For the cookies:
9 tablespoons unsalted butter, softened
1/4 cup pumpkin puree
3/4 cup sugar
3/4 cup brown sugar
3 large eggs
3 1/2 cups all-purpose flour
1 teaspoon baking soda
1 teaspoon pumpkin spice mix
1/4 teaspoon salt
Orange food coloring (or a mix of red and yellow), optional
For the frosting:
1/4 cup unsalted butter
3 tablespoons cocoa powder
1/4 cup milk
2 cups powdered sugar
1 teaspoon vanilla
INSTRUCTIONS (via The Kitchn)
1. Preheat the oven to 325°F: Place one rack in the top third of the oven and another rack in the bottom third. Line two baking sheets with parchment or nonstick baking mats.
2. Make the cookie dough: In the bowl of a stand mixer (or in a large bowl with a hand mixer), cream together the butter and sugars until they’re smooth. Mix in the pumpkin puree. Mix in the eggs one at a time. In a separate bowl, whisk together the flour, baking soda, salt, and pumpkin pie spice, then slowly stir the dry ingredients into the creamed mixture. Mix just enough to combine the ingredients. Add a few drops of orange food coloring if you’d like a deeper orange color.
3. Chill the dough: Chill the dough in the refrigerator for 30 minutes.
4. Portion the cookie dough onto the baking sheets: Scoop up about 2 tablespoons of dough and transfer to the baking sheet. Continue with the remaining dough, positioning the cookies a few inches apart. You should have about 24 cookies.
Flatten the dough: Dip your fingers in water and use them to flatten each mound of dough to about 1/4-inch thick.
5. Bake the cookies: Bake the cookies for 10 to 12 minutes, rotating the pans and swapping shelves once during baking. The cookies are done when they’re slightly puffed and just starting to turn a darker shade of golden around the edges. Cool completely.
6. While the cookies cool, make the frosting: Melt the butter in the microwave, then whisk in the cocoa powder. Add the milk and vanilla, and whisk until frothy. Make sure the cocoa powder has completely dissolved. With a hand mixer or by hand with a whisk (and a strong arm!), work the powdered sugar into the liquids a little at a time until fully incorporated. The frosting should be thick but spreadable. If runny, add more powdered sugar; if too stiff, work in a teaspoon of milk.
7. Cut out Jack-o’-Lantern faces: Set aside half of the cookies as the “bottoms”. With the remaining cookies, use a sharp paring knife to cut a notch from the top of the cookie for the pumpkin stem and then to cut jack-o’-lantern faces.
7.5. Make the “pumpkin” lines (optional): This is optional because scoring the pumpkin lines is adorable, but can make the cookie a bit fragile. Use a paring knife to score 3 to 4 lines down each cookie to make pumpkin-like lines. Press lightly, just enough to make a clear line. The dull edge of a butter knife works well for this too, pressing the lines rather than breaking the surface of the cookie.
8. Assemble the sandwich cookies: Spread a thick layer of frosting over the “bottom” cookies. Top with Jack-o’-Lantern cookies. Add an extra dollop of frosting in the notch at the top for the stem.
Enjoy! These cookies are best if eaten within 2 to 3 days. Store in an airtight container on the counter.