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For best flavor, pour the crushed pineapple with its juice into a saucepan, and simmer for about 20 minutes, until most of the liquid has evaporated. If you want to skip this step, simply drain the pineapple, pressing to remove as much juice as possible, and discard the juice. Refrigerate the pineapple while you prepare the rest of the gelato base.
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In a saucepan, whisk together 1 cup (8 ounces) of the coconut milk; the sugar, and the nonfat dry milk. Set the remaining coconut milk aside; you'll add it later.
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Cook over medium heat, stirring frequently, until the mixture begins to simmer. It won't be totally smooth, but whisk to remove as many lumps as possible.
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While the milk/sugar mixture is heating, put the 2 egg yolks in a bowl, and whisk to combine.
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Gradually pour about 1 cup of the hot mixture into the bowl with the egg yolks. Whisk to combine, then transfer the egg yolk mixture back to the saucepan.
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Stir the custard over medium-low heat for a couple of minutes, until it thickens a bit; it should be about as thick as heavy cream.
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Remove from the heat, and stir in the remaining 2/3 cup (approx.) coconut milk. Add the vanilla or coconut flavor. Don't worry, we didn't forget the rum; you won't use it until you freeze the gelato.
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Transfer the custard to a food processor or blender, add the pineapple, and process until it's as smooth as possible; the pineapple won't become a purée, but there shouldn't be any large chunks.
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Transfer to a covered container and refrigerate overnight. Make sure the canister of your ice cream maker is in the freezer, too.
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Within about 4 hours of when you want to serve the gelato, pour it into the canister of the freezer, turn on the machine, and let it work for about 20 minutes, or until the gelato is thick enough to mound on a spoon without dripping. Towards the end of the time, add the rum, if you're using it. Make sure it's thoroughly combined with the gelato.
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Enjoy the gelato immediately; or transfer it to an airtight container, and place in your refrigerator's freezer compartment for 3 to 4 hours. If it gets too hard, simply let it sit at room temperature for about 20 minutes, or until it's soft enough to scoop.
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Serve with a garnish of toasted coconut and/or dried pineapple bits, if desired.