In a large bowl, add 1 cup canned pumpkin (not entire can), granulated sugar, brown sugar, vegetable oil, egg, and vanilla. Mix until completely smooth. If desired, add in food dye—this will give you a darker, more “pumpkin-looking” cookie. (The photos have 3 drops of orange food coloring.) Mix until completely smooth.
Without stirring between these additions, add in cinnamon, pumpkin pie spice, baking powder, baking soda, salt, flour, 3/4 cup mini chocolate chips, and regular chocolate chips. Mix by hand or with an hand mixer until just combined. Do not overmix. The dough is wet, thick, and sticky!
Cover tightly and chill dough for 30 minutes up to 10 hours. Chilling is not necessary, but it makes dough easier to work with and intensifies flavors.
Preheat oven to 350℉ and line a large sheet pan with parchment paper or a silicon baking mat. Use a 1-tablespoon measuring spoon to scoop out balls of dough onto the sheet pan. Try to smooth or round the balls, but it’s okay if they’re a bit bumpy; the dough is messy to work with. Bake for 8–11 minutes and remove. Use remaining 1/4 cup mini chocolate chips to press a few more chocolate chips on the tops of the cookies straight out of the oven.
Let cookies stand on the sheet pan for 3–4 minutes before using a spatula to transfer cookies to a cooling rack. Repeat baking process with remaining dough, keeping dough in the fridge until it’s scooped into cookies (colder dough = easier to work with!) For a fudgy pumpkin pie-type cookie, chill cooked cookies in the fridge—delish!
Video
Notes
Note 1: We like a mild amount of spice in these pumpkin cookies. If you’d prefer more, use another teaspoon of pumpkin pie spice or an additional 1/4 teaspoon nutmeg and 1/8 teaspoon ground cloves.Storage: Because of the canned pumpkin and oil, these cookies get wet and sticky when kept at room temperature for more than a day. I prefer baking what will be eaten the same day, then freezing unbaked dough (see next note). If there are baked cookies that won’t be finished, I’ve found it’s best to freeze them after the first day: Put completely cooled cookies in a freezer-safe container or bag. Freeze for 2–3 months and bring back to room temperature by warming one in the microwave for 5–10 seconds.Freezing unbaked dough: Place cookie dough balls on a large sheet pan and freeze until solid. Once solid, transfer frozen dough balls to an airtight container/bag separated by parchment paper (so they don’t all stick together) and freeze for up to 3 months. You can bake cookies straight from the freezer; just add 1–3 minutes onto the cooking time (or thaw dough in the fridge and bake according to directions).