Preheat your oven to 350°F (175°C) and line two large baking sheets with parchment paper.

Spread the ½ cup of pumpkin puree evenly onto a plate lined with 4 layers of paper towels. Press gently with additional towels to blot out excess liquid until the puree looks dense and concentrated (this guarantees chewy, non-cakey cookies).

In a medium bowl, whisk together the flour, baking soda, baking powder, cinnamon, pumpkin pie spice, and salt.

In a large mixing bowl or stand mixer fitted with paddle attachment, beat the softened butter, dark brown sugar, and granulated sugar on medium speed for 2 minutes until creamy and fluffy.

Add the egg yolk and vanilla extract, beating until incorporated. Mix in the blotted pumpkin puree just until smooth.

Add the dry ingredients on low speed, mixing just until soft dough forms. Fold in the chocolate chips with a rubber spatula.

Use a 2-tablespoon cookie scoop to drop mounds of dough 2 inches apart onto prepared baking sheets. Press a few extra chocolate chips gently into the tops of each dough ball.

Bake at 350°F for 11 to 13 minutes, until cookie edges are set and tops are matte and gently cracked. Centers will remain soft.

Let cookies cool on the hot baking sheet for 10 minutes to allow centers to finish setting, then transfer to a wire rack to cool completely.