Make Cookie Dough: Melt the butter in a medium bowl. Whisk in the molasses. Add the sugars and whisk to combine. Add the eggs and vanilla, and whisk until smooth and combined, about 30-45 seconds. Stir in the dry ingredients, making sure to get any dry bits hiding in the bottom of the bowl.

Scoop Dough Balls & Chill: Scoop dough into balls that are 70 grams each, and chill for 30 minutes in the fridge or 10 minutes in the freezer before rolling in granulated sugar & adding the indent. Make the indent with the back of a teaspoon, making sure not to press too far down so the bottom of the cookie stays intact. Return the dough balls to the freezer for 20-30 additional minutes or to the fridge for 1-2 additional hours.

Make Pumpkin Filling: Whisk together all pumpkin pie filling ingredients in a medium bowl until well combined and smooth. This can be made up to 24 hours ahead. Store in the fridge in an airtight container.

Bake: Preheat your oven to 365℉. Place 5-6 cookies on a cookie sheet lined with parchment paper. Add 1-2 tsp of pumpkin pie filling to the indent in each cookie. Don't over fill them. Bake for 12-14 minutes. The edges will appear set and the pumpkin filling will also appear just set. Let cookies cool on the baking sheet for 10+ minutes, then transfer to a wire rack to cool completely. Repeat with remaining dough until all the cookies are baked.

Make Whipped Cream: In a large bowl, beat together the powdered sugar, vanilla, nutmeg, and heavy cream on medium high to high speed with an electric mixer, until stiff peaks form. Add whipped cream to a piping bag fitted with a tip, or a ziploc bag with the tip snipped off, and pipe dollops onto the cooled cookies.

Serve & Store: Serve cookies once they're topped with the whipped cream! Store leftover cookies (with or without whipped cream) in an airtight container in the fridge for 4-5 days.