Preheat and prep: Preheat the oven to 350°F (175°C). Line a couple of baking sheets with parchment paper.
Prepare pumpkin: Line a plate with paper towels and spread the pumpkin puree in a thin layer. Gently blot with additional paper towels until reduced to about 1/3 cup.
1/2 cup 100% pumpkin puree
Whisk dry ingredients: In a medium bowl, whisk together the flour, baking soda, salt, and pumpkin pie spice. Set aside.
3½ cups all purpose flour, 1 tsp. baking soda, 1 tsp. fine salt, 3 tsp. pumpkin pie spice
Cream butter & sugars: In the bowl of a stand mixer fitted with the paddle attachment (or using a hand mixer), beat the cold, cubed butter with the dark brown sugar and granulated sugar on medium speed until well combined and slightly fluffy, 2–3 minutes. It will look more like a paste.
1 cup butter, 1 cup dark brown brown sugar, 2/3 cup granulated sugar
Add wet ingredients: Beat in the egg, egg yolk, blotted pumpkin puree, and vanilla extract until smooth and fully incorporated.
1 egg + 1 egg yolk, 1 Tbsp. vanilla extract
Combine dry & wet ingredients: Gradually add the dry ingredients into the wet mixture, mixing on low speed just until combined. Do not over-mix.
Fold in chocolate: Using a spatula, fold in 1½–2 cups of chocolate. I like to use a combination of each chocolate.
1½-2 cups Guittard super cookie chips, semi-sweet chocolate chips, mini chocolate chips, chopped chocolate, etc.
Scoop dough: Scoop dough into large balls and place onto prepared sheets (you should get about 10 large cookie dough balls in total).
Bake: Bake for 12-14 minutes, until edges are set but centers still look slightly soft. Do not over-bake. Start Timer
Cool: Gently place a few more chocolate chips on top of cookies when out of the oven. Let cookies cool on the baking sheet for 15 minutes, then transfer to a wire rack to cool completely.