DRCT

SEC source: 0001880613-25-000026 · wk-form4_1749759614.xml · derivative · entry 3

SMITH W KEITH · CIK 0001203452 · Director · President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Class A Common Stock, par value $0.001 per share · 20,300 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F3 · derivative.exercise_date: June 10, 2022, the reporting person was granted 60,900 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33 percent of the restricted stock units vested on June 10, 2023, an additional 33 percent vested on June 10, 2024, and the remaining balance of 34 percent of the restricted stock units vested on June 10, 2025.

F3 · derivative.expiration_date: June 10, 2022, the reporting person was granted 60,900 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33 percent of the restricted stock units vested on June 10, 2023, an additional 33 percent vested on June 10, 2024, and the remaining balance of 34 percent of the restricted stock units vested on June 10, 2025.

SEC source: 0001880613-25-000026 · wk-form4_1749759614.xml · nonDerivative · entry 2

SMITH W KEITH · CIK 0001203452 · Director · President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 66,370

F2 · shares: Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units for 2,300 shares.

SEC source: 0001880613-25-000026 · wk-form4_1749759614.xml · nonDerivative · entry 1

SMITH W KEITH · CIK 0001203452 · Director · President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 71,314

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

SEC source: 0001880613-25-000033 · wk-form4_1749759939.xml · derivative · entry 3

Leatherberry Antoinette Renee · CIK 0001834624 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Class A Common Stock, par value $0.001 per share · 16,462 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F3 · derivative.exercise_date: On June 10, 2022, the reporting person was granted 49,382 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33 percent of the restricted stock units vested on June 10, 2023, an additional 33 percent vested on June 10, 2024, and the remaining balance of 34 percent of the restricted stock units vested on June 10, 2025.

F3 · derivative.expiration_date: On June 10, 2022, the reporting person was granted 49,382 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33 percent of the restricted stock units vested on June 10, 2023, an additional 33 percent vested on June 10, 2024, and the remaining balance of 34 percent of the restricted stock units vested on June 10, 2025.

SEC source: 0001880613-25-000033 · wk-form4_1749759939.xml · nonDerivative · entry 2

Leatherberry Antoinette Renee · CIK 0001834624 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 68,265

F2 · shares: Represents shares sold to satisfy tax liabilities associated with the reported vesting of restricted stock units for 16,462 shares.

SEC source: 0001880613-25-000033 · wk-form4_1749759939.xml · nonDerivative · entry 1

Leatherberry Antoinette Renee · CIK 0001834624 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 72,274

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

SEC source: 0001880613-25-000022 · wk-form4_1749672094.xml · derivative · entry 1

Cohen Richard · CIK 0001298692 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 35,000

Underlying: Class A Common Stock, par value $0.001 per share · 35,000 shares

Expires not disclosed

F1 · derivative.exercise_price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F2 · derivative.exercise_date: Grant of restricted stock units under the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan. The restricted stock units will vest one year from the date of grant conditioned on continued service as of the vesting date.

F2 · derivative.expiration_date: Grant of restricted stock units under the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan. The restricted stock units will vest one year from the date of grant conditioned on continued service as of the vesting date.

SEC source: 0001880613-25-000023 · wk-form4_1749672121.xml · derivative · entry 1

Leatherberry Antoinette Renee · CIK 0001834624 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 35,000

Underlying: Class A Common Stock, par value $0.001 per share · 35,000 shares

Expires not disclosed

F1 · derivative.exercise_price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F2 · derivative.exercise_date: Grant of restricted stock units under the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan. The restricted stock units will vest one year from the date of grant conditioned on continued service as of the vesting date.

F2 · derivative.expiration_date: Grant of restricted stock units under the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan. The restricted stock units will vest one year from the date of grant conditioned on continued service as of the vesting date.

SEC source: 0001880613-25-000024 · wk-form4_1749672151.xml · derivative · entry 1

Locke Mistelle · CIK 0001960753 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 35,000

Underlying: Class A Common Stock, par value $0.001 per share · 35,000 shares

Expires not disclosed

F1 · derivative.exercise_price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F2 · derivative.exercise_date: Grant of restricted stock units under the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan. The restricted stock units will vest one year from the date of grant conditioned on continued service as of the vesting date.

