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. (This makes it easier to add the indent, and prevents the dough from cracking if you try to add it later when the dough is fully chilled.) 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.See notes below about make-ahead tips & storing the dough longer.

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 (to help contain the mess) beat together the powdered sugar, vanilla, nutmeg, and heavy cream on medium high to high speed with an electric mixer, until stiff peaks form. (To check for this, turn the mixer off and lift the beaters straight out of the bowl - if peaks are left standing where the mixers lifted out, it's ready!) Don't keep mixing past this point. 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.

Freezing Cookie Dough & Make-Ahead Tips: Cookie dough can be balled, indented, and frozen on a sheet pan until solid, then transferred to a freezer bag or airtight container. Freeze for 1-2 months. Bake from frozen, adding 1-2 mins to the bake time. You can also refrigerate the dough balls for 3-4 days, adding 1 minute or so to the bake time.