Drain the canned pineapple slices and cut each pineapple into 3 equal pieces.

Take 8 slices of bacon and cut them into 3 equal strips.

Lay the bacon strips out and place a pineapple slice in the center of each one, then fold over both ends of the bacon onto the top of the pineapple and use a toothpick to secure.

Add the brown sugar and butter to a microwave safe bowl and heat for 40 seconds, stir and continue heating in 5 second increments until fully melted and you have created a glaze.

Place half of the pineapple bacon skewers into the air fryer basket and generously brush each one with the brown sugar glaze. (You will need to cook in two batches to keep from crowding while cooking)

Place the basket in air fryer and cook for 10 minutes at 400 degrees. Check after 10 minutes and cook for 2-3 minutes more depending on your desired level of crispiness!