Preheat oven to 350°F. Grease half of a 12-cup muffin tin with non-stick cooking spray (this recipes makes 6 cups). 

In a large mixing bowl, whisk together melted butter, sugars, pumpkin puree, and vanilla until creamy. Add flour, pumpkin spice, baking soda, and salt. Use a wooden spoon or rubber spatula to fold dry ingredients into wet until a soft dough forms. Fold in chocolate chips.

Scoop 2 ½-3 tbsp dough into each muffin cup and lightly press dough down so it sits evenly in the bottom (do not press up the sides yet). 

Bake for 14-15 min until edges are set. The center should still look soft and slightly underbaked. Remove from oven and immediately use the bottom of a ¼ cup measuring cup to gently press into the center of each cookie to form a cup shape. 

Cool cookie cups for 15 minutes before carefully removing. Cool completely before adding filling.

Prepare the filling. In a medium mixing bowl, use a handheld mixer to combine the cream cheese, sugar, pumpkin puree, vanilla, and pumpkin spice until creamy. Fill each cooled cookie cup with cream cheese filling. Top with whipped cream, drizzle of caramel, and sprinkle of pumpkin spice.