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Whisk together sugar, cocoa, and cornstarch in a microwave-safe bowl. Whisk in milk, a little at a time, until no dry lumps remain.
Cook in the microwave on high for 3 minutes. Stir well. Continue cooking and stirring at 1-minute intervals until shiny and thick, 2 to 4 minutes. Mix in vanilla.
Press a piece of plastic wrap directly on surface of pudding to prevent skin from forming. Place in the refrigerator to chill. Serve cold.