Preheat oven to 350 degrees F and line a 24 cup muffin pan with paper liners, or grease with cooking spray.
In a stand mixer, or with an electric mixer, mix together the butter and granulated sugar on medium for about 20 seconds, or until roughly mixed.
Add in the eggs and 1 TSP of vanilla and mix until combined.
In a separate bowl, whisk together flour, cocoa powder, baking soda, baking powder, salt, ancho chile powder, and cayenne pepper.
Slowly alternate adding flour mixture and milk to the butter/sugar mixture on medium speed.
Once combined, carefully add the boiling water on low speed.
Fill each cupcake liner 3/4 full with batter.
Bake for 20 minutes, or until toothpick inserted comes out clean.
Allow cupcakes to rest in pan for 5 minutes after removing from oven, then remove from pan and allow to cool completely on cooling rack.
When cupcakes are cool, make the frosting.
In a stand mixer, or with an electric hand mixer, cream the butter and cream cheese on medium/high for about 3 minutes, until fluffy.
Slowly add in the powdered sugar, ancho chile powder, cinnamon, cayenne, and vanilla. Mix until fluffy and spreadable.
Spread the frosting onto each cupcake and garnish with red pepper flakes, if desired. Enjoy!
