Homemade Chocolate Sandwich Cookies with Filling

I think originally this may have been a "martha" recipe - and I say that only because in my files I see that the background color to the photo is baby blue (she uses that a lot) and the little cookies have an oval tag with cute packaging and again, she uses that a lot! But it's from one of my files and although it was obviously used as a Christmas cookie at the time... that is not my plan!

This is a chocolate wafer sandwich cookie with a simple icing filling inside and I pictured using a peppermint flavored filling or a vanilla filling. Tinting the peppermint a light green and leaving the icing untinted for the vanilla to show it's white.

Now, if I had decided to make these last weekend I would have used red, white and blue fillings - all flavored with vanilla! As it is I think a fabulous idea is to tuck this away in your files and in October, use ORANGE colored icing filling for Halloween! How fun is that!?

oil cooking spray
3/4 c flour, plus more for dusting
1/3 c unsweetened cocoa powder
1/8 t salt
6 T (3/4 stick) unsalted butter, softened
3/4 c confectioners' sugar, sifted
1 large egg
1/2 t vanilla extract

Cookie Filling

Makes 1 cup (enough for 15 sandwich cookies)

6 tablespoons (3/4 stick) unsalted butter, softened
2 cups confectioners' sugar (sifted)
peppermint or vanilla extract

With an electric mixer on medium-high speed, beat butter until smooth. Add confectioners' sugar, and beat until light and fluffy. Stir in one of the flavorings.

Line baking sheets with parchment paper; lightly coat with cooking spray. Whisk together flour, cocoa, and salt. With an electric mixer on medium-high speed, cream butter and confectioners' sugar until pale and fluffy. Beat in egg and vanilla. With mixer on low speed, gradually add flour mixture, beating to combine. Divide dough in half; form into disks, and wrap in plastic. Chill until firm, at least 2 hours, or up to 2 days. (Dough can be frozen up to 2 months; thaw in the refrigerator before using.)

Working with one disk at a time, roll out dough to a 1/8-inch thickness on a lightly floured surface. Using a 1 1/2-inch square biscuit or cookie cutter, cut out shapes, transferring to prepared sheets (1 inch apart) as you work. Chill in freezer until firm, about 15 minutes. Brush off excess flour. Gather together scraps; roll, chill, and cut out more shapes.

Preheat oven to 325 degrees. Bake cookies, rotating sheets halfway through, until edges are firm, 12 to 14 minutes. Transfer cookies, on parchment, to a wire rack to cool completely.

Spread a small amount of filling on the bottom of half the cookies. Top with remaining cookies; gently press to adhere. Assembled cookies can be refrigerated up to 2 days in an airtight container.Print Friendly and PDF