Preheat oven to 350 degrees and generously grease a mini muffin pan.
Prepare the sugar cookie mix according to package.
Press the sugar cookie dough into each space, pressing it slightly up the sides.
Spoon a little of the pumpkin pie filling into the center of each cookie.
Bake the cookies 18-20 minutes, or until the edges start to turn golden brown.
Place pan on wire rack and press a Rolo into the middle of each cookie cup.
Let cookies cool completely before removing them from the pan.
To easily remove cookies, take a spoon and loosen cookie around the edges. The cookie should pop right out.
Store in fridge until ready to serve. Serve with dollop of whipped cream and sprinkle of pumpkin pie spice.