In medium saucepan over medium heat, combine cup of sugar and cup water and stir until sugar dissolves completely. Let cool 20 minutes, then mix in cranberries until coated.
Using a slotted spoon, transfer cranberries, tapping away any excess syrup, into a large resealable plastic bag. Add remaining 1 cup sugar, seal, and shake until cranberries are completely coated.
Spread out cranberries on a baking sheet and refrigerate until cranberries are completely cool and sugar hardens, 25 minutes.
Bring 2 cups water to a boil. Add Jell-O mix and whisk until completely dissolved, then remove from heat and stir in vodka and 1 cup cold water. Let cool 2 to 3 minutes.
Place 18 plastic shot glasses on a baking sheet and pour in Jell-O mixture until each is full.
Refrigerate until set, about 3 hours.
Top each shot with 1 or 2 sugared cranberries.