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.
