Pineapple Upside Down Cake Recipe from Scratch

This is by far my favorite way to make pineapple upside down cake, it is relatively easy considering it is from scratch. Everyone marvels at the topping of this cake!



  • 1 pineapple, peeled, cored, and sliced into 1/2 inch slices (1 16 ounce can of sliced pineapple may be substituted)
  • 1 jar maraschino cherries, or fresh cherries pitted
  • 1/2 cup dark brown sugar
  • 1/2 stick real butter (4 Tablespoons)
  • Cake:

  • 2 1/4 cups flour
  • 1 1/3 cup sugar
  • 3 tsp baking powder
  • 1 tsp. salt
  • 1 cup milk
  • 1/2 cup of soften butter
  • 1 tsp real vanilla extract
  • 2 eggs
  • For the cake batter, blend flour, sugar (except the brown sugar), baking powder and salt. Add the soften butter, 2/3 cup milk and vanilla. Beat 2 minutes and medium speed.

    Scrape the sides of the bowl, add the rest of the milk and the egg, and beat another 2 minutes. Set aside and prepare topping.

    For the topping, heat butter in a cast iron skillet over medium heat. Sprinkle in brown sugar and continue over medium heat until sugar is bubbly and just begins to caramelize. Be careful not to burn it.

    Once it starts to caramelize, turn off the heat. Arrange the pineapple slices in the skillet and place cherries in the center of each cored pineapple.

    Gently pour the cake batter over the pineapple, being careful not to disturb your arrangement.

    Bake the cake in a 350 degree oven for 30 to 45 minutes, or until a cake tester comes out clean.

    Allow cake to cool and invert skillet to reveal the beautiful pineapple topping.

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