, compared to $178.1 million, or 80.4% of earned premiums in 2025. Incurred losses and LAE as a percentage of earned premiums increased primarily due to a deterioration in the underlying loss and LAE ratio. Underlying losses and LAE as a percentage of earned premiums were 76.1% in the three months ended June 30, 2026, compared to 71.5% during the same period in 2025, a deterioration of 4.6 percentage points driven by higher claim severity and frequency, primarily related to bodily injury coverages, partially offset by higher average earned premium per exposure (1.6% increase year over year). Adverse loss and LAE reserve development was $17.8 million for the three months ended June 30, 2026, compared to adverse development of $18.7 million for the same period in 2025, a decrease of $0.9 million. Catastrophe losses and LAE (excluding reserve development) were $1.0 million for the three months ended June 30, 2026 and 2025, respectively. Six Months Ended June 30, 2026 Compared to the Same Period in 2025 Earned Premiums on commercial automobile insurance increased by $57.4 million for the six months ended June 30, 2026, compared to the same period in 2025, due primarily to higher average earned premium per exposure, targeted mix shifts, and higher business volumes. Incurred losses and LAE were $389.4 million, or 79.9% of earned premiums in 2026, compared to $338.4 million, or 78.7% of earned premiums in 2025. Incurred losses and LAE as a percentage of earned premiums increased primarily due to a deterioration in the underlying loss and LAE ratio. Underlying losses and LAE as a percentage of earned premiums were 74.8% for the six months ended June 30, 2026, compared to 72.7% during the same period in 2025, a deterioration of 2.1 percentage points driven by higher claim severity, primarily related to bodily injury coverages, partially offset by higher average earned premium per exposure (2.0% increase year over year). Adverse loss and LAE reserve development was $23.9 million for the six months ended June 30, 2026, compared to adverse development of $24.0 million for the same period in 2025, a decrease of $0.1 million. Catastrophe losses and LAE (excluding reserve development) were $1.2 million for the six months ended June 30, 2026, compared to $2.1 million for the same period in 2025, a decrease of $0.9 million. Life Insurance Selected financial information for the Life Insurance segment is presented below. Three Months Ended Six Months Ended (Dollars in Millions) Jun 30, 2026 Jun 30, 2025 Jun 30, 2026 Jun 30, 2025 Earned Premiums $ 102.7 $ 100.5 $ 203.5 $ 200.2 Net Investment Income 49.3 44.7 98.0 93.1 Other Income 0.4 0.3 0.7 1.0 Total Revenues 152.4 145.5 302.2 294.3 Policyholders’ Benefits and Incurred Losses and LAE 63.5 63.5 127.5 125.7 Insurance Expenses 67.3 67.7 131.9 134.1 Segment Adjusted Operating Income 21.6 14.3 42.8 34.5 Income Tax Expense 3.3 1.7 6.5 4.7 Total Segment Adjusted Net Operating Income $ 18.3 $ 12.6 $ 36.3 $ 29.8 54 Life Insurance (Continued) Insurance Reserves (Dollars in Millions) Jun 30, 2026 Dec 31, 2025 Insurance Reserves: Future Policyholder Benefits $ 3,238.1 $ 3,248.1 Incurred Losses and LAE Reserves: Life 35.3 35.0 Accident and Health 4.7 4.4 Property 1.8 1.9 Total Incurred Losses and LAE Reserves 41.8 41.3 Total Insurance Reserves $ 3,279.9 $ 3,289.4 Overall Three Months Ended June 30, 2026 Compared to the Same Period in 2025 The Life Insurance segment reported Total Segment Adjusted Net Operating Income of $18.3 million for the three months ended June 30, 2026, compared to $12.6 million for the same period in 2025. The increase in segment net operating results was due primarily to higher Net Investment Income and Earned Premiums. Earned Premiums increased by $2.2 million for the three months ended June 30, 2026, compared to the same period in 2025, due primarily to higher average premiums per policy on life insurance products. Net Investment Income increased by $4.6 million for the three months ended June 30, 2026, compared to the same period in 2025, due primarily to increased earnings on alternative investments. Policyholders’ Benefits and Incurred Losses and LAE were flat for the three months ended June 30, 2026, compared to the same period in 2025, due to lower Incurred Losses and LAE on property insurance products offset by an increase in insurance reserves related to favorable changes in mortality experience. Insurance Expenses decreased by $0.4 million for the three months ended June 30, 2026, compared to the same period in 2025, due to management actions to lower operating expenses and lower commission expense. The Life Insurance segment’s three months ended June 30, 2026 effective income tax rate was 15.1% compared to 12.7% for the