Preheat your oven to 350°F. Line a baking sheet with aluminum foil to catch any drips and make cleanup a breeze. If you have a wire rack, place it on top of the foil-lined pan to help the bacon cook evenly and crisp up nicely.

Cut the bacon slices in half so they’re just the right size for wrapping. Take one chunk of pineapple and wrap it with a half slice of bacon. Secure it with a toothpick so it stays together during baking.

Pour the brown sugar into a shallow dish or plate. Gently roll each bacon-wrapped pineapple in the sugar until it’s well coated. The sugar will caramelize in the oven, giving these bites a sweet and sticky glaze that pairs perfectly with the savory bacon.

Place the brown sugar-coated bites on your prepared baking sheet, leaving a little space between them. Bake for 30-35 minutes, or until the bacon is cooked through and starting to crisp. Keep an eye on them toward the end - they go from perfect to too dark quickly!

Remove the baking sheet from the oven and let the bites cool for about 5 minutes. This helps the caramelized sugar set a bit and makes them easier to handle.

Transfer to a serving platter and enjoy warm.