Sec Form 4 Filing - Frein Summer @ Turning Point Brands, Inc. - 2025-03-03

FORM 4 Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934, Section 17(a) of the Public Utility Holding Company Act of 1935 or Section 30(h) of the Investment Company Act of 1940

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1. Name and Address of Reporting Person Frein Summer 2. Issuer Name and Ticker or Trading Symbol Turning Point Brands, Inc. [ TPB] 5. Relationship of Reporting Person(s) to Issuer (Check all applicable) _____ Director _____ 10% Owner X __ Officer (give title below) _____ Other (specify below) Chief Revenue Officer (Last) (First) (Middle) 5201 INTERCHANGE WAY 3. Date of Earliest Transaction (MM/DD/YY) 03/03/2025 (Street) LOUISVILLE, KY40229 4. If Amendment, Date Original Filed (MM/DD/YY) 6. Individual or Joint/Group Filing (Check Applicable Line) __ X __ Form filed by One Reporting Person _____ Form filed by More than One Reporting Person (City) (State) (Zip)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned 1.Title of Security (Instr. 3) 2. Transaction Date (MM/DD/YY) 2A. Deemed Execution Date, if any (MM/DD/YY) 3. Transaction Code (Instr. 8) 4. Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5) 5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4) 6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4) Code V Amount (A) or (D) Price Common Stock 03/03/2025 A 2,175 A $ 70.34 19,378 ( 2 ) D Common Stock 03/03/2025 F 1,512 D $ 70.34 17,866 ( 3 ) D Common Stock 03/03/2025 A 650 A $ 70.34 18,516 ( 4 ) D Common Stock 03/03/2025 A 2,063 A $ 70.34 20,579 ( 5 ) D Common Stock 03/03/2025 A 1,730 A $ 70.34 22,309 ( 6 ) D Common Stock 03/03/2025 F 1,710 D $ 70.34 20,599 ( 7 ) D

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned ( e.g. , puts, calls, warrants, options, convertible securities) 1. Title of Derivative Security (Instr. 3) 2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (MM/DD/YY) 3A. Deemed Execution Date, if any (MM/DD/YY) 4. Transaction Code (Instr. 8) 5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4, and 5) 6. Date Exercisable and Expiration Date (MM/DD/YY) 7. Title and Amount of Underlying Securities (Instr. 3 and 4) 8. Price of Derivative Security (Instr. 5) 9. Number of Derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form of Derivative Security: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4) Code V (A) (D) Date Exercisable Expiration Date Title Amount or Number of Shares Options ( 1 ) $ 31.39 ( 1 ) 04/29/2032 Common Stock 6,273 6,273 D

Reporting Owners Reporting Owner Name / Address Relationships Director 10% Owner Officer Other Frein Summer 5201 INTERCHANGE WAY LOUISVILLE, KY40229 Chief Revenue Officer Signatures /s/ Summer Frien 03/05/2025 Signature of Reporting Person Date

Explanation of Responses:

( 1 )Options granted under the Turning Point Brands, Inc. 2021 Equity Incentive Plan. The options vest and become exercisable as to 34% of the underlying shares on January 1, 2023, 33% of the underlying shares on January 1, 2024 and 33% of the underlying shares on January 1, 2025. ( 2 )The reported transaction involved the reporting person's receipt of a grant of 2,175 restricted stock units under Turning Point Brands, Inc,'s 2021 Equity Incentive Plan. The total reported in Column 5 includes 14,396 restricted stock units and 4,982 shares of common stock. ( 3 )The reported transaction involves shares withheld for the payment of taxes related to restricted stock units that have vested on March 3, 2025. The total reported in Column 5 includes 10,166 restricted stock units and 7,700 shares of common stock. ( 4 )Represents shares issued upon settlement of performance restricted stock units granted to the reporting person in March 2022. The compensation committee of the Board of Directors determined that the performance criteria were met on March 3, 2025. The total reported in Column 5 includes 10,166 restricted stock units and 8,350 shares of common stock. ( 5 )Represents shares issued upon settlement of performance restricted stock units granted to the reporting person in May 2023. The compensation committee of the Board of Directors determined that the performance criteria were met on March 3, 2025. The total reported in Column 5 includes 10,166 restricted stock units and 10,413 shares of common stock. ( 6 )Represents shares issued upon settlement of performance restricted stock units granted to the reporting person in March 2024. The compensation committee of the Board of Directors determined that the performance criteria were met on March 3, 2025. The total reported in Column 5 includes 10,166 restricted stock units and 12,143 shares of common stock. ( 7 )The reported transaction involves shares withheld for the payment of taxes related to performance restricted stock units that the performance criteria were met on March 3, 2025. The total reported in Column 5 includes 10,166 restricted stock units and 10,433 shares of common stock.

Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.

* If the form is filed by more than one reporting person, see Instruction 4(b)(v).

** Intentional misstatements or omissions of facts constitute Federal Criminal Violations. See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).

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