same period in 2025. The effective income tax rate for the second quarters of 2026 and 2025 differs from the federal statutory income tax rate primarily due to investments in Company-Owned Life Insurance, tax-exempt investment income and nondeductible stock and executive compensation. The increase in the effective tax rate from the three months ended June 30, 2025 is primarily due to an increase in pretax income and an increase in tax expense related to nondeductible stock and executive compensation, partially offset by an increase in tax benefits from Company-Owned Life Insurance. Six Months Ended June 30, 2026 Compared to the Same Period in 2025 The Life Insurance segment reported Total Segment Adjusted Net Operating Income of $36.3 million for the six months ended June 30, 2026, compared to $29.8 million for the same period in 2025. The increase in segment net operating results was due primarily to higher Net Investment Income, higher Earned Premiums, and lower Insurance Expenses, partially offset by higher Policyholders’ Benefits from life insurance products. Earned Premiums increased by $3.3 million for the six months ended June 30, 2026, compared to the same period in 2025, due primarily to higher average premiums per policy on life insurance products. Net Investment Income increased by $4.9 million for the six months ended June 30, 2026, compared to the same period in 2025, due primarily to increased earnings on alternative investments and higher earnings on Company-Owned Life Insurance, partially offset by lower yields on fixed maturities. 55 Life Insurance (Continued) Policyholders’ Benefits and Incurred Losses and LAE increased by $1.8 million for the six months ended June 30, 2026, compared to the same period in 2025, due to an increase in insurance reserves related to favorable changes in mortality experience. Insurance Expenses decreased by $2.2 million for the six months ended June 30, 2026, compared to the same period in 2025, due to management actions to lower operating expenses and lower commission expense. The Life Insurance segment’s six months ended June 30, 2026 effective income tax rate was 15.1% compared to 14.0% for the same period in 2025. The effective income tax rate for the six months ended June 30, 2026 and 2025 differs from the federal statutory income tax rate due to investments in Company-Owned Life Insurance, tax-exempt investment income and nondeductible stock and executive compensation. The increase in the effective tax rate from the six months ended June 30, 2025 is primarily due to an increase in pretax income and an increase in tax expense related to nondeductible stock and executive compensation, partially offset by an increase in tax benefits from Company-Owned Life Insurance. 56 Investment Results Net Investment Income Net Investment Income for the three and six months ended June 30, 2026 and 2025 is presented below: Three Months Ended Six Months Ended (Dollars in Millions) Jun 30, 2026 Jun 30, 2025 Jun 30, 2026 Jun 30, 2025 Investment Income: Interest on Fixed Maturities1 $ 80.9 $ 76.9 $ 160.3 $ 153.3 Dividends on Equity Securities Excluding Alternative Investments 2.1 0.7 2.8 1.5 Alternative Investments: Equity Method Limited Liability Investments 1.2 (5.3) 1.8 (6.0) Limited Liability Investments Included in Equity Securities 3.5 3.1 10.6 6.8 Total Alternative Investments 4.7 (2.2) 12.4 0.8 Short-term Investments 2.7 6.0 5.8 14.6 Loans to Policyholders 5.2 5.1 10.5 10.4 Real Estate 2.7 2.3 5.0 4.5 Company-Owned Life Insurance 12.1 10.5 23.6 20.7 Other 3.3 3.3 7.3 5.3 Total Investment Income 113.7 102.6 227.7 211.1 Investment Expenses: Real Estate 2.7 2.2 4.5 4.3 Other Investment Expenses 5.6 4.5 10.7 9.7 Total Investment Expenses 8.3 6.7 15.2 14.0 Net Investment Income $ 105.4 $ 95.9 $ 212.5 $ 197.1 1 Reduced by interest expense incurred on FHLB borrowings used for spread lending purposes of $3.5 million and $4.8 million for the three months ended June 30, 2026 and 2025, respectively, and $7.4 million and $9.6 million for the six months ended June 30, 2026 and 2025, respectively. Net Investment Income increased by $9.5 million and $15.4 million for the three and six months ended June 30, 2026, respectively, compared to the same periods in 2025, primarily driven by increased earnings on alternative investments and higher levels and yields from fixed maturity securities, partially offset by lower average Short-term invested assets. Change in Unrealized Gains and Losses on Investments Unrealized losses on investments decreased $50.9 million for the three months ended June 30, 2026 and increased $38.6 million for the six months ended June 30, 2026, driven by changes in interest rates. 