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Old Fashioned Pineapple Upside Down Cake

Old Fashioned Pineapple Upside Down Cake

A deeply comforting, nostalgic dessert baked in a cast iron skillet. Golden pineapple tidbits, ruby cherries, and a spiced cake batter bake together under a rich brown sugar and maple glaze.
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Ingredients
  

  • 1 15.25 oz box yellow cake mix
  • 1 large can pineapple tidbits reserve the juice
  • 1/2 cup brown sugar for the pan, packed to cover
  • 2 tablespoons brown sugar for the batter
  • 2 tablespoons maple syrup
  • 1 jar maraschino cherries drained and patted dry
  • Vegetable oil amount as called for on cake mix box
  • Eggs amount as called for on cake mix box
  • 1/2 teaspoon ground cinnamon
  • 1/4 teaspoon ground allspice
  • 1 teaspoon vanilla extract
  • Pan spray

Instructions
 

  • Preheat and Prep: Preheat your oven to 350°F. Generously coat a 10-inch or 12-inch cast iron skillet with baking pan spray.
  • Build the Base: Pack the 1/2 cup of brown sugar evenly across the bottom of the skillet to completely cover the iron. Drizzle the maple syrup evenly over the sugar.
  • Add the Fruit: Drain the pineapple tidbits, reserving all the juice in a separate bowl. Scatter the tidbits evenly over the sugar layer. Nestle the dried cherries among the pineapple.
  • Mix the Batter: In a large mixing bowl, combine the yellow cake mix, the oil, and the eggs according to the box instructions. Instead of water, use the reserved pineapple juice. Add the remaining 2 tablespoons of brown sugar, cinnamon, allspice, and vanilla extract. Blend well.
  • Assemble: Carefully pour the spiced batter over the fruit in the skillet, spreading it gently to the edges.
  • Bake: Bake for 40 minutes, or until the edges are bubbling and the center springs back to the touch.
  • Flip and Serve: Remove from the oven and let the skillet rest for exactly 5 minutes. Place a large plate upside down over the skillet and carefully, using oven mitts, flip the pan over. Lift the skillet away to reveal the fruit topping.