Preheat the oven to 350 degrees. Lightly grease a cookie sheet, or line it with parchment paper.
In a large bowl or stand mixer, combine the sugar, oil, vanilla, egg, and pumpkin puree. Mix well.
In a separate bowl, combine the cinnamon, salt, baking powder, baking soda, and milk.
Add the wet ingredients with the dry ingredients and mix until thoroughly combined.
Next add the chocolate chips and fold them in until they are mixed in.
Spoon about one tablespoon of cookie batter onto the sheet pan. Be sure to keep about an inch between each scoop, as cookies will spread as they bake.
Bake for 7-10 minutes. Remove them from the oven, use a spatula to place each cookin in a single layer on a cooling rack.
Repeat steps 6 and 7 until all of the batter has been used.