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A pineapple upside down cake with cherries

Pineapple Upside Down Cake

  • Author: Lindsay
  • Prep Time: 30 minutes
  • Cool Time: 20 minutes
  • Cook Time: 45 minutes
  • Total Time: 95 minutes
  • Yield: 8-10 slices
  • Category: Dessert
  • Method: Baking
  • Cuisine: American


Soft and buttery with caramelized pineapple and cherries, this Pineapple Upside Down Cake is just what you need to impress your guests. And, contrary to popular belief, it’s a not a difficult cake to make!


For the Topping

  • 1/4 cup butter, melted
  • 1/2 cup packed brown sugar
  • 10 canned pineapple slices
  • 13 maraschino cherries

For the Cake

  • 1 1/4 cups (163g) all-purpose flour
  • 1 tsp baking powder
  • 1/4 tsp salt
  • 6 tbsp (84g) unsalted butter, room temperature
  • 2 tbsp (30ml) vegetable oil
  • 1/2 cup (104g) sugar
  • 1/4 cup (56g) packed brown sugar
  • 1 1/2 tsp vanilla extract
  • 2 large eggs
  • 1/4 cup (60ml) milk
  • 1/4 cup (60ml) pineapple juice


  1. Preheat oven to 350°F (176°C).
  2. Combine the melted butter and brown sugar and spread evenly in the bottom and up the sides of a 9×2 inch cake pan.
  3. Drain the pineapple, reserving 1/4 cup of juice. Set juice aside and pat the pineapple slices dry so that you don’t add excess liquid to the topping. Arrange the pineapple slices and cherries over the brown sugar, using the photos above for visual reference.
  4. To make the cake batter, combine the flour, baking powder and salt in a medium sized bowl and set aside.
  5. Add the butter, oil, sugars and vanilla extract to a large mixer bowl and beat together until light in color and fluffy, about 2-3 minutes. Do not skimp on the creaming time.
  6. Add the eggs one at a time, mixing until mostly combined after each. Scrape down the sides of the bowl as needed to be sure all ingredients are well incorporated.
  7. Add half of the dry ingredients to the batter and mix until mostly combined.
  8. Slowly add the milk and reserved pineapple juice and mix until well combined. The batter may look a little curdled, but that’s ok.
  9. Add the remaining dry ingredients and mix until well combined and smooth. Scrape down the sides of the bowl as needed to be sure all ingredients are well incorporated. Do not over mix the batter.
  10. Add the batter to the prepared cake pan and spread evenly. Bake for 30 minutes, then cover with foil and bake another 10-15 minutes to prevent the top from over-browning. The cake is done when a toothpick inserted in the middle comes out clean.
  11. Remove the cake from the oven and press the cake down gently to help flatten any dome. I placed a dish cloth on top of the cake to help press on the hot cake.
  12. Let the cake cool in the pan for 20 minutes, then invert onto a cooling rack. Allow the cake to cool a bit before serving. It’s best served warm, but if you allow it to cool completely to room temperature, you can heat individual slices for 10-15 seconds to warm them back up a bit.