Preheat the oven to 350°F. Line a cookie sheet with parchment paper and set aside.
In a medium-sized mixing bowl, whisk to combine the flour, cinnamon, salt, baking soda, nutmeg, baking powder and cloves. Set aside.
In the bowl of a stand mixer, fitted with a paddle attachment, combine the brown sugar, sugar, butter and shortening. Beat on a medium speed until smooth and creamy.
Add in eggs and mix to combine. Add milk and vanilla and mix until incorporated, then add pumpkin puree and mix to combine. Add dry ingredients and mix until just combined.
Remove the bowl from the stand mixer and add chocolate chips. Fold in using a rubber spatula.
Scoop 2-3 tablespoons of dough out and roll it into a ball, then slightly flatten it to make a disc. Place onto the prepared baking sheet and top with additional chocolate chips.
Once you have 6 cookies on the baking sheet, place them into the preheated oven on the center rack. Bake for 15 minutes, until the edges just start to turn.
Once baked, remove from the oven and let sit for a few minutes to set before placing them into a wire cooling rack to let cool.
Repeat the baking process with the remaining dough.
Room Temperature: Store in an airtight container for up to 5 days. Store cookies with a piece of white bread to help keep them moist and chewy.
Freezing Baked Cookies: You can store the baked cookies in an air-tight container or freezer-friendly bag for up to 3 months in the freezer.
Freezing the Dough: I personally like cookies fresh out of the oven, so this option works well for that. You can freeze the dough and then bake however many cookies you want, when you want them! I like to shape the dough in to balls, freeze them on a cookie sheet, and then, once they are solid, put them in a container or baggie. After that, you can freeze the dough for up to 3 months. I recommend letting the cookie dough balls thaw for a few minutes on the cookie sheet before baking them.