In a large mixing bowl, beat together butter and 2/3 cup powdered sugar with electric mixer on medium speed until well combined. Beat in vanilla.
In a separate small mixing bowl, mix together flour, 1/4 cup cocoa powder, 2 teaspoons cinnamon, ancho chile pepper, and salt until well combined. Beat into butter/sugar mixture. Stir in almonds and chocolate until well combined and dough forms.
In a large shallow bowl, whisk together remaining 1 cup of powdered sugar, 2 tablespoons cocoa powder, and 1 teaspoon cinnamon until combined. Set aside.
Form dough into 1 tablespoon balls. Place cookies on ungreased cookie sheets (or silpats or parchment paper). Bake cookies at 325 degrees F for about 15-20 minutes or until lightly browned on the bottom being careful not to overbake. Cookies will harden as they cool. Cool cookies about 1-2 minutes then roll in sugar mixture while still warm. Cool completely on wire rack then roll cookies in sugar mixture again.