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The Ultimate Classic Pineapple Upside Down Cake (From Scratch)

A close-up of a slice cut from a moist pineapple upside down cake, showing caramelized topping.

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Bake this classic, nostalgic Pineapple Upside Down Cake from scratch for a moist, tender crumb and a perfect, buttery caramelized topping. This recipe ensures your fruit releases cleanly from the pan every time.

Ingredients

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

Instructions

  1. Preheat your oven to 350°F (175°C). You will need a 9-inch round cake pan.
  2. Prepare the topping: Pour the 1/2 cup melted butter into the bottom of the cake pan. Sprinkle the 3/4 cup brown sugar evenly over the butter.
  3. Arrange the fruit: Place one pineapple slice in the center of the pan. Arrange the remaining pineapple slices around the edge, overlapping slightly if necessary. Place one maraschino cherry in the center of each pineapple ring and fill any gaps with remaining cherries.
  4. Make the cake batter: 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 3/4 cup granulated sugar until light and fluffy. This step builds the structure for a tender crumb.
  6. Beat in the eggs one at a time, mixing well after each addition. Stir in the vanilla extract.
  7. Combine wet and dry ingredients: Gradually add the flour mixture to the butter mixture, alternating with the milk and reserved pineapple juice. Begin and end with the dry ingredients. Mix only until just combined; do not overmix.
  8. Pour the batter evenly over the fruit layer in the prepared pan.
  9. Bake for 35 to 40 minutes, or until a wooden pick inserted into the center comes out clean.
  10. Cool the cake slightly: Let the cake cool in the pan on a wire rack for exactly 10 minutes. This allows the caramel to set slightly but remain soft enough to release.
  11. Invert the cake: Place a serving plate upside down over the cake pan. Carefully flip the pan and plate over together. Lift the pan off slowly. If any fruit sticks, gently place it back onto the cake.
  12. Serve warm, perhaps with vanilla ice cream.

Notes

  • For a quick version using cake mix, prepare one box of yellow cake mix according to package directions, substituting the required liquid with the reserved pineapple juice and milk mixture. Pour this batter over the prepared fruit layer.
  • To prevent sticking, ensure the melted butter fully coats the bottom of the pan before adding the brown sugar.
  • Serve this buttery pineapple cake warm for the best flavor and texture.

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