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Classic Moist Pineapple Upside Down Cake Recipe

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

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Make this classic, moist Pineapple Upside Down Cake from scratch. You get sweet, buttery caramelization and a tender crumb, making it the best pineapple dessert for any gathering.

Ingredients

Scale
  • 1/2 cup (1 stick or 113g) unsalted butter
  • 3/4 cup packed light brown sugar
  • 1 (20 ounce) can pineapple slices in juice, drained (reserve juice)
  • 10 maraschino cherries, drained
  • 1 3/4 cups all-purpose flour
  • 1 1/2 teaspoons baking powder
  • 1/2 teaspoon salt
  • 1/2 cup (1 stick or 113g) unsalted butter, softened
  • 1 cup granulated sugar
  • 2 large eggs
  • 1 teaspoon vanilla extract
  • 1/2 cup whole milk
  • 1/4 cup reserved pineapple juice

Instructions

  1. Preheat your oven to 350°F (175°C). You will need a 9-inch round cake pan.
  2. Melt 1/2 cup of butter in the cake pan over low heat on the stovetop, or carefully in the microwave. Remove from heat.
  3. Sprinkle the brown sugar evenly over the melted butter in the pan.
  4. Arrange the pineapple slices on top of the sugar mixture. Place one maraschino cherry in the center of each pineapple ring, and place any remaining cherries around the edges. Set the pan aside.
  5. In a medium bowl, whisk together the flour, baking powder, and salt. Set this dry mixture aside.
  6. In a large bowl, use an electric mixer to cream the 1/2 cup softened butter and granulated sugar until the mixture is light and fluffy. This step helps create a moist cake.
  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. Begin and end with the dry ingredients, mixing only until just combined. Do not overmix.
  10. Carefully pour the cake batter evenly over the pineapple and cherry layer in the prepared pan.
  11. Bake for 35 to 40 minutes, or until a wooden pick inserted into the center comes out clean.
  12. Let the cake cool in the pan on a wire rack for 10 minutes.
  13. Place a serving plate upside down over the cake pan. Wearing oven mitts, carefully flip the pan and plate over together. Lift the pan off the cake. If any topping sticks, gently place the fruit back onto the cake.
  14. Serve warm or at room temperature.

Notes

  • For an extra tropical flavor, add 1 teaspoon of rum extract to the cake batter along with the vanilla.
  • To ensure a very moist pineapple upside down cake, do not overbake. Check for doneness at 35 minutes.
  • If you are using a Bundt pan, increase the baking time by about 10 to 15 minutes and check for doneness.

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