Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper.

In a mixing bowl, cream together the softened unsalted butter, vegetable oil, granulated sugar, and powdered sugar until smooth and fluffy, about 2-3 minutes.

Incorporate the room temperature egg and vanilla extract into your creamed mixture, beating until fully combined, about 1-2 minutes.

Gradually add the flour, salt, and baking powder while mixing on low speed. Mix until just combined to avoid overworking the dough.

Using a large cookie scoop, portion out 9 balls of dough on the baking sheet. Flatten them slightly and create a small well in the center, then bake for 8-9 minutes.

Beat the softened cream cheese and brown sugar together until smooth, then add pumpkin puree and pumpkin pie spice, mixing until creamy. Optionally add orange food coloring.

In a separate bowl, whip the cold heavy cream with white sugar until stiff peaks form, about 3-5 minutes.

Pipe the creamy pumpkin filling into each cookie's center and optionally top with whipped cream. Chill before serving.