57 Investment Results (Continued) Change in Fair Value of Equity and Convertible Securities The components of Change in Fair Value of Equity and Convertible Securities for the three and six months ended June 30, 2026 and 2025 are presented below: Three Months Ended Six Months Ended (Dollars in Millions) Jun 30, 2026 Jun 30, 2025 Jun 30, 2026 Jun 30, 2025 Preferred Stocks $ 0.3 $ (0.3) $ 0.3 $ 0.5 Common Stocks 0.8 0.4 0.9 0.7 Other Equity Interests: Exchange Traded Funds (0.4) — 0.4 — Limited Liability Companies and Limited Partnerships (2.4) (0.6) (4.6) (1.6) Total Other Equity Interests (2.8) (0.6) (4.2) (1.6) Change in Fair Value of Equity Securities (1.7) (0.5) (3.0) (0.4) Change in Fair Value of Convertible Securities — — — — Change in Fair Value of Equity and Convertible Securities $ (1.7) $ (0.5) $ (3.0) $ (0.4) Net Realized Gains (Losses) on Sales of Investments The components of Net Realized Investment Gains (Losses) for the three and six months ended June 30, 2026 and 2025 are presented below: Three Months Ended Six Months Ended (Dollars in Millions) Jun 30, 2026 Jun 30, 2025 Jun 30, 2026 Jun 30, 2025 Fixed Maturities: Gains on Sales $ 1.3 $ 0.4 $ 3.9 $ 1.7 Losses on Sales (0.7) (0.5) (3.1) (1.0) Equity Securities: Gains on Sales — — 0.2 — Losses on Sales — — — — Other Investments: Gains on Sales — — — 0.1 Losses on Sales — — — — Net Realized Investment Gains (Losses) $ 0.6 $ (0.1) $ 1.0 $ 0.8 Gross Gains on Sales $ 1.3 $ 0.4 $ 4.1 $ 1.8 Gross Losses on Sales (0.7) (0.5) (3.1) (1.0) Net Realized Investment Gains (Losses) $ 0.6 $ (0.1) $ 1.0 $ 0.8 Impairment Losses The Company regularly reviews its investment portfolio to determine whether a decline in the fair value of an investment has occurred from credit or other, non-credit related factors. If the decline in fair value is due to credit factors and the Company does not expect to receive cash flows sufficient to support the entire amortized cost basis, the credit loss is reported in the Condensed Consolidated Statements of (Loss) Income in the period that the declines are evaluated. Conversely, an increase in the fair value or disposal of an investment with a previously established credit allowance will result in the reversal of impairment losses reported in the Condensed Consolidated Statements of (Loss) Income in the period. 58 Investment Results (Continued) The components of Impairment Losses in the Condensed Consolidated Statements of (Loss) Income for the three and six months ended June 30, 2026 and 2025 were: Three Months Ended Six Months Ended Jun 30, 2026 Jun 30, 2025 Jun 30, 2026 Jun 30, 2025 (Dollars in Millions) Amount Number of Issuers Amount Number of Issuers Amount Number of Issuers Amount Number of Issuers Other Assets1 $ (21.0) 1 $ — — $ (21.0) 1 $ — — Fixed Maturities (2.7) 12 (3.6) 18 (3.5) 15 (3.3) 18 Real Estate (0.6) 2 — — (0.8) 3 — — Other 0.6 1 — — (0.1) 9 — — Impairment Losses2 $ (23.7) $ (3.6) $ (25.4) $ (3.3) 1 During the second quarter of 2026, the Company established an allowance for credit loss for the surplus notes related to the Reciprocal Exchange. See Note 9, "Variable Interest Entities" to the Condensed Consolidated Financial Statements for more information. 2 Includes losses from intent-to-sell securities and direct write-down securities of $0.7 million and $1.2 million for the three and six months ended June 30, 2026, respectively, and $0.1 million and $1.3 million for the three and six months ended June 30, 2025, respectively. Investment Quality and Concentrations The Company’s fixed maturity investment portfolio is comprised primarily of high-grade corporate, municipal and agency bonds. At June 30, 2026, approximately 93.3% of the Company’s fixed maturity investment portfolio was rated investment-grade, which the Company defines as a security issued by a high quality obligor with at least a relatively stable credit profile and where it is highly likely that all contractual payments of principal and interest will timely occur and carry a rating from the National Association of Insurance Commissioners (“NAIC”) of 1 or 2. Securities with a rating of 1 or 2 from the NAIC typically are rated by one or more Nationally Recognized Statistical Rating Organizations and either have a rating of AAA, AA, A or BBB from Standard & Poor’s (“S&P”); a rating of Aaa, Aa, A or Baa from Moody’s Investors Service (“Moody’s”); or a rating of AAA, AA, A or BBB from Fitch Ratings. The following table summarizes the credit quality of the Company’s fixed maturity investment portfolio at June 30, 2026 and December 31, 2025: (Dollars in Millions) Jun 30, 2026 Dec 31, 2025 NAIC Rating Rating Amortized Cost Fair Value Percentage of Total Amortized Cost Fair Value Percentage of Total 1 AAA, AA, A $ 5,267.6 $ 4,674.8 69.6 % $ 5,319.9 $ 4,750.5 70.5 % 2 BBB 1,746.7 1,595.3 23.7 1,710.2 1,574.4 23.3 3-4 BB, B 418.7 410.1 6.1 390.6 375.1 5.6 5-6 CCC or Lower 62.1 40.9 0.6 55.0 43.3 0.6 Total Investments in Fixed Maturities $ 7,495.1 $ 6,721.1 100.0 % $ 7,475.7 $ 6,743.3 100.0 % Gross unrealized losses on the Company’s investments in below-investment-grade fixed maturities were $11.6 million and $13.6 million at June 30, 2026 and December 31, 2025, respectively. 