RMBL / RumbleOn, Inc. - Pengajuan SECLaporan Tahunan, Pernyataan Proksi

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): August 25, 2025 RideNow Group, In

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): August 25, 2025 RideNow Group, Inc. (Exact name of registrant as specified in its charter) Nevada (State or other jurisdiction of incorporation) 001-38248 (Commission File Number) 46-

RIDENOW GROUP, INC. AMENDED AND RESTATED WARRANT TO PURCHASE CLASS B COMMON STOCK

Exhibit 4.1 THIS AMENDED AND RESTATED WARRANT (THE “WARRANT”) AND ANY SHARES ACQUIRED UPON THE EXERCISE OF THIS WARRANT HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “ACT”) OR APPLICABLE STATE SECURITIES LAWS, AND MAY NOT BE SOLD, PLEDGED, HYPOTHECATED, DONATED OR OTHERWISE TRANSFERRED WITHOUT COMPLIANCE WITH THE REGISTRATION OR QUALIFICATION PROVISIONS OF APPLICABLE F

UNSECURED PROMISSORY NOTE

Exhibit 10.1 UNSECURED PROMISSORY NOTE THE INDEBTEDNESS EVIDENCED BY THIS NOTE IS UNSECURED AND SUBORDINATE TO THE PRIOR PAYMENT IN FULL OF THE SENIOR DEBT PURSUANT TO THE TERMS OF THE SUBORDINATION AGREEMENT. $3,333,334 August 25, 2025 (the “Effective Date”) 1.Principal. FOR VALUE RECEIVED, RideNow Group, Inc., a Nevada corporation (the “Borrower”), hereby unconditionally promises to pay to [] (t

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 Current Report on Form 8-K filed on August 11, 2025).

CONFIDENTIAL August 10, 2025 RumbleOn, Inc. 901 W. Walnut Hill Ln #110A Irving, Texas 75038 Commitment Letter ([Coulter]/[Tkach]/[Stone House])1 Ladies and Gentlemen: You have advised the undersigned (the “Lender”) that RumbleOn, Inc., a Nevada corporation (“you” or the “Company”), desires to obtain proceeds of not less than $10,000,000 in the aggregate from subordinated loans, which proceeds will

Second Amended and Restated Bylaws, effective as of August 13, 2025 (incorporated by reference to Exhibit 3.2 to the Current Report on Form 8-K filed on August 11, 2025).

Exhibit 3.2 SECOND AMENDED AND RESTATED BYLAWS OF RIDENOW GROUP, INC. ARTICLE I OFFICES Section 1.1 OFFICES. RideNow Group, Inc., a Nevada corporation (the “corporation”), shall have a registered office, a principal office, and such other offices as the board of directors of the corporation (the “board of directors”) may determine. Section 1.2 OTHER OFFICES. The board of directors may at any time

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): August 9, 2025 RumbleOn, Inc. (Ex

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): August 9, 2025 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada 001-38248 46-3951329 (State or Other Jurisdiction of Incorporation) (Commission File Number

RumbleOn, Inc. Reports Second Quarter 2025 Financial Results Rebranding Initiative, including Name Change to RideNow Group, Inc., Corporate Headquarters Relocation Back to Phoenix, AZ Area, and Ticker Symbol Change Amends, Reprices and Extends Credit

Exhibit 99.1 RumbleOn, Inc. Reports Second Quarter 2025 Financial Results Rebranding Initiative, including Name Change to RideNow Group, Inc., Corporate Headquarters Relocation Back to Phoenix, AZ Area, and Ticker Symbol Change Amends, Reprices and Extends Credit Facility IRVING, Texas – August 11, 2025 – RumbleOn, Inc. (NASDAQ: RMBL), the "Company" today announced results for the second quarter e

Amendment No. 10 to the Term Loan Credit Agreement, dated August 10, 2025, by and among RumbleOn, Inc., the Subsidiary Guarantors party thereto, the Lenders party thereto, and Oaktree Fund Administration, LLC, as administrative agent and collateral agent (incorporated by reference to Exhibit 10.

Execution Version AMENDMENT NO. 10 TO TERM LOAN CREDIT AGREEMENT AMENDMENT NO. 10 TO TERM LOAN CREDIT AGREEMENT (this “Amendment”), dated as of August 10, 2025, among RUMBLEON, INC., a Nevada corporation (the “Borrower”), the guarantors party hereto (the “Subsidiary Guarantors”), OAKTREE FUND ADMINISTRATION, LLC, as administrative agent and as collateral agent (in such capacities, the “Agent”), an

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2025 TRANSITION REPORT PURS

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2025 or TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 001-

Certificate of Amendment to Articles of Incorporation, as amended, filed with Secretary of State of the State of Nevada, effective as of August 13, 2025 (incorporated by reference to Exhibit 3.1 to the Current Report on Form 8-K filed on August 11, 2025).

ex31certofamendmenttoart FRANCISCO V. AGUILAR Secretary of State 401 North Carson Street Carson City, Nevada 89701-4201 (775) 684-5708 Website: www.nvsos.gov Profit Corporation: Certificate of Amendment (PURSUANT TO NRS 78.380 & 78.385/78.390) Certificate to Accompany Restated Articles or Amended and Restated Articles (PURSUANT TO NRS 78.403) Officer's Statement (PURSUANT TO NRS 80.030) TYPE OR PR

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables Form S-8 (Form Type) RUMBLEON, INC. (Exact Name of Registrant as Specified in its Articles) Table 1: Newly Registered Securities Security Type Security Class Title Fee Calculation Rule(1) Amount Registered(2) Proposed Maximum Offering Price Per Share(1) Maximum Aggregate Offering Price(1) Fee Rate Amount of Registration Fee Equity Class B Common Stock,

As filed with the Securities and Exchange Commission on June 13, 2025

As filed with the Securities and Exchange Commission on June 13, 2025 Registration Statement No.

Sixth Amendment to the RumbleOn, Inc. 2017 Stock Incentive Plan

Exhibit 10.1 SIXTH AMENDMENT TO THE RUMBLEON, INC. 2017 STOCK INCENTIVE PLAN WHEREAS, RumbleOn, Inc., a Nevada corporation (the “Company”), currently maintains and sponsors the RumbleOn, Inc. 2017 Stock Incentive Plan (as amended, the “Plan”); and WHEREAS, Section 14(k) of the Plan provides that the Board of Directors of the Company (the “Board”) may amend the Plan from time to time; and WHEREAS,

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): June 4, 2025 RumbleOn, Inc. (Exac

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): June 4, 2025 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada (State or other jurisdiction of incorporation) 001-38248 (Commission File Number) 46-3951329

901 W. Walnut Hill Lane, Suite 110A Irving, Texas 75038

901 W. Walnut Hill Lane, Suite 110A Irving, Texas 75038 May 14, 2025 VIA EDGAR United States Securities and Exchange Commission Division of Corporation Finance 100 F Street, N.E. Washington, D.C. 20549 Re: RumbleOn, Inc. Registration Statement on Form S-3 File No. 333-287116 Request for Acceleration Ladies and Gentlemen: Pursuant to Rule 461 promulgated under the Securities Act of 1933, as amended

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Table Form S-3 (Form Type) RumbleOn, Inc. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered and Carry Forward Securities Security Type Security Class Title Fee Calculation or Carry Forward Rule Amount Registered(1) Proposed Maximum Offering Price Per Unit(2) Maximum Aggregate Offering Price(2) Fee Rate Amount of Registration Fee

As filed with the Securities and Exchange Commission on May 9, 2025

As filed with the Securities and Exchange Commission on May 9, 2025 Registration No.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2025 TRANSITION REPORT PUR

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2025 or TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 001

RumbleOn Reports First Quarter 2025 Financial Results

Exhibit 99.1 RumbleOn Reports First Quarter 2025 Financial Results IRVING, Texas – May 7, 2025 – RumbleOn, Inc. (NASDAQ: RMBL), the "Company" or "RumbleOn", today announced results for the first quarter ended March 31, 2025. Key First Quarter 2025 Highlights (Compared to First Quarter 2024): •Revenue of $244.7 million decreased 20.5%, driven by a 3,399 decline in unit sales in the Company's powers

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): May 7, 2025 RumbleOn, Inc. (Exact

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): May 7, 2025 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada 001-38248 46-3951329 (State or Other Jurisdiction of Incorporation) (Commission File Number) (

Separation Agreement, effective as of May 1, 2025, by and between RumbleOn, Inc. and Tiffany Kice (incorporated by reference to Exhibit 10.1 to the Current Report on Form 8-K/A filed on May 1, 2025).

Exhibit 10.1 Execution Version RUMBLEON, INC. SEPARATION AGREEMENT This Separation Agreement (the “Agreement”) is by and between RumbleOn, Inc., a Nevada corporation (the “Company”), and Tiffany Kice (“Executive”). Executive and the Company are collectively referred to as the “Parties.” WHEREAS, Executive and the Company have agreed that Executive’s employment with the Company terminated effective

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K/A (Amendment No. 1) CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): March 31, 202

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K/A (Amendment No. 1) CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): March 31, 2025 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada (State or other jurisdiction of incorporation) 001-38248 (Commission Fi

Separation Agreement, effective as of May 1, 2025, by and between RumbleOn, Inc. and Brandy Treadway (incorporated by reference to Exhibit 10.2 to the Current Report on Form 8-K/A filed on May 1, 2025).

Exhibit 10.2 Execution Version RUMBLEON, INC. SEPARATION AGREEMENT This Separation Agreement (the “Agreement”) is by and between RumbleOn, Inc., a Nevada corporation (the “Company”), and Brandy Treadway (“Executive”). Executive and the Company are collectively referred to as the “Parties.” WHEREAS, Executive and the Company have agreed that Executive’s employment with the Company terminated effect

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, For Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Defin

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. 1)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. 1) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, For Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defi

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. __)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, For Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

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): March 31, 2025 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada 001-38248 46-3951329 (State or other jurisdiction (Commission File Number) (I.R.S. Employer

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): March 17, 2025 RumbleOn, Inc. (Ex

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): March 17, 2025 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada (State or other jurisdiction of incorporation) 001-38248 (Commission File Number) 46-395132

RESTRICTED STOCK UNIT AWARD

Exhibit 10.22 RESTRICTED STOCK UNIT AWARD TO: You (“Grantee”) have been granted this restricted stock unit (“RSU”) award (the “Award”) by RumbleOn, Inc. (the “Company”) pursuant to the RumbleOn 2017 Stock Incentive Plan (as amended to date, the “Plan”). This Restricted Stock Unit Award Agreement (the “Agreement”) confirms the understanding between the Company and you as of the Effective Date. The

FLOOR PLAN FACILITY AGREEMENT

Exhibit 10.29 FLOOR PLAN FACILITY AGREEMENT This Floor Plan Facility Agreement dated as of December 6, 2024 (as it may be amended or modified from time to time, this “Agreement”), is among RUMBLEON DEALERS, INC., a Delaware corporation (the “Borrower”), RUMBLEON, INC., a Nevada corporation (“Holdings”), WILLILAM R. COULTER (“Coulter”), MARK A. TKACH (“Tkach”, together with Coulter, the “Lenders”),

PERFORMANCE RESTRICTED STOCK UNIT AWARD

Exhibit 10.23 PERFORMANCE RESTRICTED STOCK UNIT AWARD TO: You (“Grantee”) have been granted this restricted stock unit (“RSU”) award (the “Award”) by RumbleOn, Inc. (the “Company”) pursuant to the RumbleOn 2017 Stock Incentive Plan (as amended to date, the “Plan”). This Restricted Stock Unit Award Agreement (the “Agreement”) confirms the understanding between the Company and you as of the Effectiv

Subsidiaries (as of December 31, 2024)

Exhibit 21 Subsidiaries (as of December 31, 2024) Subsidiary Name Jurisdiction DBA’s APS of Georgetown, LLC Delaware Central Texas Powersports Ride Now Georgetown Ridenow Georgetown RideNow Powersports RideNow Powersports Georgetown APS of Ohio, LLC Delaware Powder Keg Harley-Davidson APS of Oklahoma LLC Delaware Fort Thunder Harley-Davidson APS of Texas LLC Delaware Central Texas Harley-Davidson Round Rock RideNow Powersports BJ Motorsports, LLC Nevada RideNow Powersports on Boulder C&W Motors, Inc.

