Preheat oven to 375°F and line 2 large baking sheets with parchment paper and set aside.
In a large bowl or stand mixer (I highly recommend a stand mixer for this recipe) fitted with a paddle attachment, cream together the 1½ cups unsalted butter, 1½ cups dark brown sugar, and 1 cup granulated sugar on medium speed for 2 minutes, scraping down the sides of the bowl halfway through.
1½ cups unsalted butter, 1 cup granulated sugar, 1½ cups dark brown sugar
Add the 2 large eggs one at a time, mixing after each one just until the yolk is streaky throughout the dough. Add the ¾ cup 100% pumpkin and 1½ teaspoon vanilla extract and mix just until combined.
2 large eggs, 1½ teaspoon vanilla extract, ¾ cup 100% pumpkin
In a medium mixing bowl, whisk together the 4½ cups bread flour, 1 (3.4oz.) box instant vanilla pudding mix, 2 tablespoons powdered milk, 2 teaspoons pumpkin pie spice, 1½ teaspoons salt, 1 teaspoon ground cinnamon, and 1 teaspoon baking soda. With the mixing beating at low (stir) speed, slowly add the flour mixture a cup at a time. If you have a flour shield for your mixer, I recommend using it as this recipe creates a lot of dough. Increase to medium speed and mix just until combined, then remove from the mixer and use a rubber spatula to mix up any loose flour from the bottom of the bowl into the dough.
4½ cups bread flour, 1 (3.4oz.) box instant vanilla pudding mix, 2 tablespoons powdered milk, 1½ teaspoons salt, 2 teaspoons pumpkin pie spice, 1 teaspoon baking soda, 1 teaspoon ground cinnamon
Add 1½ cups of the 2 cups chocolate chips and mix at low speed just until combined, be careful not to overmix. You can finish mixing with a rubber spatula or with your hands until the dough is fully combined and the chips are evenly incorporated.
2 cups chocolate chips
Use a large #16 cookie scoop to portion out the dough on the prepared baking sheets, leaving 4 inches between each (6 cookies will fit on a 12x17-inch cookie sheet). Press the remaining chocolate chips into the tops and sides of the balls of dough.
Bake the cookies one cookie sheet at a time for 11 to 13 minutes or until the edges are just turning light brown. The centers should still be very soft and look slightly puffy and underdone. Remove from the oven and allow them to cool for 5 minutes on the pan before transferring them to a wire rack to cool completely. While they are still warm, you can add more chocolate chips to fill in any gaps for appearances.