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A whole, beautifully caramelized Pineapple Upside Down Cake with maraschino cherries centered in each ring, resting on a white ruffled plate.

Pineapple Upside Down Cake

A classic, moist, golden cake topped with caramelized pineapple rings and cherries—beautiful, nostalgic, and irresistibly fruity.
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Prep Time 15 minutes
Cook Time 40 minutes
Total Time 55 minutes
Servings: 8 servings
Course: Dessert
Cuisine: American
Calories: 310
Ingredients Equipment Method Notes

Ingredients
  

Topping
  • 0.25 cup unsalted butter melted
  • 0.5 cup brown sugar
  • 6-8 pineapple rings
  • 10-12 maraschino cherries optional, alcohol-free
Cake Batter
  • 1.5 cups all-purpose flour
  • 1 cup granulated sugar
  • 0.5 cup unsalted butter softened
  • 2 eggs
  • 0.5 cup milk
  • 1 tsp vanilla extract
  • 2 tsp baking powder
  • 0.25 tsp salt

Equipment

  • 9-inch Round Cake Pan
  • Saucepan
  • Mixing bowls

Method
 

  1. Preheat oven to 350°F (175°C). Grease a 9-inch round cake pan.
  2. Melt 1/4 cup butter in a small saucepan over low heat. Stir in the brown sugar until dissolved, then pour the mixture evenly into the prepared cake pan.
  3. Arrange the pineapple rings on top of the sugar mixture, placing a cherry in the center of each ring if desired.
  4. In a mixing bowl, cream the softened butter and granulated sugar until light and fluffy.
  5. Add the eggs one at a time, beating well after each addition. Stir in the vanilla extract.
  6. In a separate bowl, whisk together flour, baking powder, and salt.
  7. Add the dry mixture to the butter mixture alternately with the milk, mixing just until smooth.
  8. Pour the batter evenly over the pineapple layer.
  9. Bake for 35–40 minutes, or until a toothpick inserted into the center comes out clean.
  10. Allow the cake to rest for 5 minutes, then carefully invert onto a serving plate. Let cool slightly before slicing.

Notes

Best enjoyed warm for maximum caramelized pineapple goodness!