RUMBLEON, INC. 2024 Annual Report on Form 10-K Power of Attorney

Exhibit 24 RUMBLEON, INC. 2024 Annual Report on Form 10-K Power of Attorney KNOW ALL PERSONS BY THESE PRESENTS: That each person whose name is signed below has made, constituted and appointed, and by this instrument does make, constitute and appoint Michael Quartieri and Tiffany Kice, and each of them severally, his or her true and lawful attorney and agent, for him or her and in his or her name,

INSIDER TRADING POLICY

Exhibit 19 INSIDER TRADING POLICY RumbleOn, Inc. and its wholly owned subsidiaries (together, the “Company”) are subject to federal securities laws that impose certain obligations on the Company regarding the disclosure of material information to the public and certain prohibitions on trading the Company’s securities by any person in possession of undisclosed material information. As a director or

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-K x ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934For the fiscal year ended December 31, 2024 ¨ TRANSITION REPORT PURSUANT TO SECTIO

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-K x ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934For the fiscal year ended December 31, 2024 ¨ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934For the transition period from to Commission file number 001-38248 RumbleOn, Inc

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):March 11, 2025 RumbleOn, Inc. (Exa

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):March 11, 2025 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada (State or Other Jurisdiction of Incorporation) 001-38248 (Commission File Number) 46-3951329

RumbleOn Reports Fourth Quarter and Full Year 2024 Financial Results

Exhibit 99.1 RumbleOn Reports Fourth Quarter and Full Year 2024 Financial Results IRVING, Texas – March 11, 2025 – RumbleOn, Inc. (NASDAQ: RMBL), ("RumbleOn" or "the Company"), today announced financial results for its fourth quarter and full year ended December 31, 2024. Key Fourth Quarter 2024 Highlights (Compared to Fourth Quarter 2023): •Revenue of $269.6 million decreased 13.4% •Net loss tota

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 8-K/A (Amendment No. 1) CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): January 13, 2025 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada (State or other jurisdiction of incorporation) 001-38248 (Commission

Employment Agreement, effective as of January 13, 2025, by and among RumbleOn, Inc. and Cameron Tkach

Exhibit 10.3 EMPLOYMENT AGREEMENT This Employment Agreement (“Agreement”) is made and entered into by and between RumbleOn, Inc. (the “Company”), and Cameron Tkach (“Employee”), effective as of January 13, 2025 (the “Effective Date”). 1.Employment. During the Employment Period (as defined in Section 4), the Company shall employ Employee, and Employee shall serve, as Executive Vice President and Ch

RumbleOn, Inc. and Michael Kennedy (incorporated by reference to Exhibit 10.1 to the Current Report on Form 8-K/A filed on January 29, 2025).

Exhibit 10.1 RUMBLEON, INC. SEPARATION AGREEMENT This Separation Agreement (the “Agreement”) is by and between RumbleOn, Inc., a Nevada corporation (the “Company”), and Michael Kennedy (“Executive”). Capitalized terms used herein but not otherwise defined shall have the meanings ascribed thereto in the Employment Agreement between the Company and Executive, dated as of November 1, 2023 (the “Emplo

Employment Agreement, effective as of January 13, 2025, by and among RumbleOn, Inc. and Michael Quartieri

Exhibit 10.2 EMPLOYMENT AGREEMENT This Employment Agreement (“Agreement”) is made and entered into by and between RumbleOn, Inc. (the “Company”), and Michael Quartieri (“Employee”), effective as of January 13, 2025 (the “Effective Date”). 1.Employment. (a)During the Employment Period (as defined in Section 4), the Company shall employ Employee, and Employee shall serve, as Chief Executive Officer

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing, Financial Statements and Exhibits, Other Events

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): January 13, 2025 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada (State or other jurisdiction of incorporation) 001-38248 (Commission File Number) 46-3951

RUMBLEON, INC. ANNOUNCES LEADERSHIP CHANGES Michael Quartieri, Chairman of the Board, Appointed as Chief Executive Officer Cameron Tkach Promoted to Executive Vice President and Chief Operating Officer Becca Polak Named as Vice Chairman and Lead Inde

Exhibit 99.1 RUMBLEON, INC. ANNOUNCES LEADERSHIP CHANGES Michael Quartieri, Chairman of the Board, Appointed as Chief Executive Officer Cameron Tkach Promoted to Executive Vice President and Chief Operating Officer Becca Polak Named as Vice Chairman and Lead Independent Director IRVING, Texas – January 13, 2025 - RumbleOn, Inc. (NASDAQ: RMBL) (the “Company” or “RumbleOn”), the largest powersports

Financial Statements and Exhibits, Other Events

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): January 2, 2025 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada (State or other jurisdiction of incorporation) 001-38248 (Commission File Number) 46-39513

Registration Rights Agreement dated December 19, 2024

Exhibit 10.1 REGISTRATION RIGHTS AGREEMENT THIS REGISTRATION RIGHTS AGREEMENT (this “Agreement”), dated as of December 19, 2024, is made and entered into by and among RumbleOn, Inc., a Nevada corporation (the “Company”), and each of the Persons listed on Schedule A attached hereto (the “Schedule of Holders”) as of the date hereof (together with any of their Permitted Transferees (as defined herein

Entry into a Material Definitive Agreement, Unregistered Sales of Equity Securities, Financial Statements and Exhibits, Other Events

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): December 19, 2024 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada (State or other jurisdiction of incorporation) 001-38248 (Commission File Number) 46-395

RumbleOn Announces Final Results of $10.0 Million Fully Backstopped Registered Rights Offering

Exhibit 99.1 RumbleOn Announces Final Results of $10.0 Million Fully Backstopped Registered Rights Offering Irving, Texas – December 17, 2024 - RumbleOn, Inc. (NASDAQ: RMBL) (the “Company,” “RumbleOn,” “we,” “us,” or “our”) today announced the final results of its $10.0 million fully backstopped registered equity rights offering (the “Rights Offering”) for shares of the Company’s Class B common st

RumbleOn Announces Preliminary Results of $10.0 Million Fully Backstopped Registered Rights Offering

Exhibit 99.1 RumbleOn Announces Preliminary Results of $10.0 Million Fully Backstopped Registered Rights Offering Irving, Texas – December 13, 2024 - RumbleOn, Inc. (NASDAQ: RMBL) (the “Company,” “RumbleOn,” “we,” “us,” or “our”) today announced the preliminary results of its $10.0 million fully backstopped registered equity rights offering (the “Rights Offering”) for shares of the Company’s Class

Financial Statements and Exhibits, Other Events

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): December 13, 2024 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada (State or other jurisdiction of incorporation) 001-38248 (Commission File Number) 46-395

RMBL / RumbleOn, Inc. / Tkach Mark - SC 13D/A Activist Investment

SC 13D/A 1 tm2430607d1sc13da.htm SC 13D/A SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13D UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 9)* RumbleOn, Inc. (Name of Issuer) Class B Common Stock, par value $0.001 per share (Title of Class of Securities) 781386305 (CUSIP Number) Mark Tkach 1188 East Camelback Road Phoenix, AZ 85014 (602) 532-4600 with a copy to: Kell

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

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): December 6, 2024 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada (State or other jurisdiction of incorporation) 001-38248 (Commission File Number) 46-3951

INSTRUCTIONS AS TO USE OF RUMBLEON, INC. NON-TRANSFERABLE SUBSCRIPTION RIGHTS CERTIFICATES PLEASE CONSULT THE SUBSCRIPTION AND INFORMATION AGENT FOR ANY QUESTIONS

Exhibit 99.1 THE TERMS AND CONDITIONS OF THE RIGHTS OFFERING ARE SET FORTH IN THE COMPANY’S PROSPECTUS SUPPLEMENT DATED NOVEMBER 26, 2024 AND THE ACCOMPANYING BASE PROSPECTUS AND ARE INCORPORATED HEREIN BY REFERENCE. COPIES OF THE PROSPECTUS SUPPLEMENT AND THE ACCOMPANYING BASE PROSPECTUS ARE AVAILABLE ON THE WEBSITE OF THE SECURITIES AND EXCHANGE COMMISSION AT HTTP://WWW.SEC.GOV OR UPON REQUEST F

Form of Rights Certificate

Exhibit 4.1 THE TERMS AND CONDITIONS OF THE RIGHTS OFFERING ARE SET FORTH IN THE COMPANY’S PROSPECTUS SUPPLEMENT DATED NOVEMBER 26, 2024 AND THE ACCOMPANYING BASE PROSPECTUS AND ARE INCORPORATED HEREIN BY REFERENCE. COPIES OF THE PROSPECTUS SUPPLEMENT AND THE ACCOMPANYING BASE PROSPECTUS ARE AVAILABLE ON THE WEBSITE OF THE SECURITIES AND EXCHANGE COMMISSION AT HTTP://WWW.SEC.GOV OR UPON REQUEST FR

RUMBLEON, INC. NOTICE TO STOCKHOLDERS WHO ARE RECORD HOLDERS Up to 2,392,344 Shares of Class B Common Stock Issuable Upon Exercise of Non-Transferable Subscription Rights

Exhibit 99.2 RUMBLEON, INC. NOTICE TO STOCKHOLDERS WHO ARE RECORD HOLDERS Up to 2,392,344 Shares of Class B Common Stock Issuable Upon Exercise of Non-Transferable Subscription Rights November 26, 2024 Dear Stockholder: Enclosed for your consideration is a prospectus supplement dated November 26, 2024 and the accompanying base prospectus (as amended from time to time, together, the “Prospectus”) r

RUMBLEON, INC. SHARES OF CLASS B COMMON STOCK SUBSCRIBED FOR UPON EXERCISE OF SUBSCRIPTION RIGHTS NOMINEE HOLDER CERTIFICATION

Exhibit 99.5 THE TERMS AND CONDITIONS OF THE RIGHTS OFFERING ARE SET FORTH IN THE COMPANY’S PROSPECTUS SUPPLEMENT DATED NOVEMBER 26, 2024 AND THE ACCOMPANYING BASE PROSPECTUS AND ARE INCORPORATED HEREIN BY REFERENCE. COPIES OF THE PROSPECTUS SUPPLEMENT AND THE ACCOMPANYING BASE PROSPECTUS ARE AVAILABLE ON THE WEBSITE OF THE SECURITIES AND EXCHANGE COMMISSION AT HTTP://WWW.SEC.GOV OR UPON REQUEST F

Entry into a Material Definitive Agreement, Unregistered Sales of Equity Securities, Financial Statements and Exhibits, Other Events

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): November 26, 2024 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada 001-38248 46-3951329 (State or other jurisdiction of incorporation) (Commission File Num

Subscription Rights to Purchase Up to 2,392,344 Shares of Class B Common Stock at $4.18 Per Share

PROSPECTUS SUPPLEMENT (To Prospectus dated September 10, 2024) Filed Pursuant to Rule 424(b)(5) Registration No.

