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Form 8-K

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HIPOW HIPO The company reported a significant improvement in net income and adjusted net income compared to the previous year. Gross Written Premium increased by 58%, and the Net Loss Ratio and Combined Ratio showed substantial improvement, indicating strong operational performance and underwriting efficiency.

8-K — Hippo Holdings Inc.

Accession: 0001828105-26-000023

Filed: 2026-04-30

Period: 2026-04-30

CIK: 0001828105

SIC: 6331 (FIRE, MARINE & CASUALTY INSURANCE)

Item: Results of Operations and Financial Condition

Item: Financial Statements and Exhibits

Documents

8-K — hippo-20260430.htm (Primary)

EX-99.1 (q126earningsreleasefinal.htm)

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8-K

8-K (Primary)

Filename: hippo-20260430.htm · Sequence: 1

hippo-20260430

0001828105FALSE00018281052026-04-302026-04-30

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

Form 8-K

CURRENT REPORT

PURSUANT TO SECTION 13 OR 15(D)

OF THE SECURITIES EXCHANGE ACT OF 1934

Date of Report (Date of earliest event reported): April 30, 2026

Hippo Holdings Inc.

(Exact Name of Registrant as Specified in Its Charter)

Delaware   001-39711   32-0662604

(State or other jurisdiction of

incorporation or organization)

(Commission

File Number)

(I.R.S. Employer

Identification Number)

One Almaden Blvd., Suite 400

San Jose, California 95113

650 294-8463

(Address, including zip code, and telephone number, including area code, of Registrant’s principal executive offices)

(Former name or former address, if changed since last report)

Check the appropriate box below if the Form 8-K is intended to simultaneously satisfy the filing obligation of the registrant under any of the following provisions:

☐ Written communications pursuant to Rule 425 under the Securities Act

☐ Soliciting material pursuant to Rule 14a-12 under the Exchange Act

☐ Pre-commencement communications pursuant to Rule 14d-2(b) under the Exchange Act

☐ Pre-commencement communications pursuant to Rule 13e-4(c) under the Exchange Act

Securities registered pursuant to Section 12(b) of the Act:

Title of each class

Trading

Symbol(s)

Name of each exchange

on which registered

Common stock, $0.0001 par value per share   HIPO   New York Stock Exchange

Indicate by check mark whether the registrant is an emerging growth company as defined in Rule 405 of the Securities Act of 1933 (§230.405 of this chapter) or Rule 12b-2 of the Securities Exchange Act of 1934 (§240.12b-2 of this chapter).

Emerging growth company ☐

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act. o

Item 2.02 Results of Operations and Financial Condition

On April 30, 2026, Hippo Holdings Inc. (the “Company”) issued a press release announcing certain financial results for the quarter ended March 31, 2026, as well as an investor presentation and historical supplemental financial information. A copy of the press release, investor presentation and historical supplemental financial information are furnished as Exhibits 99.1, 99.2 and 99.3 to this report, respectively.

The Company is making reference to non-GAAP financial information in the press release, investor presentation, historical supplemental financial information and the related conference call. A reconciliation of these non-GAAP financial measures to their nearest GAAP equivalents is provided in each of the press release, investor presentation and historical supplemental financial information.

The information in Item 2.02 of this Current Report on Form 8-K, including Exhibits 99.1, 99.2 and 99.3 to this Current Report on Form 8-K, shall not be deemed to be “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended, or otherwise subject to the liabilities of that section or Section 11 and 12(a)(2) of the Securities Act of 1933, as amended. The information contained in this Item 2.02 and in the accompanying Exhibits 99.1, 99.2 and 99.3 shall not be incorporated by reference into any registration statement or other document filed by the Company with the Securities and Exchange Commission, whether made before or after the date of this Current Report, regardless of any general incorporation language in such filing, except as shall be expressly set forth by specific reference to this Item 2.02 and Exhibit 99.1, Exhibit 99.2 or Exhibit 99.3 in such filing.

Item 9.01 Financial Statements and Exhibits

(d) Exhibits.

Exhibit Number Exhibit Title or Description

99.1

Press Release Announcing Financial Results for the First Quarter Ended March 31, 2026.

99.2

Quarterly Investor Presentation dated April 30, 2026.

99.3

Historical Supplemental Financial Information.

104 Cover Page Interactive Data File (embedded within the Inline XBRL document)

SIGNATURES

Pursuant to the requirements of the Securities Exchange Act of 1934, the registrant has duly caused this report to be signed on its behalf by the undersigned hereunto duly authorized.

Date: April 30, 2026

HIPPO HOLDINGS, INC.

By:   /s/ GUY ZELTSER

Guy Zeltser

Chief Financial Officer

EX-99.1

EX-99.1

Filename: q126earningsreleasefinal.htm · Sequence: 2

q126earningsreleasefinal

Hippo Reports First Quarter 2026 Financial Results April 30, 2026 SAN JOSE, Calif. (PRNewswire) -- Hippo Holdings Inc. (NYSE: HIPO), a technology-native insurance platform reported net income of $7 million, or $0.27 per diluted share and adjusted net income of $17 million, or $0.65 per diluted share, for the quarter ended March 31, 2026. First Quarter Highlights • Gross Written Premium increased 58% to $332 million over 1Q25 • Net Income of $7 million vs. a Net Loss of $48 million in 1Q25 • Adjusted Net Income of $17 million vs. an Adjusted Net Loss of $35 million in 1Q25 • Net Loss Ratio improved 58 percentage points to 48.0% compared to 1Q25 • Combined Ratio improved 60 percentage points to 99.5% compared to 1Q25 • Revenue grew 10% to $122 million compared to 1Q25 • Book Value per share of $17.23 up 2% from year-end 2025 "We got off to a fast start in 2026, significantly advancing our strategies on both growth and operational efficiencies. The launch of our strategic distribution relationship with Progressive, when—combined with our existing Westwood partnership —creates a truly differentiated distribution network for Hippo’s homeowners product that is both tech- enabled and scaled. Technology, which has long been a source of strength for Hippo, is core to supporting these new expanded distribution channels. Our AI-powered transformation across claims, services and underwriting should both support growth and increase profitability for Hippo over time,” said Rick McCathron, Hippo President and CEO. He continued, “For the quarter, Hippo grew gross written premium by 58%, significantly improved our underwriting results with a 60 point reduction in our combined ratio, and continued to deliver positive net income $7 million of and adjusted net income of $17 million for the quarter. We are operating as a unified, technology-native carrier platform that is driving profitable growth, broadening diversification, and positioning us for long-term success.” 1

Key Operating and Financial Metrics Three Months Ended March 31, 2026 2025 ($ in millions) Gross Written Premium $ 332.4 $ 210.9 Net Written Premium 101.4 100.3 Net Retention 31 % 48 % Total Revenue $ 121.5 $ 110.3 Net Income (Loss) (1) 7.1 (47.7) Adjusted Net Income (Loss) (1) (2) 17.2 (35.1) Basic Earnings (Loss) per Share (1) 0.27 (1.91) Diluted Earnings (Loss) per Share (1) 0.27 (1.91) Diluted Adjusted Earnings (Loss) per Share (1) (2) 0.65 (1.41) Net Loss Ratio 48.0 % 105.9 % Expense Ratio 51.5 % 53.3 % Combined Ratio 99.5 % 159.2 % As of March 31, 2026 December 31, 2025 Book Value Per Share (BVPS) $17.23 $16.97 Tangible Book Value Per Share (TBVPS) (2) $15.09 $14.76 (1) Attributable to Hippo (2) Indicates non-GAAP financial measure; see “Reconciliation of Non GAAP Financial Measures to Their Most Directly Comparable GAAP Financial Measures" First Quarter Operating Summary Net income of $7 million, or $0.27 per diluted share, compared to a $48 million net loss in Q1 of last year. The improvement was driven primarily by stronger underwriting performance. The first quarter of 2025 included a $45 million loss from California wildfires, and the absence of a comparable event this period more than offset the reduction in fee income following the sale of the builders distribution network. Adjusted net income of $17 million, or $0.65 a diluted share, compared to a $35 million net adjusted loss in Q1 of last year. This quarter's results equate to a 16% annualized adjusted return on average shareholders equity. Gross written premium of $332 million for the quarter increased 58% year over year, up from $211 million in Q1 of last year. Growth was driven by both the Casualty and Commercial Multi-Peril (CMP) lines which were up 193% and 89% over last year, to $101 million and $96 million, respectively. The overall growth strategy is focused on improving underwriting profitability and reducing volatility, including through greater portfolio diversification. For 2