59 Investment Quality and Concentrations (Continued) The following table summarizes the fair value of the Company’s investments in governmental fixed maturities at June 30, 2026 and December 31, 2025: Jun 30, 2026 Dec 31, 2025 (Dollars in Millions) Fair Value Percentage of Total Investments Fair Value Percentage of Total Investments U.S. Government and Government Agencies and Authorities $ 641.8 7.4 % $ 622.4 7.2 % States and Political Subdivisions: Revenue Bonds 1,106.4 12.8 1,128.5 13.0 States 67.8 0.8 68.7 0.8 Political Subdivisions 59.1 0.7 56.1 0.6 Foreign Governments 8.5 0.1 11.0 0.1 Total Investments in Governmental Fixed Maturities $ 1,883.6 21.8 % $ 1,886.7 21.7 % The following table summarizes the fair value of the Company’s investments in non-governmental fixed maturities by range of amounts invested at June 30, 2026: (Dollars in Millions) Number of Issuers Aggregate Fair Value Below $5 753 $ 1,420.7 $5 -$10 187 1,360.5 $10 - $20 106 1,411.9 $20 - $30 19 436.9 Greater Than $30 6 207.5 Total 1,071 $ 4,837.5 The Company’s short-term investments primarily consist of money market funds, U.S. Treasury bills and short-term bonds. At June 30, 2026, the Company had $198.5 million invested in money market funds, which primarily invest in U.S. Treasury securities, and $72.9 million invested in U.S. Treasury bills and short-term bonds. 60 Investments in Limited Liability Companies and Limited Partnerships The Company owns investments in various limited liability investment companies and limited partnerships that primarily invest in senior debt, mezzanine debt, and leveraged buyouts. Investments in limited liability investment companies and limited partnerships are reported either as Equity Method Limited Liability Investments, Other Equity Interests included in Equity Securities at Fair Value, or Other Investments, depending on the accounting method used to report the investment. Additional information pertaining to these investments at June 30, 2026 and December 31, 2025 is presented below. (Dollars in Millions) Unfunded Commitment Reported Value Asset Class Jun 30, 2026 Jun 30, 2026 Dec 31, 2025 Reported as Equity Method Limited Liability Investments: Senior Debt $ 54.2 $ 21.2 $ 21.1 Mezzanine Debt 39.4 118.8 115.5 Leveraged Buyout 11.9 7.1 6.5 Real Estate — 26.0 24.1 Other 1.8 9.9 8.8 Total Equity Method Limited Liability Investments 107.3 183.0 176.0 Reported as Other Equity Interests at Fair Value: Mezzanine Debt 83.5 120.1 115.8 Leveraged Buyout 41.9 44.0 40.5 Distressed Debt 17.5 9.5 10.8 Senior Debt 7.3 24.5 25.5 Growth Equity 4.7 11.9 10.7 Other 3.9 11.5 7.0 Total Reported as Other Equity Interests at Fair Value 158.8 221.5 210.3 Reported as Other Investments: Other Equity Investments — 4.5 5.9 Total Investments in Limited Liability Companies and Limited Partnerships $ 266.1 $ 409.0 $ 392.2 The Company expects that it will be required to fund its commitments over the next several years. The Company expects that the proceeds from distributions from these investments will be the primary source of funding of such commitments. 61 Insurance, Interest, and Other Expenses Expenses for the three and six months ended June 30, 2026 and 2025 were: Three Months Ended Six Months Ended (Dollars in Millions) Jun 30, 2026 Jun 30, 2025 Jun 30, 2026 Jun 30, 2025 Insurance and Other Expenses: Insurance Expenses: Policy Acquisition Costs $ 156.8 $ 177.1 $ 309.5 $ 341.4 Business Unit Operating Costs 58.6 71.4 127.8 146.5 Corporate Overhead Costs 43.4 44.6 89.8 91.3 Insurance Expenses 258.8 293.1 527.1 579.2 Other Expenses: Acquisition and Disposition Related Transaction, Integration, Restructuring and Other Costs 10.6 4.8 16.9 10.1 Other Corporate Costs 3.0 2.1 5.4 5.2 Other Expenses 13.6 6.9 22.3 15.3 Insurance and Other Expenses 272.4 300.0 549.4 594.5 Interest Expense 8.9 9.0 18.2 20.4 Goodwill Impairment 460.0 — 460.0 — Total Insurance, Interest, and Other Expenses $ 741.3 $ 309.0 $ 1,027.6 $ 614.9 Insurance and Other Expenses Insurance and Other Expenses decreased by $27.6 million and $45.1 million for the three and six months ended June 30, 2026, respectively, compared to the same periods in 2025, primarily driven by lower Insurance Expenses, partially offset by higher Other Expenses. Policy acquisition costs decreased by $20.3 million and $31.9 million for the three and six months ended