RUMBLEON, INC. NOTICE TO CLIENTS OF STOCKHOLDERS WHO ARE ACTING AS NOMINEES Up to 2,392,344 Shares of Class B Common Stock Issuable Upon Exercise of Non-Transferable Subscription Rights

Exhibit 99.4 RUMBLEON, INC. NOTICE TO CLIENTS OF STOCKHOLDERS WHO ARE ACTING AS NOMINEES Up to 2,392,344 Shares of Class B Common Stock Issuable Upon Exercise of Non-Transferable Subscription Rights November 26, 2024 Dear Stockholder: Enclosed for your consideration is a prospectus supplement dated November 26, 2024 and the accompanying base prospectus (as amended from time to time, together, the

RUMBLEON, INC. NOTICE TO STOCKHOLDERS WHO ARE ACTING AS NOMINEES Up to 2,392,344 Shares of Class B Common Stock Issuable Upon Exercise of Non-Transferable Subscription Rights

Exhibit 99.3 RUMBLEON, INC. NOTICE TO STOCKHOLDERS WHO ARE ACTING AS NOMINEES Up to 2,392,344 Shares of Class B Common Stock Issuable Upon Exercise of Non-Transferable Subscription Rights November 26, 2024 Dear Stockholder: This letter is being distributed to custodian banks, broker, dealers, and other nominees in connection with the rights offering by RumbleOn, Inc. (the “Company”) of non-transfe

RUMBLEON, INC. BENEFICIAL OWNER ELECTION FORM

Exhibit 99.6 THE TERMS AND CONDITIONS OF THE RIGHTS OFFERING ARE SET FORTH IN THE COMPANY’S PROSPECTUS SUPPLEMENT DATED NOVEMBER 26, 2024 AND THE ACCOMPANYING BASE PROSPECTUS AND ARE INCORPORATED HEREIN BY REFERENCE. COPIES OF THE PROSPECTUS SUPPLEMENT AND THE ACCOMPANYING BASE PROSPECTUS ARE AVAILABLE ON THE WEBSITE OF THE SECURITIES AND EXCHANGE COMMISSION AT HTTP://WWW.SEC.GOV OR UPON REQUEST F

RumbleOn Announces Commencement of $10.0 Million Fully Backstopped Registered Rights Offering

Exhibit 99.7 RumbleOn Announces Commencement of $10.0 Million Fully Backstopped Registered Rights Offering Irving, Texas – November 26, 2024 - RumbleOn, Inc. (NASDAQ: RMBL) (the “Company” or “RumbleOn”) announced today that it has commenced a $10.0 million fully backstopped registered equity rights offering (the “Rights Offering”), pursuant to which the Company is expected to receive aggregate gro

Support and Standby Purchase Agreement, dated as of November 26, 2024, by and among the Company, Mark Tkach, William Coulter and Stone House Capital Management, LLC

Exhibit 10.1 SUPPORT AND STANDBY PURCHASE AGREEMENT This SUPPORT AND STANDBY PURCHASE AGREEMENT (this “Agreement”) is made and entered into on November 26, 2024, by and among Mark Tkach (“Tkach”), William Coulter (“Coulter” and, together with Tkach, the “Support Purchasers”) and Stone House Capital Management, LLC, a Delaware limited liability company (the “Standby Purchaser” and, collectively wit

Amendment No. 9 to the Term Loan Credit Agreement, dated August 11, 2024, by and among RumbleOn, Inc., the Subsidiary Guarantors party thereto, the lenders party thereto, and Oaktree Fund Administration, LLC, as administrative agent and collateral agent*

Exhibit 10.2 Execution Version AMENDMENT NO. 9 TO TERM LOAN CREDIT AGREEMENT AMENDMENT NO. 9 TO TERM LOAN CREDIT AGREEMENT (this “Amendment”), dated as of November 11, 2024, among RUMBLEON, INC., a Nevada corporation (the “Borrower”), the guarantors party hereto (the “Subsidiary Guarantors”), OAKTREE FUND ADMINISTRATION, LLC, as administrative agent and as collateral agent (in such capacities, the

RMBL / RumbleOn, Inc. / Stone House Capital Management, LLC - SC 13D/A Activist Investment

SC 13D/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 3)* RumbleOn, Inc. (Name of Issuer) Class B Common Stock, $0.001 par value (Title of Class of Securities) 781386305 (CUSIP Number) Kellie L. Bobo, Esq. Haynes and Boone, LLP 98 San Jacinto Boulevard, Suite 1500 Austin, Texas 78701 (512) 867-8411 (Na

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q/A (Amendment No. 1) (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 20

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q/A (Amendment No. 1) (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2024 or TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Com

RMBL / RumbleOn, Inc. / Tkach Mark - SC 13D/A Activist Investment

SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13D UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 8)* RumbleOn, Inc. (Name of Issuer) Class B Common Stock, par value $0.001 per share (Title of Class of Securities) 781386305 (CUSIP Number) Mark Tkach 1188 East Camelback Road Phoenix, AZ 85014 (602) 532-4600 with a copy to: Kellie L. Bobo, Esq. Haynes and Boone, LLP 98

Financial Statements and Exhibits, Other Events

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): November 15, 2024 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada (State or other jurisdiction of incorporation) 001-38248 (Commission File Number) 46-395

RumbleOn Announces Record Date for Proposed $10.0 Million Rights Offering

Exhibit 99.1 RumbleOn Announces Record Date for Proposed $10.0 Million Rights Offering Irving, Texas – November 15, 2024 - RumbleOn, Inc. (NASDAQ: RMBL) (the “Company” or “RumbleOn”) announced today that the close of business (4:00 p.m. Central Time) on November 25, 2024 has been fixed as the record date (the “Record Date”) for its previously announced proposed $10.0 million registered equity righ

RumbleOn Reports Third Quarter 2024 Financial Results

Exhibit 99.1 RumbleOn Reports Third Quarter 2024 Financial Results IRVING, Texas – November 12, 2024 – RumbleOn, Inc. (NASDAQ: RMBL), the "Company" or "RumbleOn", today announced results for the third quarter ended September 30, 2024. Key Third Quarter 2024 Highlights (Compared to Third Quarter 2023): •Revenue of $295.0 million decreased 12.7% •Net loss totaled $11.2 million compared to net loss o

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

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): November 11, 2024 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada (State or other jurisdiction of incorporation) 001-38248 (Commission File Number) 46-395

Amendment No. 9 to the Term Loan Credit Agreement, dated August 11, 2024, by and among RumbleOn, Inc., the Subsidiary Guarantors party thereto, the lenders party thereto, and Oaktree Fund Administration, LLC, as administrative agent and collateral agent*

Execution Version AMENDMENT NO. 9 TO TERM LOAN CREDIT AGREEMENT AMENDMENT NO. 9 TO TERM LOAN CREDIT AGREEMENT (this “Amendment”), dated as of November 11, 2024, among RUMBLEON, INC., a Nevada corporation (the “Borrower”), the guarantors party hereto (the “Subsidiary Guarantors”), OAKTREE FUND ADMINISTRATION, LLC, as administrative agent and as collateral agent (in such capacities, the “Agent”), an

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2024 TRANSITION REPORT

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2024 or TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number:

Financial Statements and Exhibits, Results of Operations and Financial Condition

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): November 12, 2024 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada 001-38248 46-3951329 (State or Other Jurisdiction of Incorporation) (Commission File Num

901 W. Walnut Hill Lane, Suite 110A Irving, Texas 75038

901 W. Walnut Hill Lane, Suite 110A Irving, Texas 75038 September 6, 2024 VIA EDGAR United States Securities and Exchange Commission Division of Corporation Finance 100 F Street, N.E. Washington, D.C. 20549 Re: RumbleOn, Inc. Registration Statement on Form S-3 File No. 333-281862 Request for Acceleration Ladies and Gentlemen: Pursuant to Rule 461 promulgated under the Securities Act of 1933, as am

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables Form S-3 (Form Type) RumbleOn, Inc. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered and Carry Forward Securities Security Type Security Class Title(1) Fee Calculation or Carry Forward Rule Amount Registered Proposed Maximum Offering Price Per Unit Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee Carry

As filed with the Securities and Exchange Commission on August 30, 2024

As filed with the Securities and Exchange Commission on August 30, 2024 Registration No.

Form of Senior Indenture, to be entered into by RumbleOn, Inc.

Exhibit 4.4 RUMBLEON, INC. AND [TRUSTEE] Trustee INDENTURE DATED AS OF , 20 SENIOR DEBT SECURITIES RUMBLEON, INC. RECONCILIATION AND TIE BETWEEN TRUST INDENTURE ACT OF 1939, AS AMENDED, AND INDENTURE, DATED AS OF , 20 TRUST INDENTURE ACT SECTION INDENTURE SECTION Section 310(a)(1) 6.9 (a)(2) 6.9 (a)(3) Not Applicable (a)(4) Not Applicable (a)(5) 6.9 (b) 6.8 Section 311 6.13 Section 312(a) 7.1, 7.2

Form of Subordinated Indenture, to be entered into by RumbleOn, Inc.

Exhibit 4.5 RUMBLEON, INC. AND [TRUSTEE] Trustee INDENTURE DATED AS OF , 20 SUBORDINATED DEBT SECURITIES RUMBLEON, INC. RECONCILIATION AND TIE BETWEEN TRUST INDENTURE ACT OF 1939, AS AMENDED, AND INDENTURE, DATED AS OF , 20 TRUST INDENTURE ACT SECTION INDENTURE SECTION Section 310(a)(1) 6.9 (a)(2) 6.9 (a)(3) Not Applicable (a)(4) Not Applicable (a)(5) 6.9 (b) 6.8 Section 311 6.13 Section 312(a) 7.

RMBL / RumbleOn, Inc. / Nantahala Capital Management, LLC - SC 13G/A Passive Investment

SC 13G/A 1 tm2423053d1sc13ga.htm SC 13G/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 4)* RumbleOn, Inc. (Name of Issuer) Class B Common Stock, $0.001 par value (Title of Class of Securities) 781386305 (CUSIP Number) August 30, 2024 (Date of Event which Requires Filing of this Statement) Check the app

, by and among RumbleOn, Inc., the Subsidiary Guarantors party thereto, the lenders party thereto, and Oaktree Fund Administration, LLC, as administrative agent and collateral agent.*

Execution Version AMENDMENT NO. 8 TO TERM LOAN CREDIT AGREEMENT AMENDMENT NO. 8 TO TERM LOAN CREDIT AGREEMENT (this “Amendment”), dated as of August 6, 2024, among RUMBLEON, INC., a Nevada corporation (the “Borrower”), the guarantors party hereto (the “Subsidiary Guarantors”), OAKTREE FUND ADMINISTRATION, LLC, as administrative agent and as collateral agent (in such capacities, the “Agent”), and t

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2024 TRANSITION REPORT PURS

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2024 or TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 001-

Financial Statements and Exhibits, Results of Operations and Financial Condition

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): August 7, 2024 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada (State or Other Jurisdiction of Incorporation) 001-38248 (Commission File Number) 46-395132

RumbleOn Reports Second Quarter 2024 Financial Results

Exhibit 99.1 RumbleOn Reports Second Quarter 2024 Financial Results IRVING, Texas – August 7, 2024 – RumbleOn, Inc. (NASDAQ: RMBL), the "Company" or "RumbleOn", today announced results for the second quarter ended June 30, 2024. Key Second Quarter 2024 Highlights (Compared to Second Quarter 2023): •Revenue of $336.8 million decreased 12.0% •Net loss totaled $0.7 million compared to net loss of $13

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): June 25, 2024 RumbleOn, Inc. (Exa

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): June 25, 2024 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada (State or other jurisdiction of incorporation) 001-38248 (Commission File Number) 46-3951329

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): June 4, 2024 RumbleOn, Inc. (Exac

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): June 4, 2024 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada (State or other jurisdiction of incorporation) 001-38248 (Commission File Number) 46-3951329

effective as of June 24

rumbleon-kiceemploymenta 4858-9732-6242v.3 EMPLOYMENT AGREEMENT This Employment Agreement (“Agreement”) is made and entered into by and between RumbleOn, Inc. (the “Company”), and Tiffany Kice (“Employee”), effective as of June 24, 2024 (the “Effective Date”). 1. Employment. During the Employment Period (as defined in Section 4), the Company shall employ Employee, and Employee shall serve, as Seni

RumbleOn Remains Focused on Strategic Plan with Appointment of Tiffany Kice as Chief Financial Officer

Exhibit 99.1 FOR IMMEDIATE RELEASE RumbleOn Remains Focused on Strategic Plan with Appointment of Tiffany Kice as Chief Financial Officer IRVING, TX – June 4, 2024 – RumbleOn, Inc. (NASDAQ: RMBL), the nation's largest retailer of new and used powersports products, today announced the appointment of Tiffany Kice as its new Chief Financial Officer (CFO), effective June 24, 2024. Kice brings over 25

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): June 3, 2024 RumbleOn, Inc. (Exac

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): June 3, 2024 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada (State or other jurisdiction of incorporation) 001-38248 (Commission File Number) 46-3951329

RumbleOn Reports First Quarter 2024 Financial Results 8.3% Improvement in Adjusted EBITDA on 8.0% Lower Revenue Operating Income of $5.2 Million Versus Operating Loss of $0.7 Million Last Year

Exhibit 99.1 RumbleOn Reports First Quarter 2024 Financial Results 8.3% Improvement in Adjusted EBITDA on 8.0% Lower Revenue Operating Income of $5.2 Million Versus Operating Loss of $0.7 Million Last Year Financial and Operational Highlights (compared to last year's first quarter) •New powersports unit retail sales of 10,503 versus 10,436 or up 0.6%. •Pre-owned powersports unit retail sales of 5,

Form of 2024 Performance Stock Unit Award Agreement, effective March 19, 2024

PERFORMANCE RESTRICTED STOCK UNIT AWARD TO: You (“Grantee”) have been granted this restricted stock unit (“RSU”) award (the “Award”) by RumbleOn, Inc.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2024 TRANSITION REPORT PUR

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2024 or TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 001

Form of 2024 Restricted Stock Unit Award Agreement, effective March 19, 2024

RESTRICTED STOCK UNIT AWARD TO: You (“Grantee”) have been granted this restricted stock unit (“RSU”) award (the “Award”) by RumbleOn, Inc.

