Nothing could be more tender and delicate than these chocolate cookies.  That’s why I like to sandwich them with delicate milk chocolate.  The dough is quite soft – I recommend rolling it, then chilling it again before cutting to make the process easier – it takes a little longer but it’s much easier then dealing with the frustration of trying to handle a really soft dough.

Makes about 24 sandwich cookies

Chocolate Cookie Dough

8 ounces (2 sticks) unsalted butter, very soft

6 ounces semisweet chocolate (no more than 55% cocoa solids), melted and cooled

2 1/2 cups all-purpose flour (spoon flour into dry-measure cup and level off)

1/2 cup confectioners’ sugar, sifted after measuring

Milk Chocolate Filling

3 ounces milk chocolate, melted and cooled

3 tablespoons unsalted butter, very soft

2 cookie sheets or jellyroll pans covered with parchment or foil

  1. For the dough, place the butter in a bowl and use a large rubber spatula to beat it smooth.  Scrape in the chocolate and stir it into the butter (if the chocolate is still warm the butter will melt and the dough will be ruined).  Add the flour and confectioners’ sugar and stir in to form a soft dough.
  2. Scrape the dough out onto a piece of plastic wrap and cover with more wrap.  Press the dough with the palm of your hand to make it about 1/2-inch thick.  Slide the dough onto a cookie sheet and refrigerate it until firm, an hour or two or up to 3 days.
  3. When you are ready to bake the cookies, set racks in the upper and lower thirds of the oven and preheat to 350 degrees.
  4. Remove the dough from the refrigerator and divide it into 3 pieces. Place one piece of dough on a floured work surface and return he remaining pieces to the refrigerator.  Lightly flour the dough and gently press it with the rolling pin to soften slightly before rolling.
  5. Roll the dough about 1/4-inch thick.  Use a  2 to 2 1/2-inch fluted  round cutter to cut the dough into disks, lifting them with a small spatula and arranging them about 2 inches apart all around on the prepared pans.  Place the scraps from cutting the cookie in a small bowl and refrigerate them.  Repeat with the remaining dough, then re-roll the scraps to make more cookies.
  6. Bake the cookies until they are firm and dull looking, about 15 to 20 minutes.  After the first 7 or 8 minutes, place the pan from the lower rack on the upper one and vice versa, turning the pans back to front at the same time.  Slide the cookies to racks to cool. 
  7. While the cookies are baking, whisk the chocolate and butter together. 
  8. To fill the cookies, turn half the bases over so that the flattest sides are facing upward.  Pipe or spoon a dab of the filling on each upturned cookie.  Top with the other cookies, gently pressing them together.  Immediately before serving dust very lightly with confectioners’ sugar.  Keep the cookies between sheets or wax paper in a tin or plastic container with a tight-fitting cover, in a cool place.