Combine flour, baking powder, baking soda, salt, and cinnamon in a medium bowl, set aside.
Combine pumpkin and sugar in a large bowl.
Add oil, egg, milk, and vanilla extract. Mix well.
Add dry ingredients and mix until combined.
Fold in chocolate chips.
Drop rounded tablespoons onto cookie sheets - the rounded tablespoons will turn out bit bigger than a standard cookie so bake 8 per tray.
Bake at 350 degrees (F) for 12-14 minutes until the tops are set and the cookies are slightly firm. The cookies bake up more fluffy if baked one tray at a time on the middle rack in the oven.