HIPOW

The following discussion and analysis of our financial condition and results of our operations addresses the consolidated financial condition as of June 30, 2026, compared with December 31, 2025, and consolidated results of operations for the three months and six months ended June 30, 2026 and 2025. This should be read in conjunction with our unaudited interim condensed consolidated financial statements and notes thereto included in Item 1 of this report and also our Management’s Discussion and Analysis of Financial Condition and Results of Operations, the “Risk Factors” section, and the audited consolidated financial statements included in our Annual Report on Form 10-K for the year ended December 31, 2025. This discussion contains forward-looking statements based upon current expectations that involve risks and uncertainties. Our actual results may differ materially from those anticipated in these forward-looking statements as a result of various factors, including those set forth in the section titled “Risk Factors” in our Annual Report and may be updated from time to time in our other filings with the SEC. Certain percentages herein may not sum or recalculate due to rounding. Overview Hippo is an insurance holding company with subsidiaries that provide property and casualty insurance products to both individuals and business customers primarily in the United States. We conduct insurance underwriting through our regulated carrier subsidiaries and generate revenue from a combination of insurance underwriting activities and fee- and commission-based services. Our operations include providing insurance capacity and related services for our owned managing general agent (“MGA”) and in partnership with third-party MGAs and fee-based and commission-based services that support the placement and servicing of insurance policies. We continue to execute actions to support balanced diversified growth, leveraging both third-party MGAs and our owned MGA to source and underwrite a diversified portfolio of risk across personal and commercial lines. We participate in MGA programs when they align with our risk appetite, and assess performance through disciplined underwriting, selective risk retention, reinsurance, and ongoing portfolio management. Over time, the mix of our written premium base has evolved, and we expect it may continue to evolve, with a lower proportion attributable to homeowners insurance as we further diversify our portfolio across less catastrophe exposed lines of business. Line of business disclosure Line-of-business information represents supplemental premium-related information and is not presented as separate reportable segments. For comparability, certain line-of-business information is presented for all periods shown, including periods prior to the initial introduction of this presentation in our disclosures. Gross written premium and net written premium by line of business are presented in the Key Operating and Financial Metrics section below. Net earned premium by line of business is presented in the Results of Operations section immediately below. Reinsurance We maintain a comprehensive reinsurance program to manage risk exposure, reduce earnings volatility, and safeguard capital. By ceding a portion of our underwriting risk to highly rated reinsurers and alternative capital providers, we limit the financial impact of catastrophe events and large loss activity. Nevertheless, we remain ultimately responsible for policyholder claims should a reinsurer fail to perform. Our reinsurance strategy includes a mix of quota share and excess of loss (“XOL”) structures, alongside collateralized protection through catastrophe bonds. We work with reinsurers rated “A-” (Excellent) or better by A.M. Best or require appropriate collateral. Contracts often include provisions allowing for replacement of reinsurers whose financial condition deteriorates. Our catastrophe reinsurance program supports property risks underwritten by us on behalf of our MGA and third-party MGAs. These risks are protected mainly by a corporate level group catastrophe XOL (the “Group Cat”) and in some cases by program-specific XOL treaties, catastrophe bonds, and quota share reinsurance. We are also protected by participation in the Florida Hurricane Catastrophe Fund (“FHCF”). Our catastrophe reinsurance 22 Table of Contents structure is designed to provide protection against severe loss events across the portfolio. Effective June 1, 2026, the catastrophe reinsurance program has an occurrence limit of $512.9 million and an aggregate limit of $776.9 million. Our 2026 program, established in the second quarter of 2026, reflects a shift in the way we purchase catastrophe reinsurance. We consolidated multiple program level XOL contracts into a single Group Cat structure. The new structure also incorporates the previous corporate catastrophe cover. The Group Cat covers all catastrophe exposed business written by us and attaches after inuring any program specific reinsurance, the FHCF, and the catastrophe bonds. The change to portfolio level management of our reinsurance program allowed us to place a whole account quota share that provides coverage for both property and casualty programs. The whole account quota share was a strategic reinsurance program placed on June 1, 2026. The contract covers all lines of business, of which we have a retention of at least equal to the reinsurance participation. This aligns our interests with that of the reinsurer. While the whole account quota share provides some property catastrophe relief below the attachment of the Group Cat, it was mainly placed to increase future growth optionality and manage the business on portfolio basis. For business written by our MGA, we strategically retain a significant level of risk, reflecting our confidence in the portfolio’s underwriting performance. The business written by our MGA is primarily covered by catastrophe XOL protection. We also utilize collateralized reinsurance through Mountain