Preheat your oven to 350 degrees. Line a rimmed baking sheet with parchment paper or foil. Set aside.

Wrap a pineapple piece in one piece of bacon.

Repeat with remaining bacon and pineapple pieces.

Roll each bite in brown sugar.

Place wrapped pineapple pieces onto the prepared baking sheet, seam side down.

Bake for 20-30 minutes, rotating half way through until bacon is nice and crispy.