How To Make Halloween Pumpkin Cookies

Directions

1. Set your oven to 325°F. Position one rack in the top third and another in the bottom third. Line two baking sheets with parchment paper or silicone baking mats.
2. In a stand mixer or a large bowl using a hand mixer, beat the softened butter, granulated sugar, and brown sugar until smooth. Add the pumpkin puree and mix. Beat in the eggs one at a time. In another bowl, whisk together the flour, baking soda, salt, and pumpkin pie spice. Gradually add the dry mixture to the wet mixture, stirring until just combined. If you want a more vibrant orange, add a few drops of orange food coloring.
3. Place the dough in the refrigerator and chill for 30 minutes.
4. Scoop up about 2 tablespoons of dough per cookie and place onto the prepared baking sheets, spacing them a few inches apart. You should end up with roughly 24 cookies.
5. Moisten your fingers with water and press each dough mound flat to about 1/4 inch thickness.
6. Bake for 10 to 12 minutes, rotating the pans and swapping their shelves halfway through. The cookies are ready when they are slightly puffed and the edges have just started to turn a deeper golden. Let them cool completely.
7. While the cookies cool, prepare the frosting. Melt the 1/4 cup butter in the microwave, then whisk in the cocoa powder. Add the milk and vanilla and whisk until frothy and the cocoa is fully dissolved. Using a stand mixer with the beater attachment, a hand mixer, or a whisk (and some elbow grease), gradually incorporate the powdered sugar into the liquid mixture until smooth. The frosting should be thick but spreadable. If it's too thin, add more powdered sugar; if too stiff, mix in a teaspoon of milk.
8. Set aside half of the cookies to serve as the bottoms. For the remaining cookies, use a sharp paring knife to cut a small notch from the top of each to create a stem, then cut out jack-o'-lantern faces.
9. Optionally, use the paring knife to lightly score 3 to 4 lines down each cookie to mimic pumpkin ridges. Press gently—just enough to leave a clear mark. The dull edge of a butter knife also works well for pressing lines without cutting into the cookie.
10. Spread a generous layer of frosting on the bottom cookies. Place the jack-o'-lantern cookies on top. Add an extra dab of frosting in the stem notch to finish.
11. These are best enjoyed within 2 to 3 days. Store them in an airtight container at room temperature.