In the bottom of a cocktail shaker, carefully muddle the sugar, bitters, and one orange slice. Remove the orange rind once muddled.
Next, add the bourbon and ice into the cocktail shaker.
Using the smoker gun, pump smoke into the cocktail shaker for 15 seconds, before capping it off with the shaker lid. Allow it to rest for a minute.
Shake the cocktail until the shaker is cold and frosty on the exterior.
Pour into an old fashioned cocktail glass and garnish with the remaining orange slice and a maraschino cherry. Enjoy!