F2 · derivative.expiration_date: Grant of restricted stock units under the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan. The restricted stock units will vest one year from the date of grant conditioned on continued service as of the vesting date.

SEC source: 0001628280-25-018563 · wk-form4_1745265698.xml · nonDerivative · entry 1

Walker Mark D · CIK 0001896664 · Director · Chairman and CEO · 10% owner

10b5-1 filing: Plan reported

Ownership: Indirect · By AJN Energy & Transport Ventures, LLC

Disclosed balance after: 28,323

F1 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 11, 2024. This transaction was executed in multiple trades at prices ranging from $0.52 to $0.57 per share. The price reported above reflects the weighted average purchase price on the date indicated. The reporting person hereby undertakes to provide upon request to the SEC staff, the issuer or a security holder of the issuer full information regarding the number of shares.

F2 · balance_after: Due to administrative error, the number of non-derivative securities beneficially owned by the Reporting Person was incorrectly reported as 31,518 instead of 31,508 on a Form 4 filed on March 19, 2025. This column reflects the corrected balance, as effected by the transactions reported on this Form 4.

SEC source: 0001628280-25-016871 · wk-form4_1743803313.xml · derivative · entry 2

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 22,500

Underlying: Class A Common Stock, par value $0.001 per share · 22,500 shares

Expires 2035-04-01

F3 · derivative.exercise_date: This option is scheduled to vest in three equal annual installments beginning on April 1, 2026.

SEC source: 0001628280-25-016871 · wk-form4_1743803313.xml · derivative · entry 1

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 22,500

Underlying: Class A Common Stock, par value $0.001 per share · 22,500 shares

Expires not disclosed

F1 · derivative.exercise_price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F2 · derivative.exercise_date: The restricted stock units will vest in three annual installments, with 33% to vest on each of the first and second anniversary of the grant date and the remaining 34% to vest on the third anniversary of the grant date. 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).

F2 · derivative.expiration_date: The restricted stock units will vest in three annual installments, with 33% to vest on each of the first and second anniversary of the grant date and the remaining 34% to vest on the third anniversary of the grant date. 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).

SEC source: 0001628280-25-016874 · wk-form4_1743803360.xml · derivative · entry 2

Walker Mark D · CIK 0001896664 · Director · Chairman and CEO · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 45,000

Underlying: Class A Common Stock, par value $0.001 per share · 45,000 shares

Expires 2035-04-01

F3 · derivative.exercise_date: This option is scheduled to vest in three equal annual installments beginning on April 1, 2026.

SEC source: 0001628280-25-016874 · wk-form4_1743803360.xml · derivative · entry 1

Walker Mark D · CIK 0001896664 · Director · Chairman and CEO · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 45,000

Underlying: Class A Common Stock, par value $0.001 per share · 45,000 shares

Expires not disclosed

F1 · derivative.exercise_price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F2 · derivative.exercise_date: The restricted stock units will vest in three annual installments, with 33% to vest on each of the first and second anniversary of the grant date and the remaining 34% to vest on the third anniversary of the grant date. 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).

F2 · derivative.expiration_date: The restricted stock units will vest in three annual installments, with 33% to vest on each of the first and second anniversary of the grant date and the remaining 34% to vest on the third anniversary of the grant date. 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).

SEC source: 0001628280-25-016868 · wk-form4_1743803270.xml · derivative · entry 2

Diaz Diana P · CIK 0001493839 · CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 22,500

Underlying: Class A Common Stock, par value $0.001 per share · 22,500 shares

Expires 2035-04-01

F3 · derivative.exercise_date: This option is scheduled to vest in three equal annual installments beginning on April 1, 2026.

SEC source: 0001628280-25-016868 · wk-form4_1743803270.xml · derivative · entry 1

Diaz Diana P · CIK 0001493839 · CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 22,500

Underlying: Class A Common Stock, par value $0.001 per share · 22,500 shares

Expires not disclosed

F1 · derivative.exercise_price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F2 · derivative.exercise_date: The restricted stock units will vest in three annual installments, with 33% to vest on each of the first and second anniversary of the grant date and the remaining 34% to vest on the third anniversary of the grant date. 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).

F2 · derivative.expiration_date: The restricted stock units will vest in three annual installments, with 33% to vest on each of the first and second anniversary of the grant date and the remaining 34% to vest on the third anniversary of the grant date. 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).

