This delightful pineapple upside-down cake is a classic dessert that never fails to impress. The moist, flavorful cake pairs perfectly with the caramelized pineapples and brown sugar, creating a symphony of flavors in every bite. Whether you’re hosting a gathering or simply craving a sweet treat, this recipe is a surefire way to satisfy your dessert cravings.

Why You’ll Love This Recipe

This pineapple upside-down cake is a timeless favorite, loved for its perfect balance of sweet, tangy pineapple and rich, buttery cake. The combination of caramelized fruit and moist cake creates a delightful dessert that’s both comforting and indulgent. Plus, it’s a great way to showcase fresh pineapple in a unique and delicious way.


  • 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. Preheat the oven to 350°F (175°C).
  2. Place the butter in a 9×13 glass baking pan and place the pan in the oven to melt the butter. Once melted, sprinkle the brown sugar evenly over the melted butter, followed by an even layer of the pineapple chunks. Set the pan aside.
  3. In the bowl of a countertop mixer, combine flour, sugar, baking powder, and salt. Mix by hand, using a wire whisk.
  4. Add oil, milk and vinegar mixture, eggs, and vanilla. Using the whisk attachment, mix on low for 30 seconds just to combine the ingredients.
  5. Turn the mixer to high and beat for 3 minutes, scraping the sides of the bowl a couple of times during the process. Pour the batter into the cake pan over the pineapple.
  6. Place the cake pan on a jelly roll pan or line the rack with aluminum foil to catch any drips.
  7. Bake for 55 to 65 minutes or just until a toothpick inserted into the center of the cake comes out with a couple of moist crumbs on it.
  8. Once done, remove the cake from the oven. Gently loosen the sides of the cake from the pan using a butter knife.
  9. Place a clean jelly roll pan or large rectangular platter over the cake pan and carefully flip the cake over while still in the pan.
  10. Allow the cake pan to rest over the cake for 3 minutes prior to removing it so the caramelized brown sugar can drizzle over the top of the cake.
  11. Serve warm, at room temperature, or cold with sweetened whipped cream and maraschino cherries.


This cake can be stored at room temperature for up to 3 days. If you have leftovers, it’s best to refrigerate the cake in an airtight container for up to 5 days.

Recipe Tips

  • For an extra burst of flavor, consider adding a sprinkle of cinnamon or a splash of rum to the pineapple mixture before adding the batter.
  • Ensure the cake is completely cooled before storing it to maintain its texture and flavor.
  • When flipping the cake, be careful to avoid any hot caramelized sugar that may drip from the pan.
  • Feel free to customize the cake by adding other fruits such as cherries or even a touch of coconut for a tropical twist.

Enjoy this classic pineapple upside-down cake as a delightful ending to any meal or as a special treat for any occasion.

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