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Beat 1/4 cup butter until smooth and creamy.
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Mix in 1/2 cup peanut butter, then 1 cup powdered sugar, milk and 1/4 tsp vanilla until combined.
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Gradually mix in remaining 1/2 cup powdered sugar until smooth and spreadable.
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Spread 1 tbsp filling on the flat side of one cookie, top with another cookie to make sandwiches.