One day in advance, make cookies. Prepare cookie dough and roll out 1/8 in. thick. Cut cookies using pumpkin cutter from set. Bake and cool completely.
Prepare royal icing. Tint portions orange and green. Use tip 3 and full-strength orange icing to outline pumpkin. Use tip 3 and thinned orange icing to fill-in pumpkin. Let set. Use tip 6 and full-strength green icing to fill-in stem. Let set.
Bake mini pumpkin pies in mini muffin pan following recipe directions. Cool completely.
Fill standard cupcake baking cup 1/4 full with cupcake batter. Place cooled mini pumpkin pie in center of cupcake batter. Cover pie with cupcake batter, filling cavity 3/4 in. full. Bake and cool completely.
Prepare whipped icing mix following package directions. Use tip 1M, disposable decorating bag and whipped icing to pipe swirl on top of cupcake. Cover with sprinkles.