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Pineapple Upside-Down Cake

Prep Time:

30 mins.

Cook Time:

50 mins.


1 (9-inch) cake

The Pineapple Upside Down Cake was originally a “skillet cake.” Fruit and syrup were arranged in the bottom of a cast-iron skillet, topped with cake batter, and cooked on the stovetop. This homespun cake is a sweet slice of Americana that is making a comeback.



  • 1 ripe pineapple
  • 1 1/2 cups sugar
  • 1/4 cup rum


  • 1/2 stick (1/4 cup) unsalted butter
  • 1/2 cup brown sugar
  • 6 pineapple rings (as prepared from pineapple, above)
  • 12 maraschino cherries, stems removed


  • 1 1/2 cup Swans Down® Cake Flour
  • 1 teaspoon baking powder
  • 1/2 teaspoon salt
  • 1/2 stick (1/4 cup) unsalted butter, softened
  • 1 cup sugar
  • 2 large eggs
  • 1/2 cup buttermilk


  1. PREPARE PINEAPPLE: Remove rind from pineapple and slice into 6 (1/2-inch thick) rounds. Place a 3-inch round cookie cutter over each round to trim off outer edges; reserve the trimmed pieces. Place a 1-inch round cookie cutter on the center of each round and cut out the core, creating 6 pineapple rings; set rings aside. Dice remaining pineapple and trimmed pieces and place in a medium saucepan with granulated sugar and rum; heat over medium-high heat, reducing until liquid is the consistency of syrup. Remove from heat and strain diced pineapple from syrup, reserving both pineapple syrup and diced pineapple in separate containers; set both aside.
  2. MAKE TOPPING: Grease a 9-inch round cake pan with pan spray. Melt butter over medium heat, add brown sugar and cook and stir until it starts to bubble. Pour into prepared pan, spread out evenly and top with the 6 pineapple rings. Place cherries in the center of and between pineapple rings. Set aside.
  3. MAKE CAKE: Preheat oven to 350℉. Whisk flour, baking powder and salt in a medium bowl. Cream butter and sugar until light and fluffy. Add eggs and mix until combined. Add flour mixture intermittently with buttermilk, starting and ending with flour mixture. Fold reserved diced pineapple into batter. Pour batter evenly into pan to cover pineapple rings and bake for 40 to 50 minutes or until tester comes out clean. Remove from oven and brush top of cake with reserved pineapple syrup. Run a knife around sides of cake and cool for 10 minutes in pan. Place a plate or serving platter over cake, bottom side up. Carefully flip the plate and cake over so the cake is sitting on the plate.