The flavors of Mexican hot chocolate inspired these Chocolate Diabolo Thumbprint Cookies. They are my riff on the holiday cookie tray staple, the chocolate snowball.  If you love surprises, this cookie might be for you. It’s got warm spices and a kick from cayenne pepper. The trick is to build flavor at each step. Use quality dark cocoa powder such as Ghirardelli. And use fresh spices. Toasting the nuts before adding them to the dough also builds their flavor so they can stand up to the rich chocolate.

Rifling the fridge for a jar of jam, I found some hot pepper jelly. (It’s the fruitcake of homemade gifts; there’s only so many times one can serve crackers, cream cheese and pepper jelly.) It works and might keep Uncle Al from talking politics. Or consider a tamer choice like raspberry jam.

A few planning tips. Make the dough. Form it into balls using a cookie scoop while the dough is still soft.  Then refrigerate it overnight or longer before baking. This gives any moisture in the dough time to settle so that your cookies will hold together.

Looking for more tips for baking holiday cookies.  Visit Holiday baking for Smart Cookies.

Kitchen Notebook:

Cocoa powder, I used half and half, Ghirardelli cocoa powder from the grocery store and half Extra Brute Ambree from Cacao Barry. The latter is the kind of black cocoa powder used to make Oreo cookies.  Its color is intense almost burnt, a little goes a long way.

Chocolate Diabolo Thumbprint Cookies

Yield: about 3 dozen


1 ¾ cups pecans, walnuts or a combination

2 sticks (8 ounces) unsalted butter, softened

½ cup granulated sugar, not superfine

1 teaspoon vanilla

1 2/3 cups all-purpose flour

½ cup dark cocoa powder, such as Ghirardelli or Cacao Barry

2 heaping teaspoons ground cinnamon

1/8 teaspoon cayenne pepper, more if you are brave

¼ teaspoon salt

Powdered sugar, as needed

Raspberry jam or hot pepper jelly, as needed


  1. Preheat the oven to 350°F. Place the nuts on a sheet pan and toast them in the oven until lightly brown and fragrant, for 8 – 10 minutes. Cool.
  2. Place the cooled nuts in the bowl of a food processor. Run the machine for about a minute then pulse until the nuts are chopped into small if irregularly sized pieces.
  3. Sift the flour, cocoa powder, cinnamon, salt and cayenne together.
  4. Cream the butter in the bowl of a mixer fitted with the paddle for 3 – 5 minutes, scraping the bowl three or four times. You want the butter to be light in color, smooth and fluffy. Then add the sugar and cream another 3 – 4 minutes. Add the vanilla.
  5. Add the dry ingredients and mix on medium speed until the flour is blended in but the dough is still crumbly, for 1 – 2 minutes. Add the chopped nuts and mix on low speed until the dough comes together, for another minute or two. Gather the dough into a ball.
  6. Portion the dough using a small cookie scoop. Roll each ball of dough between the palms of your hands. Store the formed dough on a sheet pan or in a covered container in the refrigerator overnight. (Or freeze for up to a month before using.)
  7. Preheat the oven to 375°F. Place the portioned cookie dough spaced 2 inches apart onto a parchment-paper lined sheet pan. Bake until the cookies puff slightly and cook through. Small cracks will appear on the surface, for about 14 – 16 minutes.
  8. Cool the cookies for 5 minutes on the pan set on a cooling rack. Gently push the end of a wooden spoon into the center of each warm cookie for the jam.
  9. Dust the cooled cookie with powdered sugar. Fill the cavity of each cookie with jam.