Peel, core, and cut the pineapple into 1/2-inch-thick chunks.
Place a chunk of pineapple on top of a shrimp, then wrap the whole thing in a 1/2 slice of bacon. Secure the pineapple, shrimp and bacon with a toothpick.
Repeat with the remaining shrimp.
Place the wrapped shrimp in the air fryer basket. Brush generously with barbecue sauce on both sides.
Air fry at 400 °F for 10 minutes, flipping at the halfway point, or until the shrimp registers at 120 °F with an instant read thermometer and the bacon and pineapple are cooked to your liking.