June 30, 2026, respectively, compared to the same periods in 2025, primarily driven by reduced business volumes in the Specialty Property & Casualty Insurance segment. Business unit operating costs decreased by $12.8 million and $18.7 million for the three and six months ended June 30, 2026, respectively, compared to the same periods in 2025, primarily due to lower expenses in the Specialty Property & Casualty Insurance Segment resulting from lower business volumes. Additionally, expenses in Non-Core Operations decreased as the business continued to run off. Other Expenses increased by $6.7 million and $7.0 million for the three and six months ended June 30, 2026, respectively, compared to the same periods in 2025, primarily due to higher Acquisition and Disposition Related Transaction, Integration, Restructuring and Other Costs. These costs included $15.9 million and $19.9 million of restructuring charges to achieve operational and organizational efficiencies for the three and six months ended June 30, 2026, respectively. The Company continues to evaluate additional efficiency opportunities through 2027. These costs were partially offset by a pre-tax gain of $7.5 million related to the sale of Newins in the second quarter of 2026. The costs for the three and six months ended June 30, 2025 primarily consisted of integration expenses due to continued investments in information technology. Interest Expense Interest Expense decreased by $2.2 million for the six months ended June 30, 2026, compared to the same period in 2025, primarily due to the redemption of $450 million of 4.350% senior notes in the first quarter of 2025. Goodwill Impairment Goodwill Impairment increased by $460.0 million for the three and six months ended June 30, 2026, respectively, compared to the same periods in 2025, due to the impairment of goodwill related to the Specialty & Property Casualty Insurance segment. See Note 3, "Goodwill" to the Condensed Consolidated Financial Statements for more information. 62 Income Taxes The federal corporate statutory income tax rate was 21% for the six months ended June 30, 2026 and June 30, 2025. The Company’s effective income tax rate, which was 0.2% and 20.2% for the three months ended June 30, 2026 and 2025, respectively, and 1.0% and 19.6% for the six months ended June 30, 2026 and 2025, respectively, differs from the federal corporate income tax rate due primarily to (1) nondeductible goodwill impairment, (2) tax-exempt investment income, (3) nontaxable income associated with the change in cash surrender value on Company-Owned Life Insurance, (4) general business tax credits, (5) a permanent difference between the amount of long-term equity-based compensation expense recognized under GAAP and the amount deductible for Federal tax purposes, (6) nondeductible executive compensation, (7) impact of deferred taxes in foreign jurisdictions, and (8) a change in valuation allowance related to foreign deferred tax assets. The Company reported nondeductible goodwill expense of $467.2 million for the three and six months ended June 30, 2026. The Company reported no nondeductible goodwill expense for the same periods in 2025. Tax-exempt investment income and dividends received deductions were $3.5 million for the three months ended June 30, 2026, compared to $3.9 million for the same period in 2025. Tax-exempt investment income and dividends received deductions were $7.1 million for the six months ended June 30, 2026, compared to $7.7 million for the same period in 2025. The nontaxable increase in cash surrender value on Company-Owned Life Insurance was $11.9 million for the three months ended June 30, 2026, compared to $10.5 million for the same period in 2025. The nontaxable increase in cash surrender value on Company-Owned Life Insurance was $23.5 million for the six months ended June 30, 2026, compared to $20.7 million for the same period in 2025. The Company realized investment tax credits and other federal income tax credits of $0.2 million for the three months ended June 30, 2026, compared to realized investment tax credits and other federal income tax credits of $0.3 million for the same period in 2025. The Company realized investment tax credits and other federal income tax credits of $0.5 million for the six months ended June 30, 2026, compared to realized investment tax credits and other federal income tax credits of $0.6 million for the same period in 2025. The amount of expense recognized for long-term equity-based compensation expense was $1.3 million higher than the amount that would be deductible under the IRC for the three months ended June 30, 2026, compared to $0.2 million lower for the same period in 2025. The amount of expense recognized for long-term