• 1/2 cup real, unsalted butter
  • 1 and 1/3 cups packed brown sugar
  • 3 and 1/2 cups fresh pineapple chunks
  • 2 and 2/3 cups 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 9Γ—13 glass baking pan. Put the pan in the oven to melt it. Once melted, sprinkle the brown sugar evenly over the melted butter, followed by an even layer of 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, milk and vinegar mixture, eggs, and vanilla. Using the whisk attachment, mix on low for 30 seconds just to combine ingredients. Then, turn the mixer to high and beat for 3 minutes, scraping the downsides of the bowl a couple of times during the process. Pour the batter into the cake pan over pineapple.
  4. Place the cake pan on a jelly roll pan or line the rack with aluminum foil.
  5. 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.
  6. Once done, remove the cake from the oven. Gently loosen the sides of the cake from the pan using a butter knife.
  7. 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.
  8. Allow the cake pan to rest over the cake for 3 minutes before removing it so the caramelized brown sugar can drizzle over the top of the cake.
  9. Serve warm, at room temperature, or cold with sweetened whipped cream and maraschino cherries.

Indulge in the deliciousness of this Pineapple Upside-Down Cake, featuring a perfect blend of caramelized brown sugar and fresh pineapple chunks, creating a delightful treat for any occasion! 🍍🍰

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