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Classic Moist Pineapple Upside Down Cake

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, moist pineapple upside down cake from scratch. It features a buttery cake base topped with glossy, caramelized pineapple rings and cherries for a nostalgic, crowd-pleasing dessert.

Ingredients

Scale
  • 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
  • 1 1/2 cups all-purpose flour
  • 1 1/2 teaspoons baking powder
  • 1/4 teaspoon salt
  • 1/2 cup granulated sugar
  • 1/2 cup unsalted butter, softened
  • 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 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.
  5. In a medium bowl, whisk together the flour, baking powder, and salt. Set aside.
  6. In a large bowl, cream together the 1/2 cup softened butter and 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 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. 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 invert the cake onto the plate. Lift the pan off slowly. If any topping sticks, gently place the fruit back into position.
  14. Serve warm or at room temperature.

Notes

  • For guaranteed success, make sure your butter and eggs are at room temperature before mixing the batter.
  • If you want a richer caramel, use dark brown sugar instead of light brown sugar for the topping.
  • This cake keeps well covered at room temperature for up to two days.

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