Chocolate Shortbread Sandwich Cookies Recipe

Chocolate does double duty in these crunchy shortbread cookies sandwiched with a creamy and decadent dark chocolate ganache.

Chocolate shortbread sandwich cookies arranged around a pint-size canning jar of milk.

Serious Eats / Yvonne Ruperti

Around this time of year, the inn that I worked at many years ago used to host a holiday tree lighting on their front lawn. As pastry chef and resident cookie elf, I'd be responsible for baking close to a thousand cookies for the event. Some might find that kind of a task a chore, but for some reason I get a lot of pleasure from turning out cookies in high volume. From composing the cookie list to seeing the cookies all neatly arranged on platters, it just never felt like work.

Among my favorite cookies from the trays were the chocolate on chocolate versions. When tossed into a cookie assortment, anything doubly chocolatey stands out as the gem, and never fails to be the first to get swiped up. Chocolate on chocolate is pure decadence. Take these chocolate shortbread sandwich cookies—crisp, buttery, chocolatey shortbread is already a super rich, appealing cookie. But sandwich that together with a luscious piping of creamy, ultra dark chocolate ganache? Now this is a cookie that will make any chocolate cookie lover weak.

To make these cookies even more irresistible, I pulled out an adorable flower shaped cutter from my bento box cutter collection. After cutting out the cookies from the rolled dough and placing them on the baking sheets, I used the back end of a pastry tip to cut out the center of half of the cookies. That way, the pretty swirl of ganache would show through the top cookie. If you want to go over the top, dip the edge of the finished cookie in melted chocolate. And if you're looking to really jazz them up for the holidays, do what I like to do: dunk the chocolate-dipped cookie in sprinkles.

November 2012

Recipe Details

Chocolate Shortbread Sandwich Cookies Recipe

Prep 30 mins
Cook 15 mins
Active 30 mins
Cooling Time 40 mins
Total 85 mins
Makes 18 to 24 cookies
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Ingredients

  • 8 ounces bittersweet chocolate, finely chopped (see note)

  • 3/4 cup heavy cream

  • 2/3 cup (2 2/3 ounces) plus 1 tablespoon confectioners sugar, divided

  • 16 tablespoons (8  ounces) unsalted butter, softened

  • 1/2 cup (3 1/2 ounces) granulated sugar

  • 1/2 teaspoon pure vanilla extract

  • 1/4 teaspoon salt

  • 2 cups (10 ounces) all purpose flour

  • 1/2 cup (1 1/2 ounces) cocoa powder

Directions

  1. Place chocolate in medium bowl. Heat cream in small saucepan over medium heat until simmering. Pour over chocolate and let sit 5 minutes. Add 1 tablespoon confectioners' sugar, whisk until smooth, then chill until set, about 1 hour.

  2. In stand mixer fitted with paddle attachment, mix remaining 2/3 cup confectioners' sugar, butter, granulated sugar, vanilla, and salt on medium low speed until creamy. Mix in flour and cocoa until completely combined. Wrap dough in plastic wrap, forming a 6-inch disc and chill until firm, about 30 minutes.

  3. Adjust oven racks to medium low and medium high positions. Preheat oven to 350°F (175°C). Line two rimmed baking sheets with parchment paper.

  4. Divide dough in half. On lightly floured surface, roll dough to 1/8-inch thick. Cut out cookies with cutter (see note) and place evenly on baking sheets. Cut centers out of half of the cookies (see note). Bake until firm, 10 to 12 minutes, rotating pans from top to bottom and front to back halfway through baking. Let cool 5 minutes on pans, then transfer cookies and parchment to cooling rack to cool completely before filling. Repeat with any remaining dough.

  5. Place pastry tip in pastry bag and fill bag with chocolate mixture. Pipe a thin layer onto each of the cookie bottoms. Sandwich together with the top cookies and serve. See note.

Special Equipment

Standing mixer, 2 rimmed baking sheets, cookie cutter, pastry bag, pastry tip

Notes

For best flavor, use a good quality bittersweet chocolate.

Any size or shape cookie cutter will work here. I used a 2 1/2-inch cutter.

The wide end of a pastry tip is useful to stamp the centers from the top cookies.

For extra chocolate appeal, dunk the cookie in melted chocolate.

Nutrition Facts (per serving)
29674 Calories
3,131g Fat
424g Carbs
101g Protein
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Nutrition Facts
Amount per serving
Calories 29674
% Daily Value*
Total Fat 3131g 4,014%
Saturated Fat 1947g 9,735%
Cholesterol 8008mg 2,669%
Sodium 1039mg 45%
Total Carbohydrate 424g 154%
Dietary Fiber 48g 172%
Total Sugars 136g
Protein 101g
Vitamin C 1mg 5%
Calcium 1262mg 97%
Iron 59mg 326%
Potassium 3232mg 69%
*The % Daily Value (DV) tells you how much a nutrient in a food serving contributes to a daily diet. 2,000 calories a day is used for general nutrition advice.
(Nutrition information is calculated using an ingredient database and should be considered an estimate.)