Add the pumpkin puree, egg, vanilla extract, sugar, and brown sugar to the bowl of a stand mixer with the paddle attachment or in a large bowl with an electric hand mixer. Mix until well combined.
Add the flour, pumpkin pie spice, cinnamon, baking powder, baking soda, and salt and mix until well combined, but don't overmix.
Fold in 1 cup of chocolate chips, cover the cookie dough, and refrigerate for 1 hour.
Once the hour is up, preheat your oven to 350 degrees F and line a baking sheet with parchment paper.
Using a mini cookie scoop, drop the dough about 3 inches apart on the baking sheet. Bake for 9-12 minutes or until the tops are set. These cookies don't spread much.
Immediately place the cookies onto a cold countertop, and use the parchment paper to help slide them off the sheet tray.
Press in the remaining chocolate chips on top for a pretty presentation. Enjoy warm!