Preheat the oven to 350 degrees Fahrenheit. Line a couple baking sheets with parchment paper.
Add the butter, brown sugar, and granulated sugar to a large bowl and mix (the bowl of a stand mixer with a paddle attachment is best). Cream them together at medium speed for a couple of minutes. 1 cup unsalted butter, 1 cup brown sugar, 1/2 cup granulated sugar
Add the pumpkin puree to a plate and press it with paper towels to dry out as much of the extra moisture from it as you can. 2/3 cup pumpkin puree
Add the pumpkin, egg, and vanilla extract to the creamed butter and sugars and mix them together until combined. Scrape down the sides and bottom of the bowl as needed. 1 large egg, 2 tsp vanilla extract
Add the old fashioned oats to a blender or food processor and pulse 4 to 5 times until you have a variety of texture, with some still holding their shape, and some smaller pieces. 2 cups old fashioned oats
Add the oats, flour, pumpkin spice, cinnamon, baking soda, and salt to a medium bowl and whisk them together. 1 3/4 cups all purpose flour, 2 tsp pumpkin pie spice , 1 tsp ground cinnamon, 1 tsp baking soda , 1/2 tsp salt
Add the dry ingredients to the wet ingredients and mix them together until you have a sticky cookie dough.
Add in the chocolate chips and mix on low speed until combined and the chips are mixed evenly into the dough. 2 cups chocolate chips
Scoop the dough into 2 TBS sized balls, placing them about 2 to 3 inches apart on a parchment paper lined cookie sheet.
Bake the cookies in the preheated oven for 11 to 14 minutes, or until the tops are set and the edges are slightly golden.
Remove from the oven and let the cookies cool on the sheet for 10 minutes, then transfer them to a wire rack to cool.