Financial Statements and Exhibits, Results of Operations and Financial Condition

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): May 8, 2024 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada (State or Other Jurisdiction of Incorporation) 001-38248 (Commission File Number) 46-3951329 (

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. __)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, For Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Defin

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

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 18, 2024 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada (State or other jurisdiction of incorporation) 001-38248 (Commission File Number) 46-395132

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Financial Statements and Exhibits

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 16, 2024 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada (State or other jurisdiction of incorporation) 001-38248 (Commission File Number) 46-395132

Amendment No. 2 to Amended and Restated Bylaws of RumbleOn, Inc., dated April 16, 2024 (Incorporated by reference to Exhibit 3.1 in the Company’s Current Report on Form 8-K, filed on April 19, 2024).

Exhibit 3.1 AMENDMENT NO. 2 TO THE AMENDED AND RESTATED BYLAWS OF RUMBLEON, INC. Pursuant to resolutions duly adopted by the Board of Directors of RumbleOn, Inc., a Nevada corporation (the “Company”) on April 16, 2024, the Company does hereby amend the Amended and Restated Bylaws of the Company effective as of October 8, 2021, as amended on May 9, 2023 (the “Bylaws”) as follows: 1.Article III, Sec

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables Form S-8 (Form Type) RUMBLEON, INC. (Exact Name of Registrant as Specified in its Articles) Table 1: Newly Registered Securities Security Type Security Class Title Fee Calculation Rule(1) Amount Registered(2) Proposed Maximum Offering Price Per Share(1) Maximum Aggregate Offering Price(1) Fee Rate Amount of Registration Fee Equity Class B Common Stock,

As filed with the Securities and Exchange Commission on April 16, 2024

As filed with the Securities and Exchange Commission on April 16, 2024 Registration Statement No.

As filed with the Securities and Exchange Commission on April 16, 2024

As filed with the Securities and Exchange Commission on April 16, 2024 Registration Statement No.

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables Form S-8 (Form Type) RUMBLEON, INC. (Exact Name of Registrant as Specified in its Articles) Table 1: Newly Registered Securities Security Type Security Class Title Fee Calculation Rule(1) Amount Registered(2) Proposed Maximum Offering Price Per Share(1) Maximum Aggregate Offering Price(1) Fee Rate Amount of Registration Fee Equity Class B Common Stock,

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

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 8, 2024 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada (State or other jurisdiction of incorporation) 001-38248 (Commission File Number) 46-3951329

Execution Version AMENDMENT NO. 7 TO TERM LOAN CREDIT AGREEMENT AMENDMENT NO. 7 TO TERM LOAN CREDIT AGREEMENT (this “Amendment”), dated as of February 5, 2024 and effective as of the Seventh Amendment Effective Date, among RUMBLEON, INC., a Nevada co

Execution Version AMENDMENT NO. 7 TO TERM LOAN CREDIT AGREEMENT AMENDMENT NO. 7 TO TERM LOAN CREDIT AGREEMENT (this “Amendment”), dated as of February 5, 2024 and effective as of the Seventh Amendment Effective Date, among RUMBLEON, INC., a Nevada corporation (the “Borrower”), the other guarantors party hereto (the “Subsidiary Guarantors”), OAKTREE FUND ADMINISTRATION, LLC, as administrative agent

Option Award Agreement between Michael Kennedy and RumbleOn, Inc., dated November 1, 2023 (Incorporated by reference to Exhibit 10.22 in the Company's Annual Report on Form 10-K, filed on March 28, 2024).

Exhibit 10.22 OPTION AWARD AGREEMENT TO: MICHAEL KENNEDY You (“Grantee” or “you”) have been granted an award (the “Award”) of nonqualified stock options (the “Options”) to purchase shares of Common Stock (“Shares”) at the applicable Exercise Price and subject to the terms and conditions described herein, as a material inducement to, and in connection with, Grantee’s acceptance of an offer of emplo

RUMBLEON, INC. (the “Company”) Compensation Clawback Policy Effective Date: November 30, 2023

Exhibit 97 RUMBLEON, INC. (the “Company”) Compensation Clawback Policy Effective Date: November 30, 2023 1.Purpose. The Company has adopted this Policy to comply with Section 954 of the Dodd-Frank Wall Street Reform and Consumer Protection Act of 2010, as codified by Section 10D of the Exchange Act, and Nasdaq New Listing Rule 5608 which require the recovery of certain forms of executive compensat

Subsidiaries (as of December 31, 2023)

Exhibit 21.1 Subsidiaries (as of December 31, 2023) Subsidiary Name Jurisdiction DBA’s America's PowerSports, Inc. Delaware APS Austin Holdings, LLC Texas APS of Georgetown, LLC Delaware Central Texas Powersports Ride Now Georgetown Ridenow Georgetown RideNow Powersports RideNow Powersports Georgetown APS of Ohio, LLC Delaware Powder Keg Harley-Davidson APS of Oklahoma LLC Delaware Fort Thunder Ha

2023 Annual Report on Form 10-K Power of Attorney RUMBLEON, INC. 2023 Annual Report on Form 10-K Power of Attorney KNOW ALL PERSONS BY THESE PRESENTS: That each person whose name is signed below has made, constituted and appointed, and by this instru

2023 Annual Report on Form 10-K Power of Attorney RUMBLEON, INC. 2023 Annual Report on Form 10-K Power of Attorney KNOW ALL PERSONS BY THESE PRESENTS: That each person whose name is signed below has made, constituted and appointed, and by this instrument does make, constitute and appoint Michael W. Kennedy and Blake Lawson, and each of them severally, his or her true and lawful attorney and agent,

Execution Version AMENDMENT NO. 6 TO TERM LOAN CREDIT AGREEMENT AMENDMENT NO. 6 TO TERM LOAN CREDIT AGREEMENT (this “Amendment”), dated as of October 31, 2023 (the “Sixth Amendment Effective Date”), among RUMBLEON, INC., a Nevada corporation (the “Bo

Execution Version AMENDMENT NO. 6 TO TERM LOAN CREDIT AGREEMENT AMENDMENT NO. 6 TO TERM LOAN CREDIT AGREEMENT (this “Amendment”), dated as of October 31, 2023 (the “Sixth Amendment Effective Date”), among RUMBLEON, INC., a Nevada corporation (the “Borrower”), the other guarantors party hereto (the “Subsidiary Guarantors”), OAKTREE FUND ADMINISTRATION, LLC, as administrative agent and as collateral

Fifth Amendment to the RumbleOn, Inc 2017 Stock Incentive Plan (Incorporated by reference to Exhibit 10.6 in the Company’s Annual Report on Form 10-K, filed on March 28, 2024).

Exhibit 10.6 FIFTH AMENDMENT TO THE RUMBLEON, INC. 2017 STOCK INCENTIVE PLAN WHEREAS, RumbleOn, Inc., a Nevada corporation (the “Company”), currently maintains and sponsors the RumbleOn, Inc. 2017 Stock Incentive Plan (the “Plan”); and WHEREAS, Section 14(k) of the Plan provides that the Board of the Directors of the Company (“Board”) may amend the Plan from time to time; and WHEREAS, the Board ha

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-K x ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934For the fiscal year ended December 31, 2023 ¨ TRANSITION REPORT PURSUANT TO SECTIO

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-K x ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2023 ¨ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-38248 RumbleOn, Inc. (Exact name of

Other Events

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): March 25, 2024 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada (State or other jurisdiction of incorporation) 001-38248 (Commission File Number) 46-395132

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 NOTIFICATION OF LATE FILING

SEC FILE NUMBER 001-38248 CUSIP NUMBER 781386 305 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

RumbleOn Reports Fourth Quarter and Full Year 2023 Financial Results & Presents Vision 2026 Strategic Plan Raised $100 Million through Rights Offering Paid Down $50 Million of Debt in the Quarter

Exhibit 99.1 RumbleOn Reports Fourth Quarter and Full Year 2023 Financial Results & Presents Vision 2026 Strategic Plan Raised $100 Million through Rights Offering Paid Down $50 Million of Debt in the Quarter IRVING, Texas – March 14, 2024 – RumbleOn, Inc. (NASDAQ: RMBL), today announced results for its quarter and full year ended December 31, 2023. FOURTH QUARTER AND FULL YEAR 2023 HIGHLIGHTS •To

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):March 14, 2024 RumbleOn, Inc. (Exa

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):March 14, 2024 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada (State or Other Jurisdiction of Incorporation) 001-38248 (Commission File Number) 46-3951329

RMBL / RumbleON, Inc. / Nantahala Capital Management, LLC - SC 13G/A Passive Investment

SC 13G/A 1 tm243309d23sc13ga.htm SC 13G/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 3)* RumbleOn, Inc. (Name of Issuer) Class B Common Stock, $0.001 par value (Title of Class of Securities) 781386305 (CUSIP Number) December 31, 2023 (Date of Event which Requires Filing of this Statement) Check the a

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): December 29, 2023 RumbleOn, Inc.

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): December 29, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada (State or other jurisdiction of incorporation) 001-38248 (Commission File Number) 46-395

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): December 21, 2023 RumbleOn, Inc.

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): December 21, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada (State or other jurisdiction of incorporation) 001-38248 (Commission File Number) 46-395

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): December 15, 2023 RumbleOn, Inc.

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): December 15, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada (State or other jurisdiction of incorporation) 001-38248 (Commission File Number) 46-395

RMBL / RumbleON Inc - Class B / Tkach Mark - SC 13D/A Activist Investment

SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13D UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 7)* RumbleOn, Inc. (Name of Issuer) Class B Common Stock, par value $0.001 per share (Title of Class of Securities) 781386305 (CUSIP Number) Mark Tkach 1188 East Camelback Road Phoenix, AZ 85014 (602) 532-4600 with a copy to: Rick A. Werner, Esq. Haynes and Boone, LLP 26t

RumbleOn Announces Final Results of Rights Offering

Exhibit 99.1 RumbleOn Announces Final Results of Rights Offering IRVING, Texas – December 6, 2023 – RumbleOn, Inc. (NASDAQ: RMBL) (the “Company” or “RumbleOn”) announced today the final results of its $100.0 million rights offering (the “Rights Offering”). The subscription period of the Rights Offering expired at 5:00 P.M. Eastern Time, on December 5, 2023. The Rights Offering resulted in subscrip

RMBL / RumbleON Inc - Class B / Stone House Capital Management, LLC - AMENDMENT NO. 2 TO SCHEDULE 13D Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 2)* RumbleOn, Inc. (Name of Issuer) Class B Common Stock, $0.001 par value (Title of Class of Securities) 781386305 (CUSIP Number) Kellie L. Bobo, Esq. Haynes and Boone, LLP 98 San Jacinto Boulevard, Suite 1500 Austin, Texas 78701 (512) 867-8411 (Name, Addre

Unregistered Sales of Equity Securities, Financial Statements and Exhibits, Other Events

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): December 6, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada (State or other jurisdiction of incorporation) 001-38248 (Commission File Number) 46-3951

Amendment No. 1 to the Standby Purchase Agreement, dated as of November 20, 2023, by and among RumbleOn, Inc., Mark Tkach, William Coulter and Stone House Capital Management, LLC

Exhibit 10.1 AMENDMENT No. 1 to STANDBY PURCHASE AGREEMENT This Amendment No. 1 to the Standby Purchase Agreement (this “Amendment”) is made and entered into on November 20, 2023, by and among Mark Tkach (“Tkach”), William Coulter (“Coulter”) and Stone House Capital Management, LLC, a Delaware limited liability company (“Stone House” and, collectively with Tkach and Coulter, the “Standby Purchaser

RumbleOn Announces Extension of $100 Million Rights Offering Subscription Period

Exhibit 99.1 RumbleOn Announces Extension of $100 Million Rights Offering Subscription Period IRVING, Texas - RumbleOn, Inc. (NASDAQ: RMBL) (the “Company” or “RumbleOn”), the largest powersports retailer in North America, today announced that its Board of Directors is extending the Rights Offering subscription period an additional week until December 5, 2023, in order to better ensure that holders

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Other Events

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): November 20, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada 001-38248 46-3951329 (State or other jurisdiction of incorporation) (Commission File Num

Subscription Rights to Purchase Up to 18,181,818 Shares of Class B Common Stock at $5.50 Per Share

PROSPECTUS Filed Pursuant to Rule 424(b)(3) Registration No.: 333-274859 Subscription Rights to Purchase Up to 18,181,818 Shares of Class B Common Stock at $5.50 Per Share RumbleOn, Inc., a Nevada corporation (the “Company,” “RumbleOn,” “we,” “us,” or “our”), is distributing at no charge to the holders of (i) our Class A common stock, par value $0.001 per share (“Class A common stock”), and (ii) C

Form of Notice to Stockholders Who Are Acting as Nominees.

