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Pineapple Upside Down Cake

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A retro classic that never goes out of style, this Pineapple Upside Down Cake is moist, buttery, and topped with caramelized pineapple rings and maraschino cherries for a gorgeous, golden finish that’s perfect for any celebration.

Ingredients

Units Scale
  • 1 (20 oz) can pineapple slices in juice (reserve 1/2 cup juice)
  • 1 jar maraschino cherries
  • 1/2 cup light brown sugar
  • 3/4 cup unsalted butter (divided: 1/4 cup melted for pan, 1/2 cup for batter)
  • 1 1/2 cups all-purpose flour
  • 1 1/2 tsp baking powder
  • 1/4 tsp salt
  • 1 cup granulated sugar
  • 2 large eggs
  • 1 tsp vanilla extract
  • 1/2 cup reserved pineapple juice
  • 1/4 cup milk

Instructions

  1. Preheat oven to 350°F (175°C). Grease a 9-inch round cake pan and pour in 1/4 cup melted butter. Sprinkle the brown sugar evenly over the butter.
  2. Arrange the pineapple slices over the brown sugar mixture and place a maraschino cherry in the center of each slice. Set aside.
  3. In a medium bowl, whisk together the flour, baking powder, and salt.
  4. In a large mixing bowl, cream together the remaining 1/2 cup softened butter and granulated sugar until light and fluffy.
  5. Add eggs one at a time, beating well after each addition. Mix in the vanilla extract.
  6. In a small bowl, combine the reserved pineapple juice and milk.
  7. Add the dry ingredients to the wet mixture in two additions, alternating with the pineapple juice-milk mixture. Mix until just combined—do not overmix.
  8. Gently pour the batter over the arranged pineapple slices and smooth the top with a spatula.
  9. Bake for 45–50 minutes, or until a toothpick inserted in the center comes out clean.
  10. Let the cake cool in the pan for 10 minutes. Carefully invert onto a serving plate. Let cool slightly before serving.

Notes

  • Use room temperature ingredients for better mixing and texture.
  • Allow the cake to rest upside down for a few minutes before lifting the pan to ensure the topping stays intact.
  • Optional: Brush a little extra reserved pineapple juice over the cake for added moisture and shine.
  • This cake is best served slightly warm or at room temperature.

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