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The Best Classic Pineapple Upside Down Cake From Scratch

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 classic pineapple upside down cake from scratch for a moist, tender crumb and a perfectly caramelized fruit topping. This recipe focuses on achieving a beautiful, non-stick release every time.

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)
  • 10 maraschino cherries, stems removed
  • 1 1/2 cups all-purpose flour
  • 1 1/2 teaspoons baking powder
  • 1/4 teaspoon salt
  • 1/2 cup (1 stick) 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 bake this cake in a 9-inch round cake pan or a 10-inch cast iron skillet.
  2. Prepare the topping: In a small bowl, mix the 1/2 cup softened butter and 1 cup brown sugar until combined. Press this mixture evenly into the bottom of your prepared pan.
  3. Arrange the fruit: Place one pineapple slice over the brown sugar mixture in the center of the pan. Place one maraschino cherry in the center hole of each pineapple slice, and arrange the remaining cherries around the edges.
  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, beat the 1/2 cup softened butter and 3/4 cup granulated sugar with an electric mixer until light and fluffy. This step builds the structure for your moist cake.
  6. Beat in the eggs one at a time, mixing well after each addition. Stir in the vanilla extract.
  7. Combine the wet and dry ingredients: Gradually add the flour mixture to the butter mixture, alternating with the milk and the 3 tablespoons of reserved pineapple juice. Mix until just combined. Do not overmix the batter.
  8. Pour the cake batter evenly over the fruit layer in the pan. Spread gently with a spatula.
  9. Bake for 35 to 40 minutes, or until a wooden pick inserted into the center comes out clean.
  10. Cool the cake in the pan on a wire rack for exactly 10 minutes. This cooling time is crucial for the caramel to set slightly but remain pourable.
  11. Place a serving plate or platter upside down over the cake pan. Carefully and quickly invert the pan and plate together. Lift the pan off the cake. If any fruit sticks, gently place it back onto the cake.
  12. Let the cake cool slightly before slicing and serving warm.

Notes

  • For the best release, line the bottom of the cake pan with parchment paper before adding the brown sugar mixture, cutting the paper to fit the circle exactly.
  • If you do not have a 9-inch round pan, a 10-inch cast iron skillet works perfectly for this recipe and adds a nice rustic touch.
  • If the caramel seems too thick when pouring the batter, warm the reserved pineapple juice slightly before adding it to the batter.

Nutrition

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