Italian Chocolate Holiday Cookies

by Rachel on December 24, 2011

Italian Chocolate Holiday Cookies

So I have this friend Jay, a riotously funny Texan. Raised Catholic by a bunch of Italians with excellent cooking skills, Jay seems to have an endless supply of extremely complicated, poorly documented family recipes that he whips up without breaking a sweat. He writes me about this or that terrific meal and I yelp – “oh please send me the recipe!” I generally get some LAUGH OUT LOUD seven-page single-spaced tome with references to crazy Italian Aunties and not enough instruction to help even Julia Child make the damn thing. This recipe was just an ingredient list and the instructions amounted to “mix and bake.” I don’t know about you – but I’m partial to slightly more developed instructions than that. So it was with some trepidation that I set out to make Jay’s Italian Auntie’s Chocolate Holiday cookies. I mixed everything together, as written, and the end result was, well, sand. I know I’m prone to exaggeration, but I am speaking the G-d’s honest truth when I say that this was not anything even approximating cookie dough – and in my book, cookie sand is just not an acceptable outcome (especially after using TWO pounds of flour, a pound of sugar and $20 bucks in other assorted ingredients).  I promise you that this revised, adapted, and adjusted version WORKS. You will NOT have cookie sand at the end. I mean it. And these cookies – the adjusted, revised, adapted version – are unusually good. They taste just like the holidays should taste, festive and wonderful. Special thanks to Jay and his amazing Italian Aunties!

Italian Chocolate Holiday Cookies (makes 6-8 dozen cookies)


  • 2 lbs all-purpose flour- (8 Cups)
  • 1 lb sugar
  • 4 teaspoons baking powder
  • ¼ teaspoon salt
  • 3 tablespoons unsweetened cocoa
  • 1 teaspoon ground cinnamon
  • 1 teaspoon ground cloves
  • 1 lb roasted almonds*
  • 3 eggs, lightly beaten
  • 6 tablespoons canola oil
  • 3 squares unsweetened chocolate, melted and cooled slightly
  • ¼ cup unsalted butter, softened
  • ½ cup whole milk
  • 1 cup strong coffee, cooled (I highly recommend Weaver’s Organic Blend Coffee – great coffee, great company, great people)
  • 1 12-oz package chocolate chips


  • ½ cup unsalted butter, softened
  • ¾ cup confectioner’s sugar
  • 2 tablespoons unsweetened cocoa
  • ¾ cup strong coffee, cold

Eat these now.

Preheat oven to 350 degrees.

*To roast the almonds place them in a dry, non-stick skillet and heat them over medium-high heat. Toss occasionally until they are light brown in color. Remove from heat and allow to cool slightly. Once cool, place on a cutting board and using a large knife, chop coarsely.

In a large mixing bowl blend together the flour, sugar, baking powder, salt, cocoa, cinnamon, cloves, and chopped roasted almonds. In the bowl of a stand mixer blend together the eggs, canola oil and softened butter. Add the melted chocolate, the milk and the coffee. Gradually add to the dry ingredients. I found this a LONG process involving a lot of brute strength as well as patience (always in short supply in my kitchen). Stir in the chocolate chips. Again, this is easier said then done. Use a strong wooden spoon and really press the chocolate chips into the dough. Roll the dough into a log and using a sharp knife cut ½ inch rounds off of the log. If you find this challenging roll it in wax paper – this will make it a bit easier to press into a roll. Bake for 7-10 minutes on an ungreased cookie sheet. You want the cookies to be moist but cooked through. The exact time will depend on how thick your cookies are and the vicissitudes of your oven. Remove from tray and allow to cool completely.

To make the frosting blend together the sugar, butter and cocoa. Do not add all of the coffee at once. Instead add it gradually until you get a relatively liquid frosting. Once your cookies are cool, dip the top of each cookie into the frosting and allow the cookies to dry overnight on a cutting board or cooling rack.

{ 2 comments… read them below or add one }

Jay December 24, 2011 at 7:36 pm

Generations of my Italian Aunties and Nonnis have been making this since the Borgias were popes. I can assure you they knew what I meant. Here’s the thing, it may look like sand, but all you have to do is add more coffee until it pulls together! But I’m glad you made this recipe your own. Did the boys like them?

Rachel December 24, 2011 at 7:38 pm

Jay – I do believe that they are Jonah’s favorite cookie EVER. He is your biggest fan!


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