X0609 4 2025-10-16 0 0001880613 Direct Digital Holdings, Inc. DRCT 0001493839 Diaz Diana P false 1177 WEST LOOP SOUTH, SUITE 1310 HOUSTON TX 77027 0 1 0 0 CFO 0 Class A Common Stock, par value $0.001 per share 2025-10-16 4 M 0 28 A 65 D Class A Common Stock, par value $0.001 per share 2026-01-24 4 M 0 102 A 167 D Class A Common Stock, par value $0.001 per share 2026-01-24 4 F 0 31 16.48 D 136 D Class A Common Stock, par value $0.001 per share 2026-04-01 4 M 0 33 A 169 D Class A Common Stock, par value $0.001 per share 2026-04-01 4 F 0 10 3.34 D 159 D Restricted Stock Units 2025-10-16 4 M 0 28 0 D Class A Common Stock, par value $0.001 per share 28 28 D Restricted Stock Units 2026-01-24 4 M 0 102 0 D Class A Common Stock, par value $0.001 per share 102 0 D Employee Stock Options (right to buy) 3.32 2026-03-24 4 A 0 4375 0 A 2036-03-24 Class A Common Stock, par value $0.001 per share 4375 4375 D Restricted Stock Units 2026-04-01 4 M 0 33 0 D Class A Common Stock, par value $0.001 per share 33 68 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 shares reported 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 October 16, 2023, the reporting person was granted 84 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 October 16, 2024, an additional 33% of the restricted stock units vested on October 16, 2025, and the remaining balance of 34% of the restricted stock units will vest on October 16, 2026. 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 18,650 restricted stock units, but was adjusted to reflect the Reverse Stock Splits. On January 24, 2025, the reporting person was granted 102 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 22,500 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 101 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 22,500 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 Diana P. Diaz 2026-06-29