Step 1: Preheat and Prepare. Preheat your oven to 350°F (175°C). Line two large baking sheets with parchment paper or silicone baking mats to prevent the cookies from sticking and ensure even browning.
Step 2: Cream Butter and Sugars. In a large mixing bowl, beat the softened butter, granulated sugar, and brown sugar together until the mixture is light and fluffy. This usually takes about 2-3 minutes using an electric mixer.
Step 3: Add Wet Ingredients. Mix in the vanilla extract and the pumpkin puree. Don’t worry if the mixture looks a bit curdled at this stage; the pumpkin adds a lot of moisture that will eventually be absorbed by the flour.
Step 4: Combine Dry Ingredients. In a separate medium bowl, whisk together the flour, baking soda, salt, cinnamon, and pumpkin pie spice. Gradually add these dry ingredients to the wet mixture, stirring until just combined. Do not overmix.
Step 5: Fold in Chocolate Chips. Use a spatula to gently fold in the semi-sweet chocolate chips. Ensure they are evenly distributed throughout the thick, orange dough.
Step 6: Scoop and Bake. Drop rounded tablespoons of dough onto the prepared baking sheets, spacing them about 2 inches apart. Bake for 10 to 12 minutes, or until the edges are set and the tops look matte. Let them cool on the pan for 5 minutes before transferring to a wire rack.