X0306 4 2020-03-18 0 0001290677 Turning Point Brands, Inc. TPB 0001794878 Purdy Graham 5201 INTERCHANGE WAY LOUISVILLE KY 40229 0 1 0 0 Chief Operating Officer Common Stock 95059 D Options (2020) 14.85 2020-03-18 4 A 0 11000 0 A 2030-03-18 Common Stock 11000 11000 D Options (2019) 47.58 2029-03-20 Common Stock 5500 5500 D Options (2018) 21.21 2028-03-07 Common Stock 8900 8900 D Options (2017) 15.41 2027-05-17 Common Stock 5000 5000 D Options (2014) 3.83 2024-08-08 Common Stock 5216 5216 D Options (2011) 3.83 2021-08-25 Common Stock 62591 62591 D Granted pursuant to the issuer's 2006 Equity Plan The options vested and became exercisable as to 50% of the underlying shares on August 25, 2011, 16.66% of the underlying shares on August 25, 2012, 16.66% of the underlying shares on August 25, 2013 and the remaining 16.66% of the underlying shares on August 25, 2014. The options vested and became exercisable as to 50% of the underlying shares on August 8, 2014, 25% of the underlying shares on August 8, 2015 and 25% of the underlying shares on August 8, 2016. 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, 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, 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, 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, 2021, 33% of the underlying shares on January 1, 2022, and 33% of the underlying shares on January 1, 2023. /s/ Graham Purdy 2020-03-20