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The Ultimate Classic & Easy Pineapple Upside Down Cake (Moist & Caramelized)

A slice cut 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 for a moist, buttery dessert with a perfectly caramelized pineapple topping. This easy recipe is a nostalgic crowd-pleaser perfect for family gatherings or potlucks.

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
  • 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 will need a 9-inch round cake pan.
  2. Pour the melted butter into the bottom of the cake pan. Sprinkle the brown sugar evenly over the 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.
  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 softened butter and granulated sugar until light and fluffy.
  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 reserved pineapple juice. Mix until just combined; do not overmix.
  8. Gently pour the cake batter over the pineapple and cherry layer in the pan. Spread the batter evenly.
  9. Bake for 35 to 40 minutes, or until a toothpick inserted into the center comes out clean.
  10. Let the cake cool in the pan on a wire rack for 10 minutes.
  11. Place a serving plate upside down over the cake pan. Carefully invert the cake onto the plate. Lift the pan away slowly. Serve warm or at room temperature.

Notes

  • For a Bundt cake variation, grease and flour a Bundt pan well before adding the butter and sugar layer. Baking time may increase slightly.
  • If you want to use a cake mix, follow the package directions for the cake batter, but substitute the required liquid with a mix of milk and reserved pineapple juice.
  • This cake keeps well covered at room temperature for up to two days.

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