Re Ltd., a Bermuda-based special purpose insurer. The catastrophe bonds issued through Mountain Re Ltd. provide multi-year per occurrence coverage for a range of perils, including hurricane and wildfire, for business written through our MGA. Results of Operations for the Three Months Ended June 30, 2026 and 2025 The following table summarizes net income for the periods presented: Three Months Ended June 30, 2026 2025 Change % Change (in millions, except percentages) Revenue: Net earned premium $ 118.7 $ 94.0 $ 24.7 26 % Commission income, net 15.7 14.7 1.0 7 % Service and fee income 3.7 2.9 0.8 28 % Net investment income 6.6 5.7 0.9 16 % Total revenue 144.7 117.3 27.4 23 % Expenses: Losses and loss adjustment expenses 59.8 44.5 15.3 34 % Insurance related expenses 38.7 32.8 5.9 18 % Technology and development expenses 10.1 8.1 2.0 25 % Sales and marketing expenses 6.3 9.2 (2.9) (32) % General and administrative expenses 18.2 17.4 0.8 5 % Impairment and restructuring charges — 1.2 (1.2) NM Interest and other expense, net 0.6 0.1 0.5 NM Total expenses 133.7 113.3 20.4 18 % Income before income taxes 11.0 4.0 7.0 175 % Income tax expense 0.9 0.1 0.8 NM Net income 10.1 3.9 6.2 159 % Net income attributable to noncontrolling interests, net of tax — 2.6 (2.6) NM Net income attributable to Hippo $ 10.1 $ 1.3 $ 8.8 677 % “NM” (not meaningful) is used where the base period is near-zero and percentage change would be misleading. 23 Table of Contents Net Earned Premium The following table summarizes our net earned premiums by line of business for each period: Three Months Ended June 30, 2026 2025 Change % Change (in millions, except percentages) Line of Business Homeowners $ 65.6 $ 62.3 $ 3.3 5 % Renters 18.0 18.7 (0.7) (4) % Commercial Multi-Peril 23.8 11.9 11.9 100 % Casualty 10.7 0.8 9.9 1238 % Other 0.6 0.3 0.3 100 % Total $ 118.7 $ 94.0 $ 24.7 26 % For the three months ended June 30, 2026, net earned premium was $118.7 million, an increase of $24.7 million, or 26% compared to $94.0 million for the three months ended June 30, 2025. The increase was due primarily to the earnings of increased gross written premiums volume and increase in retention across our Commercial Multi-Peril and Casualty lines. Commission Income, Net For the three months ended June 30, 2026, commission income was $15.7 million, an increase of $1.0 million, or 7%, compared to $14.7 million for the three months ended June 30, 2025. The increase was due primarily to an increase in fronting fee revenue of $5.6 million earned from third-party MGA program partners, driven by growth across our Commercial Multi-Peril and Casualty lines, partially offset by a decrease in agency commissions of $4.9 million due to the sale of our homebuilder distribution network in the third quarter of 2025. Service and Fee Income For the three months ended June 30, 2026, service and fee income was $3.7 million, an increase of $0.8 million, or 28%, compared to $2.9 million for the three months ended June 30, 2025. The increase was due primarily to an increase in service fees of $0.5 million. Net Investment Income For the three months ended June 30, 2026, net investment income was $6.6 million, an increase of $0.9 million, or 16%, compared to $5.7 million for the three months ended June 30, 2025. The increase was due primarily to higher average balance in cash and investments during the period. The Company’s investment portfolio is primarily comprised of securities issued by the U.S. government and agencies, money market accounts, high-grade corporate securities, asset backed securities, and residential and commercial mortgage-backed securities. 24 Table of Contents Losses and Loss Adjustment Expenses For the three months ended June 30, 2026, losses and loss adjustment expenses were $59.8 million, an increase of $15.3 million, or 34%, compared to $44.5 million for the three months ended June 30, 2025. The increase was due primarily to an increase in non-catastrophe losses related to premium growth on Commercial Multi-Peril and Casualty lines. Losses and loss adjustment expenses consisted of the following elements during the respective periods: Three Months Ended June 30, 2026 2025 Change % Change (in millions, except percentages) Catastrophe losses $ 8.0 $ 8.0 $ — — % Non-catastrophe losses 51.8 36.5 15.3 42 % Total losses and loss adjustment expenses $ 59.8 $ 44.5 15.3 34 % Catastrophe loss ratio 6.7 % 8.0 % Non-catastrophe loss ratio 43.7 % 39.0 % Net loss ratio 50.4 % 47.0 % Catastrophe loss activity for the three months ended June 30, 2026 and 2025 was primarily related to convective storm and weather activity. Included in our catastrophe loss ratio for the three months ended June 30, 2026 and 2025 was a benefit of 1 percentage point and a benefit of 2 percentage points related to prior year developments, respectively. The non-catastrophe loss ratio increased 4.7 percentage points to 43.7% for the three months ended June 30, 2026 compared to 39.0% for the three months ended June 30, 2025, due primarily to lower prior year favorable developments. Included in our non-catastrophe loss ratio for the three months ended June 30, 2026, is a net benefit of 2 percentage points related to a gain from a reinsurance commutation, partially offset by a net adverse impact of 1 percentage point related to prior year developments, whereas for the three months ended June 30, 2025, there was a benefit of 5 percentage points related to prior year developments. Insurance Related Expenses For the three months ended June 30, 2026, insurance related expenses were $38.7 million, an increase of $5.9 million, or 18%, compared to $32.8 million for the three months ended June 30, 2025. The increase was due primarily to an increase in net acquisition expenses of $3.8 million due to increased premium. Technology and Development Expenses For the three months ended June 30, 2026, technology and development expenses were $10.1 million, an increase of $2.0 million, or 25%, compared to $8.1 million for the three months ended June 30, 2025. The increase was due primarily to the transfer of headcount into technology and development related to an internal reorganization as well as an increase in headcount to support a transition services agreement with associated service fee income. Sales and Marketing Expenses For the three months ended June 30, 2026, sales and marketing expenses were $6.3 million, a decrease of $2.9 million, or 32%, compared to $9.2 million for the three months ended June 30, 2025. The decrease was due primarily to a $1.9 million reduction in employee-related costs resulting from lower headcount due to the sale of our homebuilder distribution network in the third quarter of 2025. 