Preheat oven to 350 degrees Fahrenheit. Spray a 9x13 inch pan with nonstick spray. Combine cake mix, pumpkin puree, and pumpkin pie spice — do not follow box instructions. Pour into pan and bake 30 to 35 minutes until a toothpick comes out clean. Cool completely.
Beat butter and cream cheese until smooth. Add vanilla. Add powdered sugar gradually and beat until smooth.
Remove and discard outer crust from cake. Crumble remaining cake into a large bowl.
Add 1 to 1 and 1/2 cups of frosting to crumbled cake. Stir until mixture holds together when pressed. Refrigerate 15 minutes.
Scoop and roll into 24 to 36 balls. Place on a lined baking sheet.
Melt orange candy melts with 2 tbsp shortening in 30-second microwave intervals until smooth.
Dip each lollipop stick in melted candy, insert halfway into each ball. Freeze 10 to 15 minutes.
Dip each pop in orange candy melts to coat completely. Stand upright in styrofoam. Add sprinkles immediately. Let set.
Melt chocolate candy melts with remaining 1 tbsp shortening. Drizzle over coated pops. Let set completely before serving.