Root, Inc.

Item 1.01 Entry into a Material Definitive Agreement. Warrant Cancellation and Exchange Agreement and the New Warrant On August 31, 2026, the Company entered into the Warrant Cancellation and Exchange Agreement, whereby the Company and Carvana agreed on the following: (i) Carvana surrendered, and the Company thereby cancelled, all outstanding long-term warrants that were previously issued on October 1, 2021 (the “Warrant Cancellation”) and (ii) simultaneously with the Warrant Cancellation, the Company issued Carvana a new Common Stock Purchase Warrant (the “New Warrant”). The foregoing description of the Warrant Cancellation and Exchange Agreement does not purport to be complete and is qualified in its entirety by reference to the Warrant Cancellation and Exchange Agreement, a copy of which is attached as Exhibit 10.1 to this Current Report on Form 8-K and is incorporated herein by reference. If the New Warrant is fully exercised by Carvana for cash, Carvana will have the opportunity to purchase up to 1,525,560 shares of Class A Common Stock. The New Warrant consists of five independently exercisable tranches of 305,112 shares each (each, a “Tranche”). Each Tranche is subject to certain Conditions to Exercise (as defined in the New Warrant), including, among others, certain conditions dependent on the achievement of defined milestones tied to insurance sales through the Integrated Platform. The foregoing summary of the material terms of the New Warrant does not purport to be complete and is qualified in its entirety by reference to the full text of the New Warrant, which is attached hereto as Exhibit 4.1. Second Amendment to the Commercial Agreement On August 31, 2026, a subsidiary of the Company and Carvana and certain of Carvana’s affiliates entered into the Second Amendment to the Commercial Agreement, by and among the parties thereto (the “Second Amendment to the Commercial Agreement”), amending, among other things, (i) the term and notice of non-renewal provision in the Commercial Agreement, (ii) the definition of “Company Warrants” (as defined therein) to reflect the New Warrant, and (iii) certain commercial terms, including with respect to exclusivity obligations of the parties. The foregoing description of the Second Amendment to the Commercial Agreement does not purport to be complete and is qualified in its entirety by reference to the Second Amendment to the Commercial Agreement, a copy of which is attached as Exhibit 10.2 to this Current Report on Form 8-K and is incorporated herein by reference. Second Amendment to the Investment Agreement On August 31, 2026, the Company and Carvana entered into the Second Amendment to the Investment Agreement, by and between the Company and Carvana (the “Second Amendment to the Investment Agreement”), amending, among other things, the Investment Agreement for the warrant restructuring contemplated by the Warrant Cancellation and Exchange Agreement. The foregoing description of the Second Amendment to the Investment Agreement does not purport to be complete and is qualified in its entirety by reference to the Second Amendment to the Investment Agreement, a copy of which is attached as Exhibit 10.3 to this Current Report on Form 8-K and is incorporated herein by reference. First Amendment to the Registration Rights Agreement On August 31, 2026, the Company and Carvana entered into the First Amendment to the Registration Rights Agreement, by and between the Company and Carvana (the “First Amendment”), amending, among other things, the Registration Rights Agreement for the warrant restructuring contemplated by the Warrant Cancellation and Exchange Agreement. The foregoing description of the First Amendment does not purport to be complete and is qualified in its entirety by reference to the First Amendment, a copy of which is attached as Exhibit 10.4 to this Current Report on Form 8-K and is incorporated herein by reference.

Item 3.02 Unregistered Sales of Equity Securities. The information contained in Item 1.01 regarding the issuance of the New Warrant is incorporated herein by reference. The issuance of the New Warrant is exempt from registration under the Securities Act of 1933, as amended (the “Securities Act”), pursuant to Section 4(a)(2) of the Securities Act. Carvana represented to the Company that it is an “accredited investor” as defined in Rule 501 of the Securities Act and the New Warrant is being acquired for investment purposes and not with a view to, or for sale in connection with, any distribution thereof, and appropriate legends will be affixed to the New Warrant.