For the Filling:
Transfer some of the pudding to a piping bag fitted with an appropriately-sized piping tip. Set aside.
For the Frosting:
Transfer some of the frosting to a piping bag fitted with your desired tip. Set aside.
To Assemble the Cupcakes:
Insert an apple corer into the center of the top of the cupcake. Push the corer into the cupcake, stopping ¼”- ½” from the bottom of the cupcake. Remove the cored center and reserve for other use. If necessary, enlarge the hole by using a finger to gently press on the walls of the hole and remove any remaining bits of cake. Repeat for all cupcakes.
Pipe 1 fl oz of the pudding filling into the cupcake holes.
Pipe ½ cup frosting over each cupcake, being sure to cover the hole. Sprinkle 1 Tbsp of crushed chocolate cookie over each cupcake and insert a whole cookie into the frosting.