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

Cut each slice of bacon into three strips.

Place one chunk of pineapple in the center of each bacon strip, fold both ends over, and secure with a toothpick.

In a microwave-safe bowl, combine the brown sugar and butter. Microwave for 40 seconds and stir, then heat in five-second increments until fully melted and well combined.

Soak half of the bacon-wrapped pineapple skewers in the brown sugar glaze, ensuring they’re nicely coated.

Place them in the air fryer basket (work in batches to prevent crowding) and cook at 400°F for 10 minutes. Check for crispiness; add an additional 2-3 minutes if needed.