Using a stand mixer or hand mixer and a large bowl, beat together the butter, granulated sugar, and brown sugar until light and fluffy, about 3 minutes. Scrape down the sides of the bowl as needed.
Beat in the eggs and then scrape the side of the bowl. Turn the mixer to low and beat in the vanilla extract until combined.
In a medium-sized mixing bowl, whisk together the flour, baking soda, cream of tartar, and salt. Add the flour mixture to the wet ingredients and mix on low until just combined.
Cover cookie dough in the bowl and refrigerate for at least 1 hour.
Preheat the oven to 350 degrees F. Spray the cups of a mini muffin tin with non-stick cooking spray and set aside.
Combine 1/2 cup of granulated sugar and 1 tablespoon of ground cinnamon into a large zip-top bag. (see note) Scoop 1 tablespoon of dough and roll it into a ball. Place the dough ball in the cinnamon-sugar bag and repeat with the remaining dough.
Close the bag and gently roll and shake to coat the cookie dough balls. Place 1 dough ball into each mini muffin tin cup.
Bake for 15-20 minutes. Remove the pan from the oven and use a tart tamper (r the end of a wooden spoon) to press the center of the cookie down to create a cup.
Allow the cookie cups to cool for 5 minutes in the pan, and then transfer them to a wire rack to cool completely.
Pumpkin Cheesecake
In a stand mixer, whip the cream cheese, pumpkin puree, sugar, and pumpkin pie spice together until evenly combined and smooth.
Remove the bowl from the mixer and fold in the Cool Whip until combined and there are no more big streaks.
Assembly
Spoon or pipe the cheesecake filling into each cookie cup until it reaches the top. Cover with plastic wrap and Refrigerate for 3 hours to overnight.
Remove from the fridge and uncover. Top with a dollop of Cool Whip if desired. Serve chilled or at room temperature.
Notes
If you prefer, you can mix the sugar and cinnamon coating in a medium bowl and roll the cookie dough balls in the coating one at a time.
Store any leftover cookie cups in an airtight container in the fridge.