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Classic Moist Pineapple Upside Down Cake

A close-up of a slice removed from a moist pineapple upside down cake topped with caramelized pineapple rings and maraschino cherries.

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Make this classic Pineapple Upside Down Cake from scratch for a moist, buttery dessert with perfectly caramelized fruit topping. This retro favorite is simple to prepare and great 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 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°F (175°C). You need a 9-inch round cake pan.
  2. Pour the 1/2 cup 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 pattern. Place one maraschino cherry in the center of each pineapple ring.
  4. In a medium bowl, whisk together the flour, baking powder, and salt. Set this aside.
  5. In a large bowl, cream the 1/2 cup softened butter and granulated sugar together until light and fluffy.
  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 mixture, beginning and ending with the dry ingredients. Mix until just combined; do not overmix.
  9. Carefully spoon the cake batter over the pineapple and cherry layer in the pan, spreading it evenly without disturbing the fruit arrangement.
  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 flip the pan and plate over 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 a richer caramel flavor, use dark brown sugar in the topping.
  • If you want a moister cake, ensure you do not overmix the batter after adding the flour.
  • You can substitute the reserved pineapple juice with 1/4 cup of pineapple juice from a can of crushed pineapple if you prefer.

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