the quarter, Casualty accounted for 30% of gross written premium, compared to CMP which accounted for 29% and Homeowners which accounted for 26%. Net written premium of $101 million increased by $1 million or 1% from Q1 of last year. Growth in net written premium was lower than the growth in gross written premium due to both a mix shift and a reduction in the Renters line, which contracted by $26 million year over year, on account of a change in retention rate in 2026 vs 2025, and an accompanying unearned premium adjustment related to this change. The 31% net retention rate in the quarter was slightly below our full-year guidance, and driven primarily by the one-time unearned premium adjustment noted above. We expect retention to normalize later in the year, though it may fluctuate quarter to quarter based on growth-related mix shifts. Revenue in the quarter of $122 million increased 10% from $110 million in Q1 of last year. The increase was primarily driven by higher net earned premium up 13% to $99 million, which more than offset a $5.5 million decline in commissions following the sale of our homebuilder distribution network in Q3'25. Net Loss ratio of 48.0% improved 58 percentage points over the prior year. This improvement was driven primarily by lower CAT losses this quarter compared to Q1 of last year, which was impacted by the California wildfires. The net accident year loss ratio excluding CAT losses of 46.3% improved by 2 percentage points over the Q1 of last year. Expense ratio of 51.5% improved 2 percentage points over the prior year period driven by continued improvement of operating leverage, and despite prior year period benefiting from roughly 4.5 percentage point of profits generated by the homebuilder distribution network we sold in Q3'25. Combined ratio of 99.5% improved 60 percentage points over the prior year, similarly driven by stronger underwriting performance and a lower expense ratio noted above. Total Hippo shareholder equity of $449 million, or $17.23 per share, at March 31, 2026, was up 2%, from $436 million, or $16.97 per share, at year-end 2025. The increase was primarily driven by the first quarter net income. Guidance Update The following Guidance update is based on current expectations. The following statements are forward-looking and actual results could differ materially depending on market conditions and the factors set forth under “Forward-looking statements safe harbor” below. 3

Prior Updated 2026 FY Guidance 2026 FY Guidance Gross Written Premium $1.4 - 1.5B $1.45 - $1.525B Net Written Premium $500 - $540M $520 - $550M Revenue $560 - $570M Combined Ratio 103% - 105% 103% - 105% CAT Loss Ratio 13 % 13 % Adjusted Net Income (Loss)(1) $45 - $55M $48 - $56M Stock-based compensation + Depreciation and Amortization $41M $42M (1) Indicates non-GAAP financial measure; see “Reconciliation of Non GAAP Financial Measures to Their Most Directly Comparable GAAP Financial Measures" First Quarter Earnings Conference Call and Webcast Information  Date: Thursday, April 30, 2026 Time: 8:00 a.m. Eastern Time / 5:00 a.m. Pacific Time Dial In: +1 833 470 1428 / Global Dial-In Numbers Access: 433055350 Webcast: https://events.q4inc.com/attendee/433055350 A replay of the webcast will be made available after the call in the investor relations section of the company's website at https://investors.hippo.com/ About Hippo Hippo is a technology-native insurance group that uses its carrier platform to diversify risk across both personal and commercial lines. Through the Hippo Homeowners Insurance Program, the company applies deep industry expertise and advanced underwriting to deliver proactive, tailored coverage for homeowners. Hippo Holdings Inc. subsidiaries include Hippo Insurance Services, Spinnaker Insurance Company, Spinnaker Specialty Insurance Company, and Wingsail Insurance Company. Hippo Insurance Services is a licensed property casualty insurance agent with products underwritten by various affiliated and unaffiliated insurance companies. For more information, please visit http:// www.hippo.com. 4

Consolidated Balance Sheet (in millions, unaudited) March 31, 2026 December 31, 2025 (unaudited) Assets Investments: Fixed maturities available-for-sale, at fair value (amortized cost: $299.3 million and $291.7 million, respectively) $ 298.7 $ 293.4 Short-term investments, at fair value (amortized cost: $125.3 million and $152.5 million, respectively) 125.2 152.5 Total investments 423.9 445.9 Cash and cash equivalents 275.4 218.3 Restricted cash 29.4 31.8 Accounts receivable, net of allowance of $0.3 million and $0.2 million, respectively 282.1 250.1 Reinsurance recoverable on paid and unpaid losses and LAE 398.1 346.6 Prepaid reinsurance premiums 386.7 353.7 Ceding commissions receivable 132.8 98.7 Capitalized internal use software 42.3 43.0 Intangible assets 13.6 13.8 Other assets 77.6 103.6 Total assets $ 2,061.9 $ 1,905.5 Liabilities and stockholders’ equity Liabilities: Loss and loss adjustment expense reserve $ 482.6 $ 420.4 Unearned premiums 615.3 579.7 Reinsurance premiums payable 356.3 304.4 Provision for commission 39.3 36.3 Surplus note 47.9 47.9 Accrued expenses and other liabilities 71.8 80.7 Total liabilities 1,613.2 1,469.4 Commitments and contingencies (Note 12) Stockholders’ equity: Common stock, $0.0001 par value per share; 80,000,000 shares authorized as of March 31, 2026 and December 31, 2025; 26,035,917 and 25,699,704 shares issued and outstanding as of March 31, 2026 and December 31, 2025, respectively — — Additional paid-in capital 1,659.4 1,651.5 Accumulated other comprehensive (loss) income (0.6) 1.8 Accumulated deficit (1,210.1) (1,217.2) Total stockholders’ equity 448.7 436.1 Total liabilities and stockholders’ equity $ 2,061.9 $ 1,905.5 5

Consolidated Statement of Operations (in millions, unaudited) Three Months Ended March 31, 2026 2025 Revenue: Net earned premium $ 98.9 $ 87.3 Commission income, net 12.7 14.4 Service and fee income 3.2 2.8 Net investment income 6.7 5.8 Total revenue 121.5 110.3 Expenses: Losses and loss adjustment expenses 47.5 92.4 Insurance related expenses 34.9 30.2 Technology and development expenses 9.4 8.1 Sales and marketing expenses 6.3 8.9 General and administrative expenses 16.2 16.5 Interest and other (income) expense, net — (0.2) Total expenses 114.3 155.9 Income (loss) before income taxes 7.2 (45.6) Income tax expense (benefit) 0.1 (0.2) Net income (loss) 7.1 (45.4) Net income attributable to noncontrolling interests, net of tax — 2.3 Net income (loss) attributable to Hippo $ 7.1 $ (47.7) Other comprehensive income (loss): Change in net unrealized gain (loss) on investments, net of tax (2.4) 2.1 Comprehensive income (loss) attributable to Hippo $ 4.7 $ (45.6) Per share data: Net income (loss) attributable to Hippo - basic and diluted $ 7.1 $ (47.7) Weighted-average shares used in computing net income (loss) per share attributable to Hippo Basic 25,840,004 24,978,901 Diluted 26,354,271 24,978,901 Net income (loss) per share attributable to Hippo Basic $ 0.27 $ (1.91) Diluted $ 0.27 $ (1.91) 6

Consolidated Statement of Cash Flow (in millions, unaudited) Three Months Ended March 31, 2026 2025 Cash flows from operating activities: Net cash provided by (used in) operating activities $ 8.5 $ (35.6) Cash flows from investing activities: Capitalized internal use software costs (3.1) (2.8) Purchases of property and equipment (0.1) (0.1) Purchases of fixed maturities (29.4) (15.7) Maturities of fixed maturities 20.9 11.2 Sales of fixed maturities 1.1 — Purchases of short-term investments (65.3) (50.4) Maturities of short-term investments 91.4 46.8 Sales of short-term investments 2.0 — Proceeds from deferred consideration 25.0 — Net cash provided by (used in) investing activities 42.5 (11.0) Cash flows from financing activities: Taxes paid related to net share settlement of equity awards — (3.3) Proceeds from issuance of common stock 1.0 1.0 Payments of contingent consideration — (0.2) Distributions to noncontrolling interests — (2.5) Other 2.7 (1.0) Net cash provided by (used in) financing activities 3.7 (6.0) Net increase (decrease) in cash, cash equivalents, and restricted cash 54.7 (52.6) Cash, cash equivalents, and restricted cash at the beginning of the period 250.1 232.8 Cash, cash equivalents, and restricted cash at the end of the period $ 304.8 $ 180.2 7

RECONCILIATION OF NON-GAAP FINANCIAL MEASURES TO THEIR MOST DIRECTLY COMPARABLE GAAP FINANCIAL MEASURES (in millions, unaudited) Adjusted Net Income (Loss) Three Months Ended March 31, 2026 2025 Net income (loss) attributable to Hippo $ 7.1 $ (47.7) Adjustments: Depreciation and amortization 4.8 5.6 Stock-based compensation 6.5 7.7 Fair value adjustments — (0.5) Other one-off transactions (1.2) (0.2) Adjusted net income (loss) $ 17.2 $ (35.1) Diluted Adjusted Earnings (Loss) per Share Three Months Ended March 31, 2026 2025 Adjusted net income (loss) $ 17.2 $ (35.1) Weighted-average common shares outstanding, diluted 26,354,271 24,978,901 Diluted Adjusted Earnings (Loss) per Share $ 0.65 $ (1.41) Annualized Adjusted Return on Equity Three Months Ended March 31, 2026 2025 Annualized Adjusted net income (loss) $ 68.8 $ (140.4) Average Hippo Stockholders' Equity 442.4 342.5 Annualized Adjusted Return on Equity 16 % (41) % Tangible Book Value Per Share As of March 31, 2026 As of December 31, 2025 Hippo Stockholders' Equity $ 448.7 $ 436.1 Less: Intangible assets 13.6 13.8 Less: Capitalized Internal Use Software $ 42.3 $ 43.0 Tangible stockholders’ equity $ 392.8 $ 379.3 Shares outstanding 26,035,917 25,699,704 Tangible book value per share $ 15.09 $ 14.76 8

