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Cut the pineapple into 1 inch cubes.
Line a baking pan with aluminum foil (for easy clean up), then place a cooling rack onto the lined baking sheet.
Wrap each piece of pineapple with a piece of bacon and secure with a toothpick. For thick cut bacon, ⅓ of a slice is enough. For regular bacon, use ½ of a slice for each piece of pineapple.
Dip each bacon wrapped pineapple bite into some brown sugar, patting it on as needed.
Bake at 350 degrees F for 25-35 minutes, until the bacon is slightly crispy and the sugar is caramelized.
Allow to cool for 5-10 minutes before serving.