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3.67 from 21 votes

Ultimate Fresh Pineapple Upside Down Cake

This Ultimate Fresh Pineapple Upside Down Cake has caramelized fresh pineapple basking in a rich butter brown sugar gooiness atop a fluffy vanilla cake and it's INSANE!
Servings: 12 Slices
Calories: 157kcal
Author: Kim Lange


Bottom of Cake:

  • 2 Tablespoons brown sugar

Caramelized Pineapple:

  • 3/4 cup brown sugar
  • 1/2 stick unsalted butter softened
  • 1 large pineapple—peeled quartered, cored and sliced 1/3 inch thick

Vanilla Cake

  • 1 stick (1/2 cup) unsalted butter very softened
  • 3/4 cup granulated sugar
  • 1/2 cup Greek yogurt or sour cream
  • 2 large eggs
  • 1 teaspoon vanilla extract
  • 1 1/4 cups all-purpose flour
  • 1/2 teaspoon baking powder
  • 1/4 teaspoon baking soda
  • 1/2 teaspoon salt


  • Pan Preparation:
  • Preheat the oven to 350°.
  • Butter an deep dish 8-inch or 9-inch round cake pan. Sprinkle the bottom with 2 tablespoons of the brown sugar.

Carmelized Pineapple:

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

Vanilla Cake:

  • In a medium bowl, whisk together the flour baking powder, baking soda and salt, set aside.
  • In a large bowl, whisk together yogurt, eggs, vanilla, set aside.
    Using mixer, mix together the softened butter and sugar for 2 minutes on medium speed and then add in the yogurt/egg mixture and mix together.
    Add flour mixture to the yogurt mixture and mix just until combined and no lumps appear.
  • 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.


Canned pineapple can be used as well.


Calories: 157kcal | Carbohydrates: 38g | Protein: 1g | Fat: 1g | Saturated Fat: 1g | Sodium: 125mg | Potassium: 49mg | Fiber: 1g | Sugar: 28g | Calcium: 22mg | Iron: 1mg