These are buttery chocolate shortbreads smashed together with a sweetened thick icing.
Better-than-Oreo Chocolate Sandwich Cookies
adapted from the Totally Chocolate Cookbook
2 sticks butter, softened (I used one salted, one unsalted and it was perfect)
1 cup powdered sugar, sifted
1 tsp. vanilla
1+1/2 cups cake flour OR 1 cup + 2 T. all purpose flour AND 2 T. cornstarch (I used the cornstarch)
1/2 cup unsweetened cocoa powder, sifted
1/4 tsp. salt
1/3 cup vegetable shortening
1+2/3 cup powdered sugar
2 T. milk or heavy cream
pinch of salt
1/2 tsp. vanilla extract
For the cookies, beat butter with an electric mixer until smooth and fluffy. Add sugar and vanilla and mix in. In a separate bowl combine flour, cocoa powder, and salt. Add the flour mixture to butter mixture and mix until there are no streaks of white. Do not over mix. If it is sticky (which it should be) wrap in plastic wrap in a flattened disc and refrigerate until somewhat firm – 30 minutes to an hour.
Divide the dough in half and keep one half in the fridge while you roll out the other. Turn out onto a well-floured surface and roll until 1/4 inch thick. Be sure to check the dough as you are rolling it out to make sure it isn’t sticking. Flip over and re-flour as necessary. Cut out rounds of dough (about 2 inches) using a cookie cutter, drinking glass, or champagne glass (if you’re feeling fancy). It is very helpful to flour your cookie cutter every few cookies so the dough doesn’t get stuck. Space the cookies apart about a 1/2 inch on an unlined, ungreased cookie sheet. Be careful transferring them as the dough is fragile. I used a thin metal spatula to keep from crushing the edges. Refrigerate the cookies on the sheet until firm again, while you finish rolling out the rest of the dough (10 minutes should be about right). Re-roll scraps and use as much as possible without overworking the dough.
With the cookie sheets of cookie rounds still in the fridge, preheat the oven to 350 degrees F. When preheated, remove the cookie sheets from the fridge and bake the cookies for 18-20 minutes, switching racks and rotating the sheets halfway through to ensure even baking. Cookies should be slightly firm to the touch. Be careful not to over cook them. Since they are already dark, it can be hard to see if they’re done by their color. Let cool and prepare the filling.
For the filling beat the shortening with an electric mixer to loosen it up. Add sugar and half the milk, beating to incorporate. Add remaining ingredients and stir until smooth.
To frost, dab a spoonful of the filling on the bottom of a cooled cookie. Top with another cookie and gently wiggle and smoosh it to distribute the frosting evenly or just spread it on one cookie evenly before putting the second cookie on top. Repeat with remaining cookies. Enjoy with milk. I found this made just the right amount of filling for my cookies, but it depends how much you put on and how many cookies you end up with. You can always measure out the filling and divide it exactly between the cookies.
As a side note: I decided to get rid of the post numbering. Does anyone really care how many “posts” I’ve written? Probably not. If you do, let me know 🙂 Thanks for reading as always.