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Classic Pineapple Upside-Down Cake

Classic Pineapple Upside-Down Cake

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This Classic Pineapple Upside-Down Cake features caramelized pineapple rings and cherries over a moist, buttery vanilla cake. A timeless dessert with a glossy brown sugar topping that makes every slice sweet, tender, and nostalgic.

Ingredients

Scale
  • 1/2 cup unsalted butter, melted and divided
  • 1 cup brown sugar, packed
  • 1 (20 ounce) can pineapple rings, drained
  • 8 to 10 maraschino cherries, drained
  • 1 1/2 cups all purpose flour
  • 3/4 cup granulated sugar
  • 1 1/2 teaspoons baking powder
  • 1/4 teaspoon salt
  • 2 large eggs
  • 1/2 cup milk
  • 1 teaspoon vanilla extract

Instructions

  1. Preheat the oven to 350°F and generously grease a 9 inch round cake pan.
  2. Pour 1/4 cup of the melted butter into the prepared pan and sprinkle the brown sugar evenly over it.
  3. Arrange the drained pineapple rings over the brown sugar layer and place a maraschino cherry in the center of each ring.
  4. In a bowl, whisk together the flour, baking powder, and salt.
  5. In a separate bowl, mix the remaining 1/4 cup melted butter with the granulated sugar until combined.
  6. Add the eggs, milk, and vanilla extract and mix until smooth.
  7. Gradually add the dry ingredients to the wet ingredients and mix until just combined.
  8. Pour the batter evenly over the pineapple layer and smooth the top.
  9. Bake for 40 to 45 minutes, until a toothpick inserted into the center comes out clean.
  10. Allow the cake to cool in the pan for 10 minutes, then run a knife around the edges and carefully invert onto a serving plate.

Notes

  • Pat the pineapple rings dry before arranging to prevent excess moisture.
  • Let the cake rest 10 minutes before flipping for a clean release.
  • Store covered at room temperature for up to 2 days or refrigerate for up to 5 days.