equity-based compensation expense was $6.7 million higher than the amount that would be deductible under the IRC for the six months ended June 30, 2026, compared to $2.2 million lower for the same period in 2025. The amount of nondeductible executive compensation was $5.2 million for the three months ended June 30, 2026, compared to $5.2 million for the same period in 2025. The amount of nondeductible executive compensation was $6.7 million for the six months ended June 30, 2026, compared to $10.5 million for the same period in 2025. Tax expense of $8.0 million was recorded for the three months ended June 30, 2026, compared to a tax benefit of $5.2 million for the same period in 2025 related to income taxes imposed in the foreign jurisdiction in which the Company operates. Tax expense of $0.2 million was recorded for the six months ended June 30, 2026, compared to a tax benefit of $4.4 million for the same period in 2025 related to income taxes imposed in the foreign jurisdiction in which the Company operates. The Company recorded a decrease in valuation allowance of $6.6 million for the three months ended June 30, 2026, compared to an increase of $3.6 million for the same period in 2025 for those foreign deferred tax assets it determined were not more-likely-than-not to be realized. The Company recorded an increase in valuation allowance of $1.6 million for the six months ended June 30, 2026, compared to $4.4 million for the same period in 2025 for those foreign deferred tax assets it determined were not more-likely-than-not to be realized. Recently Issued Accounting Pronouncements The Company has adopted all recently issued accounting pronouncements with effective dates prior to July 1, 2026. There were no adoptions of such accounting pronouncements during the six months ended June 30, 2026 that had a material impact on the Company’s Condensed Consolidated Financial Statements. 63 Liquidity and Capital Resources Amended and Extended Credit Agreement On March 15, 2022, the Company entered into an amended and extended credit agreement. The amended and extended credit agreement increased the borrowing capacity of the existing unsecured credit agreement to $600.0 million and extended the maturity date to March 15, 2027. Furthermore, the amended and extended credit agreement provided for an accordion feature whereby the Company could increase the revolving credit borrowing capacity by an additional $200.0 million for a total of maximum capacity of $800.0 million. On May 4, 2026, the Company reduced the borrowing capacity under the credit agreement from $600.0 million to $350.0 million in accordance with terms of the agreement. The accordion feature remained unchanged and permits the Company to increase total borrowing capacity up to $550.0 million. Financial covenants within the agreement may limit the Company from accessing the maximum capacity. The amount available as of June 30, 2026 was $350.0 million, the maximum capacity. There were no outstanding borrowings under the credit agreement at either June 30, 2026 or December 31, 2025. Subsequently, on August 3, 2026, the Company entered into an amendment to the credit agreement. The Amendment, among other things, (i) replaces the consolidated net worth financial covenant contained in the agreement with a consolidated tangible net worth financial covenant, effective as of June 29, 2026, and (ii) adds a quarterly-tested financial covenant requiring each of Trinity and United Insurance to maintain a minimum risk-based capital ratio. Long-term Debt The Company designates debt obligations as either short-term or long-term based on maturity date at issuance. Total amortized cost of Long-term Debt, Non-Current outstanding on June 30, 2026 and December 31, 2025 was: (Dollars in Millions) Jun 30, 2026 Dec 31, 2025 Non-Current: 2.400% Senior Notes due September 30, 2030 $ 398.1 $ 397.9 3.800% Senior Notes due February 23, 2032 397.2 396.9 5.875% Fixed-Rate Reset Junior Subordinated Debentures due 2062 149.2 148.7 Total Long-term Debt Outstanding $ 944.5 $ 943.5 See Note 16, "Debt" to the Condensed Consolidated Financial Statements for more information regarding the Company’s long-term debt. Federal Home Loan Bank Agreements Kemper’s subsidiaries, United Insurance, Trinity, and AAC are members of the Federal Home Loan Banks (“FHLBs”) of Chicago, Dallas and Chicago, respectively. AAC became a member of the FHLB of Chicago in May 2022. United Insurance and Trinity became members of the FHLBs of Chicago and Dallas, respectively, in 2013. Under their memberships, United Insurance, Trinity and AAC may borrow through the advance program of their respective FHLB. The Company’s investments in FHLB common stock are reported at cost and included in