Pineapple Upside-Down Cake


Fresh pineapple pieces are infused with vanilla bean, sugar, and baked with a sour cream vanilla cake for this show-stopping dessert.

Pineapple Upside-Down Cake
Photo: © Tina Rupp
Active Time:
30 mins
Total Time:
1 hrs 30 mins
1 8-inch cake

Slices of fresh pineapple set this cake apart from the usual, and you'll find the extra effort well worth it. Cook the pineapple with vanilla bean and sugar to create the topping for this fruity and decadent pineapple upside-down cake. The fluffy cake has sour cream and added vanilla extract for richness and a deeper flavor profile. 

You can make this into one eight-inch cake or make individual cakes the way Kristin Ferguson, pastry consultant at Firefly Bistro in South Pasadena, California, does. To top it off, she serves her pineapple upside-down cake with homemade buttermilk ice cream. You can also serve it with a dollop of whipped cream or your favorite store-bought ice cream.


  • 3/4 cup plus 2 tablespoons light brown sugar

  • 1 1/2 sticks unsalted butter, softened

  • 1 vanilla bean, split, seeds scraped

  • 1/2 large pineapple—peeled, quartered, cored and sliced 1/3 inch thick

  • 1/2 cup sour cream

  • 2 large eggs

  • 1 teaspoon pure vanilla extract

  • 1 1/4 cups all-purpose flour

  • 3/4 cup granulated sugar

  • 1/2 teaspoon baking powder

  • 1/4 teaspoon baking soda

  • 1/2 teaspoon salt


  1. Preheat the oven to 350°. Butter an 8-inch round cake pan. Sprinkle the bottom with 2 tablespoons of the brown sugar.

  2. In a large skillet, combine the remaining 3/4 cup of brown sugar with the 1/2 stick of butter and the vanilla bean and seeds and cook over moderately low heat until the butter is melted. Add the pineapple and cook over moderately low heat, stirring occasionally, until the pineapple is tender, about 20 minutes. Using a slotted spoon, arrange the slices in the cake pan, overlapping them if necessary. Remove the vanilla bean and pour the pan juices over the pineapple.

  3. In a bowl, whisk 1/4 cup of the sour cream with the eggs and vanilla. In another bowl, beat the flour, granulated sugar, baking powder, baking soda and salt. Add the remaining stick of butter and 1/4 cup of sour cream and beat at low speed until smooth, then beat at medium speed until fluffy. Add the sour cream–egg mixture and beat again until fluffy, 2 minutes.

  4. Spoon the batter over the pineapple and spread it evenly. Bake for about 40 minutes, until the cake is deep golden. Let cool for 5 minutes on a rack. Run a knife around the edge of the cake, invert it onto a plate and remove the pan. Replace any pineapple that may have stuck to the pan. Serve warm or at room temperature.

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