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Pineapple Upside Down Cake

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This classic Pineapple Upside Down Cake features a simple, moist vanilla cake base topped with caramelized pineapples and cherries in a buttery brown sugar glaze. A vintage favorite that’s as beautiful as it is delicious, this pineapple upside down cake recipe is always a crowd-pleaser and perfect for any occasion!

Ingredients

  • Topping:
  • 1/4 cup unsalted butter (melted)
  • 1/2 cup packed light brown sugar
  • Pineapple rings (canned or fresh, drained if using canned)
  • Maraschino cherries
  • Cake Batter:
  • 1 1/2 cups all-purpose flour
  • 1 tsp baking powder
  • 1/2 tsp baking soda
  • 1/4 tsp salt
  • 1/2 cup unsalted butter (softened)
  • 3/4 cup granulated sugar
  • 2 large eggs
  • 1 tsp vanilla extract
  • 1/2 cup sour cream
  • 1/4 cup whole milk

Instructions

  • Preheat your oven to 350°F (175°C).
  • Pour melted butter into a 9-inch round cake pan. Sprinkle brown sugar evenly over the butter.
  • Arrange pineapple rings over the brown sugar. Place a cherry in the center of each ring.
  • In a medium bowl, whisk together flour, baking powder, baking soda, and salt.
  • In a large bowl, cream butter and sugar until light and fluffy. Add eggs one at a time, beating well after each. Stir in vanilla.
  • Mix in sour cream, then milk. Gradually add dry ingredients and mix until just combined.
  • Carefully spoon batter over the pineapples and spread evenly.
  • Bake for 40–45 minutes, or until a toothpick inserted in the center comes out clean.
  • Cool for 10 minutes in the pan, then invert onto a serving plate.
  • Serve warm or at room temperature.

Notes

  • Make sure to let the cake rest for a few minutes before flipping to allow the caramel topping to set slightly.
  • You can substitute fresh pineapple or use pineapple tidbits for a different look.
  • For added flavor, brush the cake with a bit of pineapple juice before serving.