Chocolate Cinnamon Chipotle Sugar Cookies
Yield: About 12 large cookies
For the Chocolate Cinnamon Chipotle Cookies
  • 2 cups (255 g) all-purpose flour
  • ½ teaspoon kosher salt
  • ½ teaspoon ground cinnamon
  • ¼ teaspoon baking powder
  • ¼ teaspoon chipotle chile powder, or ancho chile powder
  • 6 ounces (1½ sticks/170 g) unsalted butter, cool but not cold
  • 2 tablespoons cold (unflavored, nonhydrogenated) vegetable shortening
  • 2⁄3 cup (130 g) granulated sugar
  • 1 large egg
  • 1 teaspoon pure vanilla extract
  • 2 ounces (55 g) dark chocolate (60 to 72% cacao), melted and cooled
For the Filler Icing
  • 3½ to 4 cups (395 to 450 g) confectioners’ sugar
  • ½ teaspoon cream of tartar
  • 3 large egg whites, plus more if needed
  • 1 teaspoon fresh lemon juice
For the Royal Icing
  • 3 cups (340 g) confectioners’ sugar
  • 2 large egg whites
  • 1 to 2 teaspoons fresh lemon juice
  • Various food gels
Make the Chocolate Cinnamon Chipotle Cookies
  1. In a medium bowl, whisk together the flour, salt, cinnamon, baking powder, and chipotle. Set aside.
  2. In the bowl of a standing mixer fitted with the paddle attachment, beat the butter and shortening together on medium speed until just combined. Add the sugar and cream together until the mixture is light and fluffy, about 3 minutes. Scrape down the bowl, add the egg and vanilla, and beat until just combined. Add the melted and cooled chocolate and beat until uniform in color. Scrape down the sides and bottom of the bowl, add half of the flour mixture, and beat for 15 seconds. Again, scrape down the bowl, then add the remaining flour mixture and beat until just incorporated. Loosely shape the dough into two disks (it will be sticky, so work quickly and feel free to flour your hands first), wrap them tightly in plastic wrap, and refrigerate for at least 2 hours.
  3. Preheat the oven to 325°F (165°C). Line two baking sheets with parchment paper.
  4. Unwrap one disk of dough, leaving the other in the refrigerator while you are working, and place it on a lightly flour-dusted work surface. Dust your hands and rolling pin with a little flour. Roll the dough ¼ inch (6 mm) thick, flipping and lightly flouring the dough a few times, as needed, while you work. Using your favorite Day of the Dead cookie cutter (we use the easy-to-find skull), cut shapes in the dough, then transfer them to the prepared baking sheets, leaving about 1 inch (2.5 cm) of space around each cookie. Dough scraps can be rerolled and recut, if desired. Continue the process with the remaining dough. Place the cut dough on the baking sheets in the freezer for about 15 minutes.
  5. Bake the cookies, rotating the baking sheets halfway through the baking time, until the tops of the cookies look set and are just beginning to appear dry, 10 to 12 minutes. Place the baking sheets on a cooling rack for 5 minutes. Using a spatula, transfer the cookies to the rack to cool completely.
Make the Filler Icing
  1. In the bowl of a standing mixer fitted with the paddle attachment, combine 3½ cups (395 g) confectioners’ sugar and the cream of tartar; turn the mixer to the lowest speed to mix them together and remove any possible lumps. Increase the speed to medium-low, add the egg whites and lemon juice, and mix until the icing is completely smooth. It should have the texture of a thick, shiny glaze, but be just thin enough to pour. If the mixture is too thick, add additional egg whites to thin it. If the mixture is too thin, add the additional sugar a tablespoon at a time. Scrape the icing into a piping bag fitted with a large round tip (#3). First, outline each of the cookies with the icing and wait 15 minutes for the outlines to harden.
  2. After 15 minutes, return to the first cookie and flood the icing within the outline. If you feel confident and steady, you can flood each cookie just by using a pastry bag filled with the icing; I recommend using less icing in the flooding process than you imagine you will need, as it should spread to the outline and fill it in. If you are not quite confident using just the pastry bag, or if you want to be extra careful, squeeze a few dollops of the icing over the top of the cookie and use a dry paintbrush or the back of a spoon to gently spread it to the outline. (We don’t recommend pastry brushes; craft-store paintbrushes with synthetic bristles work best.) Let the frosting dry completely before adding the décor (royal icing), at least 8 hours or overnight.
Make the Royal Icing
  1. In the bowl of a standing mixer fitted with the paddle attachment, combine the confectioners’ sugar with the egg whites and 1 teaspoon lemon juice and beat on low to medium-low speed until the icing is completely smooth, 3 to 5 minutes. When the paddle is lifted from the icing, a peak in the icing should be created, which should fall over just a bit; it’s slightly thicker than the filler icing. To reach the right consistency, add ½ teaspoon more egg white and/or lemon juice at a time to thin the icing, or 1 teaspoon more confectioners’ sugar at a time to thicken the icing.
  2. Divide this icing into five or six small prep bowls. Add pea-size amounts of food gel to all of the bowls save one, and mix, adding more gel as needed to achieve the colors you desire. Keep the last bowl plain (white). Place each color in a pastry bag fitted with a small tip (#1). (Alternatively, though we don’t wholly recommend this method, as you will get cleaner lines using pastry bags and tips, you can place the icing in zip-tight plastic bags, cut off just a tiny bottom corner of the bag—as small as possible—and use the bag to pipe.)
  3. Apply the royal icing to the outlined, filled, and completely dry cookies. Use the accompanying photo as a guide for traditional Day of the Dead décor or (obviously) decorate as you want. If you need to or want to overlap decorating colors, just make sure the bottom color is dry before applying the top color over it. Let the décor harden completely before serving, at least an hour or up to overnight.
How to store: The cookies can be kept in an airtight container in a cool and dry environment for 3 to 5 days; do not wrap in plastic wrap.
Recipe by Baked Sunday Mornings at