Entry into a Material Definitive Agreement. On August 26, 2026, Direct Digital Holdings, LLC (“ DDH LLC ”), as borrower, entered into the Thirteenth Amendment to Term Loan and Security Agreement (the “ Thirteenth Amendment ”) with Direct Digital Holdings, Inc. (the “ Company "), Colossus Media, LLC, Huddled Masses LLC and Orange142, LLC, as guarantors (collectively with DDH LLC, the “ Credit Parties ”), Lafayette Square Loan Servicing, LLC, as administrative agent (the “ Agent ”), and Lafayet…

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

Entry into a Material Definitive Agreement. On August 18, 2026, Direct Digital Holdings, LLC (“ DDH LLC ”), as borrower, entered into a waiver letter (the “ Waiver Letter ”) related to the Term Loan and Security Agreement, dated December 3, 2021, as amended (the “ Term Loan Facility ”) with Direct Digital Holdings, Inc. (the “ Company ”), Colossus Media, LLC, Huddled Masses LLC and Orange142, LLC, as guarantors (collectively with DDH LLC, the “ Credit Parties ”), Lafayette Square Loan Servici…

of this report, including Exhibit 99.1, shall not be deemed to be “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended, or otherwise subject to the liabilities of that section, nor shall it be deemed incorporated by reference in any filing under the Securities Act of 1933, as amended, except as shall be expressly set forth by specific reference.

The filing describes the terms of an incentive plan and equity plan amendment.

Independent Director — Ohad Harlev: Mr. Ohad Harlev was appointed as an Independent Director to satisfy the Company's obligations under its Amended and Restated Certificate of Designation of Series A Convertible Preferred Stock.

Entry into a Material Definitive Agreement. Amendment to Term Loan Facility On May 15, 2026, Direct Digital Holdings, LLC (“ DDH LLC ”), as borrower, entered into the Twelfth Amendment and Waiver to Term Loan and Security Agreement (the “ Twelfth Amendment ”) to the Term Loan and Security Agreement dated December 3, 2021 (the “ Term Loan Facility ”) with Direct Digital Holdings, Inc. (the “ Company ”), Colossus Media, LLC, Huddled Masses LLC and Orange142, LLC, as guarantors (such guarantors…

of this report, including Exhibit 99.1, shall not be deemed to be “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended, or otherwise subject to the liabilities of that section, nor shall it be deemed incorporated by reference in any filing under the Securities Act of 1933, as amended, except as shall be expressly set forth by specific reference.

Termination of a Material Definitive Agreement. On April 23, 2026, the Company and New Circle Principal Investments LLC (“ New Circle ”) mutually agreed to terminate effective immediately the Share Purchase Agreement dated October 18, 2024 and amended on October 24, 2025 and January 23, 2026 (as amended, the “ Equity Line of Credit ”) between the Company and New Circle pursuant to which New Circle had committed to purchase, subject to certain limitations, up to $100 million of the Company’s C…

Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing. On April 23, 2026, the Company received an Additional Staff Delisting Determination Letter from the Listing Qualifications Department of The Nasdaq Stock Market LLC (“ Nasdaq ”), notifying the Company that it is not in compliance with Nasdaq Listing Rule 5550(a)(2) (the “ Bid Price Rule ”), which could serve as an additional basis for the delisting of the Company’s securities from Nasdaq. The…

Entry into a Material Definitive Agreement. On April 28, 2026, Direct Digital Holdings, Inc. (the “ Company ”) entered into a Common Stock Purchase Agreement (the “ Purchase Agreement ”) and a related Registration Rights Agreement (the “ Registration Rights Agreement ”), each dated as of April 28, 2026, with Roth Principal Investments, LLC (“ Roth Principal Investments ”). Upon the terms and subject to the satisfaction of the conditions set forth in the Purchase Agreement, the Company will ha…

Material Modification to Rights of Security Holders. On April 23, 2026, the Company filed a Certificate of Amendment (the “ Amendment ”) to its Amended and Restated Certificate of Incorporation, as amended, with the Secretary of State of the State of Delaware to effect a 4-to-1 reverse stock split (the “ Reverse Stock Split ”) of the Company’s shares of Class A Common Stock and Class B common stock, $0.001 par value. The Company’s stockholders approved the Reverse Stock Split at a Special Mee…

Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing. On April 2, 2026, Direct Digital Holdings, Inc. (the “ Company ”) received a Staff Delisting Determination letter (the “ Nasdaq Letter ”) from the Listing Qualifications Department of The Nasdaq Stock Market LLC (“ Nasdaq ”), notifying the Company that it is not in compliance with Nasdaq Listing Rule 5550(b)(1), which requires the Company to maintain a minimum of $2.5 million in stockholders’…

of this report, including Exhibit 99.1, shall not be deemed to be “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended, or otherwise subject to the liabilities of that section, nor shall it be deemed incorporated by reference in any filing under the Securities Act of 1933, as amended, except as shall be expressly set forth by specific reference.

