Jack-O-Lantern Chocolate Cookie Sandwiches

Prep & Cook Time 1 hr
Serves 1 dz


Chocolate Cookies:

1 cup unsalted butter softened

1 cup granulated sugar

1 egg

2½ cups all-purpose flour

½ cup Kemps Chocolate Milk

⅓ cup cocoa powder

⅓ cup semi-sweet chocolate melted (2.6 ounces)

½ teaspoon baking powder

¼ teaspoon salt

Buttercream Filling:

1 cup unsalted butter softened

4½ cups powdered sugar

2 teaspoons vanilla extract

4 tablespoons heavy cream

3-4 drops orange food coloring

How to

To make the chocolate cookies:

Preheat oven to 350 degrees.

In a stand mixer fitted with the paddle attachment or a hand mixer, beat the butter and sugar on high until fluffy (1 minute).

Add in egg, chocolate milk and melted chocolate, mix until combined. Scrape down the bowl once complete.

In a separate bowl, whisk dry ingredients (flour, cocoa powder, baking powder, salt).

Add dry ingredients to wet ingredients in 4 portions, mixing well after each addition. Scrape down the bowl once complete.

Pour the dough on to a well-floured surface. Sprinkle flour over the dough and on a rolling pin, and roll the dough out until about ~1 cm thick. Add more flour as you roll if the dough seems sticky.

Use a large pumpkin cookie cutter (at least 4-5 inches wide) to cut out cookies. Place them on a well-greased cookie sheet or line with parchment paper.

Once the cookies are placed on the pan, use the tip of a sharp knife to cut out jack-o-lantern faces in half of the cookies.

Bake at 350 degrees for 8-10 minutes or until the edges start to crisp.

Remove them from the oven and allow to cool to for 10-15 minutes, then transfer them to a cooling rack for assembly.

To make the buttercream filling:

In a stand mixer fitted with the paddle attachment or a hand mixer, beat the butter until smooth.

Add 1 cup of powdered sugar, heavy cream and vanilla extract. Mix until combined.

Add remaining powdered sugar, 1 cup at a time, mixing well after each addition.

After using 4 cups of powdered sugar, taste the frosting and add more if desired.

Add 3-4 drops of orange food coloring and mix well. Add additional drops to achieve desired color.

To assemble the cookies:

Place the frosting in a piping bag or gallon bag. Cut a 1 cm tip.

Pipe frosting evenly throughout the bottom half of the cookie sandwich (the cookie without the jack-o-lantern cutout).

Place the cookie with the jack-o-lantern cutout over the frosting and press lightly.

Enjoy at room temperature.