Preheat an outdoor grill for medium-high heat.
Place a 12×12-inch sheet of aluminum foil on a work surface. Spoon brown sugar and butter in the center of the foil. Arrange pineapple ring over sugar and place cherry in the center. Top pineapple ring with inverted shortcake shell. Fold foil around cake to form a packet.
Grill packet sugar-side down in the preheated grill until sugar is caramelized and cake is hot, about 12 minutes.
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