2 cups all-purpose flour
cup Cocoa Powder, unsweetened
3/4 teaspoon Baking Soda
1/4 teaspoon Salt
1/2 cup Butter, unsalted, at room temperature
1 teaspoon Vanilla Extract
3 ounces Semi-Sweet Chocolate, melted and cooled
1 cup Milk, at room temperature
1/2 cup Butter
1 cup Packed Brown Suger
3/4 cup Milk, divided
3 cups Powdered Confectioners' Sugar, plus a little extra if needed
Preheat oven to 350 degrees. Prepare the cupcake pans by greasing or placing paper liners in them.
In a large bowl with an electric hand mixer on medium beat butter until creamy, about 2 minutes. Add sugar gradually, beating until light and fluffy, about 3 minutes, scraping down bowl occasionally. Beat in Vanilla Extract. Beat in eggs one at a time. Beat in cooled chocolate.
Beat in the flour mixture in 4 additions alternating with the milk. Begin and end with the flour mixture and beat briefly until smooth on low-medium.
Fill cupcake wells 3/4 of the way. Bake about 22 minutes or until a toothpick in middle shows a few moist crumbs.
To make frosting: in a 2-quart saucepan melt butter over medium heat. Stir in brown sugar. Heat to boiling, stirring constantly, reduce heat to low.
Boil and stir 2 minutes. Stir in 1/2 cup Milk. Heat to boiling, remove from heat. Cool to lukewarm, about 30 minutes.
Pour the caramel into a large mixing bowl gradually stir in powdered sugar and milk. Beat with an electric hand mixer on low about 6 minutes until light and fluffy. If too stiff add milk a teaspoon at a time to get the right consistency. If too watery add additional powdered sugar beating on low until it reaches the right consistency.