25 Table of Contents General and Administrative Expenses For the three months ended June 30, 2026, general and administrative expenses were $18.2 million, an increase of $0.8 million, or 5%, compared to $17.4 million for the three months ended June 30, 2025. The increase was due primarily to an increase in employee-related expenses of $0.7 million due to an increase in headcount. Impairment and Restructuring Charges For the three months ended June 30, 2026, we incurred no impairment and restructuring charges, compared to $1.2 million for the three months ended June 30, 2025 which resulted from the impairment of a lease right-of-use asset due to termination of leased office space. Interest and other expense (income), net For the three months ended June 30, 2026, interest and other expense, net was $0.6 million, an increase of $0.5 million, compared to interest and other expense, net of $0.1 million for the three months ended June 30, 2025. The current period reflects interest expense of $1.2 million on our surplus note issued in June 2025, partially offset by a $0.6 million gain from litigation settlement. Income Taxes For the three months ended June 30, 2026 and 2025, income tax expense was $0.9 million and $0.1 million, respectively. The increase was due primarily to an increase in current expense for state income taxes. Net Income Attributable to Noncontrolling Interest, net of tax For the three months ended June 30, 2026, there is no net income attributable to noncontrolling interest, compared to $2.6 million for the three months ended June 30, 2025. The decrease was due to the elimination of the remaining noncontrolling interests related to the sale of our homebuilder distribution network. Net Income Attributable to Hippo For the three months ended June 30, 2026, net income attributable to Hippo was $10.1 million, a change of $8.8 million compared to a net income attributable to Hippo of $1.3 million for the three months ended June 30, 2025 due to the factors described above. 26 Table of Contents Results of Operations for the Six Months Ended June 30, 2026 and 2025 The following table summarizes net income (loss) for the periods presented: Six Months Ended June 30, 2026 2025 Change % Change (in millions, except percentages) Revenue: Net earned premium $ 217.6 $ 181.3 $ 36.3 20 % Commission income, net 28.4 29.1 (0.7) (2) % Service and fee income 6.9 5.7 1.2 21 % Net investment income 13.3 11.5 1.8 16 % Total revenue 266.2 227.6 38.6 17 % Expenses: Losses and loss adjustment expenses 107.3 136.9 (29.6) (22) % Insurance related expenses 73.6 63.0 10.6 17 % Technology and development expenses 19.5 16.2 3.3 20 % Sales and marketing expenses 12.6 18.1 (5.5) (30) % General and administrative expenses 34.4 33.9 0.5 1 % Impairment and restructuring charges — 1.2 (1.2) NM Interest and other expense (income), net 0.6 (0.1) 0.7 NM Total expenses 248.0 269.2 (21.2) (8) % Income (loss) before income taxes 18.2 (41.6) 59.8 144 % Income tax (benefit) expense 1.0 (0.1) 1.1 NM Net income (loss) 17.2 (41.5) 58.7 141 % Net income attributable to noncontrolling interests, net of tax — 4.9 (4.9) NM Net income (loss) attributable to Hippo $ 17.2 $ (46.4) $ 63.6 137 % “NM” (not meaningful) is used where the base period is near-zero and percentage change would be misleading. Net Earned Premium The following table summarizes our net earned premiums by line of business for each period: Six Months Ended June 30, 2026 2025 Change % Change (in millions, except percentages) Line of Business Homeowners $ 128.3 $ 123.9 $ 4.4 4 % Renters 35.0 35.3 (0.3) (1) % Commercial Multi-Peril 39.7 18.5 21.2 115 % Casualty 13.9 1.3 12.6 969 % Other 0.7 2.3 (1.6) (70) % Total $ 217.6 $ 181.3 $ 36.3 20 % For the six months ended June 30, 2026, net earned premium was $217.6 million, an increase of $36.3 million, or 20% compared to $181.3 million for the six months ended June 30, 2025. The increase was due primarily to the earnings of increased gross written premiums volume across our Commercial Multi-Peril and Casualty lines. Commission Income, Net For the six months ended June 30, 2026, commission income was $28.4 million, a decrease of $0.7 million, or 2%, compared to $29.1 million for the six months ended June 30, 2025. The decrease was due primarily to a decrease in agency commissions of $10.3 million due to the sale of our homebuilder distribution network in the third 27 Table of Contents quarter of 2025, partially offset by an increase in fronting fee revenue of $9.8 million earned from third-party MGA program partners driven by growth across our Commercial Multi-Peril and Casualty lines. Service and Fee Income For the six months ended June 30, 2026, service and fee income was $6.9 million, an increase of $1.2 million, or 21%, compared to $5.7 million for the six months ended June 30, 2025. The increase is due primarily to an increase in service fees of $0.8 million. Net Investment Income For the six months ended June 30, 2026, net investment income was $13.3 million, an increase of $1.8 million, or 16%, compared to $11.5 million for the six months ended June 30, 2025. The increase was due primarily to higher average balance in cash and investments during the period. The Company’s investment portfolio is primarily comprised of securities issued by the U.S. government and agencies, money market accounts, high-grade