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Pineapple Upside Down Cake

Pineapple Upside Down Cake

  • Author: The Commish
  • Prep Time: 20 min
  • Cook Time: 40 min
  • Total Time: 1 hr + 15 min cooling
  • Yield: 10 servings 1x
  • Category: Dessert



For the pineapple mixture:

  • 4 tablespoons butter
  • 1/2 cup brown sugar
  • 1/4 cup dark rum
  • 1 fresh pineapple, peeled and sliced into 1/4-inch rounds, then quartered

For the cake:

  • 1 1/3 cups flour
  • 2 teaspoons baking powder
  • 1/4 teaspoon salt
  • 1/4 teaspoon nutmeg
  • 1/4 teaspoon ginger
  • 1/2 cup finely shredded coconut
  • 1/3 cup butter, room temperature
  • 2/3 cup sugar
  • 1 teaspoon vanilla
  • 1 teaspoon dark rum
  • 1 egg, room temperature
  • 1/2 cup milk


  1. In a 10-inch cast iron skillet over low heat, melt the butter. Using a wooden spoon, stir in the brown sugar. After the mixture begins to caramelize, remove from heat. Stir in the rum. Arrange the pineapple wedges on top of the caramelized layer so that none of the wedges overlap. Set aside.
  2. Preheat the oven to 350 degrees F.
  3. In a medium bowl, sift together the flour, baking powder, salt, nutmeg and ginger. Carefully stir in the shredded coconut.
  4. In the bowl of a stand mixer fitted with a paddle attachment, cream the butter and sugar on medium speed. Add the vanilla and rum, then add the egg. Alternately add the milk and dry ingredients until fully combined.
  5. Spread the batter over the pineapple slices. Bake until the top is golden brown and a cake tester comes out clean, about 40 minutes.
  6. Transfer the cake to a wire rack, and allow to cool for 15 minutes. Run an offset spatula around the edges to loosen the cake. Carefully invert the cake onto a serving plate. Allow to cool to room temperature, then serve.


Optional: Serve with a scoop of whipped cream and toasted coconut.