Jack-o'-Lantern Chocolate Sugar Cookies

Directions

1. In a medium bowl, whisk together the 2 1/2 cups (318g) flour, 1/2 cup (50g) Dutch-process cocoa, 1 teaspoon baking powder, and 1/4 teaspoon fine sea salt.
2. Using an electric mixer on medium-high, beat 1 1/2 sticks (170g) butter and 1 cup (200g) granulated sugar in a large bowl until smooth, about 1–2 minutes. Add 2 eggs one at a time, mixing well after each, then stir in 1 teaspoon vanilla. Reduce speed to low and gradually add the flour mixture, mixing just until combined.
3. Place the dough between two large sheets of parchment paper or silicone baking mats on a flat surface. Roll to a 1/4-inch thickness. Refrigerate until firm, at least 1 hour, or freeze for about 30 minutes.
4. Line large baking sheets with parchment. Using a pumpkin-shaped cookie cutter, cut shapes from the dough and transfer to the prepared sheets. For half of the pumpkins, cut out triangle eyes and a mouth shape.
5. Gently gather the dough scraps, reroll to 1/4-inch thickness, and repeat the cutting process. If the dough becomes too soft, chill it again in the freezer or fridge until firm before cutting and moving shapes.
6. Chill the baking sheets of cut cookies in the refrigerator for 30 minutes or in the freezer for 15 minutes, until firm. Meanwhile, preheat the oven to 350°F.
7. Bake for 8–9 minutes, until the cookies are set but not overdone. Let cool on the baking sheets for 5 minutes, then transfer to a wire rack to cool completely. Plain cookies can be stored in an airtight container at room temperature for up to 3 days or frozen for up to 2 months.
8. In a stand mixer with the paddle attachment, beat 4 ounces (113g) cream cheese, 4 tablespoons (57g) butter, and 2 teaspoons vanilla on medium-high until very light and creamy, about 2–3 minutes. Reduce speed to low and gradually add 1 1/2 cups (188g) sifted powdered sugar, beating until fluffy, about 2 minutes more. Add a few drops of orange gel food coloring until you reach the desired shade.
9. Place a dollop of the cream cheese frosting in the center of each plain pumpkin cookie. Do not frost the bottom side so the stem outlines align. Top each with a jack-o'-lantern cookie (the one with the face cutouts), pressing gently to sandwich the filling. Serve immediately or store in an airtight container at room temperature for up to 2 days (the sugar in the frosting acts as a preservative, but do not keep at room temperature longer).