X0508 4 2024-04-01 0001290677 Turning Point Brands, Inc. TPB 0001734429 Wigginton Brian 5201 INTERCHANGE WAY LOUISVILLE KY 40229 true Sr VP Finance & CAO false Common Stock 2024-04-01 4 F 0 380 29.12 D 10981 D Options 30.46 2032-03-14 Common Stock 2500 2500 D Options 45.05 2031-05-17 Common Stock 2500 2500 D Options 51.75 2031-02-18 Common Stock 1750 1750 D Options 14.85 2030-03-18 Common Stock 2500 2500 D Options 47.58 2029-03-20 Common Stock 400 400 D Options 21.21 2028-03-07 Common Stock 400 400 D Options 15.41 2027-05-15 Common Stock 750 750 D 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, 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 vest and become 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, 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, 2022, 33% of the underlying shares on January 1, 2023 and 33% of the underlying shares on January 1, 2024. Granted pursuant to the issuer's 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. The reported transaction involves shares withheld for the payment of taxes related to restricted stock units that have vested on 4/1/2024. The total reported in Column 5 includes 7,464 awarded restricted stock units and 3,517 shares of common stock. /s/ Brian Wigginton 2024-04-03