Prep the pan: Lightly grease the cake pan with cooking spray or butter. Cut a parchment round for the bottom if you like, though it’s not required.

Make the topping: Stir melted butter and brown sugar together until the mixture looks like wet sand. Spread it evenly over the bottom of the pan.

Arrange fruit: Lay pineapple rings over the sugar layer, snug but not overlapping. Nestle a cherry in the center of each ring. Patting the fruit dry helps prevent excess moisture.

Mix dry ingredients: In a bowl, whisk flour, baking powder, salt, and optional cinnamon until combined.

Mix wet ingredients: In another bowl, whisk sugar, milk, oil, egg, vanilla, and optional almond extract until smooth.

Make the batter: Add dry ingredients to wet and whisk just until no dry streaks remain. Do not overmix; a few tiny lumps are fine.

Assemble: Gently pour batter over the fruit. Spread to the edges with a spatula to create an even layer.

Preheat the air fryer: Set it to 320°F (160°C) for 3 minutes with the empty basket to warm up.

Bake: Place the pan in the basket. Air fry at 320°F (160°C) for 22–28 minutes. Start checking at 20 minutes. The cake is done when the center springs back and a toothpick comes out clean.

Prevent over-browning: If the top browns too quickly, tent a small piece of foil over the pan for the last 5–8 minutes, leaving space for air to circulate.

Cool briefly: Let the cake rest in the pan for 10 minutes. This helps the caramel set slightly so it unmolds cleanly.

Invert: Run a thin knife around the edge. Place a plate over the pan and flip confidently. Lift the pan to reveal the glossy pineapple top.

Serve: Slice warm or at room temperature. A dollop of whipped cream or vanilla ice cream is a great finish.