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

To Make The Cookies:

• In the bowl of a stand mixer, combine the butter, oil, granulated sugar, and powdered sugar. Cream until smooth.
• Mix in the egg and vanilla and combine.
• Add in the flour, salt, and baking powder. Change the mixer attachment to the paddle rather than the whisk. Mix until combined and the dough pulls away from the bowl.
• Divide the dough equally into nine balls. Flatten the dough into a disc and place it on a baking sheet lined with parchment.
• Using the bottom of a ¼ cup measuring cup, press the measuring cup into the disc and reshape the dough around the base of the cup. Gently remove the measuring cup from the dough and ensure the cup leaves an impression. Bake in the preheated oven for about 9 minutes; the edges should just be slightly starting to turn golden and set. Do not over bake. Allow to cool completely before filling.

To Make The Filling:

• In the bowl of a stand mixer, combine the softened cream cheese and the brown sugar. Cream until lighter in color and smooth.
• Add in the pumpkin puree, pumpkin pie spice, and orange food coloring. Combine well. Transfer to another bowl and wipe out the mixing bowl.
• In the bowl of the stand mixer, combine the heavy cream, granulated sugar, and vanilla. Mix on high speed with the whip attachment until stiff peaks form. It should take about 2–3 minutes. Do not overmix.
• Transfer about½cup worth of the whipped cream to a piping bag fitted with a large star tip. The remaining whipped cream can be added to the bowl with the pudding mixture.
• Fold in the whipped cream by hand until the pudding mixture is combined and light in color. Transfer the pudding mixture to another piping bag with a small, round tip.
• Pipe a mound of the pumpkin mixture into the cavity of each cookie. Gently tap the cookie on the counter to settle the pumpkin mixture.
• Pipe a small dollop of whipped cream into the center of the pumpkin mixture.