• Preheat oven to 350°F and line a baking sheet with parchment paper
• In a stand mixer, cream together butter, oil, sugar, and powdered sugar until smooth
  
• Mix in egg and vanilla until combined
  
• Add flour, salt, and baking powder, then switch to the paddle attachment and mix until dough pulls away from the bowl
  
• Divide dough into 9 balls, flatten each into a disc, and place on the prepared sheet
  
• Press a ¼ cup measuring cup into the center of each disc to form an impression, reshape edges if needed, then remove the cup
  
• Bake for 9 minutes until edges just begin to turn golden, then cool completely before filling

Filling:

• Beat cream cheese and brown sugar in a stand mixer until smooth and light
• Add pumpkin puree, pumpkin pie spice, and food coloring, then mix well and set aside
  
• In a clean mixing bowl, whip heavy cream, granulated sugar, and vanilla until stiff peaks form, about 2 to 3 minutes
  
• Transfer about ½ cup of whipped cream to a piping bag fitted with a large star tip
  
• Fold the remaining whipped cream into the pumpkin mixture until fully combined and lighter in color
• Transfer the pumpkin mixture to another piping bag without a tip or fitted with a large round tip
• Pipe a mound of pumpkin mixture into each cookie cavity and gently tap to settle
  
• Before serving top each cookie with a small dollop of whipped cream in the center