Make the best pineapple upside down cake from scratch with caramelized pineapple rings, maraschino cherries, and a moist buttery cake. Easy classic recipe with step-by-step photos, storage tips, and skillet option. Ready in about 1 hour!
Prepare the topping: Pour melted butter into a 9-inch cake pan or 10-inch cast iron skillet. Sprinkle brown sugar evenly over the butter. Arrange pineapple slices on top. Place a maraschino cherry in the center of each ring. Add extra cherries in any gaps if desired.
Make the cake batter: In a large bowl, whisk together flour, baking powder, baking soda, salt, and sugar. In a separate bowl or measuring cup, whisk buttermilk, melted butter, pineapple juice, eggs, and vanilla. Pour wet ingredients into dry and stir until just combined. Fold in chopped pineapple pieces.
Assemble and bake: Pour batter over the pineapple topping and spread evenly. Bake 45–60 minutes until a toothpick inserted in the center comes out clean. You can follow my tips for how to tell when your cake is done.
Cool and flip: Remove from oven and let rest 5–10 minutes. Run a knife around the edges, place a serving plate or cake stand on top, and carefully invert the cake. Lift the pan slowly.
Notes
Storage & Make-Ahead:Room Temperature: Up to 1 day.Refrigerator: Covered up to 5 days. Bring to room temp before serving.Freezer: Wrap tightly and freeze up to 3 months. Thaw overnight in the fridge.Make-Ahead: Bake the cake a day ahead and store covered in the fridge.