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Classic Pineapple Upside Down Cake From Scratch

A close-up of a moist slice of pineapple upside down cake topped with caramelized pineapple rings and bright red maraschino cherries.

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Make this classic pineapple upside down cake from scratch for a moist, tender dessert with a perfect caramelized fruit topping. This recipe ensures the cake releases cleanly from the pan.

Ingredients

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  • 1/2 cup unsalted butter
  • 1 cup packed light brown sugar
  • 1 (20 ounce) can pineapple slices in juice, drained (reserve juice)
  • 10 maraschino cherries, drained
  • 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
  • 1/4 cup reserved pineapple juice

Instructions

  1. Preheat your oven to 350°F (175°C). Do not grease your 9-inch round cake pan.
  2. In a small saucepan over medium heat, melt the 1/2 cup of butter. Pour the melted butter into the bottom of the cake pan.
  3. Sprinkle the brown sugar evenly over the melted butter.
  4. Arrange the pineapple slices on top of the brown sugar mixture. Place one maraschino cherry in the center of each pineapple ring, and scatter the remaining cherries around the edges.
  5. In a medium bowl, whisk together the flour, baking powder, and salt. Set this aside.
  6. In a separate large bowl, cream together the 1/2 cup softened butter and the granulated sugar until light and fluffy.
  7. Beat in the eggs one at a time, mixing well after each addition. Stir in the vanilla extract.
  8. In a small bowl, whisk together the milk and the reserved pineapple juice.
  9. Gradually add the dry ingredients to the wet ingredients, alternating with the milk mixture, beginning and ending with the dry ingredients. Mix until just combined; do not overmix.
  10. Carefully pour the cake batter over the pineapple and cherry layer in the pan. Spread the batter evenly.
  11. Bake for 35 to 40 minutes, or until a wooden pick inserted into the center comes out clean.
  12. Remove the cake from the oven and let it cool in the pan on a wire rack for exactly 10 minutes.
  13. Place a serving plate upside down over the cake pan. Wearing oven mitts, carefully invert the pan and plate together. Let the pan sit for a minute, then gently lift the pan off the cake. If any fruit sticks, place it back onto the cake.
  14. Serve warm.

Notes

  • For best results and to prevent sticking, do not grease the pan before adding the butter and sugar topping. The butter and sugar create a natural non-stick caramel layer.
  • If you want a richer caramel flavor, you can use dark brown sugar instead of light brown sugar.
  • This moist pineapple dessert is excellent served with a scoop of vanilla ice cream or whipped cream.

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