Combine the cookie ingredients in a bowl and mix. Use a cookie scoop to scoop into 18 dough balls and place them on a parchment-lined baking sheet. Refrigerate for 30 minutes.
Preheat your oven to 350°F/175°C.
Whisk together the pumpkin pie filling ingredients.
Once the cookie dough has chilled, use a spoon to press down on the cookie dough and create a deep well into each cookie. If the cookie starts to fall apart at the edges, use your fingers to push it back together (see vid for visual).
Generously fill each cookie with pumpkin pie filling. Bake the cookies for 9 minutes, until the edges start to slightly become golden-brown.
Allow the cookies to *fully* chill.
While the cookies are baking/ chilling, whisk together the whipping cream ingredients until stiff peaks form.
Top each cookie with whipped cream, and enjoy!