Preheat oven to 375 degrees. Line a baking sheet with parchment paper or a silicone baking mat, set aside.
In the bowl of a stand mixer(or a large mixing bowl using a hand mixer), add the pumpkin puree, sugar, oil, and vanilla. Mix until combined, about 30 seconds.
In a medium mixing bowl, whisk together the flour, pumpkin pie spice, baking powder, baking soda, salt, and cinnamon. With mixing speed on low, gradually add the dry ingredients. Mix until combined.
Using a large spatula or wooden spoon, fold in the mini chocolate chips.
Using a standard size cookie scoop, scoop the dough onto the prepared baking sheet. Place in the oven and bake for 14-16 minutes or until they are firm and start to turn brown on the edges.
Remove and allow to cool for 5 minutes on the sheet before transferring them to a wire rack to cool completely. Do not store until cookies have cooled for at least 30 minutes at room temperature.