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Classic Pineapple Upside Down Cake: Moist and Buttery

A moist slice of pineapple upside down cake topped with caramelized pineapple rings and bright red maraschino cherries.
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Bake this classic Pineapple Upside Down Cake from scratch for a moist, buttery dessert with perfectly caramelized fruit. This retro favorite is simple to make and always impresses at gatherings.

Ingredients

Scale
  • 1/2 cup unsalted butter, softened
  • 3/4 cup packed light brown sugar
  • 1 (20 ounce) can pineapple slices in juice, drained (reserve juice)
  • 14 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). You will need a 9-inch round cake pan.
  2. In a small saucepan over medium heat, melt the 1/2 cup of butter. Stir in the brown sugar until it dissolves slightly, creating a thick syrup. Pour this mixture evenly into the bottom of your cake pan.
  3. Arrange the pineapple slices over the brown sugar mixture in the pan. Place one maraschino cherry in the center of each pineapple ring.
  4. In a medium bowl, whisk together the flour, baking powder, and salt. Set this dry mixture aside.
  5. In a large bowl, beat the remaining 1/2 cup of softened butter and the granulated sugar with an electric mixer until the mixture is light and fluffy. This step helps create a moist cake.
  6. Beat in the eggs one at a time, mixing well after each addition. Stir in the vanilla extract.
  7. In a small bowl, whisk together the milk and the reserved pineapple juice.
  8. Gradually add the dry ingredients to the wet ingredients, alternating with the milk and juice mixture. Mix only until just combined; do not overmix the batter.
  9. Gently spoon the cake batter over the pineapple and cherries in the pan, spreading it evenly without disturbing the fruit layer underneath.
  10. Bake for 35 to 40 minutes, or until a wooden pick inserted into the center comes out clean.
  11. Let the cake cool in the pan on a wire rack for 10 minutes.
  12. Place a serving plate upside down over the cake pan. Carefully and quickly invert the cake onto the plate. Lift the pan away slowly. If any topping sticks, gently place the fruit or cherry back into position.
  13. Allow the cake to cool slightly before slicing and serving.

Notes

  • For an extra tropical flavor, substitute 1/4 cup of the milk with an equal amount of coconut milk.
  • To ensure the caramelization is perfect, make sure the butter and brown sugar mixture covers the entire bottom of the pan evenly before adding the fruit.
  • If you want a richer flavor, use dark brown sugar instead of light brown sugar for the topping.

Nutrition

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