Exhibit 99.4 RUMBLEON, INC. NOTICE TO STOCKHOLDERS WHO ARE ACTING AS NOMINEES Up to 18,181,818 Shares of Class B Common Stock Issuable Upon Exercise of Non-Transferable Subscription Rights [●], 2023 Dear Stockholder: This letter is being distributed to custodian banks, broker, dealers, and other nominees in connection with the rights offering by RumbleOn, Inc. (the “Company”) of non-transferable s

Form of Notice to Stockholders Who Are Record Holders.

Exhibit 99.3 RUMBLEON, INC. NOTICE TO STOCKHOLDERS WHO ARE RECORD HOLDERS Up to 18,181,818 Shares of Class B Common Stock Issuable Upon Exercise of Non-Transferable Subscription Rights [●], 2023 Dear Stockholder: Enclosed for your consideration is a prospectus dated [●], 2023 (as amended from time to time, the “Prospectus”) relating to the offering by RumbleOn, Inc. (the “Company”) of non-transfer

Form of Rights Certificate.

Exhibit 4.7 THE TERMS AND CONDITIONS OF THE RIGHTS OFFERING ARE SET FORTH IN THE COMPANY’S PROSPECTUS DATED [●], 2023 AND ARE INCORPORATED HEREIN BY REFERENCE. COPIES OF THE PROSPECTUS ARE AVAILABLE UPON REQUEST FROM BROADRIDGE CORPORATE ISSUER SOLUTIONS, LLC, THE SUBSCRIPTION AND INFORMATION AGENT, BY CALLING (888) 789-8409. RUMBLEON, INC. NON-TRANSFERABLE SUBSCRIPTION RIGHTS CERTIFICATE Evidenci

Form of Beneficial Owner Election Form.

Exhibit 99.7 THE TERMS AND CONDITIONS OF THE RIGHTS OFFERING ARE SET FORTH IN THE COMPANY’S PROSPECTUS DATED [●], 2023 AND ARE INCORPORATED HEREIN BY REFERENCE. COPIES OF THE PROSPECTUS ARE AVAILABLE UPON REQUEST FROM BROADRIDGE CORPORATE ISSUER SOLUTIONS, LLC, THE SUBSCRIPTION AND INFORMATION AGENT, BY CALLING (888) 789-8409. RUMBLEON, INC. BENEFICIAL OWNER ELECTION FORM I (We), the beneficial ow

Form of Notice to Clients of Stockholders Who Are Acting as Nominees.

Exhibit 99.5 RUMBLEON, INC. NOTICE TO CLIENTS OF STOCKHOLDERS WHO ARE ACTING AS NOMINEES Up to 18,181,818 Shares of Class B Common Stock Issuable Upon Exercise of Non-Transferable Subscription Rights [●], 2023 Dear Stockholder: Enclosed for your consideration is a prospectus dated [●], 2023 (as amended from time to time, the “Prospectus”) relating to the offering by RumbleOn, Inc. (the “Company”)

As filed with the Securities and Exchange Commission on November 9, 2023

As filed with the Securities and Exchange Commission on November 9, 2023 Registration No.

RMBL / RumbleON Inc - Class B / Nantahala Capital Management, LLC - SC 13G/A Passive Investment

SC 13G/A 1 tm2329848d1sc13ga.htm SC 13G/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 2)* RumbleOn, Inc. (Name of Issuer) Class B Common Stock, $0.001 par value (Title of Class of Securities) 781386305 (CUSIP Number) October 31, 2023 (Date of Event which Requires Filing of this Statement) Check the ap

Instructions as to Use of Subscription Rights Certificate.

Exhibit 99.2 THE TERMS AND CONDITIONS OF THE RIGHTS OFFERING ARE SET FORTH IN THE COMPANY’S PROSPECTUS DATED [●], 2023 AND ARE INCORPORATED HEREIN BY REFERENCE. COPIES OF THE PROSPECTUS ARE AVAILABLE UPON REQUEST FROM BROADRIDGE CORPORATE ISSUER SOLUTIONS, LLC, THE SUBSCRIPTION AND INFORMATION AGENT, BY CALLING (888) 789-8409. INSTRUCTIONS AS TO USE OF RUMBLEON, INC. NON-TRANSFERABLE SUBSCRIPTION

Form of Nominee Holder Certification.

Exhibit 99.6 THE TERMS AND CONDITIONS OF THE RIGHTS OFFERING ARE SET FORTH IN THE COMPANY’S PROSPECTUS DATED [●], 2023 AND ARE INCORPORATED HEREIN BY REFERENCE. COPIES OF THE PROSPECTUS ARE AVAILABLE UPON REQUEST FROM BROADRIDGE CORPORATE ISSUER SOLUTIONS, LLC, THE SUBSCRIPTION AND INFORMATION AGENT, BY CALLING (888) 789-8409. RUMBLEON, INC. SHARES OF CLASS B COMMON STOCK SUBSCRIBED FOR UPON EXERC

901 W. Walnut Hill Lane, Suite 110A Irving, Texas 75038

901 W. Walnut Hill Lane, Suite 110A Irving, Texas 75038 November 9, 2023 VIA EDGAR United States Securities and Exchange Commission Division of Corporation Finance 100 F Street, N.E. Washington, D.C. 20549 Re: RumbleOn, Inc. Registration Statement on Form S-3 File No. 333-274859 Request for Acceleration Ladies and Gentlemen: Pursuant to Rule 461 promulgated under the Securities Act of 1933, as ame

1 Exhibit 99.1 RumbleOn Announces Subscription Price for its $100.0 Million Rights Offering Irving, Texas – November 9, 2023 – RumbleOn, Inc. (NASDAQ: RMBL) (the “Company” or “RumbleOn”) announced today that it has set a subscription price of $5.50 p

1 Exhibit 99.1 RumbleOn Announces Subscription Price for its $100.0 Million Rights Offering Irving, Texas – November 9, 2023 – RumbleOn, Inc. (NASDAQ: RMBL) (the “Company” or “RumbleOn”) announced today that it has set a subscription price of $5.50 per share (the “Subscription Price”) of the Company’s Class B common stock to be paid upon exercise of the Subscription Rights (as defined below) to be

Financial Statements and Exhibits, Other Events

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): November 9, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada (State or Other Jurisdiction of Incorporation) 001-38248 (Commission File Number) 46-3951

UNITARY MASTER LEASE AGREEMENT NNN REIT, LP, a Delaware limited partnership, as Landlord, Freedom Powersports Fort Worth, LLC, a Texas limited liability company; Freedom Powersports, LLC, a Texas limited liability company; Freedom Powersports McKinne

UNITARY MASTER LEASE AGREEMENT Between NNN REIT, LP, a Delaware limited partnership, as Landlord, and Freedom Powersports Fort Worth, LLC, a Texas limited liability company; Freedom Powersports, LLC, a Texas limited liability company; Freedom Powersports McKinney, LLC, a Texas limited liability company; Freedom Powersports Johnson County, LLC, a Texas limited liability company; Freedom Powersports Dallas, LLC, a Texas limited liability company; Freedom Powersports Lewisville, LLC, a Texas limited liability company; and Freedom Powersports McDonough LLC, a Delaware limited liability company, collectively, as Tenant RumbleOn (8-Site) 1 0914830\202909\12943031v7 TABLE OF CONTENTS PAGE ARTICLE I AGREEMENT TO LEASE 2 1.

Financial Statements and Exhibits, Results of Operations and Financial Condition

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): November 7, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada (State or Other Jurisdiction of Incorporation) 001-38248 (Commission File Number) 46-3951

RumbleOn Reports Third Quarter 2023 Financial Results Paid Down $47 Million of Term Debt Reiterates 2023 Outlook

Exhibit 99.1 RumbleOn Reports Third Quarter 2023 Financial Results Paid Down $47 Million of Term Debt Reiterates 2023 Outlook IRVING, Texas – November 7, 2023 – RumbleOn, Inc. (NASDAQ: RMBL) (the “Company” or “RumbleOn”), the largest powersports retailer in North America, today announced operational and financial results for the three months ended September 30, 2023. RumbleOn management is hosting

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2023 o TRANSITION REPO

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2023 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file numbe

RumbleOn Announces Record Date for Proposed $100.0 Million Rights Offering

Exhibit 99.1 RumbleOn Announces Record Date for Proposed $100.0 Million Rights Offering Irving, Texas – November 1, 2023 - RumbleOn, Inc. (NASDAQ: RMBL) (the "Company" or "RumbleOn") announced today that its Board of Directors has fixed the close of business on November 13, 2023 as the record date (the “Record Date”) for its previously announced proposed $100.0 million equity rights offering (the

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): November 1, 2023 RumbleOn, Inc. (

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): November 1, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada 001-38248 46-3951329 (State or other jurisdiction of incorporation) (Commission File Numb

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

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): October 19, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada 001-38248 46-3951329 (State or other jurisdiction of incorporation) (Commission File Numb

Executive Employment Agreement, dated October 19, 2023, between Michael Kennedy and RumbleOn, Inc.

Exhibit 10.1 EMPLOYMENT AGREEMENT This Employment Agreement (“Agreement”) is made and entered into by and between RumbleOn, Inc. (the “Company”), and Michael Kennedy (“Executive”), effective as of November 1, 2023 (the “Effective Date”). 1. Employment. During the Employment Period (as hereinafter defined) in Section 4), the Company shall employ Executive, and Executive shall serve, as Chief Execut

RumbleOn Appoints Michael Kennedy as Chief Executive Officer Mr. Kennedy brings more than 30 years of Powersports Industry Leadership Experience

Exhibit 99.1 RumbleOn Appoints Michael Kennedy as Chief Executive Officer Mr. Kennedy brings more than 30 years of Powersports Industry Leadership Experience Irving, Texas - October 20, 2023 - RumbleOn, Inc. (NASDAQ: RMBL) (the “Company” or “RumbleOn”), the largest powersports retailer in North America, today announced that Michael “Mike” Kennedy has been appointed Chief Executive Officer effectiv

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

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): October 19, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada 001-38248 46-3951329 (State or other jurisdiction of incorporation) (Commission File Numb

As filed with the Securities and Exchange Commission on October 18, 2023

As filed with the Securities and Exchange Commission on October 18, 2023 Registration No.

RumbleOn, Inc. 901 W. Walnut Hill Lane, Suite 110A Irving, Texas 75038 (214) 771-9952

RumbleOn, Inc. 901 W. Walnut Hill Lane, Suite 110A Irving, Texas 75038 (214) 771-9952 October 18, 2023 VIA EDGAR United States Securities and Exchange Commission Division of Corporation Finance 100 F Street, N.E. Washington, D.C. 20549 Attention: Matthew Crispino Jan Woo Re: RumbleOn, Inc. Registration Statement on Form S-3 Filed October 4, 2023 File No. 333-274859 To the addressees set forth abov

Instructions as to Use of Subscription Rights Certificate.

Exhibit 99.2 THE TERMS AND CONDITIONS OF THE RIGHTS OFFERING ARE SET FORTH IN THE COMPANY’S PROSPECTUS DATED [●], 2023 AND ARE INCORPORATED HEREIN BY REFERENCE. COPIES OF THE PROSPECTUS ARE AVAILABLE UPON REQUEST FROM BROADRIDGE CORPORATE ISSUER SOLUTIONS, LLC, THE SUBSCRIPTION AND INFORMATION AGENT, BY CALLING (888) 789-8409. INSTRUCTIONS AS TO USE OF RUMBLEON, INC. NON-TRANSFERABLE SUBSCRIPTION

As filed with the Securities and Exchange Commission on October 4, 2023

As filed with the Securities and Exchange Commission on October 4, 2023 Registration No.