SEC source: 0001628280-25-016872 · wk-form4_1743803339.xml · derivative · entry 2

SMITH W KEITH · CIK 0001203452 · Director · President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 45,000

Underlying: Class A Common Stock, par value $0.001 per share · 45,000 shares

Expires 2035-04-01

F3 · derivative.exercise_date: This option is scheduled to vest in three equal annual installments beginning on April 1, 2026.

SEC source: 0001628280-25-016872 · wk-form4_1743803339.xml · derivative · entry 1

SMITH W KEITH · CIK 0001203452 · Director · President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 45,000

Underlying: Class A Common Stock, par value $0.001 per share · 45,000 shares

Expires not disclosed

F1 · derivative.exercise_price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F2 · derivative.exercise_date: The restricted stock units will vest in three annual installments, with 33% to vest on each of the first and second anniversary of the grant date and the remaining 34% to vest on the third anniversary of the grant date. 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).

F2 · derivative.expiration_date: The restricted stock units will vest in three annual installments, with 33% to vest on each of the first and second anniversary of the grant date and the remaining 34% to vest on the third anniversary of the grant date. 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).

SEC source: 0001628280-25-016869 · wk-form4_1743803292.xml · derivative · entry 2

Lowrey Maria Vilchez · CIK 0001943064 · Chief Growth Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 22,500

Underlying: Class A Common Stock, par value $0.001 per share · 22,500 shares

Expires 2035-04-01

F3 · derivative.exercise_date: This option is scheduled to vest in three equal annual installments beginning on April 1, 2026.

SEC source: 0001628280-25-016869 · wk-form4_1743803292.xml · derivative · entry 1

Lowrey Maria Vilchez · CIK 0001943064 · Chief Growth Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 22,500

Underlying: Class A Common Stock, par value $0.001 per share · 22,500 shares

Expires not disclosed

F1 · derivative.exercise_price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F2 · derivative.exercise_date: The restricted stock units will vest in three annual installments, with 33% to vest on each of the first and second anniversary of the grant date and the remaining 34% to vest on the third anniversary of the grant date. 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).

F2 · derivative.expiration_date: The restricted stock units will vest in three annual installments, with 33% to vest on each of the first and second anniversary of the grant date and the remaining 34% to vest on the third anniversary of the grant date. 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).

SEC source: 0001628280-25-015293 · wk-form4_1743119690.xml · nonDerivative · entry 6

Walker Mark D · CIK 0001896664 · Director · Chairman and CEO · 10% owner

10b5-1 filing: Plan reported

Ownership: Indirect · By AJN Energy & Transport Ventures, LLC

Disclosed balance after: 37,033

F7 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 11, 2024. This transaction was executed in multiple trades at prices ranging from $0.70 to $0.83 per share. The price reported above reflects the weighted average purchase price on the date indicated. The reporting person hereby undertakes to provide upon request to the SEC staff, the issuer or a security holder of the issuer full information regarding the number of shares.

SEC source: 0001628280-25-015294 · wk-form4_1743119721.xml · nonDerivative · entry 5

SMITH W KEITH · CIK 0001203452 · Director · President · 10% owner

10b5-1 filing: Plan reported

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 0

F5 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 12, 2024. This transaction was executed in multiple trades at prices ranging from $0.70 to $0.87 per share. The price reported above reflects the weighted average purchase price on the date indicated. The reporting person hereby undertakes to provide upon request to the SEC staff, the issuer or a security holder of the issuer full information regarding the number of shares.

SEC source: 0001628280-25-015293 · wk-form4_1743119690.xml · derivative · entry 8

Walker Mark D · CIK 0001896664 · Director · Chairman and CEO · 10% owner

10b5-1 filing: Plan reported

Ownership: Indirect · By Direct Digital Management, LLC

Disclosed balance after: 5,419,000

Underlying: Class A Common Stock, par value $0.001 per share · 70,000 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · derivative.exercise_price: Pursuant to the Second Amended and Restated Limited Liability Company Agreement of Direct Digital Holdings, LLC, dated as of February 15, 2022, Class A Common Units (as defined therein) held by the Reporting Person (indirectly through the Reporting Person's ownership interest in Direct Digital Management, LLC) are exchangeable for shares of Class A Common Stock on a one-for-one basis, subject to certain exceptions, conditions and adjustments. The Class A Common Units have no expiration date. At the time of any such exchange, an equal number of shares of Class B Common Stock of the Issuer held by the Reporting Person, which have no economic value and entitle holders thereof to one vote per share on all matters on which stockholders of the Issuer are entitled to vote generally, are cancelled.

