The Best Pineapple Upside-Down Cake: A Sweet Symphony of Flavors

Indulge in the timeless classic of Pineapple Upside-Down Cake with this exceptional recipe that promises a perfect balance of caramelized sweetness and moist cake crumb. Let the rich brown sugar, fresh pineapple chunks, and buttery goodness transport you to a world of delightful flavors. Follow the simple steps below to create The Best Pineapple Upside-Down Cake that will surely become a favorite at any gathering.


  • 1/2 cup real, unsalted butter
  • 1 and 1/3 cup packed brown sugar
  • 3 and 1/2 cups fresh pineapple chunks
  • 2 and 2/3 cup all-purpose flour
  • 2 cups sugar
  • 1 Tablespoon baking powder
  • 1 teaspoon salt
  • 2/3 cup vegetable oil
  • 1 and 1/2 cups milk + 1 Tablespoon white vinegar
  • 2 large eggs, lightly beaten
  • 1 teaspoon pure vanilla extract


  1. Place the butter in a 9×13 glass baking pan and melt it in the oven. Once melted, evenly sprinkle the brown sugar over the butter, followed by an even layer of fresh pineapple chunks. Set the pan aside.
  2. In the bowl of a countertop mixer, combine flour, sugar, baking powder, and salt. Mix by hand using a wire whisk.
  3. Add oil, the mixture of milk and white vinegar, eggs, and vanilla to the dry ingredients. Using the whisk attachment, mix on low for 30 seconds to combine, then turn the mixer to high and beat for 3 minutes. Scrape down the sides of the bowl during the process.
  4. Pour the batter into the cake pan over the pineapple, ensuring an even distribution.
  5. Place the cake pan on a jelly roll pan or line the rack with aluminum foil to catch any drips during baking.
  6. Bake for 55 to 65 minutes or until a toothpick inserted into the center of the cake comes out with a few moist crumbs.
  7. Once done, remove the cake from the oven. Gently loosen the sides of the cake from the pan using a butter knife.
  8. Place a clean jelly roll pan or a large rectangular platter over the cake pan and carefully flip the cake over while still in the pan.
  9. Allow the cake pan to rest over the cake for 3 minutes to let the caramelized brown sugar drizzle over the top of the cake.
  10. Serve The Best Pineapple Upside-Down Cake warm, at room temperature, or cold, garnished with sweetened whipped cream and maraschino cherries.

Conclusion: With its heavenly combination of pineapple, caramel, and moist cake, The Best Pineapple Upside-Down Cake is a dessert masterpiece that deserves a place at your table. Enjoy the sweet symphony of flavors and share this timeless treat with your loved ones for a delightful culinary experience.

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