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In a large bowl or standing mixer, beat buttery sticks on high until fluffy, about 4 minutes.
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With mixer on low gradually (and gently) add sugar until combined.
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Add milk a teaspoon at a time, then add vanilla a few drops at a time. Mix until combined. If the frosting consistency is too thick add an additional tablespoon of milk.
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Set mixer to high and beat until frosting is light and fluffy.
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Place in pastry bag and frost cooled cupcakes.