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In a large baking dish add pineapple rings and rub them with brown sugar and cinnamon mixture. You can add some rum too, if preferred. Allow them to stay for at least 10 minutes before grilling.
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When you're ready, heat a grill pan over medium-high heat until hot or use the outside barbecue. Lightly grease the pan with cooking spray and add pineapple slices leaving some space between the rings. Cook for 1-2 minutes per side until you see the grill marks and the color changes to brownish. Transfer to individual serving plates and allow to cool down a bit before serving.
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To serve, top each grilled pineapple ring with a big scoop of vanilla ice cream and drizzle with chocolate sauce. Serve immediately.