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

Close-up of 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

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  • 1/2 cup unsalted butter
  • 1 cup packed light brown sugar
  • 1 (20 ounce) can pineapple slices in juice, undrained
  • 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

Instructions

  1. Preheat your oven to 350°F (175°C). You will need a 9-inch round cake pan.
  2. Melt 1/2 cup of butter in the cake pan over low heat on the stovetop, or use a small saucepan.
  3. Remove the pan from the heat. Sprinkle the brown sugar evenly over the melted butter.
  4. Drain the pineapple slices, reserving the juice. Arrange the pineapple slices over the brown sugar mixture in the pan. Place one maraschino cherry in the center of each pineapple ring.
  5. In a medium bowl, whisk together the flour, baking powder, and salt. Set this dry mixture aside.
  6. In a large bowl, cream together the 1/2 cup softened butter and granulated sugar until light and fluffy. This step creates a buttery cake base.
  7. Beat in the eggs one at a time, mixing well after each addition. Stir in the vanilla extract.
  8. In a small bowl, mix the reserved pineapple juice with the milk.
  9. Alternate adding the flour mixture and the milk mixture to the butter mixture, beginning and ending with the flour. Mix only until just combined; do not overmix.
  10. Carefully spoon the cake batter over the pineapple and cherry layer in the pan, spreading it gently to cover the fruit evenly.
  11. Bake for 35 to 40 minutes, or until a wooden pick inserted into the center comes out clean.
  12. Let the cake cool in the pan on a wire rack for 10 minutes.
  13. Place a serving plate upside down over the cake pan. Carefully invert the cake onto the plate. Lift the pan away slowly. If any topping sticks, gently replace the fruit onto the cake.
  14. Serve warm or at room temperature.

Notes

  • For a Bundt cake format, increase the recipe by half and adjust baking time as needed.
  • If you want a quick hack, you can substitute the dry ingredients and wet ingredients (except the pineapple juice/milk mixture) with one box of yellow cake mix prepared according to package directions, using the reserved pineapple juice and milk for moisture.
  • This cake keeps well for up to three days at room temperature when covered.

Nutrition

Find it online: https://cravybite.link/pineapple-upside-down-cake-recipe/