Preheat the oven to 350 degrees F (177 degrees C). Line a baking sheet with parchment paper or a silicone baking mat.
In a medium sized bowl, whisk together the flour, baking powder, and salt. Set aside.
In a separate medium sized bowl, mix together the butter and sugar with an electric mixer for 2 minutes.
Beat in the vanilla and the egg.
With the mixer on low speed, slowly add the wet ingredients to the dry ingredients, mixing just until incorporated. Cover the dough and chill in the refrigerator for 1 hour.
When you are ready to bake the cookies, scoop up a quarter cup of the dough and roll it into a ball. Flatten the ball slightly and place on the prepared baking sheet. Repeat with the remaining dough and space the cookies at least 2 inches apart.
Using the tines of a fork, press gently around the edges of the flattened cookie dough so that it resembles a pie crust.
Bake 8-10 minutes. Do not overbake. The edges should be very slightly browned. Let cool on baking sheet for 2 minutes, then transfer the cookies to a cookie rack to cool completely.
Make the topping
In a small bowl, mix together the cream cheese, pumpkin puree, sugar, and spices with an electric mixer. Spoon the pumpkin topping over the cooled cookies and spread over the tops.
Make the whipped cream
With an electric mixer, whisk the cream and the sugar together until the cream thickens. Top the cookies with a spoonful of whipped cream.
Notes
Before you start baking, make sure to read the entire recipe, including the Ingredient Notes section, and examine the process photos. This detailed guide will help you understand how the recipe unfolds, ensuring your pumpkin pie cookies turn out perfect every time. All the information you need is found within the body of this recipe post, so don’t miss a thing!
Chill the Dough: Ensuring the cookie dough is thoroughly chilled is vital. A colder dough won't spread too much and will result in perfectly shaped cookies.
Double Up: This recipe is flexible – doubling the amounts will provide you with a larger batch to enjoy.
Taste to Preference: Customize the pumpkin topping by adjusting the pumpkin puree and sugar according to your taste buds. More sugar for sweetness, or more pumpkin for a bolder pumpkin flavor.
Color Pop: For a more intense orange color in your pumpkin topping, consider adding a few drops of orange food coloring. This step is optional and for visual appeal.