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Classic Pineapple Upside Down Cake: A Moist, Retro Favorite

A moist slice of pineapple upside down cake topped with a caramelized pineapple ring and a maraschino cherry.
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Bake this classic Pineapple Upside Down Cake from scratch for a moist, buttery dessert with perfectly caramelized fruit. This recipe delivers a nostalgic treat that is impressive but simple to make.

Ingredients

Scale
  • 1/2 cup unsalted butter
  • 1 cup packed light brown sugar
  • 1 (20 ounce) can pineapple slices in juice, drained (reserve juice)
  • 14 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 will need a 9-inch round cake pan. Give yourself a high-five for getting the oven on!
  2. Melt 1/2 cup of butter in the cake pan over low heat on the stovetop, or carefully in the oven. Once melted, sprinkle the brown sugar evenly over the butter.
  3. Arrange the drained pineapple slices over 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. This is a great step to celebrate!
  5. In a separate large bowl, cream together the 1/2 cup softened butter and granulated sugar until light and fluffy. You are doing great!
  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. Gently spoon the cake batter over the pineapple and cherry layer in the pan. Spread it evenly.
  10. Bake for 35 to 40 minutes, or until a toothpick inserted into the center comes out clean.
  11. Let the cake cool in the pan on a wire rack for 5 minutes. This short wait is important.
  12. Place a serving plate upside down over the cake pan. Carefully and quickly invert the cake onto the plate. Lift the pan away slowly. If any topping sticks, gently place the fruit back into position.
  13. Let the cake cool slightly before slicing and serving. You made a beautiful, moist pineapple cake!

Notes

  • For an extra layer of flavor, add 1 teaspoon of dark rum to the melted butter and brown sugar mixture before adding the pineapple.
  • If you want a truly Southern Style Pineapple Cake, use buttermilk instead of regular milk for a slightly tangier crumb.
  • To ensure a moist pineapple upside down cake, do not press the batter down over the fruit; let it settle naturally.

Nutrition

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