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Pineapple Upside Down Cake on a plate

Pineapple Upside Down Cake

Our brown sugar and rum pineapple upside down cake is a stunner! We break with tradition via brown sugar, ginger, pecans, and pineapple soaked in dark rum!
Course Dessert
Cuisine American
Keyword How Do I Make Pineapple Upside Down Cake, How To Make Pineapple Upside Down Cake, Pineapple Upside Down Cake, Pineapple Upside Down Cake Recipe
Prep Time 20 minutes
Cook Time 40 minutes
Total Time 1 hour
Servings 8 -12 servings
Calories 734kcal
Author Kathleen


  • 5 Rings Fresh Pineapple Cut Into 1/2 Rings
  • 1/2 cup dark rum
  • 6 tablespoons plus 1/2 cup unsalted butter
  • 1 ⅔ cup dark brown sugar packed, divided
  • 1/3 cup pecan halves
  • 1 ⅔ cup all-purpose flour
  • 1 teaspoon dried ground ginger
  • 1 teaspoon baking powder
  • 1 teaspoon baking soda
  • 1/2 teaspoon salt
  • 3 egg large
  • 1 tablespoon vanilla extract
  • 1 teaspoon mild flavored molasses
  • 2/3 cup buttermilk well shaken


  •  Preheat oven to 350 degrees.
  •  Pour rum in a 10X14 pyrex baking dish. Place pineapple rings in rum and flip them to coat. Let stand for about 30 minutes at room temperature.
  • Melt 6 tablespoons of butter in a 9 1/2 inch cast iron skillet over medium heat. Add 1 cup of the brown sugar and whisk until sugar dissolves and syrup boils about 2 minutes.  Drain pineapple and arrange in a skillet in a nice pattern.  Tuck pecan pieces into spaces.
  • Whisk flour, ginger, baking powder, baking soda, and salt in a medium bowl.
  • Beat 1/2 cup butter and 2/3 cup brown sugar in a large bowl.  Beat in eggs, vanilla, and molasses.  Beat in flour mixture in 3 additions alternating with 2 additions of buttermilk.  Spoon batter over pineapple.
  • Bake in preheated oven about 35-40 minutes or until a toothpick inserted in center of the cake comes out clean.
  • Allow cake to cool for about 5 minutes. Place a large plate over the cast iron pan and flip it over.  The cake should pop right out.  Be careful! I don't think anything is hotter than cast iron!


Serving: 1/8 of the recipe | Calories: 734kcal | Carbohydrates: 142g | Protein: 9g | Fat: 15g | Saturated Fat: 7g | Cholesterol: 86mg | Sodium: 348mg | Potassium: 823mg | Fiber: 9g | Sugar: 102g | Vitamin A: 713IU | Vitamin C: 270mg | Calcium: 175mg | Iron: 4mg