Preheat the oven to 325º F. In a mixer, blend the flour, sugar, cocoa, baking powder, baking soda, and salt. Mix in the eggs, vanilla, and olive oil.
Add the milk and beat to blend. Add the boiling water. Continue to beat at low speed. The batter will be thin.
Pour into cupcake cups and bake 20 to 25 minutes. Cupcakes are done with toothpick inserted in the center comes out clean. Cool in pan for 10 minutes then remove to wire rack to cool completely.
Beat the frosting ingredients together in a mixer until smooth and creamy and spread on the cooled cupcakes.