First things first, crank up your oven to 350°F. While it heats up, line a baking sheet with parchment paper to avoid a sticky mess.
Pour the brown sugar into a bowl.
Take your bacon strips and cut them in half. You want each piece to be the perfect size to wrap around a chunk of pineapple.
Grab a piece of pineapple, place it at one end of the bacon strip, and roll it up like a delicious little present. Once it’s snug, roll that baby in the brown sugar, coating it generously.
Slide a toothpick through the bacon-wrapped pineapple to keep everything in place. You don’t want your bacon unraveling in the oven!
Keep going with the rest of the bacon and pineapple chunks. It’s a little repetitive, but oh-so worth it.
If you’ve got some leftover brown sugar (and I bet you will), sprinkle it on top of your bacon-wrapped pineapple before baking.
Pop your baking sheet in the oven and bake for 30 minutes. The bacon will crisp up while the pineapple stays juicy and sweet.
Once they’re out of the oven, serve these treats warm for the best flavor. They’re perfect for snacking, appetizers, or even a fun dinner side dish.