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The Ultimate Moist Pineapple Upside Down Cake From Scratch with Perfect Caramelization

Close-up of a moist slice of pineapple upside down cake with caramelized topping on a white plate.
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This recipe translates the classic, nostalgic Pineapple Upside Down Cake into a simple, from-scratch version that guarantees a moist crumb and a perfectly caramelized topping that releases cleanly from the pan. This is the showstopper dessert you need for family gatherings.

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, undrained
  • 10 maraschino cherries, stems removed
  • 1 3/4 cups all-purpose flour
  • 1 1/2 teaspoons baking powder
  • 1/2 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
  • 1/4 cup reserved pineapple juice

Instructions

  1. Preheat your oven to 350°F (175°C). You need a 9-inch round cake pan.
  2. Make the topping: In the prepared cake pan, melt the 1/2 cup of softened butter. Sprinkle the brown sugar evenly over the melted butter.
  3. Arrange the pineapple slices over the sugar mixture. Place one maraschino cherry in the center of each pineapple ring.
  4. Prepare the cake batter: In a medium bowl, whisk together the flour, baking powder, and salt. Set this dry mix aside.
  5. In a separate large bowl, cream together the 1/2 cup softened butter and granulated sugar until the mixture is light and fluffy. This is key for a moist cake.
  6. Beat in the eggs one at a time, mixing well after each addition. Stir in the vanilla extract.
  7. Combine the dry ingredients and wet ingredients alternately with the milk and the reserved pineapple juice. Start and end with the dry ingredients (three additions of dry, two of wet). Mix only until just combined; do not overmix.
  8. Carefully pour the cake batter over the pineapple and cherry layer in the pan. Spread the batter evenly.
  9. Bake for 35 to 40 minutes, or until a toothpick inserted into the center comes out clean.
  10. Cool the cake in the pan on a wire rack for exactly 10 minutes. This short cooling time helps the caramel set slightly but keeps it soft enough to release.
  11. Place a serving plate upside down over the cake pan. Wearing oven mitts, firmly hold the plate and the pan together, and quickly flip them over. The cake should drop onto the plate with the topping facing up. If any fruit sticks, gently place it back onto the cake.
  12. Serve warm. This is the best pineapple upside down cake when served shortly after flipping.

Notes

  • To prevent sticking, make sure your butter fully coats the bottom of the pan before adding the brown sugar.
  • For a Southern Style Pineapple Cake flavor, you can substitute half the milk with buttermilk.
  • If you want a Bundt Cake variation, grease and flour a Bundt pan well before layering the topping. Increase the bake time by 10 to 15 minutes.

Nutrition

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