Preheat your oven to 350°F (175°C) and line two baking sheets with parchment paper for easy cleanup and to prevent sticking.
Combine the wet ingredients in a large bowl by whisking together the pumpkin puree, sugar, vegetable oil, egg, and vanilla extract until smooth and well incorporated.
Mix the dry ingredients in a separate bowl by whisking together the flour, pumpkin pie spice, baking soda, baking powder, and salt until evenly combined.
Gradually add the dry ingredients to the wet mixture, stirring just until combined. Be careful not to overmix, which can make the cookies tough.
Fold in the chocolate chips using a spatula, distributing them evenly throughout the soft dough.
Scoop rounded tablespoons of dough onto the prepared baking sheets, spacing them about 2 inches apart. The dough will be softer than traditional cookie dough.
Press a few extra chocolate chips onto the tops of each cookie dough mound for a more attractive finished appearance.
Bake for 10-12 minutes or until the edges are set but the centers still look slightly soft. They should spring back lightly when touched.
Allow cookies to cool on the baking sheets for 5 minutes before transferring to a wire rack to cool completely.