Ensure you have a clean workspace and gather all your ingredients and tools.

In a large mixing bowl, combine the softened butter, vegetable oil, granulated sugar, and powdered sugar. Mix at medium speed until light and fluffy, about 2-3 minutes.

Add the room temperature egg and the first teaspoon of vanilla extract, mixing until incorporated.

In a separate bowl, whisk together the flour, salt, and baking powder. Gradually add this to your wet ingredients, mixing on low speed until just combined.

Using a large cookie scoop, portion nine equally sized cookie balls onto a parchment-lined baking sheet.

Using a 1/4 measuring cup, press the center of each cookie down to create a well for the filling.

Preheat your oven to 350°F (175°C). Bake the cookies for 8-9 minutes, or until the edges are light golden brown. The centers may look slightly underbaked.

Allow the cookies to cool on the baking sheet for a few minutes before transferring them to a wire rack.

In a medium bowl, combine the softened cream cheese, brown sugar, pumpkin puree, cold heavy cream, white sugar, vanilla extract, and pumpkin pie spice. Whip until smooth and creamy.

Once the cookies have cooled, spoon the pumpkin pie filling into the center of each cookie's well.