Step 1: Preheat oven to 350 degrees F (175 degrees C).
Step 2: Line 24 muffin cups with paper liners.
Step 3: Whisk together 2 1/2 cups flour, cocoa powder, baking soda, salt, and baking powder in a large bowl until thoroughly mixed.
Step 4: Beat in white sugar, 2/3 cup butter, water, 1 teaspoon vanilla extract, and eggs to make a smooth batter.
Step 5: Divide batter between the prepared muffin cups, filling each cup about 2/3 full.
Step 6: Bake in the preheated oven until a toothpick inserted into the center of a cupcake comes out clean, about 20 minutes. Remove from oven and let cool completely.
Step 7: While cupcakes are cooling, beat 1 cup butter, 2 teaspoons vanilla extract with an electric mixer in a large bowl until mixture is smooth and thick.
Step 8: Reduce mixer speed to low and beat in confectioners' sugar, 1 cup at a time, until frosting is desired consistency. Beat in more confectioners' sugar to make a stiffer frosting.
Step 9: Thin with milk as needed.
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