Preheat your oven to 350°F. Line a baking sheet with parchment paper and set aside.

In a large bowl or a stand mixer, cream together the softened butter, vegetable oil, granulated sugar, and powdered sugar until light and fluffy.

Add the egg and vanilla extract, beating until well combined.

In a separate bowl, whisk the flour, salt, and baking powder. Gradually add the dry ingredients to the wet mixture, mixing just until a dough forms. Using a large cookie scoop, portion the dough into 9 equal balls. Place them on the prepared baking sheet and gently flatten each to about 1 inch thick. Use the bottom of a 1/4 cup measuring cup to press a well into the center of each cookie, creating a space for the filling.

Bake for 8 to 9 minutes, until the edges are lightly golden. Let the cookies cool on the baking sheet for 5 minutes, then transfer to a wire rack to cool completely.

In a medium bowl, beat the softened cream cheese and brown sugar until smooth. Mix in the pumpkin puree and pumpkin pie spice. If using, add a drop or two of orange gel food coloring and stir until evenly tinted; don't worry if it looks very orange.

In another medium bowl, whip the cold heavy cream, granulated sugar, and vanilla extract until stiff peaks form.

Gently fold the whipped cream into the pumpkin mixture until fully combined. Transfer the filling to a piping bag fitted with a large star tip. Pipe a generous dollop of filling into the center well of each cookie. Gently lift each cookie and tap it on the counter to help the filling settle. Top with additional whipped cream if desired and serve.