Preheat your oven to 350 degrees F and spray a 24-cup mini muffin tin with non-stick cooking spray.
Grab your sugar cookie dough and slice it into 24 equal squares (just follow the perforated lines), then drop one square of cookie dough into each mini muffin tin cavity.
Bake for 15-17 minutes, then immediately take the handle of a spoon or spatula and press down in the center of each cookie to create a well and set aside to cool.
In a medium mixing bowl, add softened cream cheese, heavy whipping cream, and pumpkin puree, then mix until combined.
Add in the powdered sugar, pumpkin pie spice, and vanilla extract, then mix again until smooth and creamy.
Transfer the pumpkin cheesecake filling into a piping bag or Ziploc bag, cut off one end, and generously fill each cookie cup.
Top each cookie cup with a pumpkin candy before enjoying!