Other Events. As previously disclosed, on November 7, 2025, the Company received a decision from the Nasdaq Hearings Panel (the “ Panel ”) regarding the Company’s continued listing on of The Nasdaq Stock Market LLC (“ Nasdaq ”), which among other things indicated that the Panel had granted the Company an exception through January 30, 2026, to demonstrate compliance with Nasdaq Listing Rule 5550(a)(2) (the “ Bid Price Rule ”). On January 12, 2026, the Company effected a 55-to-1 reverse stock s…

Entry into a Material Definitive Agreement. On January 27, 2026, Direct Digital Holdings, LLC (“ DDH LLC ”), as borrower, entered into the Eleventh Amendment and Waiver to Term Loan and Security Agreement (the “ Eleventh Amendment ”) to the Term Loan and Security Agreement dated December 3, 2021 (the “ Term Loan Facility ”) with Direct Digital Holdings, Inc. (the “ Company ”), Colossus Media, LLC, Huddled Masses LLC and Orange142, LLC, as guarantors (such guarantors together with DDH LLC, the…

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

Entry into a Material Definitive Agreement. Amendment to Equity Reserve Facility On January 23, 2026, Direct Digital Holdings, Inc., a Delaware Corporation (the “ Company ”), entered into an Amendment No. 2 to Share Purchase Agreement (the “ Amendment ”) with New Circle Principal Investments LLC, a Delaware limited liability company (“ New Circle ”), which amends the Share Purchase Agreement, dated October 18, 2024 and amended as of October 24, 2025, between the Company and New Circle (as ame…

Material Modification to Rights of Security Holders. On January 9, 2026, Direct Digital Holdings, Inc. (the “ Company ”) filed a Certificate of Amendment (the “ Amendment ”) to its Amended and Restated Certificate of Incorporation, as amended, with the Secretary of State of the State of Delaware to effect a 55-to-1 reverse stock split (the “ Reverse Stock Split ”) of the Company’s shares of Series A common stock, $0.001 par value and Series B common stock, $0.001 par value. The Company’s stoc…

The filing describes the terms of an incentive plan and equity plan amendment.

by Direct Digital Holdings, Inc. (“ Company ”), through December 5, 2025, the Company sold 12,600,000 shares of its Class A Common Stock, par value $0.001 per share (the “ Class A Common Stock ”) for an aggregate of $1,324,380 in cash consideration. This Current Report on Form 8-K is being filed because the aggregate number of shares of Class A Common Stock sold in unregistered transactions during the foregoing period exceeded five percent (5%) of the total number of such shares issued and ou…

Unregistered Sales of Equity Securities. On November 20, 2025, Direct Digital Holdings, Inc. (the “Company”) entered into a Settlement Agreement (the “Settlement Agreement”) with Continuation Capital, Inc. (“Continuation Capital”), pursuant to which we agreed to issue up to 50,000,000 shares of Class A Common Stock (the “Exchange Shares”) in exchange for the release of certain claims held by Continuation Capital related to third party vendor payables separately assigned to Continuation Capita…

Results of Operations and Financial Condition. On November 6, 2025, Direct Digital Holdings, Inc. (the “ Company ”) issued a press release announcing its financial results for the three and nine months ended September 30, 2025. A copy of the press release is furnished herewith as Exhibit 99.1 to this report and is incorporated herein by reference. Also on November 6, 2025, the Company held its previously announced earnings call regarding its unaudited financial results for the three and nine…

Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing.. As previously disclosed, on May 12, 2025, Direct Digital Holdings, Inc. (the “ Company ”) received a notice (the “ Notice ”) from the Staff of the Listing Qualifications Department (the “ Staff ”) of The Nasdaq Stock Market LLC (“ Nasdaq ”) notifying the Company that because the closing bid price of the Company’s Class A common stock, par value $0.001 per share (the “ Class A Common Stock ”),…

The shares of Class A Common Stock issuable upon the Exchange of the Series A Preferred Stock will be issued, without registration under the Securities Act of 1933, as amended (the “ Securities Act ”), in reliance on the exemptions provided by Section 3(a)(9) of the Securities Act and/or Section 4(a)(2) of the Securities Act as a transaction not involving a public offering, and in reliance on similar exemptions under applicable state laws.