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Prepare and bake cake mix according to package directions for cupcakes, using 20 paper-lined muffin cups. Cool completely.
Meanwhile, in a small bowl, prepare pudding mix according to package directions. Press plastic wrap onto surface of pudding; refrigerate until cold.
Cut a small hole in the tip of a pastry bag; insert a small pastry tip. Transfer pudding to bag. Using a wooden or metal skewer, poke a hole through bottom of cupcake liners. Push tip through hole and pipe filling into cupcakes.
In a microwave, melt chocolate chips and butter in a microwave-safe bowl; stir until smooth. Whisk in confectioners' sugar and water. Dip tops of cupcakes into glaze. If desired, pipe designs on cupcakes.