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Pineapple Upside Down Cake

Pineapple Upside Down Cake

Course Dessert
Cuisine American
Keyword Pineapple Upside Down Cake
Prep Time 15 minutes
Cook Time 40 minutes
Servings 8 people
Author Amanda Rettke



  • 2 1/4 cups (281g) all-purpose flour
  • 1 1/2 cups (300g) granulated sugar
  • 3 1/2 tsp. baking powder
  • 1 tsp. salt
  • 1 1/4 cup milk
  • 1/8 cup vegetable oil
  • 1/2 cup (1 stick or 113g) Challenge Butter, softened
  • 1 tbsp. vanilla extract
  • 3 large eggs


  • 1/2 cup (1 stick or 113g) Challenge Butter, melted
  • 1 cup brown sugar, packed


  • 2 pineapples, cut into long slices



  1. Preheat oven to 350°. Get out a 12-inch cast iron skillet.

  2. In a medium bowl, sift together flour, sugar, baking powder, and salt. Set aside.
  3. Place softened butter into a stand mixer and mix on medium for 1-2 minutes.
  4. Place dry ingredients into the stand mixer and combine with butter for 30 seconds.
  5. Add milk, oil, vanilla, and eggs and mix on medium-high until ingredients are combined.


  1. Pour melted butter into an ungreased skillet. Sprinkle the brown sugar evenly over the butter.


  1. Take the long slices of pineapple and start layering them around the edge of the pan, directly over the butter and brown sugar. It is fine to sneak them up the sides a bit. Continue layering pineapple around the pan working towards the center, making sure there is no brown sugar coming through.
  2. Pour prepared cake batter over the pineapple.
  3. Place skillet in the oven for 38-42 minutes, or until the bottom is browned and the center does not jiggle. You can test the cake with a toothpick; just insert it and if you remove it with any wet batter, the cake is not done.
  4. When the cake is done, remove from oven and let sit for a couple of minutes. Take a large serving platter and place it face-down on the hot skillet. With one hand held flat on the bottom of the platter and the other holding the handle of the skillet (using a hot pad! The skillet will be hot), flip the cake over. Once the platter is firmly on the counter, use both hands to gently lift the skillet away.

  5. Serve immediately.

Recipe Video

Recipe Notes

You can find Challenge Butter here. (Clickable Link)