Prep the pan and air fryer: Spray your cake pan with nonstick spray. Cut a parchment circle for the bottom if you like extra insurance. Preheat the air fryer to 320°F (160°C) for 3–5 minutes.

Make the topping: Melt 3 tablespoons butter. Stir in 1/3 cup brown sugar until sandy and glossy. Spread this mixture evenly over the bottom of the pan.

Arrange the fruit: Lay pineapple rings over the brown sugar. Tuck cherries in the centers and any gaps. Patting the fruit dry helps the topping caramelize instead of getting soupy.

Cream the butter and sugar: In a bowl, beat 1/4 cup softened butter with 1/2 cup sugar until light and fluffy, about 2 minutes.

Add egg and vanilla: Beat in the egg and 1 teaspoon vanilla until smooth and slightly thick.

Mix dry ingredients: In another bowl, whisk 1 cup flour, 1 teaspoon baking powder, 1/4 teaspoon baking soda, and 1/4 teaspoon salt.

Combine wet and dry: Stir the dry mixture into the butter mixture in two additions, alternating with 1/3 cup milk. Add 2 tablespoons pineapple juice and mix until just combined. The batter should be thick but spreadable. Don’t overmix.

Assemble: Gently dollop the batter over the pineapples and spread to the edges. Try not to disturb the fruit layer.

Air fry: Place the pan in the air fryer basket. Cook at 320°F (160°C) for 22–28 minutes, until the top is golden and a toothpick in the center comes out clean or with a few moist crumbs.

Cool and invert: Let the cake rest in the pan for 10 minutes. Run a thin knife around the sides. Place a plate over the pan and flip carefully. Lift the pan and peel off parchment if used.

Finish: Let it cool another 10–15 minutes before slicing. Spoon any syrup left in the pan over the cake.