Preheat oven 375 degrees. Lightly spray a 24-count mini muffin pan with cooking spray.
Roll dough into small balls. Place one ball into each muffin pan cup.
Bake for 10 minutes. Immediately remove from oven and press a pastry tamper or shot glass into the cookie to form the cup. You may need to spray the tamper or shot glass with cooking spray in between each cup to prevent the dough from sticking.
Allow cookie cups to cool completely.
Fill the cups with canned pumpkin and top with whipped topping. Drizzle with caramel syrup.