Chocolate Sandwich Cookies

Chocolate Sandwich Cookies

Is it Friday yet?  Boy, what a week, I still feel like I am recovering from the bunnies this weekend!  I am definitely looking forward to a bunny-free weekend.  After all, it is December – time to really start some serious baking.  I am still on the fence as to whether I am going to go with my old standbys, or if I am going to try out some new stuff.  Knowing me, I have to try at least a few new things, but I am also looking forward to these and definitely these.

I have always secretly been intrigued with sandwich cookies.  It has taken me years to figure out why – and I think I finally nailed it.  It is also why my kids seem to go nuts with them as well.  Cookies are great, but sandwich cookies are awesome – you get double the cookie with a bonus of filling.  As a kid, who never got any cookies – to get a sandwich cookie was really hitting the jack pot.  Normally I only let my kids pack one cookie in their lunch as dessert – but when I have sandwich cookies in the house – they get two cookies in one!  Wow, how has this been staring me in the face all this time?

I saw these cookies in Cooking Light, and thought these would be great to kick-start the holiday season.  The chocolate filling was delicious and rich, and the cookies were nice and chewy soft.  Plus, at 156 calories per sandwich, you are really getting a good deal.  You can choose any cookie cutter that floats your boat – we chose hearts and stars.  Then you can make baby cookies out of those shapes – just don’t let them burn, they cook faster than the bigger round cookies.  Now is it Friday yet?



  • 8 ounces cake flour (about 2 cups)
  • 1/2 teaspoon salt
  • 1/4 teaspoon baking powder
  • 1 cup powdered sugar
  • 1/2 cup butter, softened
  • 2 tablespoons 2% reduced-fat milk
  • 1 1/2 teaspoons vanilla extract


  • 1 1/2 ounces bittersweet chocolate, finely chopped
  • 2 tablespoons 2% reduced-fat milk
  • 1/2 cup powdered sugar
  • 2 tablespoons Dutch process cocoa
  • Dash of salt


Preheat oven to 350°.

To prepare cookies, weigh or lightly spoon flour into dry measuring cups; level with a knife. Combine flour, 1/2 teaspoon salt, and baking powder, stirring with a whisk. Place powdered sugar and butter in a large bowl. Beat with a mixer at medium-high speed until well blended. Add 2 tablespoons milk and vanilla; beat 1 minute or until well combined. Add the flour mixture; beat on low-speed until just combined.

Shape the dough into a 6-inch disk. Cover tightly with plastic wrap; chill 30 minutes. Discard plastic. Roll dough to a 1/4-inch thickness on a lightly floured surface. Cut out 36 (2-inch) round cookies, rerolling scraps as necessary. Using a small decorative cookie cutter, cut a heart-shaped opening in 18 rounds. Place cookies 1 inch apart on baking sheets lined with parchment paper. Bake at 350° for 14 minutes or until lightly browned. Cool on a wire rack.

To prepare filling, combine chocolate and 2 tablespoons milk in a microwave-safe dish; microwave at HIGH for 1 minute or until melted, stirring every 15 seconds. Stir just until smooth. Combine 1/2 cup powdered sugar, cocoa, and dash of salt in a bowl, stirring well with a whisk. Add chocolate mixture to sugar mixture; stir just until smooth. (Mixture will thicken as it cools.) Divide chocolate mixture evenly among 18 whole cookies; spread in a thin, even layer. Top each cookie with a cut-out cookie.

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