F3 · derivative.exercise_date: Pursuant to the Second Amended and Restated Limited Liability Company Agreement of Direct Digital Holdings, LLC, dated as of February 15, 2022, Class A Common Units (as defined therein) held by the Reporting Person (indirectly through the Reporting Person's ownership interest in Direct Digital Management, LLC) are exchangeable for shares of Class A Common Stock on a one-for-one basis, subject to certain exceptions, conditions and adjustments. The Class A Common Units have no expiration date. At the time of any such exchange, an equal number of shares of Class B Common Stock of the Issuer held by the Reporting Person, which have no economic value and entitle holders thereof to one vote per share on all matters on which stockholders of the Issuer are entitled to vote generally, are cancelled.

F3 · derivative.expiration_date: Pursuant to the Second Amended and Restated Limited Liability Company Agreement of Direct Digital Holdings, LLC, dated as of February 15, 2022, Class A Common Units (as defined therein) held by the Reporting Person (indirectly through the Reporting Person's ownership interest in Direct Digital Management, LLC) are exchangeable for shares of Class A Common Stock on a one-for-one basis, subject to certain exceptions, conditions and adjustments. The Class A Common Units have no expiration date. At the time of any such exchange, an equal number of shares of Class B Common Stock of the Issuer held by the Reporting Person, which have no economic value and entitle holders thereof to one vote per share on all matters on which stockholders of the Issuer are entitled to vote generally, are cancelled.

SEC source: 0001628280-25-015293 · wk-form4_1743119690.xml · nonDerivative · entry 5

Walker Mark D · CIK 0001896664 · Director · Chairman and CEO · 10% owner

10b5-1 filing: Plan reported

Ownership: Indirect · By AJN Energy & Transport Ventures, LLC

Disclosed balance after: 43,152

F6 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 11, 2024. This transaction was executed in multiple trades at prices ranging from $0.75 to $0.82 per share. The price reported above reflects the weighted average purchase price on the date indicated. The reporting person hereby undertakes to provide upon request to the SEC staff, the issuer or a security holder of the issuer full information regarding the number of shares.

SEC source: 0001628280-25-015293 · wk-form4_1743119690.xml · nonDerivative · entry 3

Walker Mark D · CIK 0001896664 · Director · Chairman and CEO · 10% owner

10b5-1 filing: Plan reported

Ownership: Indirect · By AJN Energy & Transport Ventures, LLC

Disclosed balance after: 70,640

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · price: Pursuant to the Second Amended and Restated Limited Liability Company Agreement of Direct Digital Holdings, LLC, dated as of February 15, 2022, Class A Common Units (as defined therein) held by the Reporting Person (indirectly through the Reporting Person's ownership interest in Direct Digital Management, LLC) are exchangeable for shares of Class A Common Stock on a one-for-one basis, subject to certain exceptions, conditions and adjustments. The Class A Common Units have no expiration date. At the time of any such exchange, an equal number of shares of Class B Common Stock of the Issuer held by the Reporting Person, which have no economic value and entitle holders thereof to one vote per share on all matters on which stockholders of the Issuer are entitled to vote generally, are cancelled.

F4 · ownership.nature: Upon receipt of the securities converted from Table II, Direct Digital Management, LLC distributed 70,000 shares of Class A Common Stock to one of its members, AJN Energy & Transport Ventures, LLC, for no consideration. The Reporting Person, as owner of AJN Energy & Transport Ventures, LLC and a Managing Partner of Direct Digital Management, LLC, may be deemed to have beneficial ownership of the securities directly held by AJN Energy & Transport Ventures, LLC and Direct Digital Management, LLC.

