Direct Digital sells 700k shares at ~$0.39 each to New Circle for $276k under facility

Since August 6, 2025, the end of the period covered by the most recent Report filed on any of Forms 8-K, 10-K or 10-Q under this Item 3.02 by Direct Digital Holdings, Inc. (“ Company ”), through September 16, 2025 , the Company sold 700,000 shares of its Class A Common Stock, par value $0.001 per share (the “ Class A Common Stock ”) for an aggregate of $275,993 in cash consideration after a total discount of $8,997. 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 outstanding as of August 6, 2025. The sales of Class A Common Stock referred to herein were made to New Circle Principal Investments LLC (“ New Circle ”) pursuant to the previously disclosed Equity Reserve Facility under the Share Purchase Agreement (the “ Purchase Agreement ”) with New Circle.