corporate securities, asset backed securities, and residential and commercial mortgage-backed securities. Losses and Loss Adjustment Expenses For the six months ended June 30, 2026, losses and loss adjustment expenses were $107.3 million, a decrease of $29.6 million, or 22%, compared to $136.9 million for the six months ended June 30, 2025. The decrease was due primarily to losses from a series of destructive wildfires affecting Los Angeles, California (the “LA Wildfires”) in January 2025. These were partially offset by an increase in non-catastrophe losses due primarily to premium growth on Commercial Multi-Peril and Casualty lines. Losses and loss adjustment expenses consisted of the following elements during the respective periods: Six Months Ended June 30, 2026 2025 Change % Change (in millions) Catastrophe losses $ 12.3 $ 62.0 $ (49.7) (80) % Non-catastrophe losses 95.0 74.9 20.1 27 % Total losses and loss adjustment expenses $ 107.3 $ 136.9 $ (29.6) (22) % Catastrophe loss ratio 5.7 % 34.2 % Non-catastrophe loss ratio 43.6 % 41.3 % Net loss ratio 49.3 % 75.5 % Catastrophe loss activity for the six months ended June 30, 2026 was primarily related to convective storm and weather activity while catastrophe loss activity for the six months ended June 30, 2025 was due primarily to the LA Wildfires. Included in our catastrophe loss ratio for the six months ended June 30, 2026 and 2025 is a benefit of 1 percentage point related to prior year developments in both periods. Non-catastrophe loss ratio increased 2.3 percentage points to 43.6% for the six months ended June 30, 2026 compared to 41.3% for the six months ended June 30, 2025 due primarily to lower prior year favorable developments. Included in our non-catastrophe loss ratio for the six months ended June 30, 2026, is an immaterial impact related to prior year developments and a net benefit of 1 percentage point related to a gain from a reinsurance commutation, whereas for the six months ended June 30, 2025, there was a benefit of 4 percentage points related to prior year developments. 28 Table of Contents Insurance Related Expenses For the six months ended June 30, 2026, insurance related expenses were $73.6 million, an increase of $10.6 million, or 17%, compared to $63.0 million for the six months ended June 30, 2025. The increase was due primarily to an increase in net acquisition expenses of $8.6 million due to increased premium. Technology and Development Expenses For the six months ended June 30, 2026, technology and development expenses were $19.5 million, an increase of $3.3 million, or 20%, compared to $16.2 million for the six months ended June 30, 2025. The increase was due primarily to the transfer of headcount into technology and development related to an internal reorganization as well as an increase in headcount to support a transition services agreement with associated service fee income. Sales and Marketing Expenses For the six months ended June 30, 2026, sales and marketing expenses were $12.6 million, a decrease of $5.5 million, or 30%, compared to $18.1 million for the six months ended June 30, 2025. The decrease was due primarily to a $3.8 million reduction in employee-related costs resulting from lower headcount due to the sale of our homebuilder distribution network in the third quarter of 2025. The decrease also reflects the elimination of $0.8 million in amortization of intangible assets acquired in connection with our homebuilder distribution network, which was sold in the third quarter of 2025. General and Administrative Expenses For the six months ended June 30, 2026, general and administrative expenses were $34.4 million, an increase of $0.5 million, or 1%, compared to $33.9 million for the six months ended June 30, 2025. The increase was due primarily to an increase in employee-related expenses of $0.4 million due to an increase in headcount. Impairment and Restructuring Charges For the six months ended June 30, 2026, we incurred no impairment and restructuring charges, compared to $1.2 million for the six months ended June 30, 2025 which resulted from the impairment of a lease right-of-use asset due to termination of leased office space. Interest and other expense (income), net For the six months ended June 30, 2026, interest and other expense, net were $0.6 million, an increase of $0.7 million, compared to interest and other income, net of $0.1 million for the six months ended June 30, 2025. The increase was due primarily to an increase in interest expense of $2.0 million on our surplus note issued in June 2025, partially offset by $1.1 million of earnout consideration received in connection with a prior divestiture and a $0.6 million gain from litigation settlement. Income Taxes For the six months ended June 30, 2026 and 2025, income tax expense was $1.0 million and benefit of $0.1 million, respectively. The increase was due primarily to an increase in current expense for state income taxes. Net Income Attributable to Noncontrolling Interest, net of tax For the six months ended June 30, 2026, there is no net income attributable to noncontrolling interest, compared to $4.9 million for the six months ended June 30, 2025. The decrease was due to the elimination of the remaining noncontrolling interests related to the sale of our homebuilder distribution network. Net Income (Loss) Attributable to Hippo For the six months ended June 30, 2026, net income attributable to Hippo was $17.2 million, a change of $63.6 million compared to a net loss attributable to Hippo of $46.4 million for the six months ended June 30, 2025 due to the factors described above. Key Operating and Financial Metrics and Non-GAAP Measures We regularly review the following operating and financial metrics to evaluate our business, measure our performance, identify trends in our business, prepare forecasts, and make capital allocation and strategic decisions. 