Form of Beneficial Owner Election Form.

Exhibit 99.7 THE TERMS AND CONDITIONS OF THE RIGHTS OFFERING ARE SET FORTH IN THE COMPANY’S PROSPECTUS DATED [●], 2023 AND ARE INCORPORATED HEREIN BY REFERENCE. COPIES OF THE PROSPECTUS ARE AVAILABLE UPON REQUEST FROM BROADRIDGE CORPORATE ISSUER SOLUTIONS, LLC, THE SUBSCRIPTION AND INFORMATION AGENT, BY CALLING (888) 789-8409. RUMBLEON, INC. BENEFICIAL OWNER ELECTION FORM I (We), the beneficial ow

Filing fee table.

Exhibit 107 Calculation of Filing Fee Tables S-3 (Form Type) RumbleOn, Inc. (Exact Name of Registrant as Specified in its Articles of Incorporation) Table 1: Newly Registered and Carry Forward Securities Security Type Security Class Title (1) Fee Calculation or Carry Forward Rule Amount Registered (2) Proposed Maximum Offering Price Per Unit (2) Maximum Aggregate Offering Price (3) Fee Rate Amount

Form of Notice to Stockholders Who Are Record Holders.

Exhibit 99.3 RUMBLEON, INC. NOTICE TO STOCKHOLDERS WHO ARE RECORD HOLDERS Up to [●] Shares of Class B Common Stock Issuable Upon Exercise of Non-Transferable Subscription Rights [●], 2023 Dear Stockholder: Enclosed for your consideration is a prospectus dated [●], 2023 (as amended from time to time, the “Prospectus”) relating to the offering by RumbleOn, Inc. (the “Company”) of non-transferable su

Form of Notice to Stockholders Who Are Acting as Nominees.

Exhibit 99.4 RUMBLEON, INC. NOTICE TO STOCKHOLDERS WHO ARE ACTING AS NOMINEES Up to [●] Shares of Class B Common Stock Issuable Upon Exercise of Non-Transferable Subscription Rights [●], 2023 Dear Stockholder: This letter is being distributed to custodian banks, broker, dealers, and other nominees in connection with the rights offering by RumbleOn, Inc. (the “Company”) of non-transferable subscrip

Form of Nominee Holder Certification.

Exhibit 99.6 THE TERMS AND CONDITIONS OF THE RIGHTS OFFERING ARE SET FORTH IN THE COMPANY’S PROSPECTUS DATED [●], 2023 AND ARE INCORPORATED HEREIN BY REFERENCE. COPIES OF THE PROSPECTUS ARE AVAILABLE UPON REQUEST FROM BROADRIDGE CORPORATE ISSUER SOLUTIONS, LLC, THE SUBSCRIPTION AND INFORMATION AGENT, BY CALLING (888) 789-8409. RUMBLEON, INC. SHARES OF CLASS B COMMON STOCK SUBSCRIBED FOR UPON EXERC

Form of Notice to Clients of Stockholders Who Are Acting as Nominees.

Exhibit 99.5 RUMBLEON, INC. NOTICE TO CLIENTS OF STOCKHOLDERS WHO ARE ACTING AS NOMINEES Up to [●] Shares of Class B Common Stock Issuable Upon Exercise of Non-Transferable Subscription Rights [●], 2023 Dear Stockholder: Enclosed for your consideration is a prospectus dated [●], 2023 (as amended from time to time, the “Prospectus”) relating to the offering by RumbleOn, Inc. (the “Company”) of non-

Form of Rights Certificate.

Exhibit 4.8 THE TERMS AND CONDITIONS OF THE RIGHTS OFFERING ARE SET FORTH IN THE COMPANY’S PROSPECTUS DATED [●], 2023 AND ARE INCORPORATED HEREIN BY REFERENCE. COPIES OF THE PROSPECTUS ARE AVAILABLE UPON REQUEST FROM BROADRIDGE CORPORATE ISSUER SOLUTIONS, LLC, THE SUBSCRIPTION AND INFORMATION AGENT, BY CALLING (888) 789-8409. RUMBLEON, INC. NON-TRANSFERABLE SUBSCRIPTION RIGHTS CERTIFICATE Evidenci

EXPLANATORY NOTE

EXPLANATORY NOTE RumbleOn, Inc. (the “Company”) is filing this Exhibit 99.1 to its Current Report on Form 8-K (including this Exhibit 99.1, the "Form 8-K") solely to recast certain financial information and related disclosures included in the Company’s Annual Report on Form 10-K for the fiscal year ended December 31, 2022, originally filed with the United States ("U.S.") Securities and Exchange Co

Financial Statements and Exhibits, Other Events

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): September 26, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada (State or Other Jurisdiction of Incorporation) 001-38248 (Commission File Number) 46-39

Changes in Registrant's Certifying Accountant

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): September 13, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada 001-38248 46-3951329 (State or other jurisdiction of incorporation) (Commission File Nu

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): September 8, 2023 RumbleOn, Inc.

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): September 8, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada 001-38248 46-3951329 (State or other jurisdiction of incorporation) (Commission File Num

Exhibit 99.19 – Coulter RSU Grant Agreement, dated September 1, 2023 (filed herewith).

Exhibit 99.19 RESTRICTED STOCK UNIT AWARD TO: WILLIAM COULTER You (“Grantee”) have been granted, this restricted stock unit (“RSU”) award (the "Award") by RumbleOn, Inc. (the " Company") pursuant to the RumbleOn 2017 Stock Incentive Plan (as amended to date, the “Plan”). This Restricted Stock Unit Award Agreement (the “Agreement”) confirms the understanding between RumbleOn and you as of the Effec

RMBL / RumbleON Inc - Class B / Tkach Mark - SC 13D/A Activist Investment

SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13D UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 6)* RumbleOn, Inc. (Name of Issuer) Class B Common Stock, par value $0.001 per share (Title of Class of Securities) 781386305 (CUSIP Number) Mark Tkach 1188 East Camelback Road Phoenix, AZ 85014 (602) 532-4600 with a copy to: Rick A. Werner, Esq. Haynes and Boone, LLP 26t

Exhibit 99.20 – Tkach RSU Grant Agreement, dated September 1, 2023 (filed herewith).

EX-99.20 3 tm2325740d1ex99-20.htm EXHIBIT 99.20 Exhibit 99.20 RESTRICTED STOCK UNIT AWARD TO: MARK TKACH You ("Grantee") have been granted, this restricted stock unit ("RSU") award (the "Award") by RumbleOn, Inc. (the "Company") pursuant to the RumbleOn 2017 Stock Incentive Plan (as amended to date, the "Plan"). This Restricted Stock Unit Award Agreement (the "Agreement") confirms the understandin

RMBL / RumbleON Inc - Class B / Stone House Capital Management, LLC - AMENDMENT NO. 1 TO SCHEDULE 13D Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 1)* RumbleOn, Inc. (Name of Issuer) Class B Common Stock, $0.001 par value (Title of Class of Securities) 781386305 (CUSIP Number) Rick A. Werner, Esq. Haynes and Boone, LLP 26th Floor New York, NY 10112 (212) 659-4974 (Name, Address and Telephone Number of

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): August 30, 2023 RumbleOn, Inc. (E

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): August 30, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada 001-38248 46-3951329 (State or other jurisdiction of incorporation) (Commission File Numbe

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): August 22, 2023 RumbleOn, Inc. (E

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): August 22, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada 001-38248 46-3951329 (State or other jurisdiction of incorporation) (Commission File Numbe

Real Estate Purchase and Sale Contract, dated August 22, 2023, by and between NNN REIT, LP, as buyer and RumbleOn, Inc., as seller.

Exhibit 10.1 REAL ESTATE PURCHASE AND SALE CONTRACT by and between NNN REIT, LP, a Delaware limited partnership, or assigns, as BUYER and RumbleOn, Inc., a Nevada corporation, as SELLER Premises: Nine (9) Properties as described in Exhibit A TABLE OF CONTENTS Page 1. Definitions 1 2. Purchase and Sale of Properties 4 3. Purchase Price for Properties 4 4. Closing Date 5 5. Seller Deliveries 5 6. In

Exhibit 99.11 – Joint Filing Agreement, dated August 17, 2023 (filed herewith)

Exhibit 99.11 JOINT FILING AGREEMENT In accordance with Rule 13d-1(k)(1)(iii) under the Securities Exchange Act of 1934, as amended, the persons named below agree to the joint filing on behalf of each of them of a Statement on Schedule 13D (including additional amendments thereto) with respect to the shares of Class B Common Stock, $0.001 par value, of RumbleOn, Inc., a Nevada corporation. This Jo

RMBL / RumbleON Inc - Class B / Tkach Mark - SC 13D/A Activist Investment

SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13D UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 5)* RumbleOn, Inc. (Name of Issuer) Class B Common Stock, par value $0.001 per share (Title of Class of Securities) 781386305 (CUSIP Number) Mark Tkach 1188 East Camelback Road Phoenix, AZ 85014 (602) 532-4600 with a copy to: Rick A. Werner, Esq. Haynes and Boone, LLP 26t

Employment Agreement, dated August 16, 2023, by and between RumbleOn, Inc. and Mark Tkach.

Exhibit 10.3 EMPLOYMENT AGREEMENT This Employment Agreement (“Agreement”) is made and entered into by and between RumbleOn, Inc. (the “Company”), and Mark Tkach (“Executive”), effective as of June 15, 2023 (the “Effective Date”). 1. Employment. During the Employment Period (as defined in Section 4), the Company shall employ Executive, and Executive shall serve, as Interim Chief Executive Officer o

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A (Amendment No. 1) CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): June 15, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada 001-38248 46-3951329 (State or other jurisdiction of incorporation) (Com

Form of 2023 Warrant (Incorporated by reference to Exhibit 4.1 in the Company’s Current Report on Form 8-K, filed on August 17, 2023).

Exhibit 4.1 THIS WARRANT AND ANY SHARES ACQUIRED UPON THE EXERCISE OF THIS WARRANT HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “ACT”) OR APPLICABLE STATE SECURITIES LAWS, AND MAY NOT BE SOLD, PLEDGED, HYPOTHECATED, DONATED OR OTHERWISE TRANSFERRED WITHOUT COMPLIANCE WITH THE REGISTRATION OR QUALIFICATION PROVISIONS OF APPLICABLE FEDERAL AND STATE SECURITIES LAWS OR A

Entry into a Material Definitive Agreement, Unregistered Sales of Equity Securities, Financial Statements and Exhibits

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): August 14, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada 001-38248 46-3951329 (State or other jurisdiction of incorporation) (Commission File Numbe

RMBL / RumbleON Inc - Class B / Stone House Capital Management, LLC - SCHEDULE 13D Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. )* RumbleOn, Inc. (Name of Issuer) Class B Common Stock, $0.001 par value (Title of Class of Securities) 781386305 (CUSIP Number) Rick A. Werner, Esq. Haynes and Boone, LLP 26th Floor New York, NY 10112 (212) 659-4974 (Name, Address and Telephone Number of P

Purchase Agreement, dated as of August 8, 2023, by and among the Company, Mark Tkach, William Coulter and Stone House Capital Management, LLC (incorporated by reference to Exhibit 10.1 of the Registrant’s Current Report on Form 8-K as filed with the SEC on August 11, 2023).

