shall be deemed to be furnished: Exhibit No. | Description 99.1 | Letter to Shareholders, dated November 4, 2026 104 | The cover page from this Current Report on Form 8-K, formatted in Inline XBRL. 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. ROOT, INC. Dated: November 4, 2026 By: | /s/ Alexander Timm Alexander Timm Chief Executive Officer and D…

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…

Unregistered Sales of Equity Securities. The information contained in

shall be deemed to be furnished: Exhibit No. Description 99.1 Letter to Shareholders, dated August 5, 2026 104 The cover page from this Current Report on Form 8-K, formatted in Inline XBRL. 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. ROOT, INC. Dated: August 5, 2026 By: /s/ Alexander Timm Alexander Timm Chief Executive Officer and Director

of this Form 8-K (including Exhibit 99.1 attached hereto) shall not be deemed "filed" for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the "Exchange Act"), or otherwise subject to the liabilities of that section, nor shall it be deemed incorporated by reference in any filing under the Securities Act of 1933, as amended, or the Exchange Act, except as expressly provided by specific reference in such a filing.

Termination of a Material Definitive Agreement. Concurrently with the Closing of the Credit Agreement, the Company prepaid all of the outstanding term loans under its term loan agreement, dated as of January 26, 2022 (as amended, the “Existing Credit Agreement”), by and among the Company, Holdings, the other loan parties party thereto, the lenders party thereto and Acquiom Agency Services, LLC, as administrative agent. The Existing Credit Agreement was terminated in connection with the entry…

Regulation FD Disclosure. On May 6, 2026, the Company issued a press release announcing the execution of the Credit Agreement and the authorization of a $75 million share repurchase program. A copy of this press release is furnished herewith as Exhibit 99.2 to this Current Report on Form 8-K. In addition, on May 6, 2026, the Company prepared an updated investor presentation containing certain information and financial highlights about the Company and its industry, a copy of which will be avai…

Entry into a Material Definitive Agreement. On May 4, 2026, Root, Inc. (the “Company”) entered into that certain Credit Agreement (the “Credit Agreement”), by and among the Company, Caret Holdings, Inc., as borrower (the “Borrower”), the lenders from time to time party thereto and The Huntington National Bank, as the administrative agent. The Credit Agreement provides for a senior secured term loan of $200.0 million, the entire amount of which was funded on May 4, 2026. Borrowings under the C…

Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant. The information set forth in

shall be deemed to be furnished: Exhibit No. Description 99.1 Letter to Shareholders, dated February 25, 2026 104 The cover page from this Current Report on Form 8-K, formatted in Inline XBRL. 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. ROOT, INC. Dated: February 25, 2026 By: /s/ Alexander Timm Alexander Timm Chief Executive Officer and Director

shall be deemed to be furnished: Exhibit No. Description 99.1 Letter to Shareholders, dated November 5, 2025 104 The cover page from this Current Report on Form 8-K, formatted in Inline XBRL. 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. ROOT, INC. Dated: November 5, 2025 By: /s/ Alexander Timm Alexander Timm Chief Executive Officer and Director

shall be deemed to be furnished: Exhibit No. Description 99.1 Letter to Shareholders, dated August 06, 2025 104 The cover page from this Current Report on Form 8-K, formatted in Inline XBRL. 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. ROOT, INC. Dated: August 6, 2025 By: /s/ Alexander Timm Alexander Timm Chief Executive Officer and Director

shall be deemed to be furnished: Exhibit No. Description 99.1 Letter to Shareholders, dated May 07, 2025 104 The cover page from this Current Report on Form 8-K, formatted in Inline XBRL. 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. ROOT, INC. Dated: May 7, 2025 By: /s/ Alexander Timm Alexander Timm Chief Executive Officer and Director

shall be deemed to be furnished: Exhibit No. Description 99.1 Letter to Shareholders, dated February 26, 2025 104 The cover page from this Current Report on Form 8-K, formatted in Inline XBRL. 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. ROOT, INC. Dated: February 26, 2025 By: /s/ Alexander Timm Alexander Timm Chief Executive Officer and Director

The filing describes equity grants to current executive officers, which is a routine compensation matter.

of this Form 8-K (including Exhibit 99.1 attached hereto) shall not be deemed "filed" for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the "Exchange Act"), or otherwise subject to the liabilities of that section, nor shall it be deemed incorporated by reference in any filing under the Securities Act of 1933, as amended, or the Exchange Act, except as expressly provided by specific reference in such a filing.

shall be deemed to be furnished: Exhibit No. Description 99.1 Letter to Shareholders, dated August 7, 2024 104 The cover page from this Current Report on Form 8-K, formatted in Inline XBRL. SIGNATURES Pursuant to the requirements of the Securities Exchange Act of 1934, as amended, the Registrant has duly caused this report to be signed on its behalf by the undersigned hereunto duly authorized. ROOT, INC. Dated: August 7, 2024 By: /s/ Alexander Timm Alexander Timm Chief Executive Officer and D…

shall be deemed to be furnished: Exhibit No. Description 99.1 Letter to Shareholders, dated April 30, 2024 104 The cover page from this Current Report on Form 8-K, formatted in Inline XBRL. SIGNATURES Pursuant to the requirements of the Securities Exchange Act of 1934, as amended, the Registrant has duly caused this report to be signed on its behalf by the undersigned hereunto duly authorized. ROOT, INC. Dated: April 30, 2024 By: /s/ Alexander Timm Alexander Timm Chief Executive Officer and D…

Chief Accounting Officer — Ryan Forish: Ryan Forish was promoted to Chief Accounting Officer within the company.

shall be deemed to be furnished: Exhibit No. Description 99.1 Letter to Shareholders, dated February 21, 2024 104 The cover page from this Current Report on Form 8-K, formatted in Inline XBRL. SIGNATURES Pursuant to the requirements of the Securities Exchange Act of 1934, as amended, the Registrant has duly caused this report to be signed on its behalf by the undersigned hereunto duly authorized. ROOT, INC. Dated: February 21, 2024 By: /s/ Alexander Timm Alexander Timm Chief Executive Officer…

shall be deemed to be furnished: Exhibit No. Description 99.1 Letter to Shareholders, dated November 1, 2023 104 The cover page from this Current Report on Form 8-K, formatted in Inline XBRL. SIGNATURES Pursuant to the requirements of the Securities Exchange Act of 1934, as amended, the Registrant has duly caused this report to be signed on its behalf by the undersigned hereunto duly authorized. ROOT, INC. Dated: November 1, 2023 By: /s/ Alexander Timm Alexander Timm Chief Executive Officer a…

Director — Donna Dorsey: Ms. Dorsey was elected as a Class I director of the Board.

The filing details equity grants and a cash retention arrangement for executive officers.

shall be deemed to be furnished: Exhibit No. Description 99.1 Letter to Shareholders, dated August 2, 2023 104 The cover page from this Current Report on Form 8-K, formatted in Inline XBRL. SIGNATURES Pursuant to the requirements of the Securities Exchange Act of 1934, as amended, the Registrant has duly caused this report to be signed on its behalf by the undersigned hereunto duly authorized. ROOT, INC. Dated: August 2, 2023 By: /s/ Alexander Timm Alexander Timm Chief Executive Officer and D…

Chief Financial Officer and Treasurer — Megan Binkley: Megan Binkley was promoted to Chief Financial Officer and Treasurer from Interim Chief Financial Officer and Treasurer.