- 1 cup butter, softened
- 1 2/3 cups confectioners' sugar, divided
- 1 teaspoon vanilla extract
- 2 cups all-purpose flour
- 1/4 cup unsweetened dark cocoa powder
- 1 tablespoon ground cinnamon, divided
- 1/2 teaspoon ground ancho chile pepper
- 1/8 teaspoon salt
- 2/3 cup finely chopped toasted almonds
- 1/3 cup finely chopped dark chocolate
- 2 tablespoons unsweetened dark cocoa powder
- Preheat oven to 325 degrees F (165 degrees C). Line baking sheets with parchment paper or silicone baking mats.
- Combine butter and 2/3 cup confectioners' sugar in a large bowl; beat with an electric mixer on medium speed until well combined. Beat in vanilla extract.
- Mix flour, 1/4 cup cocoa powder, 2 teaspoons cinnamon, ancho chile pepper, and salt together in a bowl. Beat into the butter mixture. Stir in almonds and dark chocolate until dough comes together.
- Shape 1 tablespoon of dough into a ball; place on a lined baking sheet. Repeat with remaining dough.
- Bake in the preheated oven until lightly browned on the bottom, 15 to 20 minutes. Cool for 1 to 2 minutes on the baking sheets.
- Mix remaining 1 cup confectioners' sugar, 1 teaspoon cinnamon, and 2 tablespoons cocoa powder in a bowl. Roll cookies in sugar mixture while still warm.
- Cool cookies completely on wire racks, about 15 minutes. Roll in sugar mixture again.