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Classic Pineapple Upside Down Cake: A Moist, Retro Favorite

Close-up of a moist slice of pineapple upside down cake topped with caramelized pineapple and bright red maraschino cherries.
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Recreate this sweet, buttery, and nostalgic dessert. This recipe focuses on achieving perfectly caramelized pineapple rings and a wonderfully moist cake base, making it a guaranteed crowd-pleaser for any gathering.

Ingredients

Scale
  • 1/2 cup unsalted butter, melted
  • 3/4 cup packed light brown sugar
  • 1 (20 ounce) can pineapple slices in juice, drained (reserve juice)
  • 10 maraschino cherries, drained
  • 1 1/2 cups all-purpose flour
  • 1 1/2 teaspoons baking powder
  • 1/2 teaspoon salt
  • 1/2 cup granulated sugar
  • 1/2 cup unsalted butter, softened
  • 2 large eggs
  • 1 teaspoon vanilla extract
  • 1/2 cup milk
  • 1/4 cup reserved pineapple juice

Instructions

  1. Preheat your oven to 350 degrees F (175 degrees C). You will need a 9-inch round cake pan.
  2. In the bottom of the cake pan, pour the 1/2 cup of melted butter evenly. Sprinkle the brown sugar over the butter.
  3. Arrange the pineapple slices over the brown sugar mixture in a decorative pattern. Place one maraschino cherry in the center of each pineapple ring, and place any remaining cherries in the gaps between the slices.
  4. Prepare the cake batter: In a medium bowl, whisk together the flour, baking powder, and salt. Set this aside.
  5. In a large bowl, cream together the 1/2 cup softened butter and the granulated sugar until the mixture is light and fluffy. This step helps create a moist cake.
  6. Beat in the eggs one at a time, mixing well after each addition. Stir in the vanilla extract.
  7. Gradually add the dry ingredients to the wet ingredients, alternating with the milk and the reserved pineapple juice. Mix until just combined; do not overmix the batter.
  8. Gently spoon the cake batter over the pineapple and cherry layer in the pan. Spread the batter evenly without disturbing the fruit arrangement underneath.
  9. Bake for 35 to 40 minutes, or until a wooden pick inserted into the center comes out clean.
  10. Let the cake cool in the pan on a wire rack for about 5 to 10 minutes. This short cooling time is key for easy flipping.
  11. Place a serving plate upside down over the cake pan. Carefully and quickly invert the pan and plate together. Lift the pan off the cake. If any topping sticks, gently place it back onto the cake.
  12. Serve warm or at room temperature. This classic pineapple cake is best enjoyed the day it is made.

Notes

  • For an extra rich, buttery pineapple cake flavor, use good quality butter in the topping.
  • If you want a slightly tropical twist, substitute 1/4 cup of the milk with coconut milk in the batter.
  • To ensure a moist pineapple upside down cake, avoid overbaking; check for doneness early.

Nutrition

Find it online: https://delishdiarist.com/pineapple-upside-down-cake-recipe-moist/