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Pineapple Upside Down Cake

Pineapple Upside Down Cake

A semi-homemade version of an old-fashioned pineapple upside down cake! 
Course Dessert
Cuisine American
Keyword pineapple upside down cake
Prep Time 10 minutes
Cook Time 30 minutes
Resting Time 5 minutes
Servings 10
Calories 598kcal


  • 3 cups light brown sugar
  • 3/4 cups butter (1.5 sticks)
  • 1 box pineapple (or vanilla) cake mix
  • 1 cup water
  • 3 large eggs (room temperature)
  • 1/3 cup vegetable oil
  • 1 can pineapple slices
  • 7-10 maraschino cherries (for garnish)


  • Preheat oven to 350 degrees F. 
  • Spray a standard (10”) cast iron skillet with non-stick cooking spray. Place on a medium-high stovetop. 
  • Add butter and brown sugar. Cook until fully melted and bubbling. 
  • Arrange the pineapple slices evenly over the top of the sugar (about 7 slices). 
  • Using an electric or hand mixer, combine cake mix, water, eggs, and oil. 
  • Pour cake batter over the pineapple slices. 
  • Transfer cast iron skillet to oven and bake for about 30 minutes. 
  • Remove from oven and allow to rest for 5 minutes. 
  • Carefully flip the cake onto a large plate or cake stand, and add a maraschino cherry to the center of each pineapple ring. 


Calories: 598kcal | Carbohydrates: 109g | Protein: 4g | Fat: 17g | Saturated Fat: 10g | Cholesterol: 92mg | Sodium: 521mg | Potassium: 151mg | Sugar: 88g | Vitamin A: 505IU | Vitamin C: 0.5mg | Calcium: 183mg | Iron: 1.8mg