X0508 4 2025-11-19 0001290677 Turning Point Brands, Inc. TPB 0001831600 Cushman Brittani 5201 INTERCHANGE WAY LOUISVILLE KY 40229 1 Sr VP, General Counsel 0 Common Stock 2025-11-19 4 M 0 3000 14.85 A 37687 D Common Stock 2025-11-19 4 S 0 3000 101.66 D 34687 D Common Stock 2025-11-19 4 M 0 4000 21.21 A 38687 D Common Stock 2025-11-19 4 S 0 4000 101.66 D 34687 D Common Stock 2025-11-19 4 M 0 3250 15.41 A 37937 D Common Stock 2025-11-19 4 S 0 3250 101.66 D 34687 D Common Stock 2025-11-19 4 M 0 2500 13 A 37187 D Common Stock 2025-11-19 4 S 0 2500 101.66 D 34687 D Common Stock 2025-11-19 4 M 0 2500 13 A 37187 D Common Stock 2025-11-19 4 S 0 2500 101.66 D 34687 D Common Stock 406.806 I By Spouse Options 30.4600 2032-03-14 Common Stock 8000 8000 D Options 51.7500 2031-02-18 Common Stock 7000 7000 D Options 14.85 2025-11-19 4 M 0 3000 14.85 D 2030-03-18 Common Stock 6000 3000 D Options 47.5800 2029-03-20 Common Stock 4800 4800 D Options 21.21 2025-11-19 4 M 0 4000 21.21 D 2028-03-07 Common Stock 4500 500 D Options 15.41 2025-11-19 4 M 0 3250 15.41 D 2027-05-14 Common Stock 3250 0 D Options 13 2025-11-19 4 M 0 2500 13 D 2027-02-14 Common Stock 10000 0 D Options 13 2025-11-19 4 M 0 2500 13 D 2027-02-14 Common Stock 10000 0 D The reporting person disclaims beneficial ownership of these securities, and the inclusion of these securities in this report shall not be deemed an admission of beneficial ownership for purposes of Section 16 or for any other purpose. Granted pursuant to the issuer's 2015 Equity Incentive Plan The options vest and become exercisable as to 34% of the underlying shares on January 1, 2022, 33% of the underlying shares on January 1, 2023 and 33% of the underlying shares on January 1, 2024. The options vest and become exercisable as to 34% of the underlying shares on January 1, 2021, 33% of the underlying shares on January 1, 2022 and 33% of the underlying shares on January 1, 2023. The options vest and become exercisable as to 34% of the underlying shares on January 1, 2020, 33% of the underlying shares on January 1, 2021 and 33% of the underlying shares on January 1, 2022. The options vest and become exercisable as to 34% of the underlying shares on January 1, 2019, 33% of the underlying shares on January 1, 2020 and 33% of the underlying shares on January 1, 2021. The options vested and became exercisable as to 34% of the underlying shares on January 1, 2018, 33% of the underlying shares on January 1, 2019 and 33% of the underlying shares on January 1, 2020. 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. Granted pursuant to the issuer's 2021 Equity Incentive Plan. The reported transaction involved the reporting person's exercise of 3,000 options granted under Turning Point Brands, Inc.'s 2015 Equity Incentive Plan. The total reported in Column 5 includes 9,434 restricted stock units and 32,753 shares of common stock. The reported transaction involved the reporting person's disposition of the exercised 3,000 options granted under Turning Point Brands, Inc.'s 2015 Equity Incentive Plan. The reported transaction involved the reporting person's exercise of 4,000 options granted under Turning Point Brands, Inc.'s 2015 Equity Incentive Plan. The total reported in Column 5 includes 9,434 restricted stock units and 32,753 shares of common stock. The reported transaction involved the reporting person's disposition of the exercised 4,000 options granted under Turning Point Brands, Inc.'s 2015 Equity Incentive Plan. The reported transaction involved the reporting person's exercise of 3,250 options granted under Turning Point Brands, Inc.'s 2015 Equity Incentive Plan. The total reported in Column 5 includes 9,434 restricted stock units and 32,753 shares of common stock. The reported transaction involved the reporting person's disposition of the exercised 3,250 options granted under Turning Point Brands, Inc.'s 2015 Equity Incentive Plan. The reported transaction involved the reporting person's exercise of 2,500 options granted under Turning Point Brands, Inc.'s 2015 Equity Incentive Plan. The total reported in Column 5 includes 9,434 restricted stock units and 32,753 shares of common stock. The reported transaction involved the reporting person's disposition of the exercised 2,500 options granted under Turning Point Brands, Inc.'s 2015 Equity Incentive Plan. /s/ Brittani Cushman 2025-11-21