Exhibit 10.1 STANDBY PURCHASE AGREEMENT This STANDBY PURCHASE AGREEMENT (this “Agreement”) is made and entered into on August 8, 2023, by and among Mark Tkach (“Tkach”), William Coulter (“Coulter”) and Stone House Capital Management, LLC, a Delaware limited liability company (“Stone House” and, collectively with Tkach and Coulter, the “Standby Purchasers”), and RumbleOn, Inc., a Nevada corporation

Joint Filing Agreement (filed herewith)

Exhibit 99.1 JOINT FILING AGREEMENT August 11, 2023 Pursuant to and in accordance with the Securities Exchange Act of 1934, as amended (the “Exchange Act”), and the rules and regulations thereunder, each party hereto hereby agrees to the joint filing, on behalf of each of them, of any filing required by such party under Section 13 or Section 16 of the Exchange Act or any rule or regulation thereun

RumbleOn Announces Planned $100 Million Fully Backstopped Rights Offering

Exhibit 99.1 RumbleOn Announces Planned $100 Million Fully Backstopped Rights Offering August 9, 2023 IRVING, Texas – RumbleOn, Inc. (NASDAQ: RMBL) (the “Company” or “RumbleOn”), the nation’s first and largest publicly traded powersports platform, today announced that it plans to make a $100 million rights offering to holders of the company’s Class A common stock and Class B common stock (and cert

Entry into a Material Definitive Agreement, Unregistered Sales of Equity Securities, Other Events, Financial Statements and Exhibits

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): August 8, 2023 RumbleOn, Inc. (Exact Name of Registrant as Specified in its Charter) Nevada 001-38248 46-3951329 (State or Other Jurisdiction of Incorporation) (Commission File Number

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): August 9, 2023 RumbleOn, Inc. (Ex

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): August 9, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada (State or Other Jurisdiction of Incorporation) 001-38248 (Commission File Number) 46-395132

RumbleOn Reports Second Quarter 2023 Financial Results

Exhibit 99.1 RumbleOn Reports Second Quarter 2023 Financial Results IRVING, Texas – August 9, 2023 – RumbleOn, Inc. (NASDAQ: RMBL) (the “Company” or “RumbleOn”), the nation's first, and largest, publicly traded powersports platform (dealership group), today announced operational and financial results for the three months ended June 30, 2023. RumbleOn management is hosting an earnings call to discu

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2023 o TRANSITION REPORT PU

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2023 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 00

AMENDMENT NO. 5 TO TERM LOAN CREDIT AGREEMENT

Execution Version AMENDMENT NO. 5 TO TERM LOAN CREDIT AGREEMENT AMENDMENT NO. 5 TO TERM LOAN CREDIT AGREEMENT (this “Amendment”), dated as of August 9, 2023 (the “Fifth Amendment Effective Date”), among RUMBLEON, INC., a Nevada corporation (the “Borrower”), the other guarantors party hereto (the “Subsidiary Guarantors”), OAKTREE FUND ADMINISTRATION, LLC, as administrative agent and as collateral a

Shin Lee, PhD 1989 Woodbury Court, Walnut Creek, CA 94596

Exhibit 99.1 Shin Lee, PhD 1989 Woodbury Court, Walnut Creek, CA 94596 July 29, 2023 Dear RumbleOn Board, I resign from the RumbleOn board effective today. Sincerely,

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) July 29, 2023 RumbleOn, Inc. (Exac

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) July 29, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada 001-38248 46-3951329 (State or other jurisdiction of incorporation) (Commission File Number)

Employment Agreement, dated July 20, 2023, by and between RumbleOn, Inc. and Steven Pully.

Exhibit 10.3 EMPLOYMENT AGREEMENT This Employment Agreement (“Agreement”) is made and entered into by and between RumbleOn, Inc. (the “Company”), and Steve Pully (“Executive”), effective as of July 14, 2023 (the “Effective Date”). 1. Employment. During the Employment Period (as defined in Section 4), the Company shall employ Executive, and Executive shall serve, as Executive Chairman of the Compan

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A (Amendment No. 1) CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 14, 2023

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A (Amendment No. 1) CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): July 14, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada 001-38248 46-3951329 (State or other jurisdiction of incorporation) (Com

Special Advisor Agreement, dated July 14, 2023, by and between RumbleOn, Inc and Michael Francis.

Exhibit 10.2 SPECIAL ADVISOR AGREEMENT THIS SPECIAL ADVISOR AGREEMENT (this “Agreement”) is entered into as of July , 2023 (the “Effective Date”), by and between RumbleOn, Inc. (the “Company”) and Michael Francis (“Advisor”). RECITALS The Company desires to engage Advisor, and Advisor desires to be so engaged by the Company, to perform certain independent contractor services, subject to the terms

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): July 14, 2023 RumbleOn, Inc. (Exa

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): July 14, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada 001-38248 46-3951329 (State or other jurisdiction of incorporation) (Commission File Number)

Separation Agreement, dated July 14, 2023, by and between RumbleOn, Inc. and Michael Francis.

Exhibit 10.1 RUMBLEON, INC. SEPARATION AGREEMENT This Separation Agreement (the “Agreement”) is by and between RumbleOn, Inc., a Nevada corporation (the “Company”), and Michael Francis (“Executive”). Capitalized terms used herein but not otherwise defined shall have the meanings ascribed thereto in the Executive Employment Agreement between the Company and Executive, dated as of August 31, 2021 (t

Letter from Marshall Chesrown.

Exhibit 17.1 MARSHALL R. CHESROWN 1936 WINTER DRIVE KELLER, TX 76262 July 7, 2023 Board of Directors of RumbleOn, inc. c/o Shin Lee, Chairman of the Nominating and Corporate Governance Committee Ladies and gentlemen, I hereby resign as a member of the Board of Directors of RumbleOn, Inc. While I had hoped to continue to serve the non-controlling shareholders of the company as a bona fide independe

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

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) July 7, 2023 RumbleOn, Inc. (Exact

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) July 7, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada 001-38248 46-3951329 (State or other jurisdiction of incorporation) (Commission File Number) (

Cooperation Agreement, dated as of June 30, 2023, by and among RumbleOn, Inc., William Coulter, and Mark Tkach.

Exhibit 10.1 Execution Version COOPERATION AGREEMENT This COOPERATION AGREEMENT (this “Agreement”) is made and entered into as of June 30, 2023 (the “Effective Date”), by and among RumbleOn, Inc., a Nevada corporation (the “Company”), on the one hand, and William Coulter and Mark Tkach (each a “Stockholder” and together, the “Stockholders”), on the other hand. The Company and the Stockholders are

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) June 30, 2023 RumbleOn, Inc. (Exac

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) June 30, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada 001-38248 46-3951329 (State or other jurisdiction of incorporation) (Commission File Number)

RMBL / RumbleON Inc - Class B / Tkach Mark - SC 13D/A Activist Investment

SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13D UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 4)* RumbleOn, Inc. (Name of Issuer) Class B Common Stock, par value $0.001 per share (Title of Class of Securities) 781386 206 (CUSIP Number) Mark Tkach 1188 East Camelback Road Phoenix, AZ 85014 (602) 532-4600 Carina L. Antweil Baker Botts L.L.P. 910 Louisiana Street Hou

Exhibit 99.9 – Cooperation Agreement, dated June 30, 2023, by and among RumbleOn, Inc., William Coulter and Mark Tkach

Exhibit 99.9 COOPERATION AGREEMENT This COOPERATION AGREEMENT (this “Agreement”) is made and entered into as of June 30, 2023 (the “Effective Date”), by and among RumbleOn, Inc., a Nevada corporation (the “Company”), on the one hand, and William Coulter and Mark Tkach (each a “Stockholder” and together, the “Stockholders”), on the other hand. The Company and the Stockholders are each herein referr

Exhibit 99.10 – Joint Filing Agreement, dated July 3, 2023

Exhibit 99.10 JOINT FILING AGREEMENT In accordance with Rule 13d-1(k)(1)(iii) under the Securities Exchange Act of 1934, as amended, the persons named below agree to the joint filing on behalf of each of them of a Statement on Schedule 13D (including additional amendments thereto) with respect to the shares of Class B Common Stock, $0.001 par value, of RumbleOn, Inc., a Nevada corporation. This Jo

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. __)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, For Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Defin

RMBL / RumbleON Inc - Class B / Tkach Mark - SC 13D/A Activist Investment

SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13D UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 3)* RumbleOn, Inc. (Name of Issuer) Class B Common Stock, par value $0.001 per share (Title of Class of Securities) 781386 206 (CUSIP Number) Mark Tkach 1188 East Camelback Road Phoenix, AZ 85014 (602) 532-4600 Travis J. Wofford Baker Botts L.L.P. 910 Louisiana Street Hou

Exhibit 99.8 – Joint Filing Agreement, dated June 20, 2023

Exhibit 99.8 JOINT FILING AGREEMENT In accordance with Rule 13d-1(k)(1)(iii) under the Securities Exchange Act of 1934, as amended, the persons named below agree to the joint filing on behalf of each of them of a Statement on Schedule 13D (including additional amendments thereto) with respect to the shares of Class B Common Stock, $0.001 par value, of RumbleOn, Inc., a Nevada corporation. This Joi

Exhibit 99.7 – Proxy Term Sheet, dated June 15, 2023, by and among RumbleOn, Inc., William Coulter and Mark Tkach (incorporated by reference to Exhibit 10.1 to the Issuer’s Current Report on Form 8-K, filed with the Securities and Exchange Commission on June 16, 2023)

Exhibit 10.1 Binding Term Sheet This Binding Term Sheet is made and agreed to as of June 15, 2023, by and among RumbleOn, Inc., a Nevada corporation (the “Company”), William Coulter (“Mr. Coulter”) and Mark Tkach (“Mr. Tkach,” and collectively with Coulter, the “Stockholders,” and collectively with the Company, the “Parties”). § Immediately following the execution of this Binding Term Sheet, the B

Employment Term Sheet, dated June 16, 2023, between RumbleOn, Inc. and Mark Tkach.

Exhibit 10.2 Binding Term Sheet Employment Agreement for Mark Tkach June 16, 2023 Title and Reporting: Interim Chief Executive Officer, reporting to the Board of Directors Duties: Will devote full-time working hours and efforts on behalf of the Company Initial Term: Six months unless extended by mutual agreement Salary: $700,000 per annum, prorated for the period of time employed and payable in ac

Proxy Term Sheet, dated June 15, 2023, by and among RumbleOn, Inc., William Coulter, and Mark Tkach.

Exhibit 10.1 Binding Term Sheet This Binding Term Sheet is made and agreed to as of June 15, 2023, by and among RumbleOn, Inc., a Nevada corporation (the “Company”), William Coulter (“Mr. Coulter”) and Mark Tkach (“Mr. Tkach,” and collectively with Coulter, the “Stockholders,” and collectively with the Company, the “Parties”). § Immediately following the execution of this Binding Term Sheet, the B

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) June 15, 2023 RumbleOn, Inc. (Exac

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) June 15, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada 001-38248 46-3951329 (State or other jurisdiction of incorporation) (Commission File Number)

Press release, dated June 16, 2023.

Exhibit 99.1 RumbleOn Announces Appointment of Interim CEO and Resolution of Proxy Contest Mark Tkach – Co-Founder of RideNow – Appointed Interim CEO RumbleOn and the Coulter-Tkach Group Reach Resolution to End Proxy Contest DALLAS, June 16, 2023—(BUSINESS WIRE)—RumbleOn, Inc. (NASDAQ: RMBL) (“RumbleOn” or the “Company”), the nation’s first technology-based powersports platform, today announced th

RumbleOn Announces Appointment of Interim CEO and Resolution of Proxy Contest Mark Tkach – Co-Founder of RideNow – Appointed Interim CEO RumbleOn and the Coulter-Tkach Group Reach Resolution to End Proxy Contest

Exhibit 99.1 RumbleOn Announces Appointment of Interim CEO and Resolution of Proxy Contest Mark Tkach – Co-Founder of RideNow – Appointed Interim CEO RumbleOn and the Coulter-Tkach Group Reach Resolution to End Proxy Contest DALLAS, June 16, 2023—(BUSINESS WIRE)—RumbleOn, Inc. (NASDAQ: RMBL) (“RumbleOn” or the “Company”), the nation’s first technology-based powersports platform, today announced th

Employment Term Sheet, dated June 16, 2023, between RumbleOn, Inc. and Mark Tkach.

Exhibit 10.2 Binding Term Sheet Employment Agreement for Mark Tkach June 16, 2023 Title and Reporting: Interim Chief Executive Officer, reporting to the Board of Directors Duties: Will devote full-time working hours and efforts on behalf of the Company Initial Term: Six months unless extended by mutual agreement Salary: $700,000 per annum, prorated for the period of time employed and payable in ac

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) June 15, 2023 RumbleOn, Inc. (Exac

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) June 15, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada 001-38248 46-3951329 (State or other jurisdiction of incorporation) (Commission File Number)

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) June 11, 2023 RumbleOn, Inc. (Exac

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) June 11, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada 001-38248 46-3951329 (State or other jurisdiction of incorporation) (Commission File Number)

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) May 26, 2023 RumbleOn, Inc. (Exact

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) May 26, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada 001-38248 46-3951329 (State or other jurisdiction of incorporation) (Commission File Number) (

RumbleOn Files Preliminary Proxy Statement as Board Continues to Seek Agreement with Dissident Stockholders to Avert a Costly Proxy Contest Proxy Statement Details Extensive Efforts to Refresh Board and Enhance Corporate Governance

Exhibit 99.1 RumbleOn Files Preliminary Proxy Statement as Board Continues to Seek Agreement with Dissident Stockholders to Avert a Costly Proxy Contest Proxy Statement Details Extensive Efforts to Refresh Board and Enhance Corporate Governance DALLAS, May 26, 2023 – (BusinessWire) – RumbleOn, Inc. (NASDAQ: RMBL) (“RumbleOn” or the “Company”), the nation’s first technology-based powersports platfo

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) May 26, 2023 RumbleOn, Inc. (Exact

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) May 26, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada 001-38248 46-3951329 (State or other jurisdiction of incorporation) (Commission File Number) (

Press release, dated May 26, 2023.

