Fresh Pineapple Upside Down Cake

I thought that canned pineapple was the best way to make a pineapple upside down cake.  That’s how everyone does it right?  I guess I thought fresh pineapple would be too tough, or just too much work.  It was so much better!  The texture was perfect and the fresh pineapple flavor really came through. The recipe came from Martha Stewart, but I made a few changes to suit the ingredients I had on hand.

  • 1 pineapple (I used about 3/4 of it)
  • 1 cup cake flour
  • 1 1/2 teaspoons baking powder
  • 1 1/4 cups granulated sugar
  • 12 tablespoons (1 1/2 sticks) unsalted butter at room temperature
  • 1/2 cup packed light brown sugar
  • 1 t. vanilla
  • 2 large eggs
  • 6 tablespoons whole milk
  • 1/2 teaspoon pure almond extract
  • Vanilla ice cream

Heat oven to 350 degrees. Peel the pineapple and cut off one end to form a flat base.  Cut down through the pineapple avoiding the core.  Slice the pineapple into thin (about 1/4 inch) slices.

Heat 1/2 cup of granulated sugar in a 10 1/2-inch cast-iron skillet. Cook until deep amber, about 5 minutes. Remove the pan from the heat. Add 4 tablespoons (1/2 stick) butter, stirring vigorously with a wooden spoon. Spread caramel evenly to coat the bottom of the skillet, and sprinkle with brown sugar.

Center one piece of pineapple in the skillet. Place pineapple slices in a tightly overlapping circle. Make a second ring, completely covering the bottom. Mine ended up looking sort of like a dahlia or daisy pattern.

In a standing mixer, cream the remaining butter, remaining 3/4 cup of granulated sugar, and vanilla. Add eggs one at a time, mixing well after each addition. Pour in milk and almond extract. Slowly add flour and baking soda, scraping sides as needed. Pour batter into pineapple-lined skillet. Spread batter evenly with an offset spatula.

Bake until golden brown and cake tester comes out clean, about 30 minutes.  Wait ten minutes, then invert the cake onto a platter.  Serve warm or room temperature with vanilla ice cream.

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About swellkid recipes

I am a mother of two boys, a wife, a teacher, and an avid home cook. These recipes are written, tested and created or adapted by me in my home kitchen. All photos were taken by me with my Canon Digital Rebel XT. No filters or Photoshop, usually natural light on my kitchen table. My motto is, if I can do it, you can do it!
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