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Classic Pineapple Upside Down Cake: Moist and Buttery Retro Dessert

A slice cut from a moist pineapple upside down cake showing caramelized topping and tender crumb.
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Make the best Pineapple Upside Down Cake from scratch. This recipe delivers a moist, tender crumb and perfectly caramelized pineapple rings, bringing a sweet, nostalgic flavor to your table.

Ingredients

Scale
  • 1/2 cup unsalted butter
  • 1 cup packed light brown sugar
  • 1 (20 ounce) can pineapple slices in juice, drained (reserve 3 tablespoons juice)
  • 10 maraschino cherries, stems removed
  • 1 1/2 cups all-purpose flour
  • 1 teaspoon 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 whole 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. Melt 1/2 cup of butter in the cake pan over low heat or in the microwave. Sprinkle the brown sugar evenly over the melted butter.
  3. Arrange the drained pineapple slices on top of the sugar mixture in the pan. 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 separate large bowl, beat the 1/2 cup softened butter and granulated sugar with an electric mixer until the mixture is light and fluffy. This step helps make your cake moist.
  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 1/4 cup of pineapple juice.
  8. Gradually add the flour mixture to the wet ingredients, alternating with the milk mixture, beginning and ending with the flour. Mix only until just combined; do not overmix.
  9. Carefully spoon the batter evenly over the pineapple and cherries in the prepared pan.
  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 5 minutes.
  12. Place a serving plate upside down over the cake pan. Holding both the plate and the pan firmly together, quickly flip them over. Lift the pan off carefully. If any topping sticks, gently replace the pineapple or cherry pieces.
  13. Serve warm for the best buttery pineapple flavor.

Notes

  • For an extra tropical flavor, add 1 teaspoon of rum extract to the batter when you add the vanilla.
  • If you want a richer caramel layer, use dark brown sugar instead of light brown sugar for the topping.
  • To prevent sticking, make sure the butter completely covers the bottom of the pan before adding the sugar.

Nutrition

Find it online: https://cookifyme.com/pineapple-upside-down-cake-recipe/