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Add butter, 3 tablespoons milk, and vanilla to a large mixing bowl. Using a hand mixer and starting at low speed, combine until smooth.
Add cocoa powder and mix until smooth, scraping sides of bowl with a spatula as needed.
Add about half of the powdered sugar. Start mixing on the lowest setting (so dry powdered sugar doesn't fly out of the bowl) and increase speed as everything is incorporated.
Add the remaining powdered sugar and continue mixing until fully combined.
Add more milk by the tablespoon as needed.
Mix on high speed until smooth, scraping sides of bowl as needed.
Spread or pipe onto completely cooled brownies, cupcakes, and cake.
See recipe notes for thinner frosting and stiff, pipable frosting.