Preheat your oven to 350°F. Spray a muffin pan with nonstick cooking spray. Cut parchment paper into small strips and place one in each muffin cup - this makes the cookies easier to lift out later.
Take two sugar cookie dough pieces and press them together into a single ball. Place the dough ball into each muffin cup and gently press it in to form a base.
Bake the cookie dough for about 10 minutes, until it’s puffed and lightly golden.
While the cookies bake, whisk together the pumpkin puree, egg, sweetened condensed milk, pumpkin pie spice, and a pinch of salt in a bowl until smooth.
Remove the muffin pan from the oven. Use a tart tamper or the back of a spoon to press a well into the center of each cookie cup.
Carefully spoon the pumpkin pie filling into each well, filling close to the top.
Return the pan to the oven and bake for another 10 - 15 minutes, or until the pumpkin filling is just set and doesn’t jiggle when gently shaken.
Let the cookie cups cool in the pan completely before removing them. Use the parchment strips to lift them out cleanly.
Optionally, once they’re fully cooled, top each one with a swirl of whipped cream. Serve immediately or store in the fridge until you’re ready to enjoy.