Jack-o'-Lantern Chocolate Cookies (Print Version)

Festive chocolate pumpkin cookies with orange cream cheese filling, perfect for Halloween parties and fall celebrations.

# Ingredients:

→ For the chocolate sugar cookies

01 - 2 1/2 cups (318 grams) all-purpose flour
02 - 1/2 cup (50 grams) Dutch-process cocoa powder
03 - 1 teaspoon baking powder
04 - 1/4 teaspoon fine sea salt
05 - 1 1/2 sticks (170 grams) unsalted butter, at cool room temperature
06 - 1 cup (200 grams) granulated sugar
07 - 2 large eggs, at cool room temperature
08 - 1 teaspoon pure vanilla extract

→ For the cream cheese frosting

09 - 4 ounces (113 grams) cream cheese, at room temperature
10 - 4 tablespoons (57 grams) unsalted butter, at room temperature
11 - 2 teaspoons vanilla extract
12 - 1 1/2 cups (188 grams) powdered sugar, sifted
13 - A few drops of orange gel food coloring

# Steps to Follow:

01 - Sift together the flour, cocoa powder, baking powder, and salt in a medium bowl.
02 - In a large bowl, use an electric mixer to beat the butter and sugar on medium-high speed until smooth and well combined for 1 to 2 minutes. Add the eggs, one at a time, until well combined. Add the vanilla extract. Gradually add the flour mixture on low speed, beating until thoroughly combined.
03 - Place the dough between two large pieces of parchment paper or silicone mats on a work surface. Roll it out to 1/4-inch thickness. Chill in the refrigerator for at least 1 hour, or in the freezer for about 30 minutes, until firm.
04 - Line large baking sheets with parchment paper. Use a pumpkin-shaped cookie cutter to cut out shapes from the dough and place them on the prepared baking sheets. For half of the cookies, cut out triangle eyes and mouth shapes to create the jack-o'-lantern faces. Reroll remaining scraps to 1/4-inch thickness and repeat the process. Chill the cut cookie dough in the refrigerator for 30 minutes or in the freezer for 15 minutes, or until firm.
05 - Preheat the oven to 350°F. Bake the cookies for 8 to 9 minutes, until set but not overbaked. Let them cool on the baking sheets for 5 minutes before transferring to a wire rack to cool completely.
06 - In the bowl of a stand mixer fitted with the paddle attachment, beat the cream cheese, butter, and vanilla on medium-high speed until light, creamy, and smooth for 2 to 3 minutes. Gradually add in the powdered sugar on low speed, beating until fluffy, about 2 more minutes. Add in orange gel food coloring to achieve the desired shade.
07 - Place a dollop of cream cheese frosting on the top side of the plain pumpkin-shaped cookies. Place a jack-o'-lantern cookie on top of each, pressing down slightly to sandwich the filling. Serve or store in an airtight container at room temperature for up to 2 days. For longer storage, refrigerate.

# Additional Notes:

01 - Natural unsweetened cocoa powder can be substituted for Dutch-process cocoa, though the cookies may turn out drier in texture and lighter in color.

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