These pumpkin pie cookie cups combine buttery cinnamon sugar cookie cups and creamy, spiced pumpkin pie filling into a cozy, two-bite treat that'll satisfy any pumpkin pie craving.
In a medium bowl, whisk to combine the flour, baking powder, baking soda, cinnamon, and salt. Set aside.
1 ¼ cups all-purpose flour, ½ teaspoon baking powder, ½ teaspoon baking soda, ¼ teaspoon ground cinnamon, ¼ teaspoon salt
In the bowl of a stand mixer (or in a large bowl using an electric hand mixer), beat the butter on high speed until smooth, about 30 seconds. Add the sugar and cream the sugar with the butter on high speed until light and fluffy, about 2 to 3 minutes more, scraping the sides of the bowl as needed.
½ cup unsalted butter, ⅝ cup granulated sugar
Add the egg yolks and vanilla extract and beat to combine.
2 large egg yolks, ½ teaspoon vanilla extract
Add the flour mixture to the butter mixture and mix on low speed just until combined, being careful not to over mix. The dough should be moistened throughout but still a bit crumbly.
Cover the bowl with plastic wrap and refrigerate the dough for 30 minutes.
While the dough chills, preheat the oven to 350°F. Spray a mini muffin pan with cooking spray.
Once the cookie dough has chilled, scoop 1 Tablespoon of dough, roll into a ball using your hands, and place a cookie dough ball into each greased well of the mini muffin pan. You should have 24 balls of dough.
Bake the cookies for 8 to 10 minutes or just until lightly golden.
Immediately upon removing the muffin pan from the oven, use the back side of a teaspoon measuring spoon to press down the centers of each cookie, forming a cup. Let the cookie cups cool in the muffin pan for 5 minutes while you prepare the pumpkin pie filling.
Make the pumpkin pie filling.
In a medium bowl, whisk together the sugar, cinnamon, nutmeg, and cloves.
Add pumpkin purée and heavy whipping cream and whisk to combine.
⅔ cup pumpkin purée, 2 ½ Tablespoons heavy whipping cream
Assemble and bake the cookie cups.
Scoop about 1 ½ teaspoons of pumpkin pie filling into each slightly cooled sugar cookie cup. The cookie cups should be just filled to the inner rim, and you may end up with a little bit of leftover filling. Do not overfill the cups.
Return the pan to the oven and bake for about 10 minutes.
Remove the pan from the oven and let the cookie cups cool in the pan for 5 minutes before carefully removing them from the pan and transferring them to a wire rack to cool completely.
Make the whipped cream topping.
When the cookie cups have cooled completely, make the whipped cream topping. In a medium bowl, whisk together sugar and cream of tartar.
1 ½ teaspoons confectioners' sugar, 1 pinch cream of tartar
Add heavy whipping cream and beat the mixture on medium-high speed until stiff peaks form.
¼ cup heavy whipping cream
Top the cookie cups.
Add the whipped cream to a piping bag fitted with an open star piping tip and pipe a dollop onto the top of each cookie cup.
Notes
Storage: Pumpkin pie cookie cups can be stored in an airtight container in the fridge for up to 4 days.Removing Sugar Cookie Cups from Pan: To easily remove the cookie cups from the pan, slide a cake tester or small knife between the edge of the cookie and the side of the pan and lift gently upward. The cookie cup should pop up out of the pan. Taking the cookies out of the pan before they've cooled completely is helpful.