SUPPLEMENTAL FINANCIAL INFORMATION (in millions, unaudited) Net Loss, Expense, and Combined Ratio Three Months Ended March 31, 2026 2025 Net Earned Premium $ 98.9 $ 87.3 Catastrophe losses 4.3 53.4 Non-catastrophe losses 43.2 39.0 Loss and loss adjustment expenses $ 47.5 $ 92.4 Catastrophe losses ratio 4.3 % 61.2 % Non-catastrophe losses ratio 43.7 % 44.7 % Net loss ratio 48.0 % 105.9 % Insurance related expenses $ 34.9 $ 30.2 Technology and development 9.4 8.1 Sales and marketing 6.3 8.9 General and administrative 16.2 16.5 Less: commission income, net and service and (15.9) (17.2) Total net expenses $ 50.9 $ 46.5 Expense Ratio 51.5 % 53.3 % Combined Ratio 99.5 % 159.2 % Prior accident year developments Loss and loss adjustment expenses (2.5) (3.1) Net loss ratio (2.6) % (3.6) % Net accident year loss ratio 50.6 % 109.5 % Net accident year loss ratio x catastrophe 46.3 % 48.3 % Gross and Net Loss Ratio Three Months Ended March 31, 2026 2025 Gross Losses and LAE $ 147.2 $ 211.8 Gross Earned Premium 297.3 222.8 Gross Loss Ratio 49.5% 95.1% Net Losses and LAE $ 47.5 $ 92.4 Net Earned Premium 98.9 87.3 Net Loss Ratio 48.0% 105.9% 9

Underwriting Data The Company has a single reportable segment and offers property & casualty insurance products. Gross written premiums (GWP), Net written premiums (NWP), and Net earned premiums (NEP) by line of business are presented below: Gross Written Premium (GWP) by State Three Months Ended March 31, 2026 2025 Amount % of GWP Amount % of GWP State California $ 66.0 19.9 % $ 46.0 21.8 % New York 44.2 13.3 % 12.2 5.8 % Florida 42.9 12.9 % 32.0 15.2 % Texas 36.2 10.9 % 26.0 12.3 % Illinois 12.9 3.8 % 6.0 2.8 % Georgia 9.7 2.9 % 5.6 2.7 % Ohio 7.2 2.2 % 4.6 2.2 % Colorado 7.0 2.1 % 4.5 2.1 % New Jersey 6.6 2.0 % 4.2 2.0 % Arizona 6.5 2.0 % 4.3 2.0 % Other 93.2 28.0 % 65.5 31.1 % Total $ 332.4 100.0 % $ 210.9 100 % Gross Written Premium (GWP) by Line of Business Three Months Ended March 31, 2026 2025 Amount % of GWP Amount % of GWP Change % Change Line of Business Homeowners $ 87.3 26 % $ 87.1 41 % $ 0.2 0.2 % Renters 40.8 12 % 35.0 17 % 5.8 16.6 % Commercial Multi-Peril 95.8 29 % 50.7 24 % 45.1 89.0 % Casualty 100.6 30 % 34.3 16 % 66.3 193.3 % Other 7.9 3 % 3.8 2 % 4.1 107.9 % Total $ 332.4 100 % $ 210.9 100 % $ 121.5 57.6 % 10

Net Written Premium (NWP) by Line of Business Three Months Ended March 31, 2026 2025 Amount % of NWP Amount % of NWP Change % Change Line of Business Homeowners $ 60.8 60 % $ 52.7 52.5 % $ 8.1 15.4 % Renters 10.8 11 % 37.2 37.1 % (26.4) (71.0) % Commercial Multi-Peril 17.6 17 % 12.5 12.5 % 5.1 40.8 % Casualty 12.9 13 % 1.1 1.1 % 11.8 1072.7 % Other (0.7) (1) % (3.2) (3.2) % 2.5 (78.1) % Total $ 101.4 100 % $ 100.3 100.0 % $ 1.1 1.1 % Net Earned Premium (NEP) by Line of Business Three Months Ended March 31, 2026 2025 Amount % of NEP Amount % of NEP Change % Change Line of Business Homeowners $ 62.7 63.4 % $ 61.6 70.6 % $ 1.1 1.8 % Renters 17.0 17.2 % 16.6 19.0 % 0.4 2.4 % Commercial Multi-Peril 15.9 16.1 % 6.6 7.6 % 9.3 140.9 % Casualty 3.2 3.2 % 0.5 0.6 % 2.7 540.0 % Other 0.1 0.1 % 2.0 2.2 % (1.9) (95.0) % Total $ 98.9 100.0 % $ 87.3 100.0 % $ 11.6 13.3 % 11

Information about Key Operating Metrics/Non-GAAP Financial Measures We define adjusted net income, a Non-GAAP financial measure, as net income 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 use adjusted net income as an internal performance measure in the management of our operations because we believe it gives our management and financial statement users useful insight into our results of operations and our underlying business performance. Adjusted net income does not reflect the overall profitably of our business and should not be viewed as a substitute for net income calculated in accordance with GAAP. Other companies may define adjusted net income differently. We define diluted adjusted earnings (loss) per share, a Non-GAAP financial measure, as adjusted net income 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. Diluted adjusted earnings (loss) per share should not be viewed as a substitute for diluted earnings (loss) per share calculated in accordance with GAAP. Other companies may define diluted adjusted earnings (loss) per share differently. We define annualized adjusted return on equity, a Non-GAAP financial measure, as adjusted net income (loss) expressed on an annualized basis as a percentage of average beginning and ending Hippo stockholders’ equity during the period. We use annualized adjusted return on equity as an internal performance measure in the management of our operations because we believe it gives our management and financial statement users useful insight into our results of operations and our underlying business performance. Annualized adjusted return on equity should not be viewed as a substitute for return on equity calculated in accordance with GAAP. Other companies may define annualized adjusted return on equity differently. We define tangible book value per share, a Non-GAAP financial measure, as total stockholders’ equity, less intangible assets, divided by the outstanding number of shares of our common stock at the end of the relevant period. Our definition of tangible book value per share may not be comparable to that of other companies, and it should not be viewed as a substitute for book value per share calculated in accordance with GAAP. We use tangible book value per share internally to evaluate changes from period to period in book value per share exclusive of changes in intangible assets. These Non-GAAP financial measures are in addition to, and not a substitute for, or superior to, measures of financial performance prepared in accordance with GAAP and 12

should not be considered as an alternative to net income, operating income or any other performance measures derived in accordance with GAAP. Reconciliations of these Non- GAAP financial measures to their most directly comparable GAAP counterpart is included above. We believe that these non-GAAP measures of financial results provide useful supplemental information to investors about Hippo. Cautionary Note Regarding Forward-Looking Statements Certain statements included in this press release that are not historical facts are forward- looking statements for purposes of the safe harbor provisions under the United States Private Securities Litigation Reform Act of 1995. These statements include, without limitation, statements regarding the financial position, business strategy, and the plans and objectives of management for Hippo Holdings Inc. (together with its subsidiaries, “Hippo,” the “Company,” “we,” “us” and “our”) for future operations. These statements constitute projections, forecasts, and forward-looking statements, and are not guarantees of performance. Such statements can be identified by the fact that they do not relate strictly to historical or current facts. Forward-looking statements generally are accompanied by words such as “anticipate,” “believe,” “continue,” “could,” “estimate,” “expect,” “future,” “intend,” “may,” “might,” “outlook,” “plan,” “possible,” “potential,” “predict,” “project,” “seek,” “seem,” “should,” “strive,” “will,” “would,” and similar expressions that predict or indicate future events or trends or that are not statements of historical matters, but the absence of these words does not mean that a statement is not forward-looking. Forward-looking statements in this press release include, for example, statements about: • our future results of operations and financial condition, including estimates and forecasts of financial and operating results and performance metrics, and our ability to attain and maintain profitability; • our business strategy, including our cost reduction efforts, our diversified distribution strategy, and our plans to expand into new markets and new products; • our ability to grow our business and, if such growth occurs, to effectively manage such growth, including the growth and development of our builder network and other distribution channels; • customer satisfaction and our ability to attract, retain, and expand our customer base; • our ability to maintain and enhance our brand and reputation, including the quality of our products and services; 13

