X0609 4 2026-01-24 0 0001880613 Direct Digital Holdings, Inc. DRCT 0001203452 SMITH W KEITH false C/O DIRECT DIGITAL HOLDINGS, INC. 1177 WEST LOOP SOUT, SUITE 1300 HOUSTON TX 77027 1 1 0 0 President 0 Class A Common Stock, par value $0.001 per share 2026-01-24 4 M 0 204 A 505 D Class A Common Stock, par value $0.001 per share 2026-01-24 4 F 0 61 16.48 D 444 D Class A Common Stock, par value $0.001 per share 2026-03-20 4 M 0 45 A 489 D Class A Common Stock, par value $0.001 per share 2026-03-20 4 F 0 14 3.52 D 475 D Class A Common Stock, par value $0.001 per share 2026-04-01 4 M 0 67 A 542 D Class A Common Stock, par value $0.001 per share 2026-04-01 4 M 0 20 3.29 D 522 D Class A Common Stock, par value $0.001 per share 2114 I By SKW Financial LLC Restricted Stock Units 2026-01-24 4 M 0 204 0 D Class A Common Stock, par value $0.001 per share 204 0 D Restricted Stock Units 2026-03-20 4 M 0 45 0 D Class A Common Stock, par value $0.001 per share 45 0 D Employee Stock Options (right to buy) 3.32 2026-03-24 4 A 0 8750 0 A 2036-03-24 Class A Common Stock, par value $0.001 per share 8750 8750 D Restricted Stock Units 2026-04-01 4 M 0 67 0 D Class A Common Stock, par value $0.001 per share 67 136 D On January 12, 2026, Direct Digital Holdings, Inc. (the "Company") effected a 55-to-1 reverse stock split (the "January Reverse Stock Split") and subsequently on April 27, 2026, the Company effected a 4-to-1 reverse stock split (the "April Reverse Stock Split," and together with the January Reverse Stock Split, the "Reverse Stock Splits"). The Securities Acquired reported in connection with this transaction have been adjusted to reflect the April Reverse Stock Split and the Amount of Securities Beneficially Owned Following Reported Transaction in connection with this transaction have been adjusted to reflect the Reverse Stock Splits. Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis. The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split. Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units on the applicable transaction date. On January 24, 2025, the reporting person was granted 204 restricted stock units, vesting on the first anniversary of the grant date conditioned on continued employment as of the vesting date. All of the restricted stock units vested on January 24, 2026. This grant was previously reported as covering 45,000 restricted stock units, but was adjusted to reflect the Reverse Stock Splits. On March 20, 2023, the reporting person was granted 135 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33% of the restricted stock units vested on March 20, 2024, an additional 33% of the restricted stock units vested on March 20, 2025, and the remaining balance of 34% of the restricted stock units vested on March 20, 2026. This grant was previously reported as covering 29,910 restricted stock units, but was adjusted to reflect the Reverse Stock Splits. This option is scheduled to vest in three equal annual installments beginning on March 24, 2027. On April 1, 2025, the reporting person was granted 203 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33% of the restricted stock units vested on April 1, 2026, an additional 33% of the restricted stock units will vest on April 1, 2027, and the remaining balance of 34% of the restricted stock units will vest on April 1, 2028. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan). This grant was previously reported as covering 45,000 restricted stock units, but was adjusted to reflect the Reverse Stock Splits. The Reporting Person is hereby disclosing delinquent transactions reportable on Form 4 that were not reported due to an administrative oversight. /s/ Mark Walker, attorney-in-fact for Keith W. Smith 2026-06-29