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Caramel-Rum Sauce
Pineapple
To make sauce: Pour ¼ c water into a heavy, medium-sized saucepan. Add sugar and cook over high heat, stirring just until sugar melts. Cook without stirring, occasionally swirling melted sugar in pan and brushing down any crystals that form on sides of pan with a pastry brush, until sugar has caramelized to a dark copper-brown, 3-5 minutes.
Slowly pour in hot cream; mixture will bubble up, so be very careful. Boil, stirring often, until sauce has reduced to 2 c, about 3 minutes. Remove from heat and stir in rum and vanilla. Let cool to room temperature.
Prepare an outdoor grill for direct cooking over medium (350°F) heat.
Brush pineapple slices with oil. Brush grill grate clean. Place pineapple slices on grill and close grill lid. Grill pineapple until grill-marked on bottom, about 3 minutes. Turn pineapple and cook until second side is grill-marked, 3 minutes more. Transfer pineapple to a cutting board and coarsely chop into bite-sized pieces. Let cool for 5-10 minutes.
Scoop ice cream into dessert bowls. Top with warm pineapple and its juices, then with caramel sauce. Serve at once.
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