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

Close-up of a moist slice of pineapple upside down cake topped with caramelized pineapple 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 simple recipe is ideal for family gatherings or any time you want a nostalgic treat.

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 degrees F (175 degrees C). Lightly grease a 9-inch round cake pan.
  2. Pour the 1/2 cup melted butter into the prepared cake pan. Sprinkle the 3/4 cup brown sugar evenly over the butter.
  3. Arrange the drained pineapple slices on top of the sugar mixture. 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 aside.
  5. In a large bowl, cream together the 1/2 cup softened butter and 3/4 cup 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. 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 pour the cake batter over the pineapple and cherry layer in the pan. Spread the batter evenly.
  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. Carefully invert the cake onto the plate. Remove the pan. Serve warm or at room temperature.

Notes

  • For a Bundt cake variation, prepare the topping in the Bundt pan and increase baking time by about 10-15 minutes.
  • If you want a richer caramel, you can cook the butter and brown sugar on the stovetop for 2 minutes before pouring it into the pan.
  • This cake tastes great the next day, but it is best served the day it is made.

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