Cut Pie Crust: Preheat the oven to 350°F (175°C). Unroll the pie crust and use a leaf-shaped cookie cutter to cut out the dough. Arrange the cutouts on a parchment-lined baking sheet.
1 refrigerated rolled pie crust, like Pillsubry
Cinnamon Sugar: In a small bowl, mix together the sugar and cinnamon. Lightly sprinkle the pie crust cutouts with the cinnamon-sugar mixture.
1/4 cup white sugar, 1 1/2 teaspoons ground cinnamon
Bake: Bake the pie crust cutouts for 10 minutes, or until they turn golden brown. Once done, set them aside to cool completely.
Beat Cream Cheese: While the pie crust is baking, in a stand mixer fitted with the whisk attachment or using an electric hand mixer, beat the softened cream cheese until smooth. Gradually add 1 cup of cool whip at a time, beating after each addition until the mixture is fully combined and fluffy. Be sure to scrape down the sides of the bowl between mixing.
1 8-ounce package full-fat cream cheese, 8 ounces about 3 cups cool whip, plus more for topping*
Whisk Pumpkin Mixture: In a separate bowl, whisk together the pumpkin, milk, vanilla extract, pumpkin pie spice, and ground cinnamon until smooth and well blended. Finally, whisk in the pudding mix until fully incorporated.
1 15-ounce can plain pumpkin puree, 1/2 cup milk, 1 teaspoon vanilla extract, 2 teaspoons pumpkin pie spice, 1/2 teaspoon ground cinnamon, 1 5.1-ounce family size box vanilla or cheesecake flavored instant pudding mix
Fold Filling: Gently fold the pumpkin mixture into the cream cheese mixture until everything is well combined.
Assemble: Spoon or pipe (with a zip-top bag or piping bag) the pumpkin cream mixture into 10-12 serving cups. Top each with a dollop of extra cool whip, a sprinkle of pumpkin pie spice, and a cooled pie crust leaf cutout or two.