Gently grease shot glass cups with cooking spray to help the Jell-O shots release better. Wipe away excess with a paper towel so that only trace residue remains.
In a saucepan, combine apple cider and sugar. Sprinkle gelatin over top. Let sit 2-3 minutes until the surface is wrinkled.
Heat on medium heat and stir until sugar and gelatin have dissolved. The mixture should be smooth with no graininess. Stir in spiced bourbon.
Pour into the prepared shot glasses. Refrigerate until set, about 4 hours.
Meanwhile, make the cinnamon sugar. In a medium bowl, combine sugar and ground cinnamon. Stir until evenly distributed. Pour some onto a plate for rimming the glasses. Rub a lemon wedge around the edge of the shot glasses. Roll the edge in the cinnamon sugar. Serve.
Notes
If you don't have cinnamon whiskey on hand, feel free to use Fireball or any other bourbon.