Chocolate Shortbread Sandwich Cookies Recipe

Photograph: Yvonne Ruperti

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

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.

Recipe Facts

Active: 30 mins
Total: 2 hrs
Makes: 18 to 24 cookies

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  • 8 ounces bittersweet chocolate, finely chopped
  • 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


  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. 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 and place evenly on baking sheets. Cut centers out of half of the cookies. 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.

Special equipment

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