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Classic Easy Pineapple Upside Down Cake

A moist slice of pineapple upside down cake topped with caramelized pineapple rings and maraschino cherries.

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Make this moist, buttery Pineapple Upside Down Cake from scratch. It features perfectly caramelized pineapple rings and is simple enough for any occasion.

Ingredients

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  • 1/2 cup unsalted butter, softened
  • 3/4 cup packed light brown sugar
  • 1 (20 ounce) can pineapple slices in juice, drained (reserve juice)
  • 10 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
  • 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. Melt 1/2 cup butter in a small saucepan over medium heat. Stir in the brown sugar until dissolved. Pour this mixture evenly into the bottom of the cake pan.
  3. Arrange the drained 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 aside.
  5. In a separate large bowl, cream together the remaining 1/2 cup softened butter and granulated sugar until light and fluffy.
  6. Beat in the eggs one at a time, mixing well after each addition. Stir in the vanilla extract.
  7. Gradually add the dry ingredients to the wet ingredients, alternating with the milk and reserved pineapple juice, beginning and ending with the dry ingredients. Mix until just combined. Do not overmix.
  8. Carefully pour the cake batter over the pineapple and cherry layer in the pan. Spread gently to cover the fruit evenly.
  9. Bake for 35 to 40 minutes, or until a wooden pick inserted into the center comes out clean.
  10. Let the cake cool in the pan on a wire rack for 10 minutes.
  11. Place a serving plate upside down over the cake pan. Wearing oven mitts, carefully flip the cake and plate over together. Lift the pan off the cake. If any topping sticks, gently place it back onto the cake.
  12. Serve warm or at room temperature.

Notes

  • For a Bundt cake, increase the recipe by half and adjust baking time as needed.
  • To make individual mini cakes, use muffin tins and reduce the baking time to about 20 minutes.
  • If you prefer a deeper caramel flavor, use dark brown sugar for the topping.

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