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Classic Pineapple Upside Down Cake: Moist and Caramelized

Close-up of a moist slice of pineapple upside down cake topped with caramelized pineapple rings and bright red maraschino cherries.
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Make the best Pineapple Upside Down Cake from scratch. This recipe delivers a moist cake base topped with perfectly caramelized pineapple rings and cherries, a true retro dessert favorite.

Ingredients

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  • 1/2 cup unsalted butter, softened
  • 1 cup packed light brown sugar
  • 1 (20 ounce) can pineapple slices in juice, drained (reserve 3 tablespoons juice)
  • 14 maraschino cherries, drained
  • 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
  • 3 tablespoons reserved pineapple juice

Instructions

  1. Preheat your oven to 350°F (175°C). You will need a 9-inch round cake pan.
  2. Melt 1/2 cup butter in a small saucepan over medium heat. Pour the melted butter into the bottom of the cake pan. Sprinkle the brown sugar evenly over the melted butter.
  3. Arrange the pineapple slices on top of the brown sugar mixture in the pan. Place one maraschino cherry in the center of each pineapple ring, and place any remaining cherries around the edges.
  4. In a medium bowl, whisk together the flour, baking powder, and salt. Set this dry mixture aside.
  5. In a large bowl, cream together the remaining 1/2 cup softened butter and the granulated sugar until the mixture is light and fluffy. This step helps create a moist cake.
  6. Beat in the eggs one at a time, mixing well after each addition. Stir in the vanilla extract.
  7. In a 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, beginning and ending with the dry ingredients. Mix until just combined; do not overmix.
  9. Carefully pour the cake batter over the pineapple and cherry layer in the prepared pan. Spread the batter evenly.
  10. Bake for 40 to 45 minutes, or until a wooden pick inserted into the center comes out clean.
  11. Let the cake cool in the pan on a wire rack for 10 minutes.
  12. Place a serving plate upside down over the cake pan. Wearing oven mitts, carefully invert the cake onto the plate. Lift the pan off slowly. If any topping sticks, gently place the fruit back onto the cake.
  13. Serve warm or at room temperature.

Notes

  • For a richer caramel flavor, you can use dark brown sugar for the topping layer.
  • If you want an extra moist pineapple cake, ensure your butter and eggs are at room temperature before mixing.
  • To prevent the cake from sticking when you flip it, line the bottom of the pan with parchment paper before adding the butter and sugar.

Nutrition

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