Other Investments. The carrying value of FHLB of Chicago common stock was $14.7 million and $17.7 million at June 30, 2026 and December 31, 2025, respectively. The carrying value of FHLB of Dallas common stock was $2.2 million and $2.1 million at June 30, 2026 and December 31, 2025, respectively. The Company periodically uses short-term FHLB borrowings for a combination of cash management and risk management purposes, in addition to long-term FHLB borrowings for spread lending purposes. During the first six months of 2026, United Insurance received no advances from the FHLB of Chicago and made repayments of $65.4 million. United Insurance had outstanding advances from the FHLB of Chicago totaling $448.4 million at June 30, 2026. These advances were made in connection with the Company’s spread lending program. The proceeds related to these advances were used to purchase fixed maturity securities to earn incremental net investment income. For these advances, United Insurance held pledged securities in a custodial account with the FHLB of Chicago with a fair value of $547.7 million at June 30, 2026. The fair value of the collateral pledged must be maintained at certain specified levels above the borrowed amount, which can vary depending on the assets pledged. If the fair value of the collateral declines below these specified levels of the amount borrowed, United Insurance would be required to pledge additional collateral or repay outstanding borrowings. See Note 15, "Policyholder Obligations" to the Condensed Consolidated Financial Statements for additional information about the United Insurance advances and related funding agreements. 64 Liquidity and Capital Resources (Continued) Common Stock Repurchases On August 5, 2025, Kemper’s Board of Directors approved a new share repurchase authorization, under which the Company can repurchase up to $500.0 million of its common stock (the “2025 Repurchase Program”). As of June 30, 2026, the remaining share repurchase authorization under the 2025 Repurchase Program was $304.2 million. The amount and timing of any future share repurchases under the 2025 Repurchase Program will depend on various factors, including market conditions, the Company’s financial condition, results of operations, available liquidity, particular circumstances and other considerations. No shares were repurchased during the three and six months ended June 30, 2026. During the three months ended June 30, 2025, Kemper repurchased and retired approximately 446,000 of its common stock in open market transactions under its share repurchase authorization for an aggregate cost of $28.5 million and an average cost per share of $64.04. During the six months ended June 30, 2025, Kemper repurchased and retired approximately 509,000 shares of its common stock in open market transactions under its share repurchase authorization for an aggregate cost of $32.5 million and an average cost per share of $63.90. Dividends to Shareholders Kemper paid a quarterly dividend of $0.32 per common share in the second quarter of 2026 and 2025, respectively. Dividends and dividend equivalents paid were $37.6 million and $41.0 million for the six months ended June 30, 2026 and 2025, respectively. Subsidiary Dividends Various insurance laws restrict the ability of Kemper’s insurance subsidiaries to pay dividends without regulatory approval. Such insurance laws applicable to the Company’s US based insurance subsidiaries generally restrict the amount of dividends paid in an annual period to the greater of statutory net income from the previous year or 10% of statutory capital and surplus. Kemper’s US based insurance subsidiaries paid $25.0 million of dividends to Kemper during the first six months of 2026. As of the filing date, Kemper’s US based insurance subsidiaries capacity to pay dividends without prior regulatory approval is estimated to be $6.2 million. Sources and Uses of Funds The Company directly held cash and investments totaling $130.0 million at June 30, 2026, compared to $145.4 million at December 31, 2025. The primary sources of funds available for repayment of Kemper’s indebtedness, repurchases of common stock, future shareholder dividend payments, and the payment of interest on Kemper’s senior notes, include cash and investments directly held by Kemper, receipt of dividends from Kemper’s insurance subsidiaries and borrowings under the credit agreement and from subsidiaries. The primary sources of funds for Kemper’s insurance subsidiaries are premiums, investment income, proceeds from the sales and maturity of investments, advances from the FHLBs of Chicago and Dallas, and capital contributions from Kemper. The primary uses of funds are the payment of policyholder benefits under