Chocolate Caramel Cream Sandwiches

Make these.  You won't regret it!  I was at a conference when I thought of these cookies.  I don't really remember the details of what made me think of them, but I do remember having an overwhelming urge to go home and make them.  There wasn't time that week, but a week or two later, I finally got the chance to try out the idea.  I just love how tiny and chocolaty they are.  Plus, you really can't go wrong when you add caramel frosting to something...

Notes:
If you don't have black cocoa powder, then replace it with regular cocoa powder.  I order black cocoa powder from the King Arthur Flour Company.  I only flatten the dough balls so that there are fork marks in one direction.  If you like hatch marks, then press them twice with a fork in opposite direction, but aim to keep the cookies a little more than a ¼-inch thick.  You can use non-fat milk in the frosting.  These cookies freeze well. 

Adapted from Poppin' Fresh HomeMade Cookies, October 1989(?) issue

Dough Ingredients:
1½ cups all-purpose flour
½ cup cocoa powder
2 tablespoons black cocoa powder
⅛ teaspoon salt
1 cup unsalted butter, room temperature
¾ cup light brown sugar
1 egg yolk
1 teaspoon vanilla
granulated sugar for flattening cookies

Frosting Ingredients:
2 tablespoons unsalted butter
1¼ cups powdered sugar
1 teaspoon vanilla
3-4 teaspoons milk

Yields approximately 3 dozen sandwich cookies

Sift, Mix, Chill:
In a medium-sized bowl, sift together the flour, cocoa powders, and salt, and set aside.  In a separate bowl, cream together the butter and brown sugar until it is light and fluffy.  Add the egg yolk and vanilla, and beat until they are incorporated.  Gently beat in the flour mixture in halves.  Shape the dough into a disc, wrap in plastic wrap, and refrigerate until chilled, 2-3 hours or overnight.

Roll and Bake:
Adjust the oven racks to the upper and lower thirds of the oven, and preheat to 325°F. Line 2 cookie sheets with parchment or Silpat mats.  Break off a teaspoon (~8 grams) of dough, and roll it into a ball.  Place the ball on the prepared cookie sheet, and repeat until all of the dough has been shaped or the cookie sheets are full.  Pour some granulated sugar into a shallow dish.  Dip the tines of a fork into the sugar and press down gently for three seconds on each dough ball and flatten until they are a little more than a ¼-inch thick.  Dip the fork tines in the sugar between each cookie.  Once all of the cookies have been flattened, bake them at 325°F for 10-14 minutes until the cookies are set, rotating the sheets halfway through.  Transfer the baked cookies to a wire rack to cool.   

Make the Frosting:
Sift the powdered sugar into a medium-sized bowl, and set aside.  Place the butter in a small skillet, and heat it until it is golden brown.  Pour the browned butter (along with the solids) into the bowl with the powered sugar, add the vanilla and two teaspoons of milk, and stir well.  If the frosting is too thick, add more milk, a teaspoon at a time, stirring well after each addition.  Use immediately. 

Fill the Cookies:
Take the cookies, and make pairs of the cookies that look alike (i.e., match the size and shape of the cookies).  Place the pairs side by side on a cookie sheet or plate with the bottoms facing up.  Fill a medium-sized Ziplock or piping bag with the frosting.  Try your best to place the frosting towards one of the bottom corners of the bag, as opposed to just frosting the entire bag.  Secure the top of the bag with a twist tie just above where the frosting ends, and snip off the bottom corner of the bag that you placed the frosting in.  Pipe a mound of frosting on the bottom of one of the cookies for each pair.  Don’t put the frosting all the way to the edge of the cookie, because when the cookies are sandwiched, it may ooze out.  After one cookie from each pair has frosting on it, place the second cookie on top of the frosting to form a sandwich, and gently push down so it is securely attached.  Store the filled cookies in an airtight container in the refrigerator or freezer, and bring to room temperature for serving. 

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