Exhibit 99.1 RumbleOn Files Preliminary Proxy Statement as Board Continues to Seek Agreement with Dissident Stockholders to Avert a Costly Proxy Contest Proxy Statement Details Extensive Efforts to Refresh Board and Enhance Corporate Governance DALLAS, May 26, 2023 – (BusinessWire) – RumbleOn, Inc. (NASDAQ: RMBL) (“RumbleOn” or the “Company”), the nation’s first technology-based powersports platfo

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of The Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of The Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ¨ Filed by a Party other than the Registrant x Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use

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): May 22, 2023 RumbleOn, Inc. (Exac

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): May 22, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada 001-38248 46-3951329 (State or other jurisdiction of incorporation) (Commission File Number)

Letter from Grant Thornton LLP

Exhibit 16.1 May 25, 2023 U.S. Securities and Exchange Commission Office of the Chief Accountant 100 F Street, NE Washington, DC 20549 Re: RumbleOn, Inc. File No. 001-38248 Dear Sir or Madam: We have read Item 4.01 of Form 8-K of RumbleOn, Inc. dated May 22, 2023, and agree with the statements concerning our Firm contained therein. Very truly yours, /s/ GRANT THORNTON LLP

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. __)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, For Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

RMBL / RumbleON Inc - Class B / Tkach Mark - SC 13D/A Activist Investment

SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13D UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 2)* RumbleOn, Inc. (Name of Issuer) Class B Common Stock, par value $0.001 per share (Title of Class of Securities) 781386 206 (CUSIP Number) Mark Tkach 1188 East Camelback Road Phoenix, AZ 85014 (602) 532-4600 Travis J. Wofford Baker Botts L.L.P. 910 Louisiana Street Hou

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of The Securities Exchange Act of 1934 (Amendment No.  )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of The Securities Exchange Act of 1934 (Amendment No.  ) Filed by the Registrant ¨ Filed by a Party other than the Registrant x Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use

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) May 11, 2023 RumbleOn, Inc. (Exact

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) May 11, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada 001-38248 46-3951329 (State or other jurisdiction of incorporation) (Commission File Number) (

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) May 11, 2023 RumbleOn, Inc. (Exact

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) May 11, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada 001-38248 46-3951329 (State or other jurisdiction of incorporation) (Commission File Number) (

Press release, dated May 15, 2023.

Exhibit 99.1 RumbleOn Appoints Steven J. Pully to its Board of Directors Reflects Company’s Commitment to Strengthening Corporate Governance DALLAS, May 15, 2023 – (WIRE) – RumbleOn, Inc. (NASDAQ: RMBL) (“RumbleOn” or “the Company”), the nation’s first technology-based powersports platform, today announced the appointment of Mr. Steven J. Pully to its Board of Directors (“the Board”), effective Ma

RumbleOn Appoints Steven J. Pully to its Board of Directors Reflects Company’s Commitment to Strengthening Corporate Governance

Exhibit 99.1 RumbleOn Appoints Steven J. Pully to its Board of Directors Reflects Company’s Commitment to Strengthening Corporate Governance DALLAS, May 15, 2023 – (WIRE) – RumbleOn, Inc. (NASDAQ: RMBL) (“RumbleOn” or “the Company”), the nation’s first technology-based powersports platform, today announced the appointment of Mr. Steven J. Pully to its Board of Directors (“the Board”), effective Ma

RumbleOn Reports First Quarter 2023 Financial Results Announces 17,336 Q1 Total Unit Sales $10-$15 Million Additional SG&A Expense Reduction Plan Q1 GPU $5,349 Reiterates 2023 Full Year Outlook

Exhibit 99.1 RumbleOn Reports First Quarter 2023 Financial Results Announces 17,336 Q1 Total Unit Sales $10-$15 Million Additional SG&A Expense Reduction Plan Q1 GPU $5,349 Reiterates 2023 Full Year Outlook IRVING, Texas – May 10, 2023 – RumbleOn, Inc. (NASDAQ: RMBL) (the “Company” or “RumbleOn”), the nation's first technology-based powersports platform, today announced operational and financial r

Marshall Chesrown

Exhibit 99.1 From: Marshall Chesrown To: All Company Sent: Tuesday, May 9, 2023 Cc: Board Of Directors Subject: Announcement Entire RumbleOn Team, Subject: Changes in Executive Leadership It is with significant disappointment that I let you all know, effective today, Peter Levy is no longer with RumbleOn as our President and Chief Operating Officer. Personally, and on behalf of the Company, I want

Release Agreement, dated May 9, 2023, between RumbleOn, Inc. and Peter Levy.

Exhibit 10.1 Release Agreement This Release Agreement (this “Release”) is executed pursuant to Section 5(e) of that certain Executive Employment Agreement, dated as of August 31, 2021, (the “Employment Agreement”), between RumbleOn, Inc., a Nevada corporation (“Company”), and Peter Levy (“Executive”) (the “Parties” and each a “Party”). All terms capitalized and not defined herein shall have the me

Press release, dated May 10, 2023.

Exhibit 99.2 RumbleOn Board Announces Significant Corporate Governance Enhancements Demonstrates Commitment to Board Refreshment, Diversity, and Expertise Enhancements to Advance RumbleOn’s Strategy to Drive Value Creation for All Shareholders DALLAS, May 10, 2023 – (WIRE) – RumbleOn, Inc.’s (NASDAQ: RMBL) (“RumbleOn” or “the Company”) Board of Directors (the “Board”) today announced a series of c

Amendment to Amended and Restated Bylaws of RumbleOn, Inc., dated May 9, 2023.

Exhibit 3.1 AMENDMENT TO THE AMENDED AND RESTATED BYLAWS OF RUMBLEON, INC. WHEREAS, Article IX of the Amended and Restated Bylaws (the “Bylaws”) of RumbleOn, Inc. (the “Company”) provides that the Board of Directors of the Company (the “Board”) may alter or repeal the Bylaws; and WHEREAS, the Board has determined it to be in the best interests of the Company to amend the Bylaws as hereinafter set

RumbleOn Board Announces Significant Corporate Governance Enhancements Demonstrates Commitment to Board Refreshment, Diversity, and Expertise Enhancements to Advance RumbleOn’s Strategy to Drive Value Creation for All Shareholders

Exhibit 99.2 RumbleOn Board Announces Significant Corporate Governance Enhancements Demonstrates Commitment to Board Refreshment, Diversity, and Expertise Enhancements to Advance RumbleOn’s Strategy to Drive Value Creation for All Shareholders DALLAS, May 10, 2023 – (WIRE) – RumbleOn, Inc.’s (NASDAQ: RMBL) (“RumbleOn” or “the Company”) Board of Directors (the “Board”) today announced a series of c

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2023 o TRANSITION REPORT P

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2023 or o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 0

Amendment to Amended and Restated Bylaws of RumbleOn, Inc., dated May 9, 2023 (Incorporated by reference to Exhibit 3.1 to the Company’s Current Report on Form 8-K filed with the SEC on May 10, 2023).

EX-3.1 2 ea178249ex3-1rumbleon.htm EXHIBIT 3.1 Exhibit 3.1 AMENDMENT TO THE AMENDED AND RESTATED BYLAWS OF RUMBLEON, INC. WHEREAS, Article IX of the Amended and Restated Bylaws (the “Bylaws”) of RumbleOn, Inc. (the “Company”) provides that the Board of Directors of the Company (the “Board”) may alter or repeal the Bylaws; and WHEREAS, the Board has determined it to be in the best interests of the

Employee communication, dated May 9, 2023.

Exhibit 99.1 From: Marshall Chesrown To: All Company Sent: Tuesday, May 9, 2023 Cc: Board Of Directors Subject: Announcement Entire RumbleOn Team, Subject: Changes in Executive Leadership It is with significant disappointment that I let you all know, effective today, Peter Levy is no longer with RumbleOn as our President and Chief Operating Officer. Personally, and on behalf of the Company, I want

Release Agreement, dated May 9, 2023, between RumbleOn, Inc. and Peter Levy.

Exhibit 10.1 Release Agreement This Release Agreement (this “Release”) is executed pursuant to Section 5(e) of that certain Executive Employment Agreement, dated as of August 31, 2021, (the “Employment Agreement”), between RumbleOn, Inc., a Nevada corporation (“Company”), and Peter Levy (“Executive”) (the “Parties” and each a “Party”). All terms capitalized and not defined herein shall have the me

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) May 9, 2023 RumbleOn, Inc. (Exact

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) May 9, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada (State or other jurisdiction of incorporation) 001-38248 (Commission File Number) 46-3951329 (I

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) May 9, 2023 RumbleOn, Inc. (Exact

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) May 9, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada (State or other jurisdiction of incorporation) 001-38248 (Commission File Number) 46-3951329 (I

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): May 10, 2023 RumbleOn, Inc. (Exac

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): May 10, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada (State or Other Jurisdiction of Incorporation) 001-38248 (Commission File Number) 46-3951329

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. 1)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. 1) Filed by the Registrant ☐ Filed by a Party other than the Registrant ☒ Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defi

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of The Securities Exchange Act of 1934 (Ame

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of The Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ¨ Filed by a Party other than the Registrant x Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confide

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) May 3, 2023 RumbleOn, Inc. (Exact

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) May 3, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada 001-38248 46-3951329 (State or other jurisdiction of incorporation) (Commission File Number) (I

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) May 3, 2023 RumbleOn, Inc. (Exact

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) May 3, 2023 RumbleOn, Inc. (Exact name of registrant as specified in its charter) Nevada 001-38248 46-3951329 (State or other jurisdiction of incorporation) (Commission File Number) (I

Press release, dated May 3, 2023.

Exhibit 99.1 Press Release May 3, 2023 RumbleOn, Inc. Announces Date of 2023 Annual Meeting of Stockholders DALLAS - RumbleOn, Inc. (NASDAQ: RMBL) (“RumbleOn” or the “Company”), the nation’s first technology-based powersports platform, today announced that the Company will hold its 2023 Annual Meeting of Stockholders (the “Annual Meeting”) on Friday, July 14, 2023. The board of directors establish

RumbleOn, Inc. Announces Date of 2023 Annual Meeting of Stockholders

Exhibit 99.1 Press Release May 3, 2023 RumbleOn, Inc. Announces Date of 2023 Annual Meeting of Stockholders DALLAS - RumbleOn, Inc. (NASDAQ: RMBL) (“RumbleOn” or the “Company”), the nation’s first technology-based powersports platform, today announced that the Company will hold its 2023 Annual Meeting of Stockholders (the “Annual Meeting”) on Friday, July 14, 2023. The board of directors establish

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-K/A (Amendment No. 1) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2022 ☐ TRANSITION REPO

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-K/A (Amendment No. 1) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2022 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number 001-38248 RumbleOn,

As filed with the Securities and Exchange Commission on April 14, 2023

As filed with the Securities and Exchange Commission on April 14, 2023 Registration No.

RMBL / RumbleON Inc - Class B / Stone House Capital Management, LLC - AMENDMENT NO. 1 TO SCHEDULE 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 1)* RumbleOn, Inc. (Name of Issuer) Class B Common Stock, $0.001 par value (Title of Class of Securities) 781386305 (CUSIP Number) April 10, 2023 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☐ Filed by a Party other than the Registrant ☒ Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Definitive Proxy State

Press release, dated April 5, 2023.

Exhibit 99.1 RumbleOn Acknowledges Preliminary Proxy Statement from Shareholders and Former Directors No Shareholder Action Required at this Time DALLAS, April 5, 2023 – RumbleOn, Inc. (NASDAQ: RMBL) (“RumbleOn” or the “Company”), the nation’s first technology-based powersports platform, today issued the following statement regarding the preliminary proxy statement filed by two former directors an