Pineapple Upside-Down Cakes

These individual pineapple upside-down cakes are baked in small Pyrex dishes so each person gets their own golden, caramelized dessert with a full pineapple ring on top. A homemade syrup made from the canned pineapple juice, pineapple concentrate, cinnamon, and butter goes in first, then the ring, then a thick, buttery batter.

The syrup uses cornstarch to thicken, so it clings to the cake instead of pooling on the plate when you flip. Boiling it for one full minute activates the cornstarch and gives you that sticky, glossy coating.

The batter is intentionally thick. It needs to hold its shape on top of the pineapple ring without running to the edges. Beat it just until blended and stop. Overbeating develops the gluten and you’ll end up with a tough, chewy cake instead of a tender one.

Pro Tips

• Wait exactly 10 minutes before inverting. Too soon and the syrup is still liquid. Too long and the cake sticks to the dish.
• Run a knife around the edge before flipping to release any caramelized syrup that’s adhered to the sides.
• Butter the dishes even though you’re adding syrup. The syrup doesn’t coat the sides, and that’s where sticking happens.
• Serve immediately while the syrup is warm and glossy. These lose their shine as they cool.

Variations

• Place a maraschino cherry in the center of each pineapple ring before adding batter for the classic look.
• Swap cinnamon for a pinch of ground ginger and cardamom for a warm, spiced twist.
• Use fresh pineapple slices and store-bought pineapple juice for a fresher, brighter flavor.