• our expectations about our book of business, including our ability to cross-sell and to attain greater value from each customer; • the effects of seasonal and cyclical trends on our results of operations; • our ability to compete effectively in the segments of the insurance industry in which we operate; • our ability to underwrite risks accurately and charge competitive yet profitable rates to our customers, and the sufficiency of the analytical models we use to assess and predict exposure to catastrophe losses; • our ability to maintain reinsurance contracts and our near- and long-term strategies and expectations with respect to the availability, adequacy, coverage, limits, pricing, and cession of insurance risk; • our ability to utilize, develop, and protect our proprietary technology, digital platform, and intellectual property; • our ability to leverage our data, technology, and geographic diversity to help manage risk; • our ability to expand our product offerings or improve existing ones; • our ability to attract and retain personnel, including our officers and key employees; • potential harm caused by outages or interruptions in, or delays to, services provided by our third-party providers, including our data vendors; • potential harm caused by misappropriation of our data and compromises in cybersecurity, and our ability to receive, process, store, use, and share data in compliance with laws and regulations related to data privacy and data security; • potential harm caused by changes in internet search engines’ methodologies; • our denial of claims or our failure to accurately and timely pay claims; • the effects of severe weather events and other natural or man-made catastrophes, including the effects of climate change, global pandemics, and terrorism; • any overall decline in economic activity; • regulators’ identification of errors in the policy forms we use, the rates we charge, and our customer communications, including cancellations, non-renewals, and reinstatements, through market conduct exams, complaints, or other inquiries; 14

• our ability to navigate extensive insurance industry regulations and the scrutiny of state insurance regulators, and the effects of existing or new legal or regulatory requirements on our business, including with respect to maintenance of risk-based capital and financial strength ratings, the insurance industry generally, and data privacy and cybersecurity, in the United States and internationally; • our expected use of cash on our balance sheet, our future capital needs, and our ability to raise additional capital; • fluctuations in our results of operations and operating metrics; and • our public securities’ liquidity and trading. These statements are based on the current expectations of Hippo’s management and are not predictions of actual performance. You should not rely upon forward-looking statements as predictions of future events. Actual events and circumstances are difficult or impossible to predict and will differ from assumptions, and many actual events and circumstances are beyond the control of Hippo. Although we believe that we have a reasonable basis for each forward-looking statement contained in this press release, we cannot guarantee that the future results, levels of activity, performance, events, and circumstances reflected in the forward-looking statements will be achieved or occur at all. These forward-looking statements are subject to a number of risks, uncertainties, and other factors, including those described above and other risks set forth in the sections entitled “Risk Factors” in the Company’s most recent Annual Report on Form 10-K and subsequent Quarterly Reports on Form 10-Q, and in other documents that may be filed by the Company from time to time with the Securities and Exchange Commission (the “SEC”). Moreover, we operate in a very competitive and rapidly changing environment. New risks and uncertainties emerge from time to time, and it is not possible for us to predict all risks and uncertainties that could have an impact on the forward-looking statements contained in this press release. If any of these risks materialize or our assumptions prove incorrect, actual results could differ materially from the results implied by these forward-looking statements. There may be additional risks that Hippo does not presently know or that Hippo currently believes are immaterial that could also cause actual results, events, or circumstances to differ materially from those described in the forward-looking statements. These forward-looking statements are based on information available as of the date of this press release and reflect Hippo’s expectations, plans, forecasts, and views of future events as of that date. Accordingly, forward-looking statements should not be relied upon as representing Hippo’s views as of any subsequent date, and Hippo does not undertake any obligation to update forward-looking statements to reflect events or circumstances after the date they were made, whether as a result of new information, future events, or 15

otherwise, except as may be required under applicable securities laws. While Hippo may elect to update these forward-looking statements at some point in the future, Hippo specifically disclaims any obligation to do so. Accordingly, undue reliance should not be placed upon the forward-looking statements. Rounding Certain monetary amounts, percentages, and other figures included in this release have been subject to rounding adjustments. The sum of individual metrics may not always equal total amounts indicated due to rounding. Contacts Investors: Charles Sebaski Investors@hippo.com Press: Mark Olson press@hippo.com 16

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1st Quarter 2026 Financial Results April 30th, 2026

1st Quarter 2026 Financial Results Cautionary Note Regarding Forward-Looking Statements Certain statements included in this presentation that are not historical facts are forward-looking statements for purposes of the safe harbor provisions under the United States Private Securities Litigation Reform Act of 1995. These statements include, without limitation, statements regarding the financial position, business strategy, and the plans and objectives of management for Hippo Holdings Inc. (together with its subsidiaries, “Hippo,” the “Company,” “we,” “us” and “our”) for future operations. These statements constitute projections, forecasts, and forward-looking statements, and are not guarantees of performance. Such statements can be identified by the fact that they do not relate strictly to historical or current facts. Forward-looking statements generally are accompanied by words such as “anticipate,” “believe,” “continue,” “could,” “estimate,” “expect,” “future,” “intend,” “may,” “might,” “outlook,” “plan,” “possible,” “potential,” “predict,” “project,” “seek,” “seem,” “should,” “strive,” “will,” “would,” and similar expressions that predict or indicate future events or trends or that are not statements of historical matters, but the absence of these words does not mean that a statement is not forward-looking. Forward-looking statements in this presentation include, for example, statements about: our future results of operations and financial condition, including estimates and forecasts of financial and operating results and performance metrics, and our ability to attain and maintain profitability; our business strategy, including our cost reduction efforts, our diversified distribution strategy, and our plans to expand into new markets and new products; our ability to grow our business and, if such growth occurs, to effectively manage such growth, including the growth and development of our builder network and other distribution channels; customer satisfaction and our ability to attract, retain, and expand our customer base; our ability to maintain and enhance our brand and reputation, including the quality of our products and services; our expectations about our book of business, including our ability to cross-sell and to attain greater value from each customer; the effects of seasonal and cyclical trends on our results of operations; our ability to compete effectively in the segments of the insurance industry in which we operate; our ability to underwrite risks accurately and charge competitive yet profitable rates to our customers, and the sufficiency of the analytical models we use to assess and predict exposure to catastrophe losses; our ability to maintain reinsurance contracts and our near- and long-term strategies and expectations with respect to the availability, adequacy, coverage, limits, pricing, and cession of insurance risk; our ability to utilize, develop, and protect our proprietary technology, digital platform, and intellectual property; our ability to leverage our data, technology, and geographic diversity to help manage risk; our ability to expand our product offerings or improve existing ones; our ability to attract and retain personnel, including our officers and key employees; potential harm caused by outages or interruptions in, or delays to, services provided by our third-party providers, including our data vendors; potential harm caused by misappropriation of our data and compromises in cybersecurity, and our ability to receive, process, store, use, and share data in compliance with laws and regulations related to data privacy and data security; potential harm caused by changes in internet search engines’ methodologies; our denial of claims or our failure to accurately and timely pay claims; the effects of severe weather events and other natural or man-made catastrophes, including the effects of climate change, global pandemics, and terrorism; any overall decline in economic activity; regulators’ identification of errors in the policy forms we use, the rates we charge, and our customer communications, including cancellations, non-renewals, and reinstatements, through market conduct exams, complaints, or other inquiries; our ability to navigate extensive insurance industry regulations and the scrutiny of state insurance regulators, and the effects of existing or new legal or regulatory requirements on our business, including with respect to maintenance of risk-based capital and financial strength ratings, the insurance industry generally, and data privacy and cybersecurity, in the United States and internationally; our expected use of cash on our balance sheet, our future capital needs, and our ability to raise additional capital; fluctuations in our results of operations and operating metrics; and our public securities’ liquidity and trading. These statements are based on the current expectations of Hippo’s management and are not predictions of actual performance. You should not rely upon forward-looking statements as predictions of future events. Actual events and circumstances are difficult or impossible to predict and will differ from assumptions, and many actual events and circumstances are beyond the control of Hippo. Although we believe that we have a reasonable basis for each forward-looking statement contained in this presentation, we cannot guarantee that the future results, levels of activity, performance, events, and circumstances reflected in the forward-looking statements will be achieved or occur at all. These forward-looking statements are subject to a number of risks, uncertainties, and other factors, including those described above and other risks set forth in the sections entitled “Risk Factors” in the Company’s most recent Annual Report on Form 10-K and subsequent Quarterly Reports on Form 10-Q, and in other documents that may be filed by the Company from time to time with the Securities and Exchange Commission (the “SEC”). Moreover, we operate in a very competitive and rapidly changing environment. New risks and uncertainties emerge from time to time, and it is not possible for us to predict all risks and uncertainties that could have an impact on the forward-looking statements contained in this presentation. If any of these risks materialize or our assumptions prove incorrect, actual results could differ materially from the results implied by these forward- looking statements. There may be additional risks that Hippo does not presently know or that Hippo currently believes are immaterial that could also cause actual results, events, or circumstances to differ materially from those described in the forward-looking statements. These forward-looking statements are based on information available as of the date of this presentation and reflect Hippo’s expectations, plans, forecasts, and views of future events as of that date. Accordingly, forward- looking statements should not be relied upon as representing Hippo’s views as of any subsequent date, and Hippo does not undertake any obligation to update forward-looking statements to reflect events or circumstances after the date they were made, whether as a result of new information, future events, or otherwise, except as may be required under applicable securities laws. While Hippo may elect to update these forward-looking statements at some point in the future, Hippo specifically disclaims any obligation to do so. Accordingly, undue reliance should not be placed upon the forward-looking statements. Rounding Certain monetary amounts, percentages, and other figures included in this presentation have been subject to rounding adjustments. The sum of individual metrics may not always equal total amounts indicated due to rounding. 2 Disclaimers

