Prepare the pineapple. Slice off the top and bottom. Working around the pineapple, slice off the rind. Then slice long planks, leaving the core. Cut into chunks. Place pineapple in large mixing bowl.
Add brown sugar and butter in small pan over medium heat. Stir until melted, add cinnamon and whisk again.
Pour cinnamon sugar mixture over pineapple and toss.
Add pineapple to air fryer basket one even layer. Air fry pineapple for 12 minutes total, flipping at the 5 and 10 minute mark. Remove when toasted!