Preheat oven to 375°F. In a large mixing bowl, combine the pumpkin puree, sugar, vegetable oil, vanilla extract, milk, egg, all-purpose flour, baking powder, baking soda, salt, and cinnamon. Stir until just combined, being careful not to overmix.
Gently fold the chocolate chips into the cookie dough until evenly combined.
Using a cookie scoop, scoop the cookie dough onto a parchment-lined baking sheet. I prefer to make these cookies bite-size, but you can use a medium cookie scoop for larger cookies. Add a few extra minutes to the bake time if needed.
Place the baking sheet in the preheated oven and bake for about 12 minutes, or until the cookies just begin to brown. Remove from the oven and let cool slightly before transferring to a wire rack. Repeat with the remaining cookie dough until the entire batch is baked.
Notes
Use 100% pure pumpkin puree, not pumpkin pie filling.
Don't overmix the cookie dough or the texture can become less soft and fluffy.
Baking times can vary depending on your oven and the size of your cookie scoop, so watch the first batch closely.
Store completely cooled cookies in an airtight container at room temperature for up to 4 days.