1st Quarter 2026 Financial Results Hippo-at- a-glance 3 Technology native, multi-line carrier platform Scalable and efficient capital structure Market Leader in the New Home Builder Channel Proven and Industry-Leading talent Admitted and E&S offerings in all 50 states AM Best Rated ‘A-’ (IX)(1) 1st Quarter Highlights (1) AM Best has assigned the Spinnaker group of companies a Financial Strength Rating (FSR) of A- (Excellent) and a Long-Term Issuer Credit Rating (Long-Term ICR) of "a-" (Excellent). (2) Non-GAAP financial measure; see "Reconciliation of Non-GAAP Metrics" in Appendix $332M $122M Gross Written Premium Revenue +58% vs 1Q25 +10% vs 1Q25 48.0% 99.5% Loss Ratio Combined Ratio $7.1M $17.2M Net Income Adjusted Net Income(2)

1st Quarter 2026 Financial Results ...Well-Positioned To Achieve Long-Term Vision Diversified Carrier Platform $1.1B 2025 GWP   Disciplined Approach to Portfolio Optimization and Risk Management 60-65% Long-term Loss Ratio Targets Homeowners Renters CMP Other New Lines Differentiated Distribution Tech- Forward Thinking 2028 Growth Targets >$2B GWP >$125M Adj. Net Income(1) >18% Adj. ROE(1)   4 A technology-native insurance platform driving growth across owned and partner MGAs. Casualty (1) Non-GAAP financial measure; see "Reconciliation of Non-GAAP Metrics" in Appendix

1st Quarter 2026 Financial Results 5 Claims (announced Q1’26) Hippo’s first notice of loss (Clara) and end-to-end claims processing assistant First Notice of Loss Over 70% of Homeowners Claims Are Expected to Be Filed Digitally Claims Efficiency 30% efficiency gains translates to more claims per adjuster with faster cycle times and lower leakage CAT Event Management Rapidly increase capacity to better serve our customers in catastrophic events We are fundamentally changing how we handle claims AI Claims “Clara” Launch Q1'26

1st Quarter 2026 Financial Results 6 Growing our Agentic A.I. Workforce AI Roadmap — 2026 Claims (announced Q1'26) Clara, Hippo’s First Notice of Loss agent, powers an end-to-end, AI-driven claims processing workflow Service (testing & iterating) Hannah, Hippo’s service agent, will handle customer and producer support across voice, chat, and email U/W (in development) Hippo’s agentic assistants will supercharge our underwriting teams Operations (in development) AI-powered assistants and automation across Hippo’s broader operations

1st Quarter 2026 Financial Results Personal Lines Update Return to Homeowners Growth in 2026 Homeowners ~$87M GWP in 1Q2026 ↑ Turned the corner to growth in Q1 ↑ Progressive + Westwood creates differentiated distribution ↓ E&S home under increased competition Renters ~$41M GWP +17% in 1Q2026 ✓ One of Hippo's most seasoned programs ✓ Excellent 10yr underwriting track record ~33% Loss Ratio ✓ Reduced retention in 2026 7

1st Quarter 2026 Financial Results Commercial Lines Update Increasing Risk Appetite in 2026 Casualty ~$101M GWP +193% in 1Q2026 Largest line in Q1 at 30% of GWP compared to 16% last year Retention increased to 13% up from 3% in 1Q25 Limit profile predominately $100k to $1 million Commercial Multi-Peril (CMP) ~$96M GWP +89% in 1Q2026 Growth driven by multiple existing program partners Growth driven by Commercial Property & Business Owners Policy 11 active programs in CMP 8(1) Program level combined ratio excludes allocation of overhead expenses

1st Quarter 2026 Financial Results 9 Executing with Purpose Strength of Platform World Class Team Carrying Momentum into 2026 & Beyond A technology-native insurance platform driving growth across owned and partner MGAs.

1st Quarter 2026 Financial Results $210.9 $332.4 10 Performance Drivers: Growing & Diversifying 1Q26 vs 1Q25 Premium Mix $ Million 1Q2025 GWP 1Q2026 GWP n Casualty n Commercial Multi- Peril n Renters n Homeowners n Other $100.3 $101.4 1Q2025 NWP 1Q2026 NWP 1Q2026 Driving Factors: Casualty GWP & NWP CMP Lines GWP Renters Retention

1st Quarter 2026 Financial Results 11 Improving Consolidated Net Underwriting 1Q2026 Driving Factors: CAT Losses Attritional Losses Expense Ratio Combined Ratio 1Q26 vs 1Q25 Improved by 60 points 159.2% 99.5% 53.3% 51.5% 48.3% 46.3% 61.2% 4.3% (3.6)% (2.6)% g CAT Loss Ratio g Net Accident Year Loss Ratio g Expense Ratio g Prior Year Development Ratio 1Q2025 1Q2026

1st Quarter 2026 Financial Results 12 Performance in Q1 2026 Net Income(1) $ Million Adjusted Net Income(2) $ Million Annualized Adjusted Return on Equity(2) (41%) 16% (35.1) 17.2 1Q2025 1Q2026 1Q2025 1Q20261Q2025 1Q2026 (47.7) 7.1 (1) Attributable to Hippo (2) Non-GAAP financial measure; see "Reconciliation of Non-GAAP Metrics" in Appendix

1st Quarter 2026 Financial Results $449M million shareholders equity Up 2% from year-end 2025 Growing Book Value Per Share BVPS ($) 4Q’24 BVPS 4Q’25 BVPS 1Q’26 BVPS $16.97 $17.23 14.56 13

1st Quarter 2026 Financial Results 2026 Guidance Metric 2026 Guidance(1) 2026 Guidance(1) Update Gross Written Premium $1.4 - $1.5B $1.45 – $1.525B Net Written Premium $500 - $540M $520 – $550M Revenue $560 - $570M Combined Ratio 103% – 105% 103% – 105% Adjusted Net Income(2) $45 - $55M $48 – $56M CAT Loss Ratio 13% 13% Stock-based comp + D&A $41M $42M (1) The 2026 guidance is based on current expectations. These statement are forward-looking and actual results could differ materially depending on the market conditions and factors set forth under "Forward-looking Statements Safe Harbor" on Slide 2. (2) Non-GAAP financial measure; see "Reconciliation of Non-GAAP Metrics" in Appendix, please reference slide 17 for related to forward looking statement reconciliations

Q&A

Appendix

1st Quarter 2026 Financial Results 17 Disclaimers Non-GAAP Financial Measures This presentation includes the non-GAAP financial measures (including on a forward- looking basis) Adjusted Net Income (Loss), Diluted Adjusted Earnings (Loss) per Share, Annualized Adjusted Return on Equity, and Tangible Book Value per Share. Hippo defines Adjusted Net Income, as net income excluding the impact of certain items that may not be indicative of underlying business trends, operating results, or future outlook, net of tax impact. Hippo calculates the tax impact only on adjustments which would be included in calculating its income tax expense using the estimated tax rate at which the company received a deduction for these adjustments. This non-GAAP measure is an addition, and not a substitute for, or superior to, measures of financial performance prepared in accordance with GAAP and should not be considered as an alternative to net income, operating income or any other performance measures derived in accordance with GAAP. Hippo defines Diluted Adjusted Earnings (loss) per Share 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. Hippo defines Annualized Adjusted Return on Equity as adjusted net income (loss) expressed on an annualized basis as a percentage of average beginning and ending stockholders’ equity during the period. Hippo defines Tangible Book Value Per Share 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. Reconciliations of non-GAAP measures to their most directly comparable GAAP counterparts are included in the Appendix to this presentation. Hippo believes that these non-GAAP measures of financial results (including on a forward-looking basis) provide useful supplemental information to investors about Hippo. Hippo’s management uses forward looking non-GAAP measures to evaluate Hippo’s projected financial and operating performance. However, there are a number of limitations related to the use of these non-GAAP measures and their nearest GAAP equivalents. For example other companies may calculate non-GAAP measures differently, or may use other measures to calculate their financial performance, and therefore Hippo’s non-GAAP measures may not be directly comparable to similarly titled measures of other companies. This presentation also includes certain projections of non-GAAP financial measures. Due to the high variability and difficulty in making accurate forecasts and projections of some of the information excluded from these projected measures, together with some of the excluded information not being ascertainable or accessible, Hippo is unable to quantify certain amounts that would be required to be included in the most directly comparable GAAP financial measures without unreasonable effort. Consequently, no disclosure of estimated comparable GAAP measures is included and no reconciliation of the forward looking non-GAAP financial measures is included.

