My holiday baking, when I do it, always contains at least two variants of shortbread.  One will always be the crowd pleasing shortbread cookie, like a cranberry lemon or a chocolate, and the other usually has a bit more Tina-ness to it.  This year I decided to take inspiration from one of my favorite flavor combinations, a classic Mexican mole, and serve it as a sweet rather than a savory.  

These cookies are a surprise and will likely be the most grown-up addition to my cookie plate.  They don’t beg for a tall glass of milk, they want a rich cup of bitter black coffee, or a peppery and dry glass of red…you can guess which one I prefer.  With your first bite you taste chocolate, then you get the headiness of cinnamon and spice, the bitterness of espresso, and finally a breath of heat blows in at the very end.  They’re not overly sweet, but they are decadently sophisticated and rich, asking quietly for you to take a second bite, and then a third.

I can count on two hands the people that I will be serving these cookies to this Christmas who will be as excited about them as I am.  They’re all from the ilk that would rather have a steaming cup of black coffee than a mug of saccharine hot chocolate, and if they DO take the hot chocolate route they like it spiked with chili or bourbon.  However, I also know that those who like it will like it alot.  If you’re a person who’s palette likes to play it a bit closer to the chest, or if you plan on serving this to the kidlets (because evidently I’m the type of person who endorses espresso consumption by wee tots?) you may want to omit the cayenne and increase the sugar….which also means increasing the butter and flour.  But don’t worry, just remember the golden combination of shortbread:  1 part sugar to 2 parts butter and 4 parts flour.

Espresso Mole Shortbread

Makes approximately 3 dozen cookies

• 1.5 cups + 1 tbsp unsalted butter at room temperature
• 3/4 cup confectioners sugar
• 1/2 tsp salt
• 2 tbsp instant espresso powder
• 2 tbsp very hot water
• 1 tbsp vanilla
• 3 cups sifted all purpose flour *
• 3/4 tsp cayenne pepper
• 1.5 tsp cinnamon
• 1/2 tsp allspice
• 6 oz semisweet dark chocolate

* We all know that I just lied about that, and will only sift my flour if I’m under intense public scrutiny and have no other alternative.

Cream together the 1.5 cups of butter with the confectioners sugar and salt.  You can do this easily in a large mixing bowl with a wooden spoon, but I’ve been putting my stand mixer into overdrive lately.  Beat them together  until they’re nice and fluffy with no lumps or clumps remaining.

Measure the powdered instant espresso into a small bowl and pour the hot water overtop.  Stir this until it’s nice and syrupy.

Add the espresso and vanilla to the creamed sugar and butter and mix it until combined.  

Follow that with the spices and give it another good mix.  Don’t forget to scrape down the sides of the bowl as you go!  

Add the flour and continue mixing until the dough looks uniform.  Scrape the bottom of the sides one more time with a spatula, urging it into a bit of a ball.

Turn the dough onto a generously large piece (or two) of plastic wrap and make sure that it has a nice tight seal.  Tuck the cookie dough into your fridge to chillax for at least two hours or overnight.

When the cookie dough is released from it’s winterly jail, you’ll notice something important:  it’s SOLID.  I mean, harder than The Rock’s pecs at an extreme flirting competition – and that’s pretty darn firm, if you ask my active imagination.  Let it rest until it starts to come up to room temperature, and I promise you that it will soften enough that it’s workable.  As soon as it’s just soft enough that you can cut it fairly easily, do so.  Turn that sucker into a 6 x 6 checkerboard, and preheat the oven to 325F.

If you’re like me, your dough is NOT in a perfect square…or even a perfect oval.  It’s more like that cousin with the lazy eye and slight hunchback.  This means that when you cut the checkerboard the pieces in the center will be much larger than those on the edges.  Find one of the average sized pieces from the second row in and tear chunks off the larger ones to add to the smaller pieces until they’re all about the same size.

Roll each piece into an oval egg shape, and then gently press a wooden skewer down the center to give them that distinctive coffee bean shape.  Lay the molded cookies on two baking sheets lined with parchment paper.

Aren’t they just charming all lined up like that?  Reminiscent of the military, true, but in buttery soon-to-be-baked form.

Bake the cookies for 30 – 35 minutes in the center of your oven, rotating the racks halfway through.  The cookies will be done when they’re slightly firm to the touch and the bottoms are just starting to get golden.  Let the cookies cool completely before moving on to the chocolate coating.

To make the chocolate coating, put the 5oz of semi-sweet chocolate into a glass bowl and set it over top of a pot with 1 – 2 inches of water inside.  Make sure that there is at least an inch of empty space between the water and the bottom of your bowl.  Set that over medium heat and let the chocolate slowly melt.

Stir the chocolate occasionally as it melts, and when it is almost all melted add in the reserved 1 tbsp of butter and stir until it’s melted and combined.

Using a pastry brush (or whatever you like that will achieve the same ends) brush the top and sides of each cookie with chocolate, and lay them back onto parchment or wax paper as each one is completed.

And there you have it.  These take chocolate coated espresso beans to a whole new level of goodness.

And don’t they make elegant tuxedo-like buttons on a white platter?

Except that I’m too greedy to spread them out, I’m more the fan of a deliciously piled platter.

I think I’m going to send some of these in a care package to my brother out West.  I know that he’ll dig the the spicy-sweet Mexican mole taste as much as I do.

Happy Holiday Baking!!!