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Preheat the air fryer to 375 (190 C). Slice, core and cut the fresh pineapple into slices, spears, chunks or rings. Make sure to cut the pineapple into even sized pieces. This ensures the pineapple fries or is grilled evenly and at the same time.
Toss the pineapple into a bowl with light brown sugar and ground cinnamon until all the pineapple is fully coated.
Lightly spray the air fryer tray or basket with a non stick cooking spray. Fry the pineapple for 6 - 8 minutes. Then carefully pull the air fryer basket out, flip each of the pineapple pieces and return to the air fryer for an additional 6 - 8 minutes.Air fry the pineapple for 12 - 16 minutes total or until your preferred level of caramelization.
After the pineapple is grilled or air fried, cool the pineapple slightly until warm. Serve as is or serve this delectable caramelized pineapple with ice cream, whipped cream, or to top a a stack of pancakes.