29 Table of Contents Certain metrics discussed below are non-GAAP financial measures. Management uses non-GAAP measures to evaluate operating performance and trends that may not be apparent from GAAP results alone. Non-GAAP measures should be considered supplemental to, and not a substitute for, the most directly comparable GAAP measures, and may not be comparable to similarly titled measures used by other companies. Reconciliations of the non-GAAP measures to the most directly comparable GAAP measures are provided below. For certain non-GAAP financial measures that are expressed as ratios or per-share amounts, the reconciliation to the most directly comparable GAAP financial measure is provided through the calculation of the measure using GAAP components, as presented below. How we evaluate performance We evaluate performance on both a GAAP basis and, given the nature of our business, through insurance-specific non-GAAP operating metrics, which include a combination of (i) growth and mix metrics, (ii) underwriting performance metrics, and (iii) profitability, return and capital efficiency metrics. The table below summarizes selected operating, growth and mix, underwriting, and profitability metrics that management uses to evaluate performance across periods. Three Months Ended June 30, Six Months Ended June 30, 2026 2025 2026 2025 (in millions, except per share data) Gross written premium $ 482.2 $ 298.6 $ 814.6 $ 509.5 Ceded written premium (299.0) (191.7) (530.0) (302.3) Net written premium 183.2 106.9 284.6 207.2 Total revenue 144.7 117.3 266.2 227.6 Net income (loss) attributable to Hippo 10.1 1.3 17.2 (46.4) Adjusted net income (loss)(1) 21.0 17.0 38.2 (18.1) Net income (loss) per share attributable to Hippo, basic 0.38 0.05 0.66 (1.84) Net income (loss) per share attributable to Hippo, diluted 0.38 0.05 0.65 (1.84) Diluted adjusted earnings (loss) per share(1) 0.79 0.65 1.45 (0.72) Annualized adjusted return on equity(1) 18.4 % 20.8 % 16.9 % (10.4) % Net loss ratio 50.4 % 47.0 % 49.3 % 75.5 % Catastrophe loss ratio 6.7 % 8.0 % 5.7 % 34.2 % Non-catastrophe loss ratio 43.7 % 39.0 % 43.6 % 41.3 % Expense ratio 45.4 % 53.1 % 48.2 % 53.2 % Combined ratio 95.8 % 100.1 % 97.5 % 128.7 % As of June 30, 2026 December 31, 2025 Book value per share $ 17.65 $ 16.97 Tangible book value per share(1) $ 15.56 $ 14.76 (1) Indicates a non-GAAP financial measure. Growth and mix metrics Gross Written Premium Gross written premium (“GWP”) is the amount received or to be received for insurance policies written or assumed by us and our affiliates as a carrier or captive reinsurer, without reduction for policy acquisition costs, reinsurance costs, or other deductions. The volume of our gross written premium in any given period is generally influenced by: •New business submissions; 30 Table of Contents •Binding of new business submissions into policies; •Bound policies going effective; •Renewals of existing policies; and •Average size and premium rate of bound policies. Ceded Written Premium Ceded written premium (“CWP”) is the amount of gross written premium written or assumed by us and our affiliates as a carrier that we cede to reinsurers. We enter into reinsurance contracts to limit our exposure to losses, to provide additional capacity for growth, and to support our underwriting business. Ceded written premium is treated as a reduction from gross written premium. The volume of our ceded written premium is impacted by the level of our gross written premium and decisions we make to increase or decrease retention levels, as well as the volume of our underwriting business. Net Written Premium Net written premium (“NWP”) is calculated as the amount of gross written premium written less ceded written premium. Management uses growth and mix metrics to assess growth trends, changes in business mix, retention, and the scale of underwriting activities. The following table summarizes our gross written premiums by line of business: Three Months Ended June 30, 2026 2025 Change % Change (in millions, except percentages) Line of Business Homeowners $ 106.7 $ 100.0 $ 6.7 7 % Renters 49.6 44.2 5.4 12 % Commercial Multi-Peril 137.6 83.3 54.3 65 % Casualty 179.5 64.9 114.6 177 % Other 8.8 6.2 2.6 42 % Total $ 482.2 $ 298.6 $ 183.6 61 % Six Months Ended June 30, 2026 2025 Change % Change (in millions, except percentages) Line of Business Homeowners $ 194.0 $ 187.1 $ 6.9 4 % Renters 90.4 79.2 11.2 14 % Commercial Multi-Peril 233.4 134.0 99.4 74 % Casualty 280.1 99.2 180.9 182 % Other 16.7 10.0 6.7 67 % Total $ 814.6 $ 509.5 $ 305.1 60 % For the three months ended June 30, 2026, gross written premium was $482.2 million, an increase of $183.6 million, or 61%, compared to $298.6 million for the three months ended June 30, 2025. The increase was primarily driven by growth in our Casualty and Commercial Multi-Peril lines of business. This growth was supported by growth of our business and expansion into new program relationships. For the six months ended June 30, 2026, gross written premium was $814.6 million, an increase of $305.1 million, or 60%, compared to $509.5 million for the six months ended June 30, 2025. The increase was primarily 31 Table of Contents driven by growth in our Casualty and Commercial Multi-Peril lines of business. This growth was supported by growth of our business and expansion into new program relationships. The following table summarizes our net written premiums by line of business: Three Months Ended June 30, 2026 2025 Change % Change (in millions, except percentages) Line of Business Homeowners $ 76.1 $ 63.0 $ 13.1 21 % Renters(1) 19.4 19.5 (0.1) (1) % Commercial Multi-Peril 50.7 26.0 24.7 95 % Casualty 35.0 1.5 33.5 NM Other 2.0 (3.1) 5.1 (165) % Total $ 183.2 $ 106.9 $ 76.3 71 % Six Months Ended June 30, 2026 2025 Change % Change (in millions, except percentages) Line of Business Homeowners $ 136.9 $ 115.7 $ 21.2 18 % Renters(1) 30.2 56.7 (26.5) (47) % Commercial Multi-Peril 68.3 38.5 29.8 77 % Casualty 47.9 2.6 45.3 NM Other 1.3 (6.3) 7.6 (121) % Total $ 284.6 $ 207.2 $ 77.4 37 % (1) In the first quarter of 2025, Renters net written premium exceeded gross