SEC source: 0001628280-25-015294 · wk-form4_1743119721.xml · nonDerivative · entry 4

SMITH W KEITH · CIK 0001203452 · Director · President · 10% owner

10b5-1 filing: Plan reported

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 12,186

F4 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 12, 2024. This transaction was executed in multiple trades at prices ranging from $0.75 to $0.82 per share. The price reported above reflects the weighted average purchase price on the date indicated. The reporting person hereby undertakes to provide upon request to the SEC staff, the issuer or a security holder of the issuer full information regarding the number of shares.

SEC source: 0001880613-25-000050 · wk-form4_1750450321.xml · derivative · entry 5

Direct Digital Management, LLC · CIK 0001897454 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 10,798,000

Underlying: Class A Common Stock, par value $0.001 per share · 70,000 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Pursuant to the Second Amended and Restated Limited Liability Company Agreement of Direct Digital Holdings LLC, dated as of February 15, 2022, Class A Common Units (as defined therein) held by the Reporting Person are exchangeable for shares of Class A Common Stock on a one-for-one basis, subject to certain exceptions, conditions and adjustments. The Class A Common Units have no expiration date. At the time of any such exchange, an equal number of shares of Class B Common Stock of the Issuer held by the Reporting Person, which have no economic value and entitle holders thereof to one vote per share on all matters on which stockholders of the Issuer are entitled to vote generally, are cancelled.

F1 · derivative.exercise_date: Pursuant to the Second Amended and Restated Limited Liability Company Agreement of Direct Digital Holdings LLC, dated as of February 15, 2022, Class A Common Units (as defined therein) held by the Reporting Person are exchangeable for shares of Class A Common Stock on a one-for-one basis, subject to certain exceptions, conditions and adjustments. The Class A Common Units have no expiration date. At the time of any such exchange, an equal number of shares of Class B Common Stock of the Issuer held by the Reporting Person, which have no economic value and entitle holders thereof to one vote per share on all matters on which stockholders of the Issuer are entitled to vote generally, are cancelled.

F1 · derivative.expiration_date: Pursuant to the Second Amended and Restated Limited Liability Company Agreement of Direct Digital Holdings LLC, dated as of February 15, 2022, Class A Common Units (as defined therein) held by the Reporting Person are exchangeable for shares of Class A Common Stock on a one-for-one basis, subject to certain exceptions, conditions and adjustments. The Class A Common Units have no expiration date. At the time of any such exchange, an equal number of shares of Class B Common Stock of the Issuer held by the Reporting Person, which have no economic value and entitle holders thereof to one vote per share on all matters on which stockholders of the Issuer are entitled to vote generally, are cancelled.

SEC source: 0001880613-25-000050 · wk-form4_1750450321.xml · nonDerivative · entry 2

Direct Digital Management, LLC · CIK 0001897454 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

F2 · kind: The Reporting Person distributed 70,000 shares of Class A Common Stock to one of its members for no consideration.

SEC source: 0001880613-25-000050 · wk-form4_1750450321.xml · nonDerivative · entry 1

Direct Digital Management, LLC · CIK 0001897454 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 70,000

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Pursuant to the Second Amended and Restated Limited Liability Company Agreement of Direct Digital Holdings LLC, dated as of February 15, 2022, Class A Common Units (as defined therein) held by the Reporting Person are exchangeable for shares of Class A Common Stock on a one-for-one basis, subject to certain exceptions, conditions and adjustments. The Class A Common Units have no expiration date. At the time of any such exchange, an equal number of shares of Class B Common Stock of the Issuer held by the Reporting Person, which have no economic value and entitle holders thereof to one vote per share on all matters on which stockholders of the Issuer are entitled to vote generally, are cancelled.

SEC source: 0001628280-25-015293 · wk-form4_1743119690.xml · nonDerivative · entry 4

Walker Mark D · CIK 0001896664 · Director · Chairman and CEO · 10% owner

10b5-1 filing: Plan reported

Ownership: Indirect · By AJN Energy & Transport Ventures, LLC

Disclosed balance after: 62,930

F5 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 11, 2024. This transaction was executed in multiple trades at prices ranging from $0.75 to $0.78 per share. The price reported above reflects the weighted average purchase price on the date indicated. The reporting person hereby undertakes to provide upon request to the SEC staff, the issuer or a security holder of the issuer full information regarding the number of shares.

