Preheat oven to 350°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 1 cup unsalted butter, 1¼ cup dark brown sugar, and 1 cup granulated sugar on medium speed (speed 4 on a stand mixer) for 2 minutes, scraping down the sides of the bowl halfway through.
Measure and spread the ¾ cup 100% pumpkin puree out on paper towels. I usually start with four of the select-a-size sheets on the bottom or two regular folded over, then press the pumpkin with another set of paper towels on top. Replace the top paper towel with two select-a-size sheets and flip the pumpkin so the new top towels are now on the bottom of the pumpkin. Discard the original bottom towels and replace them with two more, pressing to remove the excess moisture. You should have about 100-115g of pumpkin after squeezing.
Add the pumpkin to the mixing bowl, it should peel off the towel easily, but you can use a rubber spatula to assist. Mix until fully incorporated.
Add the 2 large eggs one at a time, mixing after each one just until the yolk is streaky throughout the dough. Add 1 tablespoon vanilla bean paste and mix just until combined.
In a medium mixing bowl, whisk together the 4 cups all-purpose flour, 1 (3.4oz.) box instant vanilla pudding mix, 2 tablespoons powdered milk, 1 tablespoon pumpkin pie spice, 2 teaspoons cream of tartar, 1 teaspoon salt, 1 teaspoon ground cinnamon, and ½ 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 the speed to medium 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.
Mix together ¼ cup granulated sugar, ¾ teaspoon ground cinnamon, and ¾ teaspoon pumpkin pie spice in a small bowl and set aside.
Use a large #16 cookie scoop to portion out the dough into 2.5-ounce portions. Roll the balls of dough between your palms, then roll the dough balls in the cinnamon sugar mixture to coat. Discard the cinnamon sugar mixture after all cookie dough balls have been rolled in it.
Place on the prepared baking sheets, leaving 2 to 3 inches between each (8 cookies will fit in offset pairs on a 13x18-inch cookie sheet). The cookies will have a slightly gooey center. If you prefer cookies that are slightly more chewy throughout, use the palm of your hand to gently press the cookies down so they are about ¾-inch thick.
Bake the cookies one cookie sheet at a time for 11 to 13 minutes.
While the cookies bake, add ¼ cup granulated sugar, ¾ teaspoon ground cinnamon, and ¾ teaspoon pumpkin pie spice to a small bowl and mix to combine.
Remove from the oven and allow them to cool for 5 minutes on the pan before dipping each one in the freshly prepared cinnamon sugar mixture and transferring them to a wire rack to cool completely.