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The Best Pineapple Upside-Down Cake

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This Pineapple Upside-Down Cake is the perfect blend of buttery caramelized pineapple and a light, fluffy cake that’s to die for! The sweetness of brown sugar and fresh pineapple, combined with a rich cake base, makes it an irresistible treat for any occasion. Serve it warm with whipped cream for an unforgettable dessert experience!

Ingredients

Scale

  1. For the Pineapple Topping:

    • 1/2 cup real, unsalted butter
    • 1 and 1/3 cup packed brown sugar
    • 3 and 1/2 cups fresh pineapple chunks

    For the Cake Batter:

    • 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

Instructions

  • Prepare the Topping:
    • Preheat the oven and place the butter in a 9×13 glass baking pan. Let the butter melt in the oven.
    • Once melted, evenly sprinkle brown sugar over the butter, then layer the pineapple chunks on top. Set aside.
  • Make the Cake Batter:
    • In a countertop mixer, combine flour, sugar, baking powder, and salt. Mix by hand using a wire whisk.
    • Add vegetable oil, milk, vinegar mixture, eggs, and vanilla. Mix on low for 30 seconds to combine.
    • Increase the speed to high and beat for 3 minutes, scraping the sides of the bowl as necessary.
  • Bake the Cake:
    • Pour the batter over the pineapple layer in the pan.
    • Place the cake pan on a jelly roll pan or line the rack with aluminum foil.
    • Bake at 350°F for 55 to 65 minutes, or until a toothpick inserted comes out with a couple of moist crumbs.
  • Flip and Serve:
    • Once baked, remove from the oven and gently loosen the sides with a butter knife.
    • Place a clean jelly roll pan or large platter over the cake and carefully flip the pan over.
    • Let the cake rest for 3 minutes before removing the pan so that the caramelized sugar drizzles over the top.
    • Serve warm, at room temperature, or cold with whipped cream and maraschino cherries.

Notes

  • For a rich, indulgent touch, serve with sweetened whipped cream or a scoop of vanilla ice cream.
  • Be careful when flipping the cake to avoid spills. The caramelized topping will be hot!

Nutrition

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