Item 3 is hereby amended to add the following: On June 4, 2025, Mr. Cohen received a grant of 61,728 restricted stock units (the "June 2025 RSUs") calculated based on the share price at the close of trading on June 4, 2025. Each June 2025 RSU represents a contingent right to receive one share of Common Stock. The June 2025 RSUs will vest on June 4, 2026, and are subject to pro rata vesting if Mr. Cohen leaves the board of directors before that date. The June 2025 RSUs are held in an account by Mr. Cohen for the benefit of Partners and upon the applicable vesting date, the shares are intended to be transferred to Partners. As previously reported, on August 9, 2024, Mr. Cohen received a grant of 28,531 August 2024 RSUs for his service on the board of directors of the issuer. On June 4, 2025, 28,531 of the August 2024 RSUs vested and were initially held in an account by Mr. Cohen for the benefit of Partners. On June 6, 2025, the shares were transferred to Partners for no consideration. The transfer represents a "bona fide gift" under Rule 16b-5 promulgated by the SEC pursuant to the Securities Exchange Act of 1934, as amended (the "Act"), and as such, the transaction is exempt for matching and short-swing liability purpose sunder Section 16(b) of the Act.

Item 4 is hereby amended to add the following: On August 10, 2025, the Issuer entered into separate commitment letters (collectively, the "Commitment Letters") with each of Stone House Capital Management, LLC, Mark Tkach and Bill Coulter (collectively, the "Commitment Parties"), pursuant to which each Commitment Party has committed to make $3,333,334 of subordinated loans to the Issuer (collectively, the "Subordinated Loans"). The aggregate gross proceeds of the Subordinated Loans, or approximately $10 million, will be used by the Issuer to prepay outstanding principal amounts owed under the Issuer's term loan credit agreement (the "Credit Agreement"). The Subordinated Loans will bear interest at a rate per annum of 13.0% per annum, payable semi-annually in-kind by increasing the principal amount of the Subordinated Loans. The Subordinated Loans will mature thirty-six months after the date of funding. The Subordinated Loans will be contractually subordinated in right of payment to the loans outstanding under the Credit Agreement (the "Senior Loans"). Each of the Commitment Parties has agreed to hold and make the commitments available until 11:59 p.m., Eastern Time, on September 5, 2025. The foregoing description of the Commitment Letters and the Credit Agreement does not purport to be complete and is qualified in its entirety by reference to the Issuer's current report on Form 8-K, dated August 11, 2025, the Issuer's press release, dated August 11, 2025, and the Form of Commitment Letter, dated as of August 10, 2025, which are each incorporated herein by reference to Exhibit 99.25, Exhibit 99.26, and Exhibit 99.27 to this Schedule 13D, respectively.

Item 5(a) is hereby amended and restated in its entirety as follows: The aggregate number and percentage of the class of securities identified pursuant to Item 1 beneficially owned by each Reporting Person is stated in Items 11 and 13 on the cover page(s) hereto. Item 13 on each cover page hereto is based upon 38,002,422 shares of Class B Common Stock, outstanding as of August 1, 2025, as disclosed in the Issuer's quarterly report on Form 10-Q, filed on August 11, 2025, by the Issuer with the U.S. Securities and Exchange Commission. Each Reporting Person declares that neither the filing of this Schedule 13D nor anything herein shall be construed as an admission that such person is, for the purposes of Section 13(d) or 13(g) of the Act or any other purpose, the beneficial owner of any securities covered by this Schedule 13D. Each Reporting Person may be deemed to be a member of a group with respect to the Issuer or securities of the Issuer for the purposes of Section 13(d) or 13(g) of the Act. Each Reporting Person declares that neither the filing of this Schedule 13D nor anything herein shall be construed as an admission that such person is, for the purposes of Section 13(d) or 13(g) of the Act or any other purpose, (i) acting (or has agreed or is agreeing to act) with any other person as a partnership, limited partnership, syndicate or other group for the purpose of acquiring, holding or disposing of securities of the Issuer or otherwise with respect to the Issuer or any securities of the Issuer or (ii) a member of any syndicate or group with respect to the Issuer or any securities of the Issuer.

Item 7 is hereby amended to add the following: 99.25 - Current Report on Form 8-K, dated August 11, 2025 (incorporated by reference to the Issuer's Current Report on Form 8-K filed on August 11, 2025 by the Issuer with the U.S. Securities and Exchange Commission). 99.26 - Press Release, dated August 11, 2025 (incorporated by reference to Exhibit 99.1 to the Issuer's Current Report on Form 8-K filed on August 11, 2025 by the Issuer with the U.S. Securities and Exchange Commission). 99.27 - Form of Commitment Letter, dated as of August 10, 2025, by and between RumbleOn, Inc. and each Lender party thereto (incorporated by reference to Exhibit 10.1 to the Issuer's Current Report on Form 8-K filed on August 11, 2025 by the Issuer with the U.S. Securities and Exchange Commission).