Chocolate Kahlúa Sandwiches

I was a little uncertain about these cookies at first.  I'd had this idea of a cookie styled after a White Russian in my head for several weeks now.  They were going to be rich, creamy, and taste exactly like the drink.  

These cookies are rich and creamy, but they certainly don't taste quite like a White Russian.  They're more like a coffee-flavored version of a Dare Chocolate Fudge cookie, which happened to be my favorite store-bought cookie when I lived in Atlanta.

When I first tried a finished cookie, I liked it, but it just wasn't what I was expecting it to be.  Sometimes it is hard to accept that a cookie tastes amazing even though it doesn't fit your vision.  Luckily I decided to share a few with friends, and they were able to confirm that these cookies are super yummy, even if they don't taste exactly like the drink that inspired them.  

Notes:
Use low speed when you add the vanilla and Kahlúa to the cookie dough to keep the liquid from splattering all over the place.  This dough freezes well.  The espresso powder may make the dough look a little speckled, but it won't be too obvious in the finished cookies.  I like to roll cookies out between a piece of parchment paper and plastic wrap, as opposed to rolling them out with flour, because it keeps the scraps from getting too floury and the "second roll" of the scraps will yield cookies more similar to the first roll of the dough.  Also, I like to freeze the rolled dough (on a cookie sheet to prevent wrinkling) before cutting it so I can get nice edges for the cookies.  Freezing the dough again, before the cut cookies are transferred to the baking sheet, keeps the cookies from getting distorted when you transfer them.  That being said, if you like to roll cookies on the countertop with flour and transfer them directly to the baking sheet, go ahead and do it that way.  If you like crispier cookies, roll the cookies so they are ⅛-inch thick like I did; if you like softer cookies, roll them to somewhere between ⅛- and ¼-inch thick. 

I like to bake the cookies one day and then fill them the next day to make the process more manageable.  The regular cocoa powder that I use is Natural High Fat Cocoa from Penzeys Spices.  The black cocoa powder that I use is from King Arthur Flour.  I used the black cocoa powder for the filling in this recipe because it made it dark and chocolaty.  If you don't have black cocoa powder, just use regular cocoa powder, but keep in mind that your filling won't be as dark as mine.  I keep the finished cookies in the refrigerator because the filling has heavy whipping cream in it.  If you'd rather keep the cookies at room temperature, replace the cream with additional Kahlúa or water. 

Dough recipe adapted from an undated newspaper clipping in my great-grandmother's 1933 datebook. 

Dough Ingredients:
3½ cups all-purpose flour
½ teaspoon salt
2 teaspoons espresso powder
1 cup unsalted butter, room temperature
1½ cups light brown sugar
2 eggs
2 tablespoons Kahlúa, or other coffee-flavored liqueur
1 teaspoon vanilla extract

Filling Ingredients:
¼ cup (½ stick) unsalted butter, room temperature
2 cups powdered sugar, sifted
3 tablespoons Kahlúa, or other coffee-flavored liqueur
1½ tablespoons heavy whipping cream
½ teaspoon vanilla
pinch of salt
¼ cup cocoa powder, sifted
¼ cup black cocoa powder, sifted

Yields about 4 dozen sandwich cookies

Mix:
In a medium-sized bowl, whisk together the all-purpose flour, salt, and espresso powder, and set aside.  In a separate bowl, cream together the butter and light brown sugar.  Add the eggs, one at a time, beating until they are fully incorporated.  On low speed, beat in the vanilla and Kahlúa, then add half the flour mixture in halves, and beat until the dough begins to come together.  Shape the dough into 3 discs and wrap them in plastic wrap.  Place the dough in the fridge to chill for at least an hour, or overnight.  At this point, you can also freeze the dough. 

Roll and Bake:
Remove the dough from the refrigerator, and allow it to warm up for a few minutes.  If the dough is too cold when it is rolled out, it will crack and be difficult to work with.  Place the dough in the middle of a piece of parchment paper, and put a sheet of plastic wrap over the top of the dough.  Roll the dough, adjusting the plastic wrap as needed to prevent large wrinkles, until it is about ⅛-inch thick.  Slide the dough (with the parchment paper and plastic wrap) onto a cookie sheet, and place the dough and the cookie sheet in the freezer.  Repeat with the remaining dough discs. 

Preheat the oven to 350°F, and line two cookie sheets with Silpat mats or parchment paper.  Remove the first piece of rolled dough from the freezer, and take off the plastic wrap.  Use a cookie cutter to cut the dough into your desired shapes, then transfer the piece of dough back to the freezer.  Repeat with the remaining rolled dough pieces.  Going back to the first piece of (now cut) dough, remove it again from the freezer and transfer the cut shapes with an off-set spatula onto the prepared cookie sheets.  Fill the two sheets, and bake the cookies at 350°F for 8-10 minutes, or until they are set and the edges are just about to turn golden brown.  Allow them to cool on the sheet for 5 minutes, then transfer the cookies to a cooling rack.  Gather the dough scraps together, and form them into a ball.  Roll out the dough ball, and repeat the process until all of the scraps are gone. 

Make the Filling:
Once the cookies are cool, make the filling.  Beat the butter until it is creamy and light.  Add half of the powdered sugar and the Kahlúa, and beat until they are incorporated into the butter.  Scrape the beater and bowl, add the remaining powdered sugar and heavy whipping cream, and beat well.  Lastly, scrape the beater and bowl again, add a pinch of salt, both types of cocoa powder, and the vanilla, and beat for 3 minutes or so until the frosting is fully mixed and fluffy.  If the frosting seems too dry, add additional Kahlúa; if it is too wet, try beating it a little longer to dry it out, or add additional powdered sugar.

Fill the Cookies:
Pairs up the cookies, and place them side by side on a cookie sheet or plate with the bottoms facing up.  Fill a large Ziplock or piping bag with the filling.  Try your best to place the filling towards one of the bottom corners of the bag, as opposed to just filling the entire bag.  Secure the top of the bag with a twist tie just above where the filling ends, and snip off the bottom corner of the bag that you placed the filling in.  Pipe some filling on the bottom of one of the cookies for each pair.  Don’t put the filling 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 filling on it, place the second cookie on top of the filling to form a sandwich, and gently push down so it is securely attached.  Store the cookies in an airtight container in the refrigerator.  Allow the filling to warm up a little bit before serving.  

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