SEC source: 0001628280-25-015294 · wk-form4_1743119721.xml · nonDerivative · entry 3

SMITH W KEITH · CIK 0001203452 · Director · President · 10% owner

10b5-1 filing: Plan reported

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 32,749

F3 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 12, 2024. This transaction was executed in multiple trades at prices ranging from $0.75 to $0.77 per share. The price reported above reflects the weighted average purchase price on the date indicated. The reporting person hereby undertakes to provide upon request to the SEC staff, the issuer or a security holder of the issuer full information regarding the number of shares.

SEC source: 0001628280-25-014571 · wk-form4_1742856260.xml · nonDerivative · entry 3

Walker Mark D · CIK 0001896664 · Director · Chairman and CEO · 10% owner

10b5-1 filing: Plan reported

Ownership: Indirect · By AJN Energy & Transport Ventures, LLC

Disclosed balance after: 640

F3 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 11, 2024. This transaction was executed in multiple trades at prices ranging from $0.73 to $0.81 per share. The price reported above reflects the weighted average purchase price on the date indicated. The reporting person hereby undertakes to provide upon request to the SEC staff, the issuer or a security holder of the issuer full information regarding the number of shares.

SEC source: 0001628280-25-014575 · wk-form4_1742856573.xml · nonDerivative · entry 3

SMITH W KEITH · CIK 0001203452 · Director · President · 10% owner

10b5-1 filing: Plan reported

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 40,449

F3 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 12, 2024. This transaction was executed in multiple trades at prices ranging from $0.74 to $0.81 per share. The price reported above reflects the weighted average purchase price on the date indicated. The reporting person hereby undertakes to provide upon request to the SEC staff, the issuer or a security holder of the issuer full information regarding the number of shares.

SEC source: 0001628280-25-014571 · wk-form4_1742856260.xml · nonDerivative · entry 2

Walker Mark D · CIK 0001896664 · Director · Chairman and CEO · 10% owner

10b5-1 filing: Plan reported

Ownership: Indirect · By AJN Energy & Transport Ventures, LLC

Disclosed balance after: 11,088

F2 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 11, 2024. This transaction was executed in multiple trades at prices ranging from $0.75 to $0.78 per share. The price reported above reflects the weighted average purchase price on the date indicated. The reporting person hereby undertakes to provide upon request to the SEC staff, the issuer or a security holder of the issuer full information regarding the number of shares.

SEC source: 0001628280-25-014575 · wk-form4_1742856573.xml · nonDerivative · entry 2

SMITH W KEITH · CIK 0001203452 · Director · President · 10% owner

10b5-1 filing: Plan reported

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 50,749

F2 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 12, 2024. This transaction was executed in multiple trades at prices ranging from $0.74 to $0.78 per share. The price reported above reflects the weighted average purchase price on the date indicated. The reporting person hereby undertakes to provide upon request to the SEC staff, the issuer or a security holder of the issuer full information regarding the number of shares.

SEC source: 0001628280-25-014571 · wk-form4_1742856260.xml · nonDerivative · entry 1

Walker Mark D · CIK 0001896664 · Director · Chairman and CEO · 10% owner

10b5-1 filing: Plan reported

Ownership: Indirect · By AJN Energy & Transport Ventures, LLC

Disclosed balance after: 16,918

F1 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 11, 2024. This transaction was executed in multiple trades at prices ranging from $0.74 to $0.85 per share. The price reported above reflects the weighted average purchase price on the date indicated. The reporting person hereby undertakes to provide upon request to the SEC staff, the issuer or a security holder of the issuer full information regarding the number of shares.

SEC source: 0001628280-25-014575 · wk-form4_1742856573.xml · nonDerivative · entry 1

SMITH W KEITH · CIK 0001203452 · Director · President · 10% owner

10b5-1 filing: Plan reported

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 56,580

F1 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 12, 2024. This transaction was executed in multiple trades at prices ranging from $0.74 to $0.85 per share. The price reported above reflects the weighted average purchase price on the date indicated. The reporting person hereby undertakes to provide upon request to the SEC staff, the issuer or a security holder of the issuer full information regarding the number of shares.

SEC source: 0001628280-25-015295 · wk-form4_1743119752.xml · derivative · entry 3

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,105

Underlying: Class A Common Stock, par value $0.001 per share · 2,105 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F4 · derivative.exercise_date: On March 20, 2023, the reporting person was granted 6,315 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 will vest on March 20, 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).

