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Rosa’s Classic Pineapple Upside Down Cake

A 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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Bake this moist, retro-style pineapple upside down cake featuring a rich, buttery caramelized topping. This recipe uses simple steps for a perfect result every time.

Ingredients

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  • 1 cup (200g) granulated sugar for topping
  • 1/4 cup (57g) unsalted butter, cut into pieces
  • 1 (20 ounce) can pineapple slices in juice, drained (reserve 3 tablespoons juice)
  • 10 maraschino cherries
  • 1 1/2 cups (180g) all-purpose flour
  • 1 1/2 teaspoons baking powder
  • 1/2 teaspoon salt
  • 1/2 cup (113g) unsalted butter, softened
  • 3/4 cup (150g) 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). If you are not using a cast iron skillet, grease and flour a 9-inch round cake pan.
  2. Prepare the topping: In a medium saucepan, melt the 1/4 cup butter over medium heat. Stir in the 1 cup sugar until it dissolves and bubbles slightly, about 2 minutes. Do not let it burn.
  3. Pour the caramel mixture evenly into the bottom of your cake pan or 10-inch cast iron skillet.
  4. Arrange the pineapple slices over the caramel layer. Place one maraschino cherry in the center of each pineapple ring, and scatter the remaining cherries around the edges.
  5. Make the cake batter: In a medium bowl, whisk together the flour, baking powder, and salt. Set aside.
  6. In a large bowl, cream together the 1/2 cup softened butter and 3/4 cup sugar until light and fluffy. Beat in the eggs one at a time, then stir in the vanilla extract.
  7. Gradually add the dry ingredients to the wet ingredients, alternating with the milk and reserved pineapple juice, beginning and ending with the flour mixture. Mix until just combined; do not overmix.
  8. Carefully pour the cake batter over the pineapple and caramel layer in the pan. Spread the batter evenly.
  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 exactly 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 topping sticks, gently place the pieces back onto the cake.
  12. Serve warm or at room temperature.

Notes

  • For a cast iron skillet, use a 10-inch size for best results. If using a regular pan, a 9-inch round works well.
  • To prevent sticking, ensure the caramel is evenly distributed across the bottom before adding the batter.
  • For a tropical flavor variation, substitute 1 tablespoon of the milk with dark rum extract in the batter.
  • Serve this buttery caramel cake with vanilla ice cream or fresh whipped cream.

Nutrition

Find it online: https://rosatasty.com/pineapple-upside-down-cake-recipe-joy/