life insurance contracts, claims under property and casualty insurance contracts and accident and health insurance contracts, the payment of commissions and general expenses, the purchase of investments and repayments of advances from the FHLBs of Chicago and Dallas. Generally, there is a time lag between when premiums are collected and when policyholder benefits and insurance claims are paid. During periods of growth, property and casualty insurance companies typically experience positive operating cash flows and can invest a portion of their operating cash flows to fund future policyholder benefits and claims. During periods in which premium revenues decline, insurance companies may experience negative cash flows from operations and may need to sell investments to fund payments to policyholders and claimants. In addition, if the Company’s property and casualty insurance subsidiaries experience several significant catastrophic events over a relatively short period of time, investments may be sold to fund payments, which could result in investment gains or losses. Management believes that its property and casualty insurance subsidiaries maintain adequate levels of liquidity in the event that they were to experience several future catastrophic events over a relatively short period of time. 65 Liquidity and Capital Resources (Continued) Information about the Company’s cash flows for the six months ended June 30, 2026 and 2025 is presented below. (Dollars in Millions) Jun 30, 2026 Jun 30, 2025 Net Cash Provided by Operating Activities $ 119.3 $ 269.6 Net Cash (Used in) Provided by Investing Activities (59.7) 361.4 Net Cash Used in Financing Activities (104.4) (519.4) Cash available for investment activities is dependent on cash flow from Operating Activities and Financing Activities and the level of cash the Company elects to maintain. Net Cash Provided by Operating Activities Net cash provided by Operating Activities was $119.3 million for the six months ended June 30, 2026, compared to net cash provided of $269.6 million for the same period in 2025. The decrease in net cash provided by Operating Activities was primarily driven by lower personal automobile volumes in the Specialty Property & Casualty business. Net Cash (Used in) Provided by Investing Activities Net cash used in Investing Activities for the six months ended June 30, 2026 was $59.7 million, compared to net cash provided of $361.4 million for the same period in 2025. The decrease in net cash provided by Investing Activities was primarily due to proceeds from sales of short term investments in the first quarter of 2025 that were primarily used to fund the redemption of the $450.0 million 4.350% Senior Notes due February 15, 2025 (the “2025 Senior Notes”). Net Cash Used in Financing Activities Net cash used in Financing Activities for the six months ended June 30, 2026 was $104.4 million, compared to net cash used of $519.4 million for the same period in 2025. This decrease in net cash used by Financing Activities was primarily due to the redemption of the 2025 Senior Notes in the first quarter of 2025 and absence of common stock repurchases in 2026, partially offset by higher net repayments under United Insurance's FHLB of Chicago spread lending program. Critical Accounting Estimates Kemper’s subsidiaries conduct their operations in two industries: property and casualty insurance and life insurance. Accordingly, the Company is subject to several industry-specific accounting principles under GAAP. The preparation of financial statements in accordance with GAAP requires the use of estimates and assumptions that affect the reported amounts of assets and liabilities, the disclosure of contingent assets and liabilities at the date of the financial statements and the reported amounts of revenues and expenses during the reporting period. The process of estimation is inherently uncertain. Accordingly, actual results could ultimately differ materially from the estimated amounts reported in a company’s financial statements. Different assumptions are likely to result in different estimates of reported amounts. The Company’s critical accounting policies most sensitive to estimates include the valuation of investments, the valuation of life insurance reserves, the valuation of reserves for property and casualty insurance incurred losses and LAE, the assessment of recoverability of goodwill, and the recoverability of deferred tax assets. The Company’s critical accounting policies are described in the MD&A included in the 2025 Annual Report. There have been no material changes to the information disclosed in the 2025 Annual Report with respect to these critical accounting estimates and the Company’s significant accounting policies.