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Pineapple Upside Down Cake from Scratch Recipe

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4.3 from 4 reviews

This Pineapple Upside Down Cake from scratch is a classic dessert featuring a buttery brown sugar topping with caramelized pineapple rings and maraschino cherries, layered under a moist and fluffy vanilla pineapple cake. The cake is baked to golden perfection and inverted to reveal a beautiful tropical topping, making it perfect for any occasion.

Ingredients

Topping

  • Cooking spray
  • 4 tablespoons unsalted butter
  • 1/2 cup light brown sugar
  • 1/4 teaspoon vanilla extract
  • 1 8-ounce can pineapple rings in 100% pineapple juice
  • 8 maraschino cherries

Cake

  • 1 1/2 cups all-purpose flour
  • 1 teaspoon baking powder
  • 1/2 teaspoon salt
  • 8 tablespoons unsalted butter, softened to room temperature
  • 1 cup sugar
  • 2 large eggs
  • 1/2 teaspoon vanilla extract
  • 1/2 cup pineapple juice (from the canned pineapple)

Instructions

  1. Preheat and Prepare Pan: Preheat your oven to 350°F (175°C). Generously spray a 9-inch round cake pan with cooking spray to ensure the cake will release easily after baking.
  2. Make the Topping: In a small saucepan over low heat, melt 4 tablespoons of butter with 1/2 cup light brown sugar, stirring occasionally until the mixture is smooth. Remove from heat and stir in 1/4 teaspoon vanilla extract. Pour this caramel mixture evenly into the bottom of the prepared cake pan.
  3. Arrange Pineapple and Cherries: Arrange pineapple rings in a single layer over the brown sugar mixture. Place one maraschino cherry in the center of each ring. Set aside.
  4. Mix Dry Ingredients: In a small bowl, whisk together 1 1/2 cups all-purpose flour, 1 teaspoon baking powder, and 1/2 teaspoon salt. Set this aside.
  5. Cream Butter and Sugar: In a medium bowl, using an electric mixer, beat 8 tablespoons softened unsalted butter with 1 cup sugar until the mixture is smooth and fluffy, about 1 minute.
  6. Add Eggs, Vanilla, and Pineapple Juice: Beat in 2 large eggs one at a time, then add 1/2 teaspoon vanilla extract and 1/2 cup pineapple juice. Mix until combined.
  7. Add Dry Ingredients: Sprinkle the flour mixture over the wet ingredients and beat just until combined. Be careful not to overmix.
  8. Assemble and Bake: Gently spread the cake batter evenly over the arranged pineapple rings in the pan. Smooth the top with a spatula. Bake in the preheated oven for about 45 minutes. Test doneness by inserting a toothpick into the top layer of the cake; it should come out mostly clean. Avoid inserting the toothpick into the fruit layer, which will be wet.
  9. Cool and Invert: Let the cake cool in the pan for about 20 minutes. Then place a serving plate over the pan and carefully invert the cake onto the plate. Tap firmly to release the cake. If it doesn’t release easily, warm the pan in the oven for a few minutes and try again.

Notes

  • Use a 9-inch round cake pan for the best results.
  • Be sure to let the cake cool slightly before inverting to prevent breaking.
  • You can substitute maraschino cherries with fresh cherries or omit if preferred.
  • For a more tropical twist, add a splash of rum to the cake batter.
  • Ensure butter is softened but not melted for proper creaming with sugar.