Preheat oven to 350 degrees. Using a greased mini muffin tin, place one sugar cookie dough piece in each slot. Bake for 15 minutes until slightly golden brown. Take out of the oven and place the muffin tin on a wired rack. Let cool for 5 minutes.
Using a utensil with a small rounded tip (I used a wooden spatula) gently press in the centers of the sugar cookies to make cups. Let cool completely.
Pumpkin Cream
Cream the cream cheese for 1 minute with a hand mixer on medium speed. Add in the pumpkin and mix to combine. Slowly, add in the powdered sugar until combined. Add in the remainging ingredients and whip for 2 minutes, set aside.
Whipped Cream
Add whipping cream to a large bowl, whip on high with a hand mixer until soft peaks form. Add in the powdered sugar and vanilla. Continue to whip until cream forms stiff peaks, set aside.
Cookie Cup Assembly
Take cookie cups out of the muffin tin and pipe in the pumpkin cream evenly among the cups. Top with a tiny dollop of whipped cream and a sprinkling of cinnamon if desired. Serve and enjoy! Store in an air tight container in the fridge.