Root, Inc.

Adjusted EBITDA We define adjusted EBITDA, a non-GAAP financial measure, as net income (loss) excluding interest expense, income tax expense, depreciation and amortization, share-based compensation, loss on extinguishment of debt, warrant compensation expense, restructuring charges, legal fees and other items that do not reflect our ongoing operating performance.

SEC original ↗Root, Inc. — Earnings release (8-K exhibit)EX-99Aug 6, 2025

These items include general and administrative, interest expense, loss on extinguishment of debt and income tax expense, which can all be found on the condensed consolidated statements of operations and comprehensive income.

SEC original ↗Root, Inc. — 10-Q Quarterly report10-QAug 5, 2026

Restricted cash equivalents consist of amounts held by our lender to satisfy the minimum cash management requirements under our senior secured term loan and short-term, highly liquid investments held by a financial institution to maintain certain collateral requirements with an unaffiliated Texas county mutual insurance company, and are stated at amortized cost, which approximates their fair value.

SEC original ↗Root, Inc. — 10-Q Quarterly report10-QAug 5, 2026

Share Repurchases We are authorized to repurchase shares of our Class A common stock under a stock repurchase program, or Repurchase Program, approved by our board of directors.

SEC original ↗Root, Inc. — 10-Q Quarterly report10-QAug 5, 2026

We retire shares of our Class A common stock immediately upon repurchase.

SEC original ↗Root, Inc. — 10-Q Quarterly report10-QAug 5, 2026

2025-12, Codification Improvements, during the second quarter of 2026, we elected to recognize the excess of the repurchase price over par value entirely as a reduction of additional paid-in capital, or APIC, provided that APIC remains positive.

SEC original ↗Root, Inc. — 10-Q Quarterly report10-QAug 5, 2026

Other highlights of the quarter include Gross combined ratio improved 6 points to 94% year-over-year, demonstrating the power of our pricing and underwriting technology Policies in force grew by 12% year-over-year to 455,493, despite increased competition in our Direct channel Partnership channel new writings nearly tripled year-over-year, validating our strategy of meeting customers where they are with a seamless, easy experience These financial results, while critical, are the result of consistent execution over many quarters and, as such, we believe are inherently lagging indicators of our performance.

SEC original ↗Root, Inc. — Earnings release (8-K exhibit)EX-99Aug 6, 2025

To better appreciate Root s future and the big 2 Letter to Shareholders Q2 2025 opportunity ahead of us, we believe it is essential to focus on how we are continuing to execute against our strategy.

SEC original ↗Root, Inc. — Earnings release (8-K exhibit)EX-99Aug 6, 2025

We also advanced our growth strategy by broadening our distribution.

SEC original ↗Root, Inc. — Earnings release (8-K exhibit)EX-99Aug 6, 2025

This channel is critical to our long-term growth strategy.

SEC original ↗Root, Inc. — Earnings release (8-K exhibit)EX-99Aug 6, 2025

We are still in the very early chapters of our journey, and as we continue to execute against our three strategic pillars pricing and automation, building differentiated access to customers, and creating experiences customers love we believe we will continue to deliver even better products at better prices.

SEC original ↗Root, Inc. — Earnings release (8-K exhibit)EX-99Aug 6, 2025

5 Letter to Shareholders Q2 2025 As mentioned last quarter, we are able to react swiftly and appropriately when it comes to the potential impact of tariffs.

SEC original ↗Root, Inc. — Earnings release (8-K exhibit)EX-99Aug 6, 2025

To date, we have not seen a meaningful impact from tariff implementations, and given that our current loss ratios remain below our long-term target of 60 to 65%, we would be able to absorb some impact without raising rates or sacrificing our long-term unit economic targets.

SEC original ↗Root, Inc. — Earnings release (8-K exhibit)EX-99Aug 6, 2025

11 Letter to Shareholders Q2 2025 Forward-looking statements This letter contains and statements made during the above-referenced webcast will contain forward-looking statements relating to, among other things, the future performance of Root and its consolidated subsidiaries that are based on Root s current expectations, forecasts, and assumptions, and involve risks and uncertainties.

SEC original ↗Root, Inc. — Earnings release (8-K exhibit)EX-99Aug 6, 2025

50 Signatures 52 i SPECIAL NOTE REGARDING FORWARD-LOOKING STATEMENTS This Quarterly Report on Form 10-Q contains forward-looking statements about us and our industry that involve substantial risks and uncertainties.

SEC original ↗Root, Inc. — 10-Q Quarterly report10-QAug 5, 2026

The outcome of the events described in these forward-looking statements is subject to risks, uncertainties and other factors described under the heading Risk Factors and elsewhere in this Quarterly Report on Form 10-Q.

SEC original ↗Root, Inc. — 10-Q Quarterly report10-QAug 5, 2026

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 herein.

SEC original ↗Root, Inc. — 10-Q Quarterly report10-QAug 5, 2026