Preheat the oven to 350F then line a baking sheet with parchment paper and set aside.
Cream the butter, oil, sugar, and powdered sugar in a large mixing bowl or a stand mixer.
1 stick butter, 1/3 cup oil, 1/2 cup granulated sugar, 1/4 cup powdered sugar
Add the egg, and vanilla extract, and mix until combined.
1 egg, 1 tsp vanilla extract
Add the flour, salt, and baking powder and mix until combined, using a large cookie scooper, scoop out 9 equally sized cookie balls, place them on the prepared baking sheet, gently flatten them to about 1 inch in thickness, then using a 1/4 measuring cup, press down the center of the cookie to make room for the pumpkin pie filling.
Bake for 8-9 minutes then cool on the baking sheet.
Make the pumpkin pie filling.
In a medium bowl, cream the cream cheese, and brown sugar. Once smooth, mix in the pumpkin puree and the pumpkin spice. Add a little gel food coloring and mix, don't worry if it's looking very orange.
3 oz cream cheese, 1/2 cup brown sugar, 5 oz pumpkin puree, 2 tsp pumpkin pie spice, orange gel food coloring
In a separate medium bowl, whip the cold whipped cream, granulated sugar, and vanilla extract until you reach stiff peaks.
2/3 cup heavy cream, 1 tbsp granulated sugar, 1 tsp vanilla extract
Fold the whipped cream into the pumpkin mixture until fully combined. Transfer to a piping bag with a large piping tip. Pipe a big dollop of pumpkin pie filling in the center of each cookie. Gently pick up the cookies and tap them on the counter to get the filling to spread.
Chill in the fridge until the filling is set, about 30 minutes. Top with whipped cream and enjoy!