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Upside Down Pineapple Cake

Updated: Jun 13, 2021

When I saw this recipe in the cookbook, it took me back to my childhood— this was one of my mother’s favorite bakes, and one of my favorite cakes to eat when I was younger. However, I felt that the recipe needed to be adapted to my tastes, and so I made a few revisions, with the help of my mother, to produce a more balanced cake. Most notably, the original recipe called for maraschino cherries, which, in my opinion, are too sweet and syrupy for the cake. Instead, we decided that fresh cherries would create less moisture in the oven and stay true to their tart and complex flavor. Furthermore, while I decided to use canned pineapple, the original recipe required both the fruit and the juice. I felt that the pineapple juices would produce a sweet, one-dimensional overall taste in the cake. Instead, I substituted the pineapple juice with apple cider for a lighter, more nuanced-tasting alternative. I found that, not only does the apple cider cut through the sweetness of the canned pineapple, it also helps to elevate the flavors of the cake since alcohol has a lower boiling temperature, and its inclusion magnified the sweet and tangy qualities of the bake.

Upside Down Pineapple Cake


  • 1/3 cup + 3 tablespoons butter, divided

  • 1/2 cup dark brown sugar

  • 6 pineapple slices (I used the canned pineapple)

  • 10 cherries

  • 1 1/2 cups all-purpose flour

  • 1 1/2 teaspoons baking powder

  • 1 cup granulated sugar

  • 1 egg

  • 1/2 cup apple cider

Yields: 1 (9-inch) round cake

Prep Time: 30 minutes

Cook Time: 45-50 minutes


  1. Preheat oven to 350°F.

  2. Melt 3 tablespoons of butter. In a round, non-stick cake 9- inch pan, place the melted butter and top with brown sugar.

  3. Add the pineapple rounds over the sugar, and fill gaps with the cherries.

  4. Set the pan aside while you prepare the batter.

  5. Sift the flour with the baking soda in a large mixing bowl. Set aside.

  6. In a stand mixer, beat the reaming 1/3 cup butter with the sugar.

  7. Add the egg.

  8. Add the flour mixture alternating with the apple cider.

  9. Beat well for 3 minutes until all the ingredients have been incorporated.

  10. Pour the batter over the pineapple in the pan.

  11. Bake for 45-50 minutes.

  12. Once done remove from the oven, and allow it to cool in the pan for 1 hour.

  13. Un-mold and enjoy.

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