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To freeze the pineapple, prepare fresh pineapple by removing the core, peeling it, and cutting it into 1-inch slices. Arrange the pineapple pieces evenly on a baking sheet and place in the freezer, ensuring they are not overlapping, for a minimum of 4 hours or overnight.
Prepare the soft serve: Combine the frozen pineapple chunks, sweetened condensed milk, and chilled heavy whipping cream in a food processor. Blend briefly to fragment the pineapple, then blend constantly until the mixture is velvety and uniform, being sure to scrape the edges as necessary. This process typically takes around 1 to 2 minutes.
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