X0306 4 2018-04-25 0001290677 Turning Point Brands, Inc. TPB 0001660136 Murray James Michael TURNING POINT BRANDS, INC. 5201 INTERCHANGE WAY LOUISVILLE KY 40229 true Sr. VP, Business Planning Common Stock 2018-04-25 4 M 0 400 1.06 A 24579 D Common Stock 2018-04-25 4 S 0 150 20.78 D 24429 D Common Stock 2018-04-26 4 M 0 400 1.06 A 24829 D Common Stock 2018-04-26 4 S 0 150 20.62 D 24679 D Common Stock 2018-04-27 4 M 0 400 1.06 A 25079 D Common Stock 2018-04-27 4 S 0 150 21.04 D 24929 D Options (2008) 1.06 2018-04-25 4 M 0 400 0 D 2018-11-04 Common Stock 400 1864 D Options (2008) 1.06 2018-04-26 4 M 0 400 0 D 2018-11-04 Common Stock 400 1464 D Options (2008) 1.06 2018-04-27 4 M 0 400 0 D 2018-11-04 Common Stock 400 1064 D Options (2018) 21.21 2028-03-07 Common Stock 7500 7500 D Options (2017) 15.41 2027-05-17 Common Stock 6000 6000 D Options (2014) 3.83 2024-08-08 Common Stock 29731 29731 D Options (2011) 3.83 2021-08-25 Common Stock 62591 62591 D 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 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. 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 November 4, 2008, 16.66% of the underlying shares on January 1, 2009, 16.66% of the underlying shares on January 1, 2010 and the remaining 16.66% of the underlying shares on January 1, 2011. Granted pursuant to the issuer's 2015 Equity Incentive Plan. Granted pursuant to the issuer's 2006 Equity Incentive Plan. /s/ James M. Murray 2018-04-27