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Classic Moist Pineapple Upside Down Cake

A moist slice cut from a homemade pineapple upside down cake, topped with caramelized pineapple rings and maraschino cherries.

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Make this classic, moist Pineapple Upside Down Cake from scratch. It features caramelized pineapple rings and cherries baked into a sweet, buttery cake base.

Ingredients

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  • 1/2 cup unsalted butter
  • 3/4 cup packed light brown sugar
  • 1 (20 ounce) can pineapple slices in juice, undrained
  • 14 maraschino cherries, stems removed
  • 1 1/2 cups all-purpose flour
  • 1 1/2 teaspoons baking powder
  • 1/2 teaspoon salt
  • 1/2 cup unsalted butter, softened
  • 3/4 cup granulated sugar
  • 2 large eggs
  • 1 teaspoon vanilla extract
  • 1/2 cup milk

Instructions

  1. Preheat your oven to 350 degrees F. Melt 1/2 cup butter in a 9-inch round cake pan. Sprinkle the brown sugar evenly over the melted butter.
  2. Arrange the pineapple slices on top of the brown sugar mixture in the pan. Place one cherry in the center of each pineapple ring, and place any remaining cherries around the edges.
  3. In a medium bowl, whisk together the flour, baking powder, and salt. Set this dry mixture aside.
  4. In a large bowl, cream together the 1/2 cup softened butter and granulated sugar until light and fluffy. Beat in the eggs one at a time, then mix in the vanilla extract.
  5. Gradually add the dry ingredients to the wet ingredients, alternating with the milk, beginning and ending with the dry mixture. Mix until just combined; do not overmix.
  6. Carefully spoon the cake batter over the pineapple and cherries in the pan, spreading it evenly.
  7. Bake for 40 to 45 minutes, or until a wooden pick inserted into the center comes out clean.
  8. Let the cake cool in the pan on a wire rack for 5 minutes. Place a serving plate over the cake pan. Invert the cake onto the plate. Remove the pan carefully. Serve warm.

Notes

  • For a richer flavor, substitute 1/4 cup of the milk with 1/4 cup of dark rum when mixing the batter.
  • If you prefer a quicker method, you can substitute the from-scratch cake batter with one box of yellow cake mix prepared according to package directions, omitting any liquid called for and using the milk specified above.
  • This retro fruit cake tastes best when served warm.

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