Prep the pineapple: Trim, peel, and core the pineapple. Cut into even spears or 1/2-inch rings. Uniform pieces cook more evenly and caramelize better.
Make the coating: In a bowl, mix the brown sugar, honey (if using), melted butter or coconut oil, vanilla, cinnamon, and a pinch of salt. You want a glossy, slightly thick mixture.
Toss to coat: Add the pineapple pieces to the bowl and toss until each piece is lightly coated. Don’t drench them—excess liquid can smoke or burn.
Preheat the air fryer: Set your air fryer to 380°F (193°C) for 3 minutes. A hot basket helps with quick caramelization.
Arrange in a single layer: Place the pineapple in the basket in one layer with a bit of space between each piece. Avoid overcrowding to ensure color and texture.
Air fry the first side: Cook at 380°F for 6–8 minutes. Check at 5 minutes if your air fryer runs hot. You’re looking for golden edges and a deepening color.
Flip and finish: Turn the pieces and cook another 4–6 minutes, until caramelized and lightly blistered in spots. Thicker pieces may need an extra minute or two.
Optional glaze: If there’s remaining syrup in the bowl, brush a little on in the final minute for added shine and sweetness.
Serve warm: Sprinkle with lime zest or a tiny pinch of flaky salt to balance the sweetness. Serve with vanilla ice cream, coconut yogurt, or over pancakes, waffles, or oatmeal.