Preheat oven to 350 degrees. Line baking sheets with silicone baking mats or parchment paper.
In a mixing bowl, whisk together flour, baking powder, baking soda, cinnamon, pumpkin pie spice, and salt for 20 seconds, set aside.
In a separate mixing bowl, with an electric mixer, blend together granulated sugar, brown sugar and vegetable oil until combined.
Mix in egg and vanilla then blend in pumpkin puree.
With mixer on low speed, slowly add in flour mixture and mix just until nearly combined, scraping down the sides of the bowl as needed (batter will be pretty wet).
With a rubber spatula, fold in chocolate chips while folding batter to evenly combined.
Drop dough 2 Tbsp at a time (either using a medium cookie dough scoop or using two spoons) at a time onto baking sheets lined with Silcone liners or parchment paper, spacing cookies two inches apart.
Bake until cookies are nearly set, about 11 - 13 minutes.
Allow to cool several minutes before transferring to a wire rack to cool.
If they last this long, store in a single layer in an airtight container (these are best once they've rested in an airtight container a few hours, they soften throughout).