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Classic Moist Pineapple Upside Down Cake Recipe

Close-up of a slice of moist pineapple upside down cake topped with caramelized pineapple rings and bright red cherries.

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Bake this classic, moist Pineapple Upside Down Cake from scratch. You get sweet, buttery caramelization and tender fruit topping a rich, golden cake base. This retro dessert is perfect for parties or family gatherings.

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 3/4 cups all-purpose flour
  • 1 1/2 teaspoons baking powder
  • 1/2 teaspoon salt
  • 1/2 cup unsalted butter, softened
  • 3/4 cup granulated sugar
  • 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. Pour the 1/2 cup of melted butter into the bottom of the cake pan. Sprinkle the brown sugar evenly over the melted butter.
  3. Arrange the pineapple slices over the sugar mixture in a decorative pattern. Place one maraschino cherry in the center of each pineapple ring, and place any remaining cherries around the edges.
  4. In a medium bowl, whisk together the flour, baking powder, and salt. Set this dry mixture aside.
  5. In a large bowl, cream together the 1/2 cup softened butter and granulated sugar with an electric mixer 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. In a small bowl, whisk together the milk and the reserved pineapple juice.
  8. Gradually add the dry ingredients to the wet ingredients, alternating with the milk/juice mixture, beginning and ending with the dry ingredients. Mix until just combined; do not overmix the batter.
  9. Carefully spoon the cake batter over the pineapple and cherry layer in the pan, spreading it gently to cover the fruit evenly without disturbing the pattern.
  10. Bake for 35 to 40 minutes, or until a wooden pick inserted into the center comes out clean.
  11. Let the cake cool in the pan on a wire rack for 10 minutes.
  12. Place a serving plate upside down over the cake pan. Wearing oven mitts, carefully invert the pan and plate together. Lift the pan off the cake. If any fruit sticks, gently place it back onto the cake.
  13. Serve warm or at room temperature.

Notes

  • For an extra buttery flavor, use high-quality butter in both the topping and the cake batter.
  • If you want a slightly tropical twist, substitute 1/4 cup of the milk with coconut milk.
  • To ensure a perfectly moist cake, measure your flour using the spoon-and-level method.

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