Preheat the oven to 400 degrees F. Cut the bacon into thirds. Place the bacon on a baking sheet lined with foil and bake for 6 minutes flipping the bacon halfway through the cook time. Remove the bacon and allow it to cool to the touch.
Then wrap each bacon around a piece of the pineapple and secure it to the pineapple with a toothpick.
Dip each one in a shallow bowl of the brown sugar to coat it with the sugar.
Place the pineapple on a baking sheet lined with foil and bake at 400 degrees F for 20-30 minutes (flipping them halfway through the cook time) until the bacon is cooked through and cripsy.
Serve warm and then enjoy!
Notes
You can use fresh or canned pineapple for this recipe. A thicker bacon works the best in this recipe. These are best served immediately but you can refrigerate the leftovers in an air tight container for up to 4 days.