1st Quarter 2026 Financial Results 18 Key Operating Metrics (in millions, except per share data, unaudited) Q1’24 Q2’24 Q3’24 Q4’24 Q1’25 Q2’25 Q3’25 Q4’25 Q1'26 (in millions, except per share data) Net earned premium $60.5 $64.4 $70.6 $77.0 $87.3 $94.0 $99.7 $99.1 $98.9 Commission income, net 15.9 16.1 15.7 15.9 14.4 14.7 10.5 11.7 12.7 Service and fee income 2.8 3.0 3.0 2.8 2.8 2.9 3.1 3.0 3.2 Net investment income 5.9 6.1 6.2 6.3 5.8 5.7 7.3 6.6 6.7 Total Revenue $85.1 $89.6 $95.5 $102.0 $110.3 $117.3 $120.6 $120.4 $121.5 Net Income (Loss) (1) (35.7) (40.5) (8.5) 44.2 (47.7) 1.3 98.1 6.0 7.1 Adjusted Net Income (Loss) (1) (2) (14.1) (19.5) (1.3) 14.7 (35.1) 17.0 18.3 17.6 17.2 Basic Earnings (Loss) per Share (1) (1.47) (1.64) (0.34) 1.78 (1.91) 0.05 3.90 0.24 0.27 Diluted Earnings (Loss) per Share (1) (1.47) (1.64) (0.34) 1.71 (1.91) 0.05 3.77 0.23 0.27 Diluted Adjusted Earnings (Loss) per Share (1) (2) (0.58) (0.79) (0.05) 0.57 (1.41) 0.65 0.70 0.67 0.65 Net Loss Ratio 87% 94% 73% 58% 106% 47% 48% 46% 48% Expense Ratio 71% 72% 55% 49% 53% 53% 52% 53% 51% Combined Ratio 158% 166% 128% 107% 159% 100% 100% 99% 100% Book Value Per Share (BVPS) $14.39 $12.96 $12.94 $14.56 $12.83 $13.02 $16.64 $16.97 $17.23 Tangible Book Value Per Share (TBVPS) (2) $11.31 $9.95 $10.28 $11.94 $10.31 $10.61 $14.37 $14.76 $15.09 (1) Attributable to Hippo (2) Indicates non-GAAP financial measure; see “Reconciliation of Non GAAP Financial Measures to Their Most Directly Comparable GAAP Financial Measures"

1st Quarter 2026 Financial Results 19 Reconciliation of Non-GAAP Metrics (in millions, except share and per share data, unaudited) Q1’24 Q2’24 Q3’24 Q4’24 Q1’25 Q2’25 Q3’25 Q4’25 Q1'26 Net income (loss) attributable to Hippo $ (35.7) $ (40.5) $ (8.5) $ 44.2 $ (47.7) $ 1.3 $ 98.1 $ 6.0 $ 7.1 Adjustments Depreciation and amortization 5.6 5.9 5.9 5.8 5.6 5.3 4.7 4.8 4.8 Stock-based compensation 8.4 11.9 9.0 8.9 7.7 7.9 7.0 6.7 6.5 Fair value adjustments 1.5 0.4 0.3 (0.5) (0.5) 0.3 — (0.4) — Other one-off transactions 2.5 2.8 0.2 2.4 (0.2) 1.0 (0.3) 0.5 (1.2) Impairment and restructuring 3.6 — — — — 1.2 3.8 — — Gain on sale of a business — — (8.2) (46.1) — — (95.0) — — Adjusted net income (loss) $ (14.1) $ (19.5) $ (1.3) $ 14.7 $ (35.1) $ 17.0 $ 18.3 $ 17.6 $ 17.2 Diluted Adjusted Earnings (Loss) Per Share Adjusted net income (loss) $ (14.1) $ (19.5) $ (1.3) $ 14.7 $ (35.1) $ 17.0 $ 18.3 $ 17.6 $ 17.2 Weighted-average common shares outstanding, diluted 24,225,650 24,633,960 25,068,472 25,889,665 24,978,901 26,023,780 26,025,069 26,245,980 26,354,271 Diluted Adjusted Earnings (loss) $ (0.58) $ (0.79) $ (0.05) $ 0.57 $ (1.41) $ 0.65 $ 0.70 $ 0.67 $ 0.65 $(14.1)M $(19.5)M $(1.3)M $14.7M $(35.1)M $17.0M $17.6M Adjusted Net Income (Loss) $18.3M $17.2M

1st Quarter 2026 Financial Results 20 Reconciliation of Non-GAAP Metrics (in millions, except share and per share data, unaudited) Q1’24 Q2’24 Q3’24 Q4’24 Q1’25 Q2’25 Q3’25 Q4’25 Q1'26 Annualized Adjusted net income (loss) $ (56.4) $ (78.0) $ (5.2) $ 58.8 $ (140.4) $ 68.0 $ 73.2 $ 70.4 $ 68.8 Average Hippo Stockholders' Equity 364.6 336.9 324.5 344.3 342.5 327.7 377.0 428.8 442.4 Annualized Adjusted Return on Equity (15%) (23%) (2%) 17% (41%) 21% 19% 16% 16% Tangible Book Value Per Share Hippo Stockholders' Equity $ 351.2 $ 322.6 $ 326.4 $ 362.1 $ 322.8 $ 332.5 $ 421.5 $ 436.1 $ 448.7 Less: Intangible assets 26.2 25.0 23.8 17.0 16.1 14.3 14.0 13.8 13.6 Less: Capitalized internal use software 48.9 49.9 43.3 48.1 47.4 47.2 43.3 43.0 42.3 Tangible stockholders’ equity $ 276.1 $ 247.7 $ 259.3 $ 297.0 $ 259.3 $ 271.0 $ 364.2 $ 379.3 $ 392.8 Shares outstanding 24,409,724 24,891,528 25,232,297 24,866,803 25,157,214 25,543,053 25,337,366 25,699,704 26,035,917 Tangible book value per share $ 11.31 $ 9.95 $ 10.28 $ 11.94 $ 10.31 $ 10.61 $ 14.37 $ 14.76 $ 15.09 Annualized Adjusted Return on Equity

1st Quarter 2026 Financial Results 21 Underwriting (in millions, unaudited) Q1’24 Q2’24 Q3’24 Q4’24 Q1’25 Q2’25 Q3’25 Q4’25 Q1'26 Net Earned Premium $60.5 $64.4 $70.6 $77.0 $87.3 $94.0 $99.7 $99.1 $98.9 Catastrophe losses 15.4 21.5 16.1 4.8 53.4 8.0 (0.3) (1.0) 4.3 Non-catastrophe losses 37.2 38.9 35.5 39.6 39.0 36.5 47.8 46.5 43.2 Loss and loss adjustment expenses $52.6 $60.4 $51.6 $44.4 $92.4 $44.5 $47.5 $45.5 $47.5 Catastrophe losses 25.5% 34.4% 22.8% 6.2% 61.2% 7.5% 0.0% (1.0%) 4.3% Non-catastrophe losses 62.5% 60.4% 50.3% 52.4% 44.7% 38.8% 48.0% 46.9% 43.7% Net loss ratio 87.0% 94.0% 73.0% 58.0% 105.9% 47.0% 48.0% 45.9% 48.0% Insurance related expenses $20.8 $24.5 $22.6 $20.9 $30.2 $32.8 $32.9 $35.4 $34.9 Technology and development 8.3 7.8 7.0 7.6 8.1 8.1 8.0 8.3 9.4 Sales and marketing 14.4 13.4 12.5 10.9 8.9 9.2 8.0 7.3 6.3 General administrative 18.3 19.9 15.3 17.2 16.5 17.4 16.5 16.7 16.2 Less: commission income, net and service and fee income (18.7) (19.1) (18.7) (18.7) (17.2) (17.6) (13.6) (14.7) (15.9) Total net expenses $43.1 $46.5 $38.7 $37.9 $46.5 $49.9 $51.8 $53.0 $50.9 Expense Ratio 71.2% 72.2% 54.8% 49.2% 53.3% 53.1% 52.0% 53.5% 51.5% Combined Ratio 158.2% 166.2% 127.8% 107.2% 159.2% 100.1% 100.0% 99.4% 99.5% Prior accident year developments Loss and loss adjustment expenses — (1.9) (1.9) (2.1) (3.1) (7.0) (0.5) 1.1 (2.5) Net loss ratio —% (3.0%) (2.7%) (2.7%) (3.6%) (7.4%) (0.5%) 1.0% (2.6%) Net accident year loss ratio 87.0% 97.0% 75.7% 60.7% 109.5% 54.4% 48.5% 44.9% 50.6% Net accident year loss ratio x catastrophe 61.5% 62.6% 52.9% 54.5% 48.3% 46.9% 48.5% 45.9% 46.3% Net Loss, Expense, And Combined Ratio

1st Quarter 2026 Financial Results 22 Underwriting (in millions, unaudited) Q1’24 Q2’24 Q3’24 Q4’24 Q1’25 Q2’25 Q3’25 Q4’25 Q1'26 Gross Losses and LAE $121.1 $123.2 $106.3 $99.5 $211.8 $87.8 $100.6 $134.8 $147.2 Gross Earned Premium 206.7 212.2 213.4 221.5 222.8 238.5 253.0 272.6 297.3 Gross Loss Ratio 59% 58% 50% 45% 95.1% 36.8% 39.8% 49.4% 49.5% Net Losses and LAE $52.6 $60.4 $51.6 $44.4 $92.4 $44.5 $47.5 $45.5 $47.5 Net Earned Premium 60.5 64.4 70.6 77.0 87.3 94.0 99.7 99.1 98.9 Net Loss Ratio 87% 94% 73% 58% 105.9% 47% 48% 45.9% 48.0% Gross & Net Loss Ratio

