Pineapple Upside Down Cake Image

Pineapple Upside Down Cake

Struggle Meals - "Vintage"

Prep Time
Cook Time


Pineapple Topping

  • 1 stick unsalted butter
  • 1 cup plus 2 tablespoons brown sugar
  • 11 rings of canned pineapple
  • 25 maraschino cherries

Vanilla Cake

  • 3 cups All Purpose flour
  • 1 teaspoon baking powder
  • 1/2 teaspoon baking soda
  • 1 teaspoon salt
  • 2 sticks unsalted butter, melted
  • 1/2 cup brown sugar
  • 1 cup granulated sugar
  • 2 eggs
  • 1/3 cup full fat greek yogurt
  • 2 teaspoons vanilla extract
  • 1 cup whole milk


Pineapple Topping

  1. Preheat the oven to 350 degrees. Grease a 9x13 inch baking dish and line the bottom with parchment paper.
  2. Heat the butter and brown sugar over low heat in a small saucepan. Stir constantly until the butter melts and brown sugar is fully incorporated. Pour the glaze into the bottom of the baking dish.
  3. Arrange the pineapple rings and cherries in a single layer on top of the butter and brown sugar glaze.

Vanilla Cake

  1. For the dry ingredients, mix the flour, baking powder, baking soda, and salt in a medium bowl.
  2. For the wet ingredients, in a separate large bowl, whisk the melted butter, brown sugar and granulated sugar together. Add the eggs, greek yogurt, and vanilla to the wet mixture, and whisk until well incorporated. Stir the dry ingredients into the wet a little at a time, alternating with the milk a little at a time as well. Whisk until batter is just incorporated.
  3. Pour the batter in the pan on top of pineapples. Bake for 40-45 minutes. Allow the cake to cool for 20 minutes before inverting. Top the pan with a cutting board that is slightly larger, and quickly and deliberately flip the pan away from you. Carefully remove parchment paper and cool completely before serving.