Remove the bacon from it's package and slice the pieces in half.
Take one piece of pineapple and wrap the bacon around it. Secure with a toothpick. Repeat until all the bacon has been wrapped around a piece of pineapple.
Add the brown sugar to a bowl. Roll each pineapple roll in the brown sugar.
Place each pineapple roll in a 9x13 baking dish.
Preheat the oven to 400 degrees. Place the dish in the oven and cook for 25 minutes.
Notes
The baking dish needs to have sides. The bacon produces lots of juices as does the brown sugar.
If you are using larger chunks of pineapple, slice the bacon in half. If you have smaller pieces of pineapple, you can cut the bacon into thirds.
Make sure to secure the bacon with a toothpick. Otherwise, you risk the bacon coming off and then you have a cooked piece of pineapple and a piece of bacon.
Use the juices from the pan as a dipping sauce for the pineapple pieces. The sauce is full of bacon goodness and brown sugar and this adds to the appetizer.