1st Quarter 2026 Financial Results 23 Q1’24 Q2’24 Q3’24 Q4’24 Q1’25 Q2’25 Q3’25 Q4’25 Q1'26 Gross Written Premium Homeowners $97.0 $118.7 $111.3 $96.1 $87.1 $100.0 $101.0 $91.0 $87.3 Renters 29.0 33.8 52.9 31.3 35.0 44.2 59.3 36.4 40.8 Commercial Multi-Peril 31.3 49.6 29.6 41.0 50.7 83.3 66.0 64.9 95.8 Casualty 33.0 39.5 32.2 32.9 34.3 64.9 76.3 88.4 100.6 Other 4.4 16.1 8.4 4.3 3.8 6.2 8.6 7.2 7.9 Total $194.7 $257.7 $234.4 $205.6 $210.9 $298.6 $311.2 $287.9 $332.4 Net Written Premium Homeowners $95.4 $68.1 $78.2 $65.5 $52.7 $63.0 $75.7 $63.5 $60.8 Renters 5.0 5.4 8.7 5.5 37.2 19.5 26.4 18.0 10.8 Commercial Multi-Peril 7.5 8.9 2.3 10.4 12.5 26.0 13.6 14.1 17.6 Casualty 0.6 0.6 0.4 0.4 1.1 1.5 3.7 2.3 12.9 Other 0.3 10.8 1.0 (2.6) (3.2) (3.1) (1.5) (0.7) (0.7) Total $108.8 $93.8 $90.6 $79.2 $100.3 $106.9 $117.9 $97.2 $101.4 Net Earned Premium Homeowners $49.1 $51.9 $57.1 $62.7 $61.6 $62.3 $63.9 $63.4 $62.7 Renters 4.9 5.3 5.7 6.4 16.6 18.7 18.7 18.4 17.0 Commercial Multi-Peril 4.1 4.6 4.1 6.2 6.6 11.9 13.8 15.5 15.9 Casualty 0.6 0.5 0.4 0.4 0.5 0.8 3.2 1.6 3.2 Other 1.8 2.1 3.3 1.3 2.0 0.3 0.1 0.2 0.1 Total $60.5 $64.4 $70.6 $77.0 $87.3 $94.0 $99.7 $99.1 $98.9 Premium by Line of Business Underwriting (in millions, unaudited)

Contact Information Charles Sebaski Head of Investor Relations IR@hippo.com

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historicalquartersnewmet

Hippo Holdings (NYSE: HIPO) Consolidated Line of Business Reporting 1Q2025 to 1Q2026 1

Key Operating and Financial Metrics (in millions, except per share data, unaudited) 2025 2026 Q1 Q2 Q3 Q4 Q1 Gross Written Premium $ 210.9 $ 298.6 $ 311.2 $ 287.9 $ 332.4 Net Written Premium 100.3 106.9 117.9 97.2 101.4 Net Retention 48 % 36 % 38 % 34 % 31 % Total Revenue $ 110.3 $ 117.3 $ 120.6 $ 120.4 $ 121.5 Net Income (Loss) (1) (47.7) 1.3 98.1 6.0 7.1 Adjusted Net Income (Loss) (1) (2) (35.1) 17.0 18.3 17.6 17.2 Basic Earnings (Loss) per Share (1) (1.91) 0.05 3.90 0.24 0.27 Diluted Earnings (Loss) per Share (1) (1.91) 0.05 3.77 0.23 0.27 Diluted Adjusted Earnings (Loss) per Share (1) (2) (1.41) 0.65 0.70 0.67 0.65 Net Loss Ratio 105.9 % 47.0 % 48.0 % 45.9 % 48.0 % Expense Ratio 53.3 % 53.1 % 52.0 % 53.5 % 51.5 % Combined Ratio 159.2 % 100.1 % 100.0 % 99.4 % 99.5 % Book Value Per Share (BVPS) $12.83 $13.02 $16.64 $16.97 $17.23 Tangible Book Value Per Share (TBVPS) (2) $10.31 $10.61 $14.37 $14.76 $15.09 (1) Attributable to Hippo (2) Indicates non-GAAP financial measure; see “Reconciliation of Non GAAP Financial Measures to Their Most Directly Comparable GAAP Financial Measures" 1

RECONCILIATION OF NON-GAAP FINANCIAL MEASURES TO THEIR MOST DIRECTLY COMPARABLE GAAP FINANCIAL MEASURES (in millions, except share and per share data, unaudited) Adjusted Net Income (Loss) 2025 2026 Q1 Q2 Q3 Q4 Q1 Net income (loss) attributable to Hippo $ (47.7) $ 1.3 $ 98.1 $ 6.0 $ 7.1 Adjustments: Depreciation and amortization 5.6 5.3 4.7 4.8 4.8 Stock-based compensation 7.7 7.9 7.0 6.7 6.5 Fair value adjustments (0.5) 0.3 — (0.4) — Other one-off transactions (0.2) 1.0 (0.3) 0.5 (1.2) Impairment and restructuring charges — 1.2 3.8 — — Gain on sale of a business — — (95.0) — — Adjusted net income (loss) $ (35.1) $ 17.0 $ 18.3 $ 17.6 $ 17.2 Diluted Adjusted Earnings (Loss) per Share 2025 2026 Q1 Q2 Q3 Q4 Q1 Adjusted net income (loss) $ (35.1) $ 17.0 $ 18.3 $ 17.6 $ 17.2 Weighted-average common shares outstanding, diluted 24,978,901 26,023,780 26,025,069 26,245,980 26,354,271 Diluted Adjusted Earnings (Loss) per Share $ (1.41) $ 0.65 $ 0.70 $ 0.67 $ 0.65 Annualized Adjusted Return on Equity 2025 2026 Q1 Q2 Q3 Q4 Q1 Annualized Adjusted net income (loss) $ (140.4) $ 68.0 $ 73.2 $ 70.4 $ 68.8 Average Hippo Stockholders' Equity 342.5 327.7 377.0 428.8 442.4 Annualized Adjusted Return on Equity (41) % 21 % 19 % 16 % 16 % Tangible Book Value Per Share 2025 2026 Q1 Q2 Q3 Q4 Q1 Hippo Stockholders' Equity $ 322.8 $ 332.5 $ 421.5 $ 436.1 $ 448.7 Less: Intangible assets 16.1 14.3 14.0 13.8 13.6 Less: Capitalized internal use software 47.4 47.2 43.3 43.0 42.3 Tangible stockholders’ equity $ 259.3 $ 271.0 $ 364.2 $ 379.3 $ 392.8 Shares outstanding 25,157,214 25,543,053 25,337,366 25,699,704 26,035,917 Tangible book value per share $ 10.31 $ 10.61 $ 14.37 $ 14.76 $ 15.09 2

SUPPLEMENTAL FINANCIAL INFORMATION (in millions, unaudited) Net Loss, Expense, and Combined Ratio 2025 2026 Q1 Q2 Q3 Q4 Q1 Net Earned Premium $ 87.3 $ 94.0 $ 99.7 $ 99.1 $ 98.9 Catastrophe losses 53.4 8.0 (0.3) (1.0) 4.3 Non-catastrophe losses 39.0 36.5 47.8 46.5 43.2 Loss and loss adjustment expenses $ 92.4 $ 44.5 $ 47.5 $ 45.5 $ 47.5 Catastrophe losses ratio 61.2 % 7.5 % — % (1.0) % 4.3 % Non-catastrophe losses ratio 44.7 % 38.8 % 48.0 % 46.9 % 43.7 % Net loss ratio 105.9 % 47.0 % 48.0 % 45.9 % 48.0 % Insurance related expenses $ 30.2 $ 32.8 $ 32.9 $ 35.4 $ 34.9 Technology and development 8.1 8.1 8.0 8.3 9.4 Sales and marketing 8.9 9.2 8.0 7.3 6.3 General and administrative 16.5 17.4 16.5 16.7 16.2 Less: commission income, net and service and fee income (17.2) (17.6) (13.6) (14.7) (15.9) Total net expenses $ 46.5 $ 49.9 $ 51.8 $ 53.0 $ 50.9 Expense Ratio 53.3 % 53.1 % 52.0 % 53.5% 51.5% Combined Ratio 159.2 % 100.1 % 100.0 % 99.4% 99.5% Prior accident year developments Loss and loss adjustment expenses $ (3.1) $ (7.0) $ (0.5) $ 1.1 $ (2.5) Net loss ratio (3.6) % (7.4) % (0.5) % 1.0 % (2.6) % Net accident year loss ratio 109.5 % 54.4 % 48.5 % 44.9 % 50.6 % Net accident year loss ratio x catastrophe losses 48.3 % 46.9 % 48.5 % 45.9 % 46.3 % Gross and Net Loss Ratio 2025 2026 Q1 Q2 Q3 Q4 Q1 Gross Losses and LAE $ 211.8 $ 87.8 $ 100.6 $ 134.8 $ 147.2 Gross Earned Premium 222.8 238.5 253.0 272.6 297.3 Gross Loss Ratio 95 % 37 % 40 % 49.4 % 49.5 % Net Losses and LAE $ 92.4 $ 44.5 $ 47.5 $ 45.5 $ 47.5 Net Earned Premium 87.3 94.0 99.7 99.1 98.9 Net Loss Ratio 105.9 % 47 % 48 % 45.9 % 48.0 % 3