written premium due to a one-time reduction in ceded unearned premium resulting from the restructuring of the Renters reinsurance program effective January 1, 2025. “NM” (not meaningful) is used where the base period is near-zero and percentage change would be misleading. For the three months ended June 30, 2026, net written premium was $183.2 million, an increase of $76.3 million, or 71%, compared to $106.9 million for the three months ended June 30, 2025. The increase was primarily driven by higher gross written premiums in our Casualty and Commercial Multi-Peril lines and higher retention levels in our Homeowners and Casualty lines. For the six months ended June 30, 2026, net written premium was $284.6 million, an increase of $77.4 million, or 37%, compared to $207.2 million for the six months ended June 30, 2025. The increase was primarily driven by higher gross written premiums in our Casualty and Commercial Multi-Peril lines and higher retention levels in our Homeowners and Casualty lines. These were partially offset by a decrease in retention in our Renters line, where changes in net written premium relative to gross written premium were influenced by changes in retention levels effective January 1, 2025. Net retention, calculated as net written premium divided by gross written premium, was 38% and 36%, for the three months ended June 30, 2026 and 2025, respectively, and 35% and 41%, for the six months ended June 30, 2026 and 2025. 32 Table of Contents Underwriting performance metrics Net Losses and Loss Adjustment Expense ratios Catastrophe loss ratio, expressed as a percentage, is the ratio of catastrophe losses and LAE to the net earned premium. Non-catastrophe loss ratio, expressed as a percentage, is the ratio of the net non-catastrophe losses and LAE to the net earned premium. Net loss ratio, expressed as a percentage, is the ratio of the net losses and LAE to the net earned premium. Management uses these metrics to assess underwriting performance, evaluate pricing adequacy, risk selection, portfolio quality and trends in loss experience. Losses and loss adjustment expenses consisted of the following components during the respective periods: Three Months Ended June 30, Six Months Ended June 30, 2026 2025 2026 2025 (in millions, except percentages) Catastrophe losses $ 8.0 $ 8.0 $ 12.3 $ 62.0 Non-catastrophe losses 51.8 36.5 95.0 74.9 Total losses and loss adjustment expenses $ 59.8 $ 44.5 $ 107.3 $ 136.9 Net earned premium $ 118.7 94.0 217.6 181.3 Net loss ratio 50.4 % 47.0 % 49.3 % 75.5 % Catastrophe loss ratio 6.7 % 8.0 % 5.7 % 34.2 % Non-catastrophe loss ratio 43.7 % 39.0 % 43.6 % 41.3 % Expense Ratio Expense ratio, expressed as a percentage, is the ratio of insurance related expenses, technology and development expenses, sales and marketing expenses, and general and administrative expenses, net of commission income, net service and fee income, to net earned premiums. Management uses this metric to evaluate operating leverage, cost efficiency, effectiveness of pricing, and expense management actions. Other companies may define expense ratio differently. Expense ratio is calculated as follows: Three Months Ended June 30, Six Months Ended June 30, 2026 2025 2026 2025 (in millions, except percentages) Net earned premium $ 118.7 $ 94.0 $ 217.6 $ 181.3 Net expenses: Insurance related expenses $ 38.7 $ 32.8 $ 73.6 $ 63.0 Technology and development expenses 10.1 8.1 19.5 16.2 Sales and marketing expenses 6.3 9.2 12.6 18.1 General and administrative expenses 18.2 17.4 34.4 33.9 Less: commission income, net and service and fee income (19.4) (17.6) (35.3) (34.8) Total net expenses $ 53.9 $ 49.9 $ 104.8 $ 96.4 Expense ratio 45.4 % 53.1 % 48.2 % 53.2 % 33 Table of Contents Combined Ratio Combined ratio is defined as the sum of the net loss ratio and the expense ratio. Management uses the combined ratio as a comprehensive measure of underwriting profitability. A combined ratio under 100% generally indicates an underwriting profit. A combined ratio over 100% generally indicates an underwriting loss. Management uses this metric to evaluate our operating performance. Three Months Ended June 30, Six Months Ended June 30, 2026 2025 2026 2025 Expense ratio 45.4 % 53.1 % 48.2 % 53.2 % Net loss ratio 50.4 % 47.0 % 49.3 % 75.5 % Combined ratio 95.8 % 100.1 % 97.5 % 128.7 % Profitability, return and capital efficiency metrics Adjusted Net Income (Loss) Adjusted Net Income (Loss) is a non-GAAP financial measure, defined as net income (loss) excluding the impact of certain items that may not be indicative of underlying business trends, operating results, or future outlook, net of tax impact. We calculate the tax impact only on adjustments which would be included in calculating our income tax expense using the estimated tax rate at which the Company received a deduction for these adjustments. We define Adjusted Net Income (Loss) as net income (loss) adjusted for, as applicable, (i) depreciation and amortization, (ii) stock-based compensation expense, (iii) the impact of other non-cash fair market value adjustments, (iv) impairment and restructuring related expenses, (v) gain or loss on the sale of a business, (vi) net realized gains or losses on investments and (vii) other one-off transactions, which primarily include the receipt of earnout consideration and certain legal fees and settlement costs (gains) that we consider to be unique in nature, net of tax impact. We calculate the tax impact only on adjustments which would be included in calculating our income tax expense using the estimated tax rate at which the company received a deduction for these adjustments. We exclude the impact of depreciation and amortization, stock-based compensation expense, and non-cash fair market value adjustments, because these are non-cash expenses or non-cash fair value adjustments and we believe that excluding these items provides meaningful information regarding performance and ongoing cash-generation potential. We exclude impairment and restructuring related