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Pineapple Vanilla Upside Down Cake


  • For the Caramelized Pineapple

  • 4 tablespoon, 2 ounces or 1/2 stick of butter

  • 1 cup dark brown sugar

  • 1 pineapple, peeled, cored and cut into thick wedges

  • For the Cake Batter

  • 1 cup of AP or pastry flour

  • 1/2 cup fine cornmeal

  • 1/2 cup brown sugar

  • 1 tablespoon baking powder

  • 1/2 teaspoon salt

  • 1 stick (8 tablespoons or 4 ounces) butter, gently melted

  • 1/2 cup milk

  • 2 eggs

  • 2 tablespoon vanilla extract


  • 1.

    Preheat your oven to 400°.

  • For the Caramelized Pineapple:

  • 1.

    Gently melt the butter in a 12” cast iron skillet over medium heat. Sprinkle the sugar evenly over the melted butter and continue heating as it melts into a bubbling brown syrup. Don’t stir the pan but as the steam disappears and it begins to bubble and brown gently swirl it for even cooking. Turn off the heat. Add the pineapple wedges, in a radial pattern, jamming them all in to make them fit. Turn the heat back to medium low. Continue cooking until the pineapple lightly browns. A medium low to medium heat will work best, a slow patient browning heat. This step takes 15 to 20 minutes but it’s worth it! Flip pineapple and gently brown the other side.

  • For the Cake Batter:

  • 1.

    Preheat your oven to 400°.

  • 2.

    Dry and wet. Whisk the flour, cornmeal, brown sugar, baking powder and salt together. In a separate bowl, whisk together the butter, milk, eggs and vanilla extract. Add the wet to the dry and combine until smooth. You may use your stand mixer or just a hand whisk and a wooden spoon. Pour the batter over the caramelized pineapple in the pan and bake for 18-20 minutes. Cool on the counter for 10 minutes or so then carefully invert onto a plate. Try using oven mitts to tightly place the plate on the edges of the skillet then clamp and flip it over in one fluid motion. It works!

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