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Classic Homemade Moist Pineapple Upside Down Cake: The Showstopper Version

A close-up of a slice of pineapple upside down cake topped with caramelized pineapple rings and bright red maraschino cherries.
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You will love this classic Pineapple Upside Down Cake recipe. It is a showstopper dessert, perfect for family gatherings, that delivers a moist, buttery crumb and sweet, caramelized pineapple topping. This retro dessert is easy to make from scratch and always impresses everyone.

Ingredients

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  • 1/2 cup unsalted butter
  • 1 cup packed light brown sugar
  • 1 (20 ounce) can pineapple slices in juice, undrained
  • 10 maraschino cherries, with stems removed
  • 1 3/4 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 whole milk

Instructions

  1. Preheat your oven to 350°F (175°C). You will use a 9-inch round cake pan or a 10-inch cast iron skillet for this recipe.
  2. In a small saucepan over medium heat, melt the 1/2 cup of butter. Stir in the brown sugar until it dissolves and forms a thick syrup. Pour this mixture evenly into the bottom of your prepared pan.
  3. Drain the pineapple slices, reserving the juice for another use if you wish. Arrange the pineapple slices over the brown sugar mixture in a decorative pattern. Place one maraschino cherry in the center of each pineapple ring, and place any remaining cherries around the fruit.
  4. In a medium bowl, whisk together the flour, baking powder, and salt. Set this aside.
  5. In a large bowl, use an electric mixer to cream together the 1/2 cup of softened butter and the granulated sugar until the mixture is light and fluffy. This step helps make your cake moist.
  6. Beat in the eggs one at a time, mixing well after each addition. Mix in the vanilla extract.
  7. Gradually add the dry ingredients to the wet ingredients, alternating with the milk. Begin and end with the flour mixture. Mix only until just combined; do not overmix the batter.
  8. Gently spoon the cake batter over the pineapple and cherry layer in the pan, spreading it evenly without disturbing the fruit arrangement underneath.
  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 about 10 minutes.
  11. Place a serving plate upside down over the cake pan. Carefully invert the cake onto the plate. Lift the pan away slowly. If any fruit sticks, gently place it back onto the cake top.
  12. Serve the cake warm or at room temperature. This cake is fantastic with a scoop of vanilla ice cream.

Notes

  • For an extra showstopper presentation, consider baking this in a Bundt pan instead of a round pan.
  • If you want a quick version, you can substitute the dry ingredients with one box of yellow cake mix, following the package directions for liquid amounts, but still prepare the topping separately.
  • This recipe is a favorite shared on Pinterest by many home cooks looking for the best pineapple upside down cake.

Nutrition

Find it online: https://kitchenuser.net/pineapple-upside-down-cake-recipe-moist/