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Classic Moist Pineapple Upside Down Cake

Two slices of moist pineapple upside down cake topped with caramelized pineapple and bright red cherries.
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Make this classic pineapple upside down cake for a show-stopping, nostalgic dessert. This recipe focuses on achieving a moist cake and a perfect caramelized pineapple topping.

Ingredients

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  • 1/2 cup unsalted butter
  • 3/4 cup packed light brown sugar
  • 1 (20 ounce) can pineapple slices in juice, drained (reserve 3 tablespoons juice)
  • 10 maraschino cherries, drained
  • 1 1/2 cups all-purpose flour
  • 1 1/2 teaspoons baking powder
  • 1/2 teaspoon salt
  • 1/2 cup granulated sugar
  • 1/2 cup unsalted butter, softened
  • 2 large eggs
  • 1 teaspoon vanilla extract
  • 1/2 cup whole milk
  • 3 tablespoons reserved pineapple juice

Instructions

  1. Preheat your oven to 350°F (175°C). You will use a 9-inch round cake pan for this recipe.
  2. In a small saucepan, melt 1/2 cup of butter over medium heat. Stir in the brown sugar until it dissolves and creates a thick syrup. Pour this mixture evenly into the bottom of your 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 this aside.
  5. In a large bowl, cream together the 1/2 cup softened butter and 1/2 cup granulated sugar until the mixture is light and fluffy. This takes about 3 minutes with an electric mixer.
  6. Beat in the eggs one at a time, mixing well after each addition. Stir in the vanilla extract.
  7. In a separate small bowl, whisk together the milk and the 3 tablespoons of reserved pineapple juice.
  8. Gradually add the dry ingredients to the wet ingredients, alternating with the milk mixture. Begin and end with the dry ingredients. Mix until just combined; do not overmix the batter.
  9. Gently spoon the cake batter over the pineapple and cherries in the pan, spreading it evenly without disturbing the fruit layer underneath.
  10. Bake for 35 to 40 minutes, or until a toothpick inserted into the center comes out clean.
  11. Remove the cake from the oven and let it cool in the pan on a wire rack for exactly 10 minutes.
  12. Place a serving plate or platter upside down over the cake pan. Carefully invert the pan and plate together. Lift the pan off the cake. If any fruit sticks, gently place it back onto the cake top.
  13. Let the cake cool slightly before slicing and serving.

Notes

  • For an easier version, substitute the dry ingredients with one box of yellow cake mix, following the box directions for liquid amounts, but still use the homemade caramel topping.
  • If you prefer baking in a cast iron skillet, use a 10-inch skillet and adjust baking time by a few minutes as needed.
  • Serve warm with vanilla ice cream for the best flavor experience.

Nutrition

Find it online: https://dishicious.com/pineapple-upside-down-cake-moist-recipe/