- 1 + 1/4 cups All-purpose flour
- 1/2 cup unsweetened natural cocoa powder
- 1 teaspoon baking soda
- 1/8 teaspoon salt
- 1/2 cup unsalted butter, softened to room temperature
- 3/4 cup granulated sugar
- 1/4 cup packed light brown sugar
- 1 large egg, at room temperature
- 1 teaspoon vanilla extract
- 1/4 cup unsalted butter, softened to room temperature
- 1/4 cup vegetable shortening, room temperature
- 1 + 3/4 cups confectioners’ sugar
- 1 teaspoon vanilla extract
- Food coloring (optional)
- Be sure to remove the butter and egg from the refrigerator and bring both to room temperature. It is really important that the butter be at room temperature because if it is too cold, then it won’t cream properly later on!
- Make the cookies: In a medium bowl, mix together the flour, cocoa powder, baking soda, and salt. Set aside.
- In a separate large bowl, use an electric handheld or stand mixer to beat the butter on high speed until creamy (about 1 minute). Scrape down the sides of the bowl, if needed. Switch the mixer to medium speed and add both the granulated and brown sugar until combined. Here’s a quick how-to if you’ve never creamed butter and sugar together. Beat in the egg and vanilla extract until just combined. Turn the mixer off.
- Gradually add the dry ingredients (1 cup at a time) to the wet ingredient mixture and mix on low until all of the dry ingredients have been combined and a dough is formed. Take the dough and gently roll in on the counter to form a ball. Place the dough back into the bowl, cover with plastic wrap, and chill for 30 minutes. Sorry, chilling is mandatory.
- Preheat oven to 350F degrees. Remove the cookie dough from the refrigerator. Line two large baking sheets with parchment paper or silicone baking mats. Set aside.
- Roll the dough into small balls (about 2 teaspoons of slightly chilled dough per ball) and place 12 on each baking sheet. Press down on the balls to flatten slightly and bake each batch for 6-8 minutes. These cookies are small and bake very quickly and they will appear soft when done. Remove from the oven and allow to cool for at least 5 minutes on the baking sheet before transferring to a wire rack to cool completely. Repeat until all of the cookie dough has been used (or eaten!).
- Make the cream filling: In a small bowl using a handheld or stand mixer, beat the butter and shortening together on high speed until creamy and combined (about 1 minute). Turn the mixer off and add the confectioners’ sugar and vanilla. If you wish to have a festive orange cream filling, then also add a few drops of red and yellow food coloring. Beat on low for 1 minute and then switch to high and beat for 1 more minute until creamy and combined. The cream filling is thick.
- Carefully spoon the filling into a quart-sized ziploc bag. Here’s a quick how-to video that shows how easy it is to make and use your own pastry bag! Pipe the cream filling between two cooled chocolate cookies. Repeat with the rest.
Cookies stay fresh covered at room temperature for up to 1 week. Cookies freeze well, up to 2 months. Cream filling may be made ahead of time (up to 2 days in advance). Cover and chill when storing. Allow to come to room temperature before using.