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Is the Secret to Making the Best Pineapple Upside Down Cake Double Brown Sugar Caramel?

Old Fashioned Pineapple Upside Down Cake

Catherine Olson
Baked in a cast iron skillet with double the brown sugar caramel topping this old fashioned pineapple upside down cake is everyone's favorite cake!
Prep Time 45 mins
Cook Time 45 mins
Course Dessert
Cuisine American
Servings 8 pieces


  • 10" Cast Iron Skillet


Double Brown Sugar Caramel Topping

  • 1 fresh pineapple
  • 12 tablespoons unsalted butter
  • 1 ½ cups packed light brown sugar

Cake Batter

  • 1 ½ cups all-purpose flour
  • 2 teaspoons baking powder
  • ¼ teaspoon salt
  • 6 tablespoons unsalted butter softened
  • 1 cup granulated sugar
  • 2 large eggs
  • 1 teaspoon vanilla
  • 1 tablespoon dark rum imitation works great
  • ½ cup unsweetened pineapple juice can use half the pineapple for juicing


Double Brown Sugar Caramel Topping

  • Cut pineapple into ½ inch thick pieces and cut out the center of each piece
  • Set aside pineapple
  • In 10” cast iron pan melt butter and add brown sugar
  • Simmer over medium-high heat until mixture comes to a boil stirring constantly
  • Cook for 5-6 minutes
  • Remove from heat and allow to cool for 10 minutes
  • Arrange pineapple on top of sugar mixture in skilet, overlapping pieces slightly until the base of the pan is covered

Cake Batter

  • Beat butter and sugar in a large bowl with an electric mixer until light and fluffy
  • Add eggs one at a time, beating well after each addition
  • Add vanilla and rum
  • Incorporate half of the flour, baking powder, and salt and mix on low just until blended
  • Add pineapple juice and beat again until blended
  • Add remaining flour, again just until blended
  • Batter may appear slightly curdled
  • Spoon batter over pineapple in the cast iron pan and spread evenly until pineapple slices are covered
  • Bake at Fahrenheit 350° for 35 to 45 minutes
  • Remove from oven and let sit for 5 minutes
  • Carefully invert cake onto a plate
  • Serve cake warm or at room temperature