Underwriting Data The Company has a single reportable segment and offers property & casualty insurance products. Gross written premiums (GWP), Net written premiums (NWP), and Net earned premiums (NEP) by line of business are presented below. Gross Written Premium (GWP) by Line of Business 2025 2026 Q1 Q2 Q3 Q4 Q1 Product Homeowners $ 87.1 $ 100.0 $ 101.0 $ 91.0 $ 87.3 Renters 35.0 44.2 59.3 36.4 40.8 Commercial Multi-Peril 50.7 83.3 66.0 64.9 95.8 Casualty 34.3 64.9 76.3 88.4 100.6 Other 3.8 6.2 8.6 7.2 7.9 Total $ 210.9 $ 298.6 $ 311.2 $ 287.9 $ 332.4 Net Written Premium (NWP) by Line of Business 2025 2026 Q1 Q2 Q3 Q4 Q1 Product Homeowners $ 52.7 $ 63.0 $ 75.7 $ 63.5 $ 60.8 Renters 37.2 19.5 26.4 18.0 10.8 Commercial Multi-Peril 12.5 26.0 13.6 14.1 17.6 Casualty 1.1 1.5 3.7 2.3 12.9 Other (3.2) (3.1) (1.5) (0.7) (0.7) Total $ 100.3 $ 106.9 $ 117.9 $ 97.2 $ 101.4 Net Earned Premium (NEP) by Line of Business 2025 2026 Q1 Q2 Q3 Q4 Q1 Product Homeowners $ 61.6 $ 62.3 $ 63.9 $ 63.4 $ 62.7 Renters 16.6 18.7 18.7 18.4 17.0 Commercial Multi-Peril 6.6 11.9 13.8 15.5 15.9 Casualty 0.5 0.8 3.2 1.6 3.2 Other 2.0 0.3 0.1 0.2 0.1 Total $ 87.3 $ 94.0 $ 99.7 $ 99.1 $ 98.9 4

Information about Key Operating Metrics/Non-GAAP Financial Measures 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, and (vi) other one-off transactions, which primarily include certain legal fees and settlement costs, that we consider to be unique in nature, net of tax impact. 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 evaluate our underlying business performance. Adjusted net income (loss) does not reflect the overall profitability of our business. 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 per share calculated in accordance with GAAP, and other companies may define diluted adjusted earnings (loss) per share differently. 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. 5

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. These Non-GAAP financial measures are in addition to, and not a substitute for, or superior to, measures of financial performance prepared in accordance with GAAP and should not be considered as an alternative to net income, operating income or any other performance measures derived in accordance with GAAP. Reconciliations of these Non- GAAP financial measures to their most directly comparable GAAP counterpart is included above. We believe that these non-GAAP measures of financial results provide useful supplemental information to investors about Hippo. Cautionary Note Regarding Forward-Looking Statements Certain statements included in this press release that are not historical facts are forward- looking statements for purposes of the safe harbor provisions under the United States Private Securities Litigation Reform Act of 1995. These statements include, without limitation, statements regarding the financial position, business strategy, and the plans and objectives of management for Hippo Holdings Inc. (together with its subsidiaries, “Hippo,” the “Company,” “we,” “us” and “our”) for future operations. These statements constitute projections, forecasts, and forward-looking statements, and are not guarantees of performance. Such statements can be identified by the fact that they do not relate strictly to historical or current facts. Forward-looking statements generally are accompanied by words such as “anticipate,” “believe,” “continue,” “could,” “estimate,” “expect,” “future,” “intend,” “may,” “might,” “outlook,” “plan,” “possible,” “potential,” “predict,” “project,” “seek,” “seem,” “should,” “strive,” “will,” “would,” and similar expressions that predict or indicate future events or trends or that are not statements of historical matters, but the absence of these words does not mean that a statement is not forward-looking. Forward-looking statements in this press release include, for example, statements about: • our future results of operations and financial condition, including estimates and forecasts of financial and operating results and performance metrics, and our ability to attain and maintain profitability; 6

• our business strategy, including our cost reduction efforts, our diversified distribution strategy, and our plans to expand into new markets and new products; • our ability to grow our business and, if such growth occurs, to effectively manage such growth, including the growth and development of our builder network and other distribution channels; • customer satisfaction and our ability to attract, retain, and expand our customer base; • our ability to maintain and enhance our brand and reputation, including the quality of our products and services; • our expectations about our book of business, including our ability to cross-sell and to attain greater value from each customer; • the effects of seasonal and cyclical trends on our results of operations; • our ability to compete effectively in the segments of the insurance industry in which we operate; • our ability to underwrite risks accurately and charge competitive yet profitable rates to our customers, and the sufficiency of the analytical models we use to assess and predict exposure to catastrophe losses; • our ability to maintain reinsurance contracts and our near- and long-term strategies and expectations with respect to the availability, adequacy, coverage, limits, pricing, and cession of insurance risk; • our ability to utilize, develop, and protect our proprietary technology, digital platform, and intellectual property; • our ability to leverage our data, technology, and geographic diversity to help manage risk; • our ability to expand our product offerings or improve existing ones; • our ability to attract and retain personnel, including our officers and key employees; • potential harm caused by outages or interruptions in, or delays to, services provided by our third-party providers, including our data vendors; • potential harm caused by misappropriation of our data and compromises in cybersecurity, and our ability to receive, process, store, use, and share data in compliance with laws and regulations related to data privacy and data security; 7

• potential harm caused by changes in internet search engines’ methodologies; • our denial of claims or our failure to accurately and timely pay claims; • the effects of severe weather events and other natural or man-made catastrophes, including the effects of climate change, global pandemics, and terrorism; • any overall decline in economic activity; • regulators’ identification of errors in the policy forms we use, the rates we charge, and our customer communications, including cancellations, non-renewals, and reinstatements, through market conduct exams, complaints, or other inquiries; • our ability to navigate extensive insurance industry regulations and the scrutiny of state insurance regulators, and the effects of existing or new legal or regulatory requirements on our business, including with respect to maintenance of risk-based capital and financial strength ratings, the insurance industry generally, and data privacy and cybersecurity, in the United States and internationally; • our expected use of cash on our balance sheet, our future capital needs, and our ability to raise additional capital; • fluctuations in our results of operations and operating metrics; and • our public securities’ liquidity and trading. These statements are based on the current expectations of Hippo’s management and are not predictions of actual performance. You should not rely upon forward-looking statements as predictions of future events. Actual events and circumstances are difficult or impossible to predict and will differ from assumptions, and many actual events and circumstances are beyond the control of Hippo. Although we believe that we have a reasonable basis for each forward-looking statement contained in this press release, we cannot guarantee that the future results, levels of activity, performance, events, and circumstances reflected in the forward-looking statements will be achieved or occur at all. These forward-looking statements are subject to a number of risks, uncertainties, and other factors, including those described above and other risks set forth in the sections entitled “Risk Factors” in the Company’s most recent Annual Report on Form 10-K and subsequent Quarterly Reports on Form 10-Q, and in other documents that may be filed by the Company from time to time with the Securities and Exchange Commission (the “SEC”). Moreover, we operate in a very competitive and rapidly changing environment. New risks and uncertainties emerge from time to time, and it is not possible for us to predict all risks and uncertainties that could have an impact on the forward-looking statements contained in this press release. If any of these risks materialize or our assumptions prove incorrect, actual results could differ materially from the results implied by these forward-looking 8

statements. There may be additional risks that Hippo does not presently know or that Hippo currently believes are immaterial that could also cause actual results, events, or circumstances to differ materially from those described in the forward-looking statements. These forward-looking statements are based on information available as of the date of this press release and reflect Hippo’s expectations, plans, forecasts, and views of future events as of that date. Accordingly, forward-looking statements should not be relied upon as representing Hippo’s views as of any subsequent date, and Hippo does not undertake any obligation to update forward-looking statements to reflect events or circumstances after the date they were made, whether as a result of new information, future events, or otherwise, except as may be required under applicable securities laws. While Hippo may elect to update these forward-looking statements at some point in the future, Hippo specifically disclaims any obligation to do so. Accordingly, undue reliance should not be placed upon the forward-looking statements. Rounding Certain monetary amounts, percentages, and other figures included in this release have been subject to rounding adjustments. The sum of individual metrics may not always equal total amounts indicated due to rounding. Contacts Investors: Charles Sebaski Investors@hippo.com Press: Mark Olson press@hippo.com 9

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Apr. 30, 2026

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