expenses, gain or loss on sale of business, and other one-off transactions because such expenses are periodic in nature and have no direct correlation to the cost of operating our business on an ongoing basis that we consider to be unique in nature. Management uses this measure to evaluate our underlying business performance. Adjusted net income (loss) does not reflect the overall profitability of our business. Shown below is the adjusted net income (loss) for the following periods and a reconciliation of this measure of performance to net income (loss) as presented in the consolidated statements of operations and comprehensive income (loss): 34 Table of Contents Three Months Ended June 30, Six Months Ended June 30, 2026 2025 2026 2025 (in millions) Net income (loss) attributable to Hippo $ 10.1 $ 1.3 $ 17.2 $ (46.4) Adjustments: Depreciation and amortization 4.8 5.3 9.6 10.9 Stock-based compensation 6.6 7.9 13.1 15.6 Fair value adjustments — 0.3 — (0.2) Other one-off transactions (0.6) 1.0 (1.8) 0.8 Impairment and restructuring charges — 1.2 — 1.2 Realized losses on investments 0.1 — 0.1 — Tax impact of adjustments — — — — Adjusted net income (loss) $ 21.0 $ 17.0 $ 38.2 $ (18.1) Diluted Adjusted Earnings (Loss) per Share Diluted Adjusted Earnings (Loss) per Share is a non‑GAAP financial measure defined as adjusted net income (loss) divided by the weighted average common shares outstanding for the period, reflecting the dilution which could occur if equity-based awards are converted into common share equivalents as calculated using the treasury stock method. Management uses this measure to assess performance on a per-share basis across periods. Diluted adjusted earnings (loss) per share should not be viewed as a substitute for diluted earnings (loss) per share calculated in accordance with GAAP, and other companies may define diluted adjusted earnings (loss) per share differently. Diluted adjusted earnings (loss) per share is calculated as follows: Three Months Ended June 30, Six Months Ended June 30, 2026 2025 2026 2025 (in millions, except share and per share data) Adjusted net income (loss) $ 21.0 $ 17.0 $ 38.2 $ (18.1) Weighted average common shares outstanding, diluted(1) 26,552,111 26,023,780 26,431,819 25,168,442 Diluted adjusted earnings (loss) per share $ 0.79 $ 0.65 $ 1.45 $ (0.72) (1)For additional information refer to Note 15, Net Income (Loss) Per Share Attributable to Common Stockholders, of the unaudited interim condensed consolidated financial statements. Annualized Adjusted Return on Equity Annualized adjusted return on equity is a non‑GAAP financial measure defined as adjusted net income (loss) expressed on an annualized basis as a percentage of average beginning and ending stockholders’ equity during the period. Management uses this measure to evaluate capital efficiency and returns generated on deployed capital. Annualized adjusted return on equity should not be viewed as a substitute for return on equity calculated using unadjusted GAAP numbers, and other companies may define adjusted return on equity differently. 35 Table of Contents Annualized adjusted return on equity is calculated as follows: Three Months Ended June 30, Six Months Ended June 30, 2026 2025 2026 2025 (in millions, except percentages) Annualized adjusted net income (loss) $ 84.0 $ 68.0 $ 76.4 $ (36.2) Average Hippo stockholders’ equity 457.2 327.7 450.9 347.3 Annualized adjusted return on equity 18.4 % 20.8 % 16.9 % (10.4) % Tangible Book Value Per Share Tangible Book Value Per Share is a non-GAAP financial measure defined as total stockholders’ equity, less intangible assets and capitalized internal use software, divided by the outstanding number of shares of our common stock at the end of the relevant period. Management uses this measure to evaluate changes from period to period in book value per share exclusive of changes in intangible assets in order to assess capital position and balance sheet strength. Tangible book value per share should not be viewed as a substitute for book value per share calculated in accordance with GAAP, and other companies may define tangible book value per share differently. Shown below are the tangible book value per share for the following periods and a reconciliation of this measure of performance to Hippo stockholders’ equity as presented in the consolidated balance sheet. As of June 30, 2026 December 31, 2025 (in millions, except share and per share data) Hippo stockholders’ equity $ 465.6 $ 436.1 Less: Intangible assets 13.4 13.8 Less: Capitalized internal use software 41.6 43.0 Tangible stockholders’ equity $ 410.6 $ 379.3 Shares outstanding 26,384,898 25,699,704 Tangible book value per share $ 15.56 $ 14.76 Liquidity and Capital Resources Sources of Liquidity Our existing sources of liquidity include cash and cash equivalents and marketable securities. As of June 30, 2026, we had $244.5 million of cash, $27.1 million of restricted cash, and $498.0 million of available-for-sale fixed income securities and short-term investments. We believe our cash, cash equivalents and short-term securities will be sufficient to fund our operations for at least the next twelve months following the date of this Quarterly Report on Form 10-Q. In addition, we are a member of the Federal Home Loan Bank (FHLB) of New York, which provides secured borrowing capacity. Our borrowing capacity as of June 30, 2026, is $58.8 million, and there were no outstanding amounts under this agreement. 