Preheat oven to 350°F (175°C) and line a 12-cup muffin pan with liners.
In a medium bowl, whisk together the flour, baking powder, baking soda, and salt.
In a large bowl, beat the cupcake butter and granulated sugar until light and fluffy, about 2–3 minutes.
Add the eggs one at a time, mixing well after each addition.
Mix in the almond extract, amaretto, and cherry juice if using.
Add the dry ingredients in two additions, alternating with the milk, mixing just until combined.
Gently fold in the chocolate chips and chopped cherries.
Divide the batter evenly among cupcake liners, filling each about three-quarters full.
Bake for 18–22 minutes, until a toothpick inserted comes out clean or with melted chocolate only.
Remove cupcakes from the pan and allow to cool completely on a wire rack.
In a large bowl, beat the buttercream butter until smooth and creamy.
Gradually add the powdered sugar, beating well after each addition.
Mix in the amaretto, vanilla extract, and salt.
Add the cream or milk one tablespoon at a time until the buttercream is light and spreadable.
Frost the cooled cupcakes and garnish as desired.