F4 · derivative.expiration_date: On March 20, 2023, the reporting person was granted 6,315 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 will vest on March 20, 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).

SEC source: 0001628280-25-015295 · wk-form4_1743119752.xml · nonDerivative · entry 2

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 17,638

F3 · shares: Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units for 2,105 shares.

SEC source: 0001628280-25-015295 · wk-form4_1743119752.xml · nonDerivative · entry 1

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 18,367

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F2 · balance_after: Due to administrative error, the number of non-derivative securities beneficially owned by the Reporting Person was incorrectly reported as 14,829 instead of 16,262 on a Form 4 filed on June 14, 2024. This column reflects the corrected balance, as effected by the transactions reported on this Form 4.

SEC source: 0001628280-25-015293 · wk-form4_1743119690.xml · derivative · entry 7

Walker Mark D · CIK 0001896664 · Director · Chairman and CEO · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 9,970

Underlying: Class A Common Stock, par value $0.001 per share · 9,970 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F8 · derivative.exercise_date: On March 20, 2023, the reporting person was granted 29,910 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 will vest on March 20, 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).

F8 · derivative.expiration_date: On March 20, 2023, the reporting person was granted 29,910 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 will vest on March 20, 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).

SEC source: 0001628280-25-015293 · wk-form4_1743119690.xml · nonDerivative · entry 2

Walker Mark D · CIK 0001896664 · Director · Chairman and CEO · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 7,013

F2 · shares: Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units for 9,970 shares.

SEC source: 0001628280-25-015293 · wk-form4_1743119690.xml · nonDerivative · entry 1

Walker Mark D · CIK 0001896664 · Director · Chairman and CEO · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 9,970

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

SEC source: 0001628280-25-015294 · wk-form4_1743119721.xml · derivative · entry 7

SMITH W KEITH · CIK 0001203452 · Director · President · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 9,970

Underlying: Class A Common Stock, par value $0.001 per share · 9,970 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F6 · derivative.exercise_date: On March 20, 2023, the reporting person was granted 29,910 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 will vest on March 20, 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).

F6 · derivative.expiration_date: On March 20, 2023, the reporting person was granted 29,910 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 will vest on March 20, 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).

SEC source: 0001628280-25-015294 · wk-form4_1743119721.xml · nonDerivative · entry 2

SMITH W KEITH · CIK 0001203452 · Director · President · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 51,014

F2 · shares: Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units for 9,970 shares.

SEC source: 0001628280-25-015294 · wk-form4_1743119721.xml · nonDerivative · entry 1

SMITH W KEITH · CIK 0001203452 · Director · President · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 53,971

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

SEC source: 0001628280-25-015297 · wk-form4_1743119795.xml · derivative · entry 3

Lowrey Maria Vilchez · CIK 0001943064 · Chief Growth Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,105

Underlying: Class A Common Stock, par value $0.001 per share · 2,105 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F3 · derivative.exercise_date: On March 20, 2023, the reporting person was granted 6,315 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 will vest on March 20, 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).

F3 · derivative.expiration_date: On March 20, 2023, the reporting person was granted 6,315 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 will vest on March 20, 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).

SEC source: 0001628280-25-015297 · wk-form4_1743119795.xml · nonDerivative · entry 2

Lowrey Maria Vilchez · CIK 0001943064 · Chief Growth Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 16,020

F2 · shares: Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units for 2,105 shares.

SEC source: 0001628280-25-015297 · wk-form4_1743119795.xml · nonDerivative · entry 1

Lowrey Maria Vilchez · CIK 0001943064 · Chief Growth Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 16,645

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

SEC source: 0001628280-25-013906 · wk-form4_1742424112.xml · nonDerivative · entry 3

Walker Mark D · CIK 0001896664 · Director · Chairman and CEO · 10% owner

10b5-1 filing: Plan reported

Ownership: Indirect · By AJN Energy & Transport Ventures, LLC

Disclosed balance after: 31,518

F3 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 11, 2024. This transaction was executed in multiple trades at prices ranging from $0.76 to $0.83 per share. The price reported above reflects the weighted average purchase price on the date indicated. The reporting person hereby undertakes to provide upon request to the SEC staff, the issuer or a security holder of the issuer full information regarding the number of shares.