36 Table of Contents The Company issued a surplus note on June 2, 2025 in the amount of $50.0 million. The surplus note issuance provides additional statutory capital and further supports our operational and growth initiatives. To date, we have funded operations primarily with issuances of convertible preferred stock, convertible promissory notes, common stock and a surplus note, as well as from asset dispositions and revenue. While we have achieved profitability in recent quarters, we cannot assure that we will continue to generate sufficient revenue and other income to cover operating expenses, working capital and capital expenditures in the longer term. We expect the funds raised as discussed above to fund our cash needs. However, our capital requirements depend on many factors, including the volume of issuances of insurance policies, the timing and extent of spending to support research and development efforts, investments in information technology systems, and the expansion of sales and marketing activities. In the future, we may raise additional funds through the issuance of debt or equity securities or through borrowing. We cannot assure that such funds will be on favorable terms, or available at all. Cash Flow Summary The following table summarizes our cash flows for the periods presented: Six Months Ended June 30, 2026 2025 Change (in millions) Net cash provided by (used in): Operating activities $ 51.6 $ (10.9) $ 62.5 Investing activities $ (34.7) $ (32.9) $ (1.8) Financing activities $ 4.6 $ 36.8 $ (32.2) Operating Activities Cash provided by operating activities was $51.6 million for the six months ended June 30, 2026, a change of $62.5 million, from cash used in operating activities of $10.9 million for the six months ended June 30, 2025. The increase was due primarily to growth in earned premium and lower levels of losses paid due to the absence of claim payments related to the January 2025 LA Wildfires, partially offset by higher cash outflows for settlements of ceded reinsurance. Variations in operating cash flow between periods are primarily driven by variations in our gross and ceded written premiums and the volume and timing of premium receipts, claim payments, reinsurance payments, and reinsurance recoveries on paid losses. In addition, fluctuations in losses and loss adjustment expenses and other insurance operating expenses impact operating cash flows. Investing Activities Cash used in investing activities was $34.7 million for the six months ended June 30, 2026, due primarily to the purchases of investment securities, partially offset by the maturities and sales of investment securities and proceeds of deferred consideration. Cash used in investing activities was $32.9 million for the six months ended June 30, 2025, due primarily to the purchases of investment securities, partially offset by the maturities of investment securities. Financing Activities Cash provided by financing activities was $4.6 million for the six months ended June 30, 2026, primarily driven by change in fiduciary liabilities and proceeds from common stock issuances. Cash provided by financing activities was $36.8 million for the six months ended June 30, 2025, primarily driven by proceeds from the surplus note and common stock issuances. These are partially offset by distributions to noncontrolling interests and change in fiduciary liabilities, and taxes paid related to net share settlement of RSUs. 37 Table of Contents Material Cash Requirements Our material cash requirements from known contractual and other obligations primarily relate to unpaid losses and loss adjustment expense, our surplus note, purchase commitments, and lease payments. There have been no material changes to our contractual obligations from those described in the Annual Report on Form 10-K for the year ended December 31, 2025, other than an increase in Unpaid Losses and Loss Adjustment Expense. The estimation of the unpaid losses and loss adjustment expenses is based on various complex and subjective judgments. Actual losses paid may differ, perhaps significantly, from the reserve estimates reflected in our unaudited interim condensed consolidated financial statements. Similarly, the timing of payment of our estimated losses is not fixed and there may be significant changes in actual payment activity. The assumptions used in estimating the likely payments due by period are based on our historical claims payment experience and industry payment patterns, but due to the inherent uncertainty in the process of estimating the timing of such payments, there is a risk that the amounts paid can be significantly different from the amounts disclosed. Critical Accounting Policies and Estimates Our discussion and analysis of our financial condition and results of operations are based upon our unaudited interim condensed consolidated financial statements, which have been prepared in accordance with GAAP. The preparation of our financial statements requires us to make estimates and judgments that affect the reported amounts in our unaudited interim condensed consolidated financial statements. We evaluate our estimates on an on-going basis, including those related to our revenue, losses and loss adjustment expense reserve, recoverability of our net deferred tax asset, and intangible assets. We base our estimates on historical experience and on various other assumptions that we believe to be reasonable under the circumstances, the results of which form the basis for making judgments about the carrying values of assets and liabilities. Although actual results have historically been reasonably consistent with management’s expectations, the actual results may differ from these estimates, or our estimates may be affected by different assumptions or conditions. Our critical accounting policies are described under the heading “Management’s Discussion and Analysis of Financial Condition and Results of Operations—Critical Accounting Estimates” in our 2025 Annual Report on Form 10-K and the notes to the unaudited interim condensed consolidated financial statements appearing elsewhere in this Quarterly Report. During the six months ended June 30, 2026, there were no material changes to our critical accounting policies from those discussed in our 2025 Annual Report on Form 10-K. Recent Accounting Pronouncements The information set forth under Note 1 to the unaudited interim condensed consolidated financial statements under the caption “